Mẹo Hướng dẫn Which condition may be the result of an adverse medication effect associated with administration of chloramphenicol in infants quizlet? Mới Nhất

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Summary

Chloramphenicol is a broad spectrum antibiotic that is effective against a variety of susceptible and serious bacterial infections but is not frequently used because of its high risk of bone marrow toxicity.

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Brand Names

Chloromycetin

Generic NameChloramphenicolDrugBank Accession
NumberDB00446Background

An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic. (From Martindale, The Extra Pharmacopoeia, 29th ed, p106)

TypeSmall MoleculeGroupsApproved, Vet approvedStructure

WeightAverage: 323.129
Monoisotopic: 322.012326918 Chemical
Formula
C11H12Cl2N2O5Synonyms

  • Chloramphénicol
  • Chloramphenicol
  • Chloramphenicolum
  • Chlornitromycin
  • Cloramfenicol
  • Cloranfenicol
  • D-(−)-2,2-dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p.-nitrophenylethyl)acetamide
  • D-(−)-threo-1-p.-nitrophenyl-2-dichloroacetylamino-1,3-propanediol
  • Laevomycetinum
  • Levomicetina
  • Levomycetin

External IDs

  • NSC-3069

Indication

Used in treatment of cholera, as it destroys the vibrios and decreases the diarrhea. It is effective against
tetracycline-resistant vibrios. It is also used in eye drops or ointment to treat bacterial conjunctivitis.

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Associated Conditions

  • Acne
  • Allergic Conjunctivitis (AC)
  • Bacterial Conjunctivitis
  • Bacterial Conjunctivitis caused by susceptible bacteria
  • Bacterial Infections
  • Bacterial Keratitis
  • Bacterial dacryocystitis
  • Bacterial diarrhoea
  • Keratitis
  • Ocular
    Inflammation
  • Trachoma
  • Anterior eye segment inflammation
  • Bacterial blepharitis
  • Bacterial corneal ulcers
  • Non-purulent ophthalmic infections caused by susceptible bacteria
  • Superficial ocular infections
  • Swelling of the eyes

Associated Therapies

  • Skin disinfection

Contraindications & Blackbox Warnings

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Pharmacodynamics

Chloramphenicol is a broad-spectrum antibiotic
that was derived from the bacterium Streptomyces venezuelae and is now produced synthetically. Chloramphenicol is effective against a wide variety of microorganisms, but due to serious side-effects (e.g., damage to the bone marrow, including aplastic anemia) in humans, it is usually reserved for the treatment of serious and life-threatening infections (e.g., typhoid fever). Chloramphenicol is bacteriostatic but may be bactericidal in high concentrations or when used against highly susceptible
organisms. Chloramphenicol stops bacterial growth by binding to the bacterial ribosome (blocking peptidyl transferase) and inhibiting protein synthesis.

Mechanism of action

Chloramphenicol is lipid-soluble, allowing it to diffuse through the bacterial cell membrane. It then reversibly binds to the L16 protein of the 50S subunit of bacterial ribosomes, where transfer of amino acids to growing peptide chains is prevented (perhaps by suppression of
peptidyl transferase activity), thus inhibiting peptide bond formation and subsequent protein synthesis.

TargetActionsOrganismU50S ribosomal protein L16

inhibitor

Escherichia coli (strain K12)
UDr hemagglutinin structural subunit

antagonist

Escherichia coli
UComplement decay-accelerating factor

other

Humans
Absorption

Rapidly and completely absorbed from gastrointestinal tract following oral administration (bioavailability 80%). Well absorbed following intramuscular administration (bioavailability 70%). Intraocular and some systemic absorption also occurs after topical application to the eye.

Volume of distribution

Not Available

Protein
binding

Plasma protein binding is 50-60% in adults and 32% is premature neonates.

Metabolism

Hepatic, with 90% conjugated to inactive glucuronide.

Route of elimination

Not Available

Half-life

Half-life in adults with normal hepatic and renal function is 1.5 – 3.5 hours. In patients with impaired renal function half-life is 3 – 4 hours. In patients
with severely impaired hepatic function half-life is 4.6 – 11.6 hours. Half-life in children 1 month to 16 years old is 3 – 6.5 hours, while half-life in infants 1 to 2 days old is 24 hours or longer and is highly variable, especially in low birth-weight infants.

Clearance

Not Available

Adverse Effects

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Toxicity

Oral, mouse: LD50 = 1500 mg/kg; Oral, rat: LD50 = 2500 mg/kg. Toxic reactions including fatalities have occurred in the premature and newborn; the signs and symptoms associated with these reactions have been referred to as the gray syndrome. Symptoms include (in order of appearance) abdominal distension with or without emesis, progressive pallid
cyanosis, vasomotor collapse frequently accompanied by irregular respiration, and death within a few hours of onset of these symptoms.

Pathways
PathwayCategoryChloramphenicol Action Pathway
Drug action
Pharmacogenomic Effects/ADRs Not
AvailableDrug Interactions

This information should not be
interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

  • Approved
  • Vet approved
  • Nutraceutical
  • Illicit
  • Withdrawn
  • Investigational
  • Experimental
  • All
    Drugs

DrugInteraction

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interactions in your software

Abatacept
The risk or severity of adverse effects can be increased when Chloramphenicol is combined with Abatacept.
Abciximab
The risk or severity of bleeding can be increased when Abciximab is combined with Chloramphenicol.
Abemaciclib
The metabolism of Abemaciclib can be decreased when combined with Chloramphenicol.
Abrocitinib
The metabolism of Abrocitinib can be decreased when combined with Chloramphenicol.
Acalabrutinib
The metabolism of Acalabrutinib can be decreased when combined with Chloramphenicol.
Acenocoumarol
The serum concentration of Acenocoumarol can be increased when it is combined with Chloramphenicol.
Acetohexamide
The metabolism of Acetohexamide can be decreased when combined with Chloramphenicol.
Acetylsalicylic acid
The risk or severity of bleeding can be increased when Acetylsalicylic acid is combined with Chloramphenicol.
Acyclovir
The excretion of Acyclovir can be decreased when combined with Chloramphenicol.
Adalimumab
The risk or severity of adverse effects can be increased when Adalimumab is combined with Chloramphenicol.
Food Interactions

  • Take on an empty stomach.

Drug product information from 10+ global regions

Our datasets provide approved
product information including:
dosage, form, labeller, route of administration, and marketing period.

Access drug product information from over 10 global regions.

International/Other BrandsBrochlor (Sanofi-Aventis) / Chloramex (Actavis) /
Chlorocid (Egyt) / Chlorocol / Chlorsig (Sigma) / Fenicol (Alcon) / Globenicol / Halomycetin (Wabosan) / Oleomycetin / Sificetina (SIFI)Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImageCebenicol Oph Liq 0.4%
Liquid
.4 %
Ophthalmic
Chauvin Pharma Inc.
1992-12-31
1997-07-15

Chloramphenicol
Solution
0.5 %
Ophthalmic
Pharma Stulln Inc.
1994-12-31
Not applicable

Chloramphenicol
Ointment
1 % w/w
Ophthalmic; Topical
Pharma Stulln Inc.
1994-12-31
2022-11-23

Chloromycetin
Ointment
10 mg/1g
Ophthalmic
PARKE-DAVIS
2006-10-08
Not applicable

Chloromycetin Oph Ont 1%
Ointment
1 %
Ophthalmic
Parke Davis Division, Warner Lambert Canada Inc.
1951-12-31
1999-04-08

Chloromycetin Oph Soln 0.5%
Liquid
.5 %
Ophthalmic
Parke Davis Division, Warner Lambert Canada Inc.
1971-12-31
1997-08-25

Chloromycetin Otic
Solution / drops
5 mg/1mL
Auricular (otic)
Monarch Pharmaceuticals, Inc.
1953-03-30
2002-02-12

Chloroptic Dps 0.5%
Solution / drops
.5 %
Ophthalmic
Allergan
1963-12-31
2011-08-04

Chloroptic Oph Ont 1%
Ointment
10 mg / g
Ophthalmic
Allergan
1988-12-31
2011-08-04

Econochlor
Ointment
10 mg/1g
Ophthalmic
ALCON LABORATORIES, INC.
2006-09-12
Not applicable

Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImageNovo-chlorocap Cap 250mg
Capsule
250 mg / cap
Oral
Novopharm Limited
1966-12-31
2005-08-10

Odan-chloramphenicol
Liquid
0.5 mg / mL
Ophthalmic
Odan Laboratories Ltd
1985-12-31
Not applicable

Odan-chloramphenicol
Ointment
10 mg / g
Ophthalmic
Odan Laboratories Ltd
1992-12-31
Not applicable

PMS-chloramphenicol Ophthalmic Soln 0.5%
Solution / drops
.5 %
Ophthalmic
Pharmascience Inc
1992-12-31
2022-10-28

Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImageOPTIVIS OPHTHALMIC OINTMENT
Ointment
1 %w/w
Ophthalmic
บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด
2004-04-04
Not applicable

VANAFEN OPTHALMIC OINTMENT
Ointment
1 %w/w
Ophthalmic
บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด
1986-06-08
Not applicable

VENAFEN-S EYE DROP
Liquid
5 mg/1ml
Ophthalmic
บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด
1985-02-06
Not applicable

ขี้ผึ้ง ยูนีซัน
Ointment
1 %w/w
Topical
บริษัท ยูนีซัน จำกัด
1985-06-18
Not applicable

ขี้ผึ้งโคลฟามีน ใส่แผล
Ointment
1 %w/w
Topical
บริษัท แลชแมน จำกัด จำกัด
1987-03-17
Not applicable

คลอรอฟ ยาหยอดตา
Liquid
5 mg/1ml
Ophthalmic
บริษัท แสงไทยกำปะนี จำกัด
1985-08-23
Not applicable

คลอร์ – ไพแร็ด
Ointment
1 %w/w
Topical
บริษัท สหการโอสถ (1996) จำกัด จำกัด
1996-11-07
Not applicable

คลออ๊อฟ ขี้ผึ้งป้ายตา
Ointment
1 %w/w
Ophthalmic
บริษัท แสงไทยกำปะนี จำกัด
1985-01-29
Not applicable

คลอแรม ออยต์เมนท์
Ointment
1 %w/w
Topical
บริษัท สหแพทย์เภสัช จำกัด
1986-05-27
Not applicable

พิซาลิน ออยเมนท์
Ointment
1 %w/w
Topical
บริษัท 2 เอ็ม.(เมด-เมเกอร์) จำกัด จำกัด
1988-06-28
Not applicable

Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImageActinac Pwr
Chloramphenicol (40 mg / g) + Allantoin (24 mg / g) + Hydrocortisone acetate (40 mg / g) + Nicoboxil (24 mg / g) + Octasulfur (320 mg / g)
Powder
Topical
Roussel Canada Inc.
1978-12-31
1996-09-09

Actinac Pws
Chloramphenicol (40 mg / g) + Allantoin (24 mg / g) + Hydrocortisone acetate (40 mg / g) + Nicoboxil (24 mg / g) + Octasulfur (320 mg / g)
Powder, for solution
Topical
Hoechst Roussel Canada Inc.
1994-12-31
2001-07-20

Ophthocort Ont
Chloramphenicol (10 mg / g) + Hydrocortisone acetate (5 mg / g) + Polymyxin B sulfate (5000 unit / g)
Ointment
Ophthalmic
Parke Davis Division, Warner Lambert Canada Inc.
1958-12-31
1998-04-07

Pentamycetin/hc
Chloramphenicol (10 mg / g) + Hydrocortisone acetate (10 mg / g)
Ointment
Auricular (otic); Ophthalmic
Sandoz Canada Incorporated
1992-12-31
2022-08-01

Pentamycetin/hc
Chloramphenicol (2 mg / mL) + Hydrocortisone acetate (10 mg / mL)
Suspension
Auricular (otic); Ophthalmic
Sandoz Canada Incorporated
1992-12-31
2022-08-01

Sopamycetin/hc Ointment
Chloramphenicol (10 mg / g) + Hydrocortisone acetate (10 mg / g)
Ointment
Auricular (otic); Ophthalmic
Laboratoires Charton Laboratories
1992-12-31
1999-01-16

Sopamycetin/hc Ont
Chloramphenicol (.2 %) + Hydrocortisone acetate (1 %)
Ointment
Auricular (otic); Ophthalmic
Laboratoires Charton Laboratories
1988-12-31
1999-01-16

Sopamycetin/hc Susp
Chloramphenicol (.2 %) + Hydrocortisone acetate (1 %)
Solution / drops
Ophthalmic
Laboratoires Charton Laboratories
1988-12-31
1999-01-16

คลอแรมเฟนิคอล เอ.เอ็น.บี. 250 มก.
Chloramphenicol (250 MG/2ML) + Lidocaine (30 MG/2ML)
Solution

บริษัท เอ.เอ็น.บี.ลาบอราตอรี่ (อำนวยเภสัช) จำกัด จำกัด
1985-12-07
Not applicable

คอร์ทิคอร์ท-ซี
Chloramphenicol (10 MG/1G) + Hydrocortisone (10 MG/1G)
Cream

ห้างหุ้นส่วนจำกัด โรงงานเลิศสิงห์เภสัชกรรม
1997-06-06
Not applicable

ATC CodesD06AX02 — Chloramphenicol

  • D06AX — Other antibiotics for topical use
  • D06A — ANTIBIOTICS FOR TOPICAL USE
  • D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
  • D — DERMATOLOGICALS

S02AA01 — Chloramphenicol

  • S02AA —
    Antiinfectives
  • S02A — ANTIINFECTIVES
  • S02 — OTOLOGICALS
  • S — SENSORY ORGANS

D10AF03 — Chloramphenicol

  • D10AF — Antiinfectives for treatment of acne
  • D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE
  • D10 — ANTI-ACNE PREPARATIONS
  • D —
    DERMATOLOGICALS

S01AA01 — Chloramphenicol

  • S01AA — Antibiotics
  • S01A — ANTIINFECTIVES
  • S01 — OPHTHALMOLOGICALS
  • S — SENSORY ORGANS

G01AA05 — Chloramphenicol

  • G01AA — Antibiotics
  • G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL.
    COMBINATIONS WITH CORTICOSTEROIDS
  • G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
  • G — GENITO URINARY SYSTEM AND SEX HORMONES

J01BA01 — Chloramphenicol

  • J01BA — Amphenicols
  • J01B — AMPHENICOLS
  • J01 — ANTIBACTERIALS FOR SYSTEMIC USE
  • J — ANTIINFECTIVES FOR SYSTEMIC USE

S03AA08 — Chloramphenicol

  • S03AA — Antiinfectives
  • S03A — ANTIINFECTIVES
  • S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
  • S — SENSORY ORGANS

Drug Categories

  • Alcohols
  • Amphenicols
  • Anti-Acne Preparations
  • Anti-Acne Preparations for Topical Use
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antibiotics for Topical Use
  • Antiinfectives for Systemic Use
  • Antiinfectives for Treatment of Acne
  • Benzene Derivatives
  • Cytochrome P-450 CYP2C19 Inhibitors
  • Cytochrome P-450 CYP2C19 Inhibitors (strong)
  • Cytochrome P-450 CYP3A Inhibitors
  • Cytochrome P-450 CYP3A4 Inhibitors
  • Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
  • Cytochrome P-450 CYP3A5 Inhibitors
  • Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
  • Cytochrome P-450 CYP3A7
    Inhibitors
  • Cytochrome P-450 CYP3A7 Inhibitors (strength unknown)
  • Cytochrome P-450 Enzyme Inhibitors
  • Dermatologicals
  • Enzyme Inhibitors
  • Genito Urinary System and Sex Hormones
  • Glycols
  • Gynecological Antiinfectives and Antiseptics
  • Immunosuppressive Agents
  • Myelosuppressive Agents
  • Nitro Compounds
  • Nitrobenzenes
  • OAT1/SLC22A6 inhibitors
  • Ophthalmological and Otological Preparations
  • Ophthalmologicals
  • Otologicals
  • Propylene Glycols
  • Protein Synthesis Inhibitors
  • Sensory Organs

Chemical TaxonomyProvided by ClassyfireDescriptionThis compound belongs to the class of organic compounds known as nitrobenzenes.
These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.KingdomOrganic compoundsSuper ClassBenzenoidsClassBenzene and substituted derivativesSub ClassNitrobenzenesDirect ParentNitrobenzenesAlternative ParentsNitroaromatic compounds / Secondary
alcohols / Propargyl-type 1,3-dipolar organic compounds /
Organic oxoazanium compounds / Carboximidic acids /
Primary alcohols /
Organopnictogen compounds / Organonitrogen
compounds / Organochlorides / Organic
zwitterions show 4 moreSubstituentsAlcohol / Alkyl chloride / Alkyl halide / Allyl-type 1,3-dipolar organic compound / Aromatic alcohol / Aromatic homomonocyclic compound / C-nitro compound / Carboximidic acid /
Carboximidic acid derivative / Hydrocarbon derivative show 17 moreMolecular FrameworkAromatic homomonocyclic compoundsExternal Descriptorsorganochlorine compound (CHEBI:17698) / Aromatic compounds (C00918) Affected organisms

  • Enteric bacteria and other eubacteria
  • Gram negative and gram positive bacteria
  • Streptococcus pneumoniae
  • Neisseria meningitidis
  • Haemophilus influenzae
  • Enterococcus faecium

UNII66974FR9Q1CAS number56-75-7InChI KeyWIIZWVCIJKGZOK-RKDXNWHRSA-NInChI

InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h2-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1

IUPAC Name

2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide

SMILES

OC[[email protected]@H](NC(=O)C(Cl)Cl)[[email protected]](O)C1=CC=C(C=C1)[N+]([O-])=O

Synthesis Reference

Guang-Zhong Wu, Wanda I. Tormos, “Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates.” U.S. Patent US5352832, issued May, 1992.

US5352832General References

  • Bhutta ZA, Niazi SK, Suria A: Chloramphenicol clearance in typhoid fever: implications for therapy. Indian J Pediatr. 1992 Mar-Apr;59(2):213-9. [Article]
  • Wali SS, Macfarlane JT, Weir WR, Cleland PG, Ball PA, Hassan-King M, Whittle HC, Greenwood BM: Single injection treatment of meningococcal meningitis. 2. Long-acting
    chloramphenicol. Trans R Soc Trop Med Hyg. 1979;73(6):698-702. [Article]
  • Puddicombe JB, Wali SS, Greenwood BM: A field trial of a single intramuscular injection of long-acting chloramphenicol in the treatment of meningococcal meningitis. Trans R Soc Trop Med Hyg. 1984;78(3):399-403. [Article]
  • Pecoul B,
    Varaine F, Keita M, Soga G, Djibo A, Soula G, Abdou A, Etienne J, Rey M: Long-acting chloramphenicol versus intravenous ampicillin for treatment of bacterial meningitis. Lancet. 1991 Oct 5;338(8771):862-6. [Article]
  • Nathan N, Borel T, Djibo A, Evans D, Djibo S, Corty JF, Guillerm M, Alberti KP, Pinoges L, Guerin PJ, Legros D: Ceftriaxone as effective as long-acting chloramphenicol in short-course
    treatment of meningococcal meningitis during epidemics: a randomised non-inferiority study. Lancet. 2005 Jul 23-29;366(9482):308-13. [Article]
  • External LinksHuman Metabolome DatabaseHMDB0014589KEGG DrugD00104KEGG CompoundC00918PubChem Compound5959PubChem Substance46505318ChemSpider5744BindingDB23447RxNav2348ChEBI17698ChEMBLCHEMBL130ZINCZINC000000113382Therapeutic Targets DatabaseDAP001356PharmGKBPA448927PDBe LigandCLMRxListRxList Drug PageDrugs.comDrugs Drug PageWikipediaChloramphenicolPDB Entries1cla / 1k01 /
    1nji / 1qhs / 1qhy /
    1usq / 2jkj / 2jkl /
    2uxp / 2xat … show 23 moreFDA labelMSDSClinical
    Trials
    PhaseStatusPurposeConditionsCount4
    Completed
    Treatment
    Ophthalmopathy , Lacrimal System
    1
    0
    Terminated
    Treatment
    Osteomyelitis
    1
    Not Available
    Completed
    Not Available
    Antibiotic Resistant Infection / Bacterial Infections / Surgical Site Infections
    1
    Manufacturers

    • John j ferrante
    • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
    • Parkedale pharmaceuticals inc
    • Armenpharm ltd
    • Parke davis pharmaceutical research div warner lambert co
    • Altana inc
    • Pharmafair inc
    • Allergan pharmaceutical
    • Alcon laboratories inc
    • Akorn inc
    • Optopics laboratories corp
    • Elkins sinn div ah robins co
      inc
    • App pharmaceuticals llc
    • Gruppo lepetit spa chăm sóc sức mạnh thể chất và làm đẹp sub merrell dow pharmaceuticals inc
    • Angus chemical co

    Packagers

    • Akorn Inc.
    • APP Pharmaceuticals
    • Darby Dental Supply Co. Inc.
    • General Injectables and Vaccines Inc.
    • Gruppo Lepetit SPA
    • Ivax Pharmaceuticals
    • Medisca Inc.
    • Professional Compounding Centers America LLC
    • Spectrum Pharmaceuticals

    Dosage Forms
    FormRouteStrengthPowder
    Topical

    Powder, for solution
    Topical

    Capsule
    Oral
    250 mg
    Syrup
    Oral

    Suppository

    Gel
    Conjunctival

    Ointment
    Conjunctival

    Solution / drops
    Conjunctival

    Suspension / drops
    Conjunctival

    Suspension / drops
    Conjunctival
    0.5 %
    Liquid
    Ophthalmic
    .4 %
    Ointment
    Ophthalmic

    Insert
    Vaginal
    250 MG
    Insert
    Vaginal
    500 MG
    Capsule
    Oral

    Cream

    Ointment
    Ophthalmic; Topical
    1 % w/w
    Solution
    Ophthalmic
    0.5 %
    Ointment
    Ophthalmic

    Solution
    Auricular (otic)
    5 %
    Solution
    Auricular (otic)
    5 % w/v
    Solution
    Ophthalmic
    25 mg/5ml
    Injection, powder, for solution
    Intravenous; Parenteral
    1 G
    Suspension
    Oral

    Ointment
    Ophthalmic
    10 mg/1g
    Capsule, liquid filled
    Oral
    250 mg
    Ointment
    Ophthalmic
    1 %
    Liquid
    Ophthalmic
    .5 %
    Solution / drops
    Auricular (otic)
    5 mg/1mL
    Solution / drops
    Ophthalmic
    .5 %
    Ointment
    Ophthalmic
    10 mg / g
    Suspension / drops
    Ophthalmic

    Capsule, coated
    Oral
    250 mg
    Injection, powder, for solution
    Intravenous
    1 G/10ML
    Ointment

    Injection, powder, for solution
    Parenteral
    1000 mg
    Solution / drops
    Ophthalmic

    Cream

    Solution / drops
    Auricular (otic)

    Ointment
    Conjunctival; Ophthalmic

    Solution
    Ophthalmic
    5 mg/1mL
    Insert
    Vaginal
    0.25 g
    Solution
    Auricular (otic)
    2.5 mg
    Ointment
    Topical

    Injection, solution
    Intramuscular; Intravenous

    Ointment

    1 % w/w
    Solution / drops
    Ophthalmic; Topical
    .5 %
    Solution
    Ophthalmic
    0.5 % w/v
    Solution / drops
    Ophthalmic
    0.5 %W/V
    Capsule
    Oral
    250 mg / cap
    Liquid
    Ophthalmic
    0.5 mg / mL
    Ointment
    Ophthalmic
    10 mg/g
    Solution
    Ophthalmic
    5.0 mg/ml
    Solution
    Ophthalmic
    2.5 mg / mL
    Solution
    Ophthalmic
    5 mg / mL
    Suspension
    Auricular (otic); Ophthalmic

    Solution / drops
    Auricular (otic)

    Solution / drops
    Ophthalmic

    Tablet, coated
    Oral

    Ointment
    Ophthalmic
    .2 %
    Solution / drops
    Auricular (otic)
    5 %
    Solution / drops
    Ophthalmic
    .2 %
    Ointment
    Auricular (otic); Ophthalmic

    Solution
    Conjunctival; Ophthalmic

    Solution / drops
    Ophthalmic
    0.5 % W/V
    Cream; ointment

    Solution / drops

    Solution
    Ophthalmic
    5 MG/ML
    Solution
    Conjunctival; Ophthalmic
    5 mg
    Ointment
    Topical
    1 %w/w
    Ointment
    Topical
    2 %w/w
    Liquid
    Ophthalmic
    5 mg/1ml
    Capsule
    Oral
    100 mg
    Solution

    Liquid
    Ophthalmic

    Liquid
    Auricular (otic)
    10 mg/1ml
    Tablet, coated
    Oral
    100 mg
    Liquid
    Auricular (otic)
    50 mg/1ml
    Liquid
    Auricular (otic)

    Tablet

    250 mg
    Ointment
    Ophthalmic
    1 %w/w
    Prices
    Unit descriptionCostUnitChloramphen na succ 1 gm vial
    28.74USD
    vial
    Chloramphenicol palm powder
    2.52USD
    g
    Chloramphenicol crystals
    1.32USD
    g

    DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

    PatentsNot AvailableStateSolidExperimental Properties
    PropertyValueSourcemelting point (°C)
    171
    Bartz, Q..R.; U.S. Patent 2,483,871; October 4, 1949; assigned to Parke, Davis & Company Crooks, H.M., Jr., Rebstock, M.C., Controulis, J. and Bartz, Q..R.; U.S. Patent 2,483,884; October 4, 1949; assigned to Parke, Davis & Company. Ehrlich, J., Smith, R.M. and Penner, M.A.; U.S. Patent 2,483,892; October 4, 1949; assigned to Parke, Davis & Company. Carrara, G.; U.S. Patent 2,776,312; January 1, 1957 Slack, R.; U.S. Patent 2,786,870; March 26, 1957; assigned to Parke, Davis
    & Company.
    water solubility
    2500 mg/L ( 25 °C)
    MERCK INDEX (2001)
    logP
    1.14
    HANSCH,C ET AL. (1995)
    logS
    -2.11
    ADME Research, USCD
    Caco2 permeability
    -4.69
    ADME Research, USCD
    Predicted Properties
    PropertyValueSourceWater Solubility
    0.461 mg/mL
    ALOGPS
    logP
    1.15
    ALOGPS
    logP
    0.88
    ChemAxon
    logS
    -2.8
    ALOGPS
    pKa (Strongest Acidic)
    8.69
    ChemAxon
    pKa (Strongest Basic)
    -2.8
    ChemAxon
    Physiological Charge
    0
    ChemAxon
    Hydrogen Acceptor Count
    5
    ChemAxon
    Hydrogen Donor Count
    3
    ChemAxon
    Polar Surface Area
    112.7 Å2
    ChemAxon
    Rotatable Bond Count
    6
    ChemAxon
    Refractivity
    72.2 m3·mol-1
    ChemAxon
    Polarizability
    28.13 Å3
    ChemAxon
    Number of Rings
    1
    ChemAxon
    Bioavailability
    1
    ChemAxon
    Rule of Five
    Yes
    ChemAxon
    Ghose Filter
    Yes
    ChemAxon
    Veber’s Rule
    No
    ChemAxon
    MDDR-like Rule
    No
    ChemAxon
    Predicted ADMET Features
    PropertyValueProbabilityHuman Intestinal Absorption
    +
    0.9157
    Blood Brain Barrier
    +
    0.9366
    Caco-2 permeable
    +
    0.7367
    P-glycoprotein substrate
    Non-substrate
    0.7305
    P-glycoprotein inhibitor I
    Non-inhibitor
    0.9216
    P-glycoprotein inhibitor II
    Non-inhibitor
    0.8822
    Renal organic cation transporter
    Non-inhibitor
    0.9477
    CYP450 2C9 substrate
    Non-substrate
    0.7775
    CYP450 2D6 substrate
    Non-substrate
    0.8934
    CYP450 3A4 substrate
    Non-substrate
    0.5936
    CYP450 1A2 substrate
    Non-inhibitor
    0.9046
    CYP450 2C9 inhibitor
    Non-inhibitor
    0.9071
    CYP450 2D6 inhibitor
    Non-inhibitor
    0.9231
    CYP450 2C19 inhibitor
    Inhibitor
    0.8994
    CYP450 3A4 inhibitor
    Non-inhibitor
    0.8309
    CYP450 inhibitory promiscuity
    Low CYP Inhibitory Promiscuity
    0.8682
    Ames test
    Non AMES toxic
    0.9133
    Carcinogenicity
    Non-carcinogens
    0.5483
    Biodegradation
    Ready biodegradable
    0.5053
    Rat acute toxicity
    2.2247 LD50, mol/kg
    Not applicable
    hERG inhibition (predictor I)
    Weak inhibitor
    0.9658
    hERG inhibition (predictor II)
    Non-inhibitor
    0.8764

    ADMET data is predicted using admetSAR, a không lấy phí tool for evaluating chemical ADMET properties. (23092397)

    Mass Spec (NIST)Download (10.9 KB)
    Spectra
    SpectrumSpectrum TypeSplash KeyPredicted GC-MS Spectrum – GC-MS
    Predicted GC-MS
    Not Available
    Predicted MS/MS Spectrum – 10V, Positive (Annotated)
    Predicted LC-MS/MS
    Not Available
    Predicted MS/MS Spectrum – 20V, Positive (Annotated)
    Predicted LC-MS/MS
    Not Available
    Predicted MS/MS Spectrum – 40V, Positive (Annotated)
    Predicted LC-MS/MS
    Not Available
    Predicted MS/MS Spectrum – 10V, Negative (Annotated)
    Predicted LC-MS/MS
    Not Available
    Predicted MS/MS Spectrum – 20V, Negative (Annotated)
    Predicted LC-MS/MS
    Not Available
    Predicted MS/MS Spectrum – 40V, Negative (Annotated)
    Predicted LC-MS/MS
    Not Available
    LC-MS/MS Spectrum – LC-ESI-qTof , Positive
    LC-MS/MS
    Not Available
    LC-MS/MS Spectrum – LC-ESI-QFT , negative
    LC-MS/MS
    splash20-0kmi-0945000000-40a09f3f9528bd669823
    LC-MS/MS Spectrum – LC-ESI-QFT , negative
    LC-MS/MS
    splash20-0udi-0900000000-64dbb16119292f4410e2
    LC-MS/MS Spectrum – LC-ESI-QFT , negative
    LC-MS/MS
    splash20-0udi-0900000000-5c8fbcad8e93fa9f2906
    LC-MS/MS Spectrum – LC-ESI-QFT , negative
    LC-MS/MS
    splash20-0uk9-1900000000-4c6518583a7488591aa3
    LC-MS/MS Spectrum – LC-ESI-QFT , negative
    LC-MS/MS
    splash20-00di-1900000000-00574ed667d64b4a45e9
    LC-MS/MS Spectrum – LC-ESI-QFT , negative
    LC-MS/MS
    splash20-00di-1900000000-d4ac63e9260ab31ac6b1
    LC-MS/MS Spectrum – LC-ESI-QTOF , negative
    LC-MS/MS
    splash20-0zml-0933000000-4ae209b29cb52d4e3844
    LC-MS/MS Spectrum – LC-ESI-QTOF , negative
    LC-MS/MS
    splash20-056r-0933000000-74ff5ec451e56526d425
    MS/MS Spectrum – Linear Ion Trap , negative
    LC-MS/MS
    splash20-0a4l-0590000000-90d108018a0f99815fb7
    MS/MS Spectrum – Linear Ion Trap , negative
    LC-MS/MS
    splash20-0a4l-0690000000-161f2afa43298fd3437a
    LC-MS/MS Spectrum – LC-ESI-QFT , negative
    LC-MS/MS
    splash20-0uk9-0923000000-86308db0ec59b40b1533
    LC-MS/MS Spectrum – LC-ESI-QFT , positive
    LC-MS/MS
    splash20-05fr-0094000000-ad8da59124745b38a76f
    LC-MS/MS Spectrum – LC-ESI-QFT , positive
    LC-MS/MS
    splash20-00di-0390000000-06fcf307f2fdb79741ad
    LC-MS/MS Spectrum – LC-ESI-QFT , positive
    LC-MS/MS
    splash20-014i-1940000000-be07d702045f4d3e05ac
    LC-MS/MS Spectrum – LC-ESI-QFT , positive
    LC-MS/MS
    splash20-014i-1910000000-55a74a828c3c9750ee1c
    LC-MS/MS Spectrum – LC-ESI-QFT , positive
    LC-MS/MS
    splash20-0159-2900000000-bf685c17ab79583133ee
    LC-MS/MS Spectrum – LC-ESI-QFT , positive
    LC-MS/MS
    splash20-0159-4900000000-e6f6ccbfffe89c345365
    LC-MS/MS Spectrum – LC-ESI-QTOF , positive
    LC-MS/MS
    splash20-00di-0191000000-41f70006e2b4e5f8d8aa
    LC-MS/MS Spectrum – LC-ESI-QTOF , positive
    LC-MS/MS
    splash20-014i-0960000000-d64346c38bebc079f066
    MS/MS Spectrum – Linear Ion Trap , positive
    LC-MS/MS
    splash20-0f89-0491000000-c7e13efc8c7ed0e68cff
    MS/MS Spectrum – Linear Ion Trap , positive
    LC-MS/MS
    splash20-0f89-0492000000-4b6f8c10f6acc0f02196
    MS/MS Spectrum – , positive
    LC-MS/MS
    splash20-014i-0920000000-96bfb1c31d89e3f10caf
    LC-MS/MS Spectrum – LC-ESI-QFT , positive
    LC-MS/MS
    splash20-0600-0592000000-129db104bb506af06de0

    Targets

    Build, predict & validate machine-learning models

    Use our structured and evidence-based datasets to unlock new
    insights and accelerate drug
    research.

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    KindProteinOrganismEscherichia coli (strain K12)Pharmacological action

    Unknown

    Actions

    Inhibitor

    General FunctionTrna bindingSpecific FunctionThis protein binds directly to 23S ribosomal RNA and is located the A site of the peptidyltransferase center. It contacts the A and P site tRNAs. It has an essential role in subunit assembly, wh…Gene NamerplPUniprot IDP0ADY7Uniprot Name50S ribosomal protein L16Molecular Weight15281.125 Da

    References

  • Murray IA, Cann PA, Day PJ, Derrick JP, Sutcliffe MJ, Shaw WV, Leslie AG: Steroid recognition by chloramphenicol acetyltransferase: engineering and structural analysis of a high affinity fusidic
    acid binding site. J Mol Biol. 1995 Dec 15;254(5):993-1005. [Article]
  • Nierhaus D, Nierhaus KH: Identification of the chloramphenicol-binding protein in Escherichia coli ribosomes by partial reconstitution. Proc Natl Acad Sci U S A. 1973 Aug;70(8):2224-8. [Article]
  • Baxter RM, Ganoza MC, Zahid N,
    Chung DG: Reconstruction of peptidyltransferase activity on 50S and 70S ribosomal particles by peptide fragments of protein L16. Eur J Biochem. 1987 Mar 16;163(3):473-9. [Article]
  • KindProteinOrganismEscherichia coliPharmacological action

    Unknown

    Actions

    Antagonist

    General FunctionNot AvailableSpecific FunctionHemagglutinins of uropathogenic E.coli mediate adherence to the upper urinary tract. These adhesins bind to the Dr blood group antigen and also agglutinate human erythrocytes in the presence of D-m…Gene NamedraAUniprot IDP24093Uniprot NameDr hemagglutinin structural subunitMolecular Weight17058.095 Da

    References

  • Swanson TN, Bilge SS, Nowicki B, Moseley SL: Molecular structure of the Dr adhesin: nucleotide sequence and mapping of receptor-binding domain by use of fusion constructs. Infect Immun.
    1991 Jan;59(1):261-8. [Article]
  • KindProteinOrganismHumansPharmacological action

    Unknown

    Actions

    Other

    General FunctionVirus receptor activitySpecific FunctionThis protein recognizes C4b and C3b fragments that condense with cell-surface hydroxyl or amino groups when nascent C4b and C3b are locally generated during C4 and c3 activation. Interaction of daf…Gene NameCD55Uniprot IDP08174Uniprot NameComplement
    decay-accelerating factorMolecular Weight41399.79 Da

    References

  • Pettigrew D, Anderson KL, Billington J, Cota E, Simpson P, Urvil P, Rabuzin F, Roversi P, Nowicki B, du Merle L, Le Bouguenec C, Matthews S, Lea SM: High resolution studies of the Afa/Dr adhesin DraE and its interaction with chloramphenicol. J Biol Chem. 2004 Nov 5;279(45):46851-7. Epub 2004 Aug 24.
    [Article]
  • Korotkova N, Chattopadhyay S, Tabata TA, Beskhlebnaya V, Vigdorovich V, Kaiser BK, Strong RK, Dykhuizen DE, Sokurenko EV, Moseley SL: Selection for functional diversity drives accumulation of point mutations in Dr adhesins of Escherichia coli. Mol Microbiol. 2007 Apr;64(1):180-94. [Article]
  • Enzymes

    KindProteinOrganismEscherichia coliPharmacological action

    Unknown

    Actions

    Substrate

    General FunctionChloramphenicol o-acetyltransferase activitySpecific FunctionThis enzyme
    is an effector of chloramphenicol resistance in bacteria.Gene Namecat3Uniprot IDP00484Uniprot NameChloramphenicol acetyltransferase 3Molecular Weight24993.32 Da

    References

  • Murray IA, Cann PA, Day PJ, Derrick
    JP, Sutcliffe MJ, Shaw WV, Leslie AG: Steroid recognition by chloramphenicol acetyltransferase: engineering and structural analysis of a high affinity fusidic acid binding site. J Mol Biol. 1995 Dec 15;254(5):993-1005. [Article]
  • Derrick JP, Lian LY, Roberts GC, Shaw WV: Analysis of the binding of 1,3-diacetylchloramphenicol to chloramphenicol acetyltransferase by isotope-edited 1H NMR and
    site-directed mutagenesis. Biochemistry. 1992 Sep 8;31(35):8191-5. [Article]
  • Murray IA, Lewendon A, Shaw WV: Stabilization of the imidazole ring of His-195 the active site of chloramphenicol acetyltransferase. J Biol Chem. 1991 Jun 25;266(18):11695-8. [Article]
  • KindProteinOrganismPseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)Pharmacological action

    Unknown

    Actions

    Substrate

    General FunctionChloramphenicol o-acetyltransferase activitySpecific FunctionThis enzyme is an effector of
    chloramphenicol (Cm) resistance in bacteria. Acetylates Cm but not 1-acetoxy-Cm.Gene NamecatUniprot IDP26841Uniprot NameChloramphenicol acetyltransferaseMolecular Weight23524.385 Da

    References

  • Potrykus J,
    Baranska S, Wegrzyn G: Inactivation of the acrA gene is partially responsible for chloramphenicol sensitivity of Escherichia coli CM2555 strain expressing the chloramphenicol acetyltransferase gene. Microb Drug Resist. 2002 Fall;8(3):179-85. [Article]
  • Potrykus J, Wegrzyn G: Chloramphenicol-sensitive Escherichia coli strain expressing the chloramphenicol acetyltransferase (cat) gene. Antimicrob
    Agents Chemother. 2001 Dec;45(12):3610-2. [Article]
  • Navia MM, Capitano L, Ruiz J, Vargas M, Urassa H, Schellemberg D, Gascon J, Vila J: Typing and characterization of mechanisms of resistance of Shigella spp. isolated from feces of children under 5 years of age from Ifakara, Tanzania. J Clin Microbiol. 1999 Oct;37(10):3113-7.
    [Article]
  • KindProteinOrganismStreptomyces venezuelae (strain ATCC 10712 / CBS 650.69 / DSM 40230 / JCM 4526 / NBRC 13096 / PD 04745)Pharmacological action

    Unknown

    Actions

    Substrate

    General
    FunctionKinase activitySpecific FunctionInactivates chloramphenicol by catalyzing the transfer of the gamma-phosphate of ATP to the antibiotic’s C-3′ hydroxyl group.Gene NameNot AvailableUniprot IDQ56148Uniprot NameChloramphenicol 3-O
    phosphotransferaseMolecular Weight18816.255 Da

    References

  • Ellis J, Campopiano DJ, Izard T: Cubic crystals of chloramphenicol phosphotransferase from Streptomyces venezuelae in complex with chloramphenicol. Acta Crystallogr D Biol Crystallogr. 1999 May;55(Pt 5):1086-8. [Article]
  • Izard T, Ellis
    J: The crystal structures of chloramphenicol phosphotransferase reveal a novel inactivation mechanism. EMBO J. 2000 Jun 1;19(11):2690-700. [Article]
  • Mosher RH, Camp DJ, Yang K, Brown MP, Shaw WV, Vining LC: Inactivation of chloramphenicol by O-phosphorylation. A novel resistance mechanism in Streptomyces venezuelae ISP5230, a chloramphenicol producer. J Biol Chem. 1995 Nov 10;270(45):27000-6.
    [Article]
  • KindProteinOrganismHumansPharmacological action

    Unknown

    Actions

    Inhibitor

    General FunctionSteroid hydroxylase activitySpecific
    FunctionResponsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im…Gene NameCYP2C19Uniprot IDP33261Uniprot NameCytochrome P450 2C19Molecular
    Weight55930.545 Da

    References

  • Park JY, Kim KA, Kim SL: Chloramphenicol is a potent inhibitor of cytochrome P450 isoforms CYP2C19 and CYP3A4 in human liver microsomes. Antimicrob Agents Chemother. 2003 Nov;47(11):3464-9. [Article]
  • Flockhart Table of Drug Interactions
    [Link]
  • KindProteinOrganismHumansPharmacological action

    Unknown

    Actions

    Inhibitor

    General FunctionVitamin d3 25-hydroxylase activitySpecific FunctionCytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react…Gene NameCYP3A4Uniprot IDP08684Uniprot NameCytochrome P450 3A4
    Molecular Weight57342.67 Da

    References

  • Park JY, Kim KA, Kim SL: Chloramphenicol is a potent inhibitor of cytochrome P450 isoforms CYP2C19 and CYP3A4 in human liver microsomes. Antimicrob Agents Chemother. 2003 Nov;47(11):3464-9. [Article]
  • Flockhart Table of Drug Interactions
    [Link]
  • KindProteinOrganismHumansPharmacological action

    Unknown

    Actions

    Inhibitor

    General FunctionOxygen bindingSpecific
    FunctionCytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un…Gene NameCYP3A5Uniprot IDP20815Uniprot NameCytochrome P450 3A5Molecular
    Weight57108.065 Da

    References

  • Flockhart Table of Drug Interactions [Link]
  • KindProteinOrganismHumansPharmacological action

    Unknown

    Actions

    Inhibitor

    General FunctionOxygen bindingSpecific FunctionCytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un…Gene NameCYP3A7Uniprot IDP24462Uniprot NameCytochrome P450 3A7Molecular Weight57525.03 Da

    References

  • Flockhart Table of Drug Interactions [Link]
  • Transporters

    KindProteinOrganismHumansPharmacological action

    Unknown

    Actions

    Inhibitor

    General FunctionSodium-independent organic anion transmembrane transporter activitySpecific FunctionInvolved in the renal elimination of endogenous
    and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one …Gene NameSLC22A6Uniprot IDQ4U2R8Uniprot NameSolute carrier family 22 thành viên 6Molecular Weight61815.78 Da

    References

  • Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [Article]
  • Drug created June 13, 2005 13:24 / Updated September 20, 2022 00:04

    Which drug class may cause kernicterus in neonates?

    Sulfonamides and medications that are highly bound to plasma protein (e.g., ceftriaxone) are contraindicated in neonates because they can displace bilirubin, which may cause kernicterus.

    Which adverse effect on pediatric clients is associated with nalidixic acid?

    Central Nervous System (CNS) effects including convulsions, increased intracranial pressure, and toxic psychosis have been reported with nalidixic acid therapy.

    Which medication may cause photophobia as an adverse effect?

    Photophobia is prevalent for patients who have taken atropine, which has multiple clinical applications—including as a treatment for dry mouth, specific eye disorders (e.g. myopia) and also as a muscle relaxant.

    Which medication is considered first line of therapy for treating Reye syndrome in pediatric clients?

    However, aspirin use in children with a viral illness has been associated with development of Reye’s syndrome. As a result, its use in children has declined in the United States. Acetaminophen is relatively không lấy phí of adverse effects and is considered first-line pharmacologic antipyresis therapy.
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    #condition #result #adverse #medication #effect #administration #chloramphenicol #infants #quizlet