Which condition may be the result of an adverse medication effect associated with administration of chloramphenicol in infants quizlet?

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.

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

Which condition may be the result of an adverse medication effect associated with administration of chloramphenicol in infants quizlet?

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.

Which condition may be the result of an adverse medication effect associated with administration of chloramphenicol in infants quizlet?

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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

Which condition may be the result of an adverse medication effect associated with administration of chloramphenicol in infants quizlet?

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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.

TargetActionsOrganism
U50S 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

Which condition may be the result of an adverse medication effect associated with administration of chloramphenicol in infants quizlet?

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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
PathwayCategory
Chloramphenicol 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.

Which condition may be the result of an adverse medication effect associated with administration of chloramphenicol in infants quizlet?

Drug product information from 10+ global regions

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dosage, form, labeller, route of administration, and marketing period.

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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 EndRegionImage
Cebenicol 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 2019-11-23
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 EndRegionImage
Novo-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 2016-10-28
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OPTIVIS 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 EndRegionImage
Actinac 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 2019-08-01
Pentamycetin/hc Chloramphenicol (2 mg / mL) + Hydrocortisone acetate (10 mg / mL) Suspension Auricular (otic); Ophthalmic Sandoz Canada Incorporated 1992-12-31 2019-08-01
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[C@@H](NC(=O)C(Cl)Cl)[C@H](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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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.com Drug PageWikipediaChloramphenicolPDB Entries1cla / 1k01 / 1nji / 1qhs / 1qhy / 1usq / 2jkj / 2jkl / 2uxp / 2xat … show 23 moreFDA labelMSDSClinical Trials
PhaseStatusPurposeConditionsCount
4 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 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
FormRouteStrength
Powder 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 descriptionCostUnit
Chloramphen 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
PropertyValueSource
melting 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 (at 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
PropertyValueSource
Water 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
PropertyValueProbability
Human 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 free tool for evaluating chemical ADMET properties. (23092397)

Mass Spec (NIST)Download (10.9 KB) Spectra
SpectrumSpectrum TypeSplash Key
Predicted 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

Which condition may be the result of an adverse medication effect associated with administration of chloramphenicol in infants quizlet?

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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 at 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

  1. 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]
  2. 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]
  3. 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

  1. 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

  1. 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]
  2. 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

  1. 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]
  2. 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]
  3. Murray IA, Lewendon A, Shaw WV: Stabilization of the imidazole ring of His-195 at 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

  1. 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]
  2. 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]
  3. 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

  1. 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]
  2. 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]
  3. 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

  1. 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]
  2. 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

  1. 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]
  2. 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

  1. 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

  1. 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 member 6Molecular Weight61815.78 Da

References

  1. 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 at June 13, 2005 13:24 / Updated at 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 free of adverse effects and is considered first-line pharmacologic antipyresis therapy.