Drug/Small Molecule:
chloramphenicol

2D structure

Overview

Generic Names: CAF; CAM; CAP; CPh; Chloramfenikol; Chloramphenicole; Chloroamphenicol; Cloroamfenicolo; D-Chloramphenicol
IUPAC Name: 2,2-dichloro-N-[1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
Trade Names: Ak-Chlor Ophthalmic Ointment; Ak-Chlor Ophthalmic Solution; Ak-chlor; Alficetyn; Ambofen; Amphenicol; Amphicol; Amseclor; Anacetin; Aquamycetin; Austracil; Austracol; Biocetin; Biophenicol; Catilan; Chemicetin; Chemicetina; Chlomin; Chlomycol; Chlora-Tabs; Chloracol Ophthalmic Solution; Chloramex; Chloramficin; Chloramfilin; Chloramsaar; Chlorasol; Chloricol; Chlornitromycin; Chloro-25 vetag; Chlorocaps; Chlorocid; Chlorocid S; Chlorocide; Chlorocidin C; Chlorocidin C tetran; Chlorocol; Chlorofair; Chlorofair Ophthalmic Ointment; Chlorofair Ophthalmic Solution; Chloroject L; Chloromax; Chloromycetin Hydrocortisone; Chloromycetin Ophthalmic Ointment; Chloromycetin Palmitate; Chloromycetin for Ophthalmic Solution; Chloromycetny; Chloromyxin; Chloronitrin; Chloroptic; Chloroptic Ophthalmic Solution; Chloroptic S.O.P.; Chloroptic-P S.O.P.; Chlorovules; Cidocetine; Ciplamycetin; Cloramfen; Cloramficin; Cloramicol; Cloramidina; Clorocyn; Cloromisan; Clorosintex; Comycetin; Cylphenicol; Desphen; Detreomycin; Detreomycine; Dextromycetin; Doctamicina; Econochlor; Econochlor Ophthalmic Ointment; Econochlor Ophthalmic Solution; Elase-Chloromycetin; Embacetin; Emetren; Enicol; Enteromycetin; Erbaplast; Ertilen; Farmicetina; Farmitcetina; Fenicol; Fenicol Ophthalmic Ointment; Globenicol; Glorous; Halomycetin; Hortfenicol; I-Chlor Ophthalmic Solution; Intramycetin; Isicetin; Ismicetina; Isophenicol; Isopto fenicol; Juvamycetin; Kamaver; Kemicetina; Kemicetine; Klorita; Klorocid S; Leukamycin; Leukomyan; Leukomycin; Levomicetina; Levomitsetin; Levomycetin; Loromisan; Loromisin; Mastiphen; Mediamycetine; Medichol; Micloretin; Micochlorine; Micoclorina; Microcetina; Mychel; Mychel-Vet; Mycinol; Normimycin V; Novochlorocap; Novomycetin; Novophenicol; Ocu-Chlor Ophthalmic Ointment; Ocu-Chlor Ophthalmic Solution; Oftalent; Oleomycetin; Opclor; Opelor; Ophtho-Chloram Ophthalmic Solution; Ophthochlor; Ophthochlor Ophthalmic Solution; Ophthoclor; Ophthocort; Ophtochlor; Optomycin; Otachron; Otophen; Pantovernil; Paraxin; Pentamycetin; Pentamycetin Ophthalmic Ointment; Pentamycetin Ophthalmic Solution; Quemicetina; Rivomycin; Romphenil; Ronphenil; Septicol; Sificetina; Sintomicetina; Sintomicetine R; Sno-Phenicol; Sopamycetin Ophthalmic Ointment; Sopamycetin Ophthalmic Solution; Spectro-Chlor Ophthalmic Ointment; Spectro-Chlor Ophthalmic Solution; Stanomycetin; Synthomycetin; Synthomycetine; Synthomycine; Tega-Cetin; Tevcocin; Tevcosin; Tifomycin; Tifomycine; Tiromycetin; Treomicetina; Tyfomycine; Unimycetin; Veticol; Viceton
Brand Mixtures: Actinac Pwr (Allantoin + Butoxyethyl Nicotinate + Chloramphenicol + Hydrocortisone Acetate + Sulfur); Actinac Pws (Allantoin + Butoxyethyl Nicotinate + Chloramphenicol + Hydrocortisone Acetate + Sulfur); Chlorasone (Chloramphenicol + Prednisolone Acetate); Elase Chloromycetin Ont (Chloramphenicol + Deoxyribonuclease Pancreatic + Fibrinolysin); Liquichlor (Chloramphenicol + Prednisolone + Squalane + Tetracaine); Ophthocort Ont (Chloramphenicol + Hydrocortisone Acetate + Polymyxin B); Sopamycetin/Hc Ointment (Chloramphenicol + Hydrocortisone Acetate); Sopamycetin/Hc Ont (Chloramphenicol + Hydrocortisone Acetate); Sopamycetin/Hc Susp (Chloramphenicol + Hydrocortisone Acetate); Zoomycetine Spray (Chloramphenicol + Isopropyl Alcohol + Methyl Violet)
PharmGKB Accession Id: PA448927

Description

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)

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.

ATC Therapeutic Categories

  • D06AX:Other antibiotics for topical use
  • D10AF:Antiinfectives for treatment of acne
  • G01AA:Antibiotics
  • J01BA:Amphenicols
  • S01AA:Antibiotics
  • S02AA:Antiinfectives
  • S03AA:Antiinfectives

Pharmacology and Interactions

Mechanism Of Action

Chloramphenicol is lipid-soluble, allowing it to diffuse through the bacterial cell membrane. It then reversibly binds to 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.

Pharmacology

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.

Food Interactions

Take on an empty stomach.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic, with 90% conjugated to inactive glucuronide.

Protein Binding

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

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.

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.

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.

Chemical Properties

Chemical Formula:

C11H12Cl2N2O5

SMILES Code:

c1cc(ccc1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)N(=O)=O

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

323.129 / 322.0123

Curated Information

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
UGT2B7
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  • PK
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Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Curated Information

The following drugs are in curated knowledge about this drug.

  Drug Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
warfarin
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Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

acenocoumarol Increases the anticoagulant effect
acetohexamide The agent increases the effect of sulfonylurea
anisindione Increases the anticoagulant effect
chlorpropamide The agent increases the effect of sulfonylurea
cyclosporine Increases the effect of cyclosporine
dicumarol Increases the anticoagulant effect
ethotoin Increases phenytoin, modifies chloramphenicol
fosphenytoin Increases phenytoin, modifies chloramphenicol
glibenclamide The agent increases the effect of sulfonylurea
gliclazide The agent increases the effect of sulfonylurea
glipizide The agent increases the effect of sulfonylurea
glisoxepide The agent increases the effect of sulfonylurea
glycodiazine The agent increases the effect of sulfonylurea
mephenytoin Increases phenytoin, modifies chloramphenicol
phenytoin Increases phenytoin, modifies chloramphenicol
rifampin Rifampin decreases the effect of chloramphenicol
tacrolimus Increases tacrolimus levels
tolazamide The agent increases the effect of sulfonylurea
tolbutamide The agent increases the effect of sulfonylurea
warfarin Increases the anticoagulant effect

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00446
ChEBI ID:
17698
KEGG Compound ID:
C00918
KEGG Drug ID:
D00104
PubChem Compound ID:
298
PubChem Substance ID:
4172

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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