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 | |
|---|---|---|---|
|
UGT2B7 |
|
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 | |
|---|---|---|---|
|
|
warfarin |
|
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.
Additional Datasets
These datasets are minimally curated and are sorted alphabetically by title.
LinkOuts
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.