Ak-chlor;Ak-Chlor Ophthalmic Ointment;Ak-Chlor Ophthalmic Solution;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 for Ophthalmic Solution;Chloromycetin Hydrocortisone;Chloromycetin Ophthalmic Ointment;Chloromycetin Palmitate;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;

CAF;CAM;CAP;Chloramfenikol;Chloramphenicole;Chloroamphenicol;Cloroamfenicolo;CPh;D-Chloramphenicol;

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)

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Synthesis Reference

Not Available

General Reference

Bhutta ZA, Niazi SK, Suria A: Chloramphenicol clearance in typhoid fever: implications for therapy. Indian J Pediatr. 1992 Mar-Apr;59(2):213-9. Pubmed 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. Pubmed 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. Pubmed 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. Pubmed 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. Pubmed

Type	small molecule

Classes

Not Available

Substructures

Not Available

antibacterials 抗细菌;

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.
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.
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
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.
Affected organisms	Enteric bacteria and other eubacteria
Pathways	Not Available

Properties
State	solid
Experimental Properties	Property Value Source melting point 150.5 °C PhysProp 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	Property Value Source water solubility 4.61e-01 g/l ALOGPS logP 1.15 ALOGPS logP 0.88 ChemAxon logS -2.9 ALOGPS pKa (strongest acidic) 7.49 ChemAxon pKa (strongest basic) -2.8 ChemAxon physiological charge 0 ChemAxon hydrogen acceptor count 5 ChemAxon hydrogen donor count 3 ChemAxon polar surface area 115.38 ChemAxon rotatable bond count 6 ChemAxon refractivity 73.2 ChemAxon polarizability 28.08 ChemAxon

Drug	Interaction
Acetohexamide	Chloramphenicol may increase the effect of sulfonylurea, acetohexamide.
Butalbital	Barbiturates such as butalbital may increase the metabolism of Chloramphenicol. Chloramphenicol may decrease the metabolism of Barbiturates. Monitor for decreased serum concentrations/therapeutic effects of chloramphenicol if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. In addition, monitor for increased effects of barbiturates if chloramphenicol is initiated/dose increased, or decreased effects if chloramphenicol is discontinued/dose decreased.
Chlorpropamide	Chloramphenicol may increase the effect of sulfonylurea, chlorpropamide.
Cyclosporine	Chloramphenicol may increase the effect of cyclosporine.
Ethotoin	Increases phenytoin, modifies chloramphenicol
Fosphenytoin	Increases phenytoin, modifies chloramphenicol
Gliclazide	Chloramphenicol may increase the effect of sulfonylurea, gliclazide.
Glipizide	Chloramphenicol may increase the effect of sulfonylurea, glipizide.
Glisoxepide	Chloramphenicol may increase the effect of sulfonylurea, glisoxepide.
Glyburide	Chloramphenicol may increase the effect of sulfonylurea, glibenclamide.
Glycodiazine	Chloramphenicol may increase the effect of sulfonylurea, glycodiazine.
Lurasidone	Concomitant therapy with a strong CYP3A4 inhibitor will increase level or effect of lurasidone. Coadministration with lurasidone is contraindicated.
Mephenytoin	Increases phenytoin, modifies chloramphenicol
Phenytoin	Increases phenytoin, modifies chloramphenicol
Rifampin	Rifampin decreases the effect of chloramphenicol
Silodosin	Chloramphenicol is a strong inhibitor of CYP3A4 may increase the serum concentration of silodosin by decreasing its metabolism thus increases the potential for adverse side effects. Combination therapy is contraindicated.
Tacrolimus	Chloramphenicol may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Chloramphenicol therapy is initiated, discontinued or altered.
Thiopental	Chloramphenicol may increase the serum concentration of Thiopental by decreasing Thiopental metabolism. Thiopental may decrease the serum concentration of Chloramphenicol by increasing Chloramphenicol metabolism. Monitor for changes in therapeutic effects of both agents if concomitant therapy is initiated, discontinued or doses are adjusted.
Tolazamide	Chloramphenicol may increase the effect of sulfonylurea, tolazamide.
Tolbutamide	Chloramphenicol may increase the effect of sulfonylurea, tolbutamide.

• Take on an empty stomach.