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QuickView for Chloramphenicol (compound)

Name: Chloramphenicol
PubChem Compound ID: 146033
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)
Molecular formula: C11H12Cl2N2O5
Molecular weight: 323.129 g/mol
Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (R-(R*,S*))-; 7384-89-6; ZINC00113389; Spectrum3_000338; KBio2_006927; Spectrum2_000884; Spectrum4_000275; (R-(R*,S*))-2,2-Dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)acetamide; KBio2_004359; Spectrum_001311.
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Name: Chloramphenicol
Name (isomeric): DB00446
Drug Type: small molecule
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)
Chloramfenikol; Chloramphenicole; CAP; Chloroamphenicol; CAF; Cloroamfenicolo; CPh; CAM; D-Chloramphenicol
Brand: Veticol, Sopamycetin Ophthalmic Solution, Detreomycine, Emetren, Ronphenil, Chloromycetin Palmitate, Quemicetina, Ophthocort, Pentamycetin Ophthalmic Ointment, Chloroptic, Fenicol Ophthalmic Ointment, Micochlorine, Tevcosin, Tega-Cetin, Septicol, Synthomycetine, Unimycetin, Ophthoclor, Sintomicetine R, Cloramicol, Novophenicol, Dextromycetin, Chloroptic-P S.O.P., Farmicetina, Ciplamycetin, Farmitcetina, Chloramex, Micoclorina, Microcetina, Mediamycetine, Chlorocidin C tetran, Ak-chlor, Cloromisan, Chloramfilin, Isopto fenicol, Levomycetin, Ertilen, Ambofen, Chlorofair Ophthalmic Ointment, Amphenicol, Levomitsetin, Econochlor Ophthalmic Solution, Chloromycetin for Ophthalmic Solution, Isicetin, Ophtho-Chloram Ophthalmic Solution, Ak-Chlor Ophthalmic Solution, Otachron, Catilan, Econochlor, Juvamycetin, Pentamycetin, Paraxin, Leukamycin, Erbaplast, Isophenicol, Chloramsaar, Desphen, Chlorocol, Glorous, Optomycin, Tyfomycine, Chlorofair, Chlornitromycin, Comycetin, Kemicetine, Tevcocin, Cidocetine, Novochlorocap, Chlorocid S, Alficetyn, Kemicetina, Mycinol, Anacetin, Clorosintex, Ophtochlor, Chlorofair Ophthalmic Solution, Synthomycetin, Spectro-Chlor Ophthalmic Ointment, Aquamycetin, Ophthochlor Ophthalmic Solution, Chlomycol, Sno-Phenicol, Chloromax, Romphenil, Klorocid S, Chlorovules, Sintomicetina, Novomycetin, Mychel-Vet, Oleomycetin, Biocetin, Mastiphen, Viceton, Treomicetina, Ocu-Chlor Ophthalmic Solution, Spectro-Chlor Ophthalmic Solution, Detreomycin, Chlorocid, Econochlor Ophthalmic Ointment, Tifomycin, Globenicol, Cylphenicol, Chloromycetny, Chlorocidin C, Intramycetin, Cloramfen, Clorocyn, Austracil, Chlomin, Ophthochlor, Ak-Chlor Ophthalmic Ointment, Enicol, Cloramficin, Austracol, Levomicetina, Fenicol, Tiromycetin, Chemicetina, Opelor, I-Chlor Ophthalmic Solution, Chloromyxin, Amphicol, Mychel, Ocu-Chlor Ophthalmic Ointment, Hortfenicol, Otophen, Chloroject L, Loromisan, Chloracol Ophthalmic Solution, Micloretin, Sopamycetin Ophthalmic Ointment, Medichol, Loromisin, Ismicetina, Kamaver, Chloromycetin Hydrocortisone, Pentamycetin Ophthalmic Solution, Biophenicol, Chloroptic Ophthalmic Solution, Normimycin V, Leukomyan, Synthomycine, Oftalent, Chlorocaps, Leukomycin, Chloroptic S.O.P., Pantovernil, Chlorocide, Chlorasol, Stanomycetin, Embacetin, Chemicetin, Elase-Chloromycetin, Chloro-25 vetag, Klorita, Sificetina, Doctamicina, Chloronitrin, Chloromycetin Ophthalmic Ointment, Halomycetin, Tifomycine, Rivomycin, Cloramidina, Opclor, Enteromycetin, Amseclor, Chloricol, Chlora-Tabs, Chloramficin
Brand name mixture:
Zoomycetine Spray(Chloramphenicol + Isopropyl Alcohol + Methyl Violet), Elase Chloromycetin Ont(Chloramphenicol + Deoxyribonuclease Pancreatic + Fibrinolysin), Actinac Pwr(Allantoin + Butoxyethyl Nicotinate + Chloramphenicol + Hydrocortisone Acetate + Sulfur), Ophthocort Ont(Chloramphenicol + Hydrocortisone Acetate + Polymyxin B), Actinac Pws(Al...
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Category: Protein Synthesis Inhibitors, Anti-Bacterial Agents
CAS number: 56-75-7
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.
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 tr...
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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 an...
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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.
Protein binding: Plasma protein binding is 50-60% in adults and 32% is premature neonates.
Biotransformation: Hepatic, with 90% conjugated to inactive glucuronide.
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.
Affected organisms: Enteric bacteria and other eubacteria
Food interaction:
Take on an empty stomach.
Drug interaction:
ThiopentalChloramphenicol 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.
ButalbitalBarbiturates 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.
TacrolimusChloramphenicol 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.
ChlorpropamideChloramphenicol may increase the effect of sulfonylurea, chlorpropamide.
FosphenytoinIncreases phenytoin, modifies chloramphenicol
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