- Molecular NameChloramphenicol
- SynonymCAF; CAM; CAP; Chloramfenikol; Chloramphenicole; Chloroamphenicol; Cloroamfenicolo; CPh; D-Chloramphenicol
- Weight323.132
- Drugbank_IDDB00446
- ACS_NO56-75-7
- Show 2D model
- LogP (experiment)1.14
- LogP (predicted, AB/LogP v2.0)0.93
- pka11.03
- LogD (pH=7, predicted)0.92
- Solubility (experiment)2.5 mg/ml
- LogS (predicted, ACD/Labs)(ph=7)-2.48
- LogSw (predicted, AB/LogsW2.0)2.37
- Sw (mg/ml) (predicted, ACD/Labs)1.06
- No.of HBond Donors3
- No.of HBond Acceptors7
- No.of Rotatable Bonds6
- TPSA118.39
- StatusFDA approved
- AdministrationTopical (ocular), oral, IV, IM
- PharmacologyA bacteriostatic antimicrobial. It is considered a prototypical broad-spectrum antibiotic, alongside the tetracyclines. Chloramphenicol is effective against a wide variety of Gram-positive and Gram-negative bacteria, including most anaerobic organisms.
- Absorption_value90.0
- Absorption (description)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.
- Caco_2N/A
- Bioavailability82.0
- Protein binding53.0
- Volume of distribution (VD)0.5 to 1 L/kg
- Blood/Plasma Partitioning ratio (D_blood)N/A
- MetabollsmThe inactive palmitate ester is hydrolysed to free drug in the gastro-intestinal tract before absorption and the inactive sodium succinate ester, given parenterally, is similarly hydrolysed in vivo. It is widely distributed in the body, giving a concentration in the CSF about 50% of that in the blood. The main metabolic pathway is conjugation with glucuronic acid; chloramphenicol is also hydrolysed to 1-(4-nitrophenyl)-2-aminopropane-1,3-diol. Both metabolites are inactive.
- Half life2~5 h
- ExcretionUp to about 90% of a dose is excreted in the urine in 24 h, mainly as the glucuronide, with about 5 to 10% of the dose in unchanged form. About 3% of the dose is excreted in the bile but this is mainly reabsorbed to give about 1% eliminated in the faeces.
- Urinary ExcretionN/A
- Clerance4 ml/min/kg.
- ToxicityToxic 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.
- LD50 (rat) LD50 = 2500 mg/kg
- LD50 (mouse) LD50 = 1500 mg/kg