Chloramphenicol |
Last updated: 11/01/2024 |
(Also known as: chloromycetin; amphenicol; chlornitromycin; CAF; D-chloramphenicol ; CAM) |
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An antiobic drug effective against a wide variety of gram-positive and gram-negative bacteria, including most anaerobic organisms | |
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1947, first isolated | |
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Typically used to treat skin infections, wound infections, bone infections, intestinal tract infections and pneumonia | |
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Cats; Dogs |
Approval status |
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Not approved | |
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Not approved |
Chemical structure |
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Isomeric | |
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C₁₁H₁₂Cl₂N₂O₅ | |
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C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-] | |
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C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-] | |
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WIIZWVCIJKGZOK-RKDXNWHRSA-N | |
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InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1 | |
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Yes |
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Common Name | Relationship | Link |
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chloramphenicol | - |
General status |
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Antibiotic, Antimicrobial, Antibacterial, Medicinal drug | |
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Amphenicol | |
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>98% | |
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Synthetic | |
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Broad spectrum, inhibits bacterial protein synthesis | |
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[50S ribosomal protein L16, Antagonist], [Dr hemagglutinin structural subunit, Antagonist], [Complement decay-accelerating factor] | |
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56-75-7 | |
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200-287-4 | |
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5959 | |
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Antiinfectants for systemic use: Antibacterials for intramammary use; Sensory organs: Ophthalmologicals | |
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QJ51BA01; QS01AA01 | |
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No | |
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Prohibited | |
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323.13 | |
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2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide | |
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Evidence of use in third world countries | |
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Colourless to pale yellow solid |
Formulations |
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Chloromycetintm Redidrops | Pharmacia Animal Health Ltd | Not licensed | Not licensed | ||||||
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2500 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
High | ||||||||
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150800 | L3 L = Pesticide manuals and hard copy reference books / other sources Propylene glycol3 = Unverified data of known source |
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151 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
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Decomposes before boiling | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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1.38 X 1001 | Calculated | - | |||||||
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1.14 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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2.30 X 10-07 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
Low volatility | ||||||||
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max @ 278nm | L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source |
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Degradation |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Soil adsorption and mobility |
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- | V1 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 1 = Estimated data with little or no verification |
Moderately mobile | |||||||
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99 | ||||||||||
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Estimated | ||||||||||
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Fate indices |
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Known soil and groundwater metabolites |
None
Other known metabolites |
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d-threo-2-amino-1-(p-nitrophenyl)-1,3-propanediol | - | Humans; Rat | - | ||||
chloramphenicol-beta-d-glucuronide | chloramphenicol 3-glucuronide | Humans; Rat | - | ||||
2-amino-1-(p-nitrophenyl)-1,3-propanediol | - | unknown | - |
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Terrestrial ecotoxicology |
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1500 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Mouse4 = Verified data |
Moderate | ||||||||
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Aquatic ecotoxicology |
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1828 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Anguilla japonica4 = Verified data |
Low | ||||||||
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3360 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Daphnia magna as umol/litre4 = Verified data |
Low | ||||||||
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General |
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High (class III) | - | - | ||||||||
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1500 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Mouse4 = Verified data |
Moderate | ||||||||
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Subcutaneous LD₅₀ > 5000 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Intravenous LD₅₀ = 171 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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In humans metabolised and approx. half excreted in urine within 8hr of an oral dosing as the glucuronide conjugate; only 6% was excreted as the unchanged parent. | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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Health issues |
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IARC Group 2A carcinogen; US NTP - suspected carcinogen; OSHA - anticipated human carcinogen Can induce childhood leukemia and aplastic anemia, although these effects are rare Toxic if ingested Blood, kidneys and liver toxicant |
Handling issues |
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No information available | |||
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Not listed (Not listed) | |||
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chloramphenicol | ||
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cloroamfenicolo | ||
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cloramfenicol | ||
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chloromycetny | ||
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Record last updated: | 11/01/2024 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |