CLM

CHLORAMPHENICOL

Created:	1999-07-08
Last modified:	2011-06-04

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Chemical Details
Formal Charge	0
Atom Count	32
Chiral Atom Count	2
Bond Count	32
Aromatic Bond Count	6

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Chemical Component Summary
Name	CHLORAMPHENICOL
Systematic Name (OpenEye OEToolkits)	2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]ethanamide
Formula	C₁₁ H₁₂ Cl₂ N₂ O₅
Molecular Weight	323.129
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	ClC(Cl)C(=O)NC(C(O)c1ccc([N+]([O-])=O)cc1)CO
SMILES	CACTVS	3.341	OC[CH](NC(=O)C(Cl)Cl)[CH](O)c1ccc(cc1)[N+]([O-])=O
SMILES	OpenEye OEToolkits	1.5.0	c1cc(ccc1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
Canonical SMILES	CACTVS	3.341	OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc(cc1)[N+]([O-])=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1cc(ccc1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
InChI	InChI	1.03	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
InChIKey	InChI	1.03	WIIZWVCIJKGZOK-RKDXNWHRSA-N

Drug Info: DrugBank

DrugBank ID	DB00446
Name	Chloramphenicol
Groups	approved withdrawn vet_approved
Description	An antibiotic first isolated from cultures of _Streptomyces venezuelae_ 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 (From Martindale, The Extra Pharmacopoeia, 29th ed, p106) The FDA has withdrawn all oral drug products containing chloramphenicol, due to the high risk of fatal aplastic anemia associated with this specific route of administration.[L43942,L44022]
Synonyms	D-(−)-2,2-dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p-nitrophenylethyl)acetamide D-(−)-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propanediol Chlornitromycin Chloramphenicolum Cloranfenicol Chloramphénicol Levomycetin Levomicetina Laevomycetinum Chloramphenicol Cloramfenicol
Brand Names	Chloromycetin Oph Ont 1% Chloromycetin Otic Cebenicol Oph Liq 0.4% Sopamycetin Solution Ophthalmique 0.2% Odan-chloramphenicol Ophthocort Ont Chloroptic Oph Ont 1% Sopamycetin/hc Ont Pentamycetin Ophthalmic Solution 0.5% - Liq Actinac Pws Actinac Pwr Ophtho-chloram Liq 0.5% PMS-chloramphenicol Ophthalmic Soln 0.5% Sopamycetin Oph Ont 0.2% Chloromycetin Oph Soln 0.5% Pentamycetin Liq 2.5mg/ml Sopamycetin/hc Susp PMS-chloramphenicol Ophthalmic Ointment Sopamycetin Soln Otique 5% Chloramphenicol Pentamycetin Ont 10mg/gm Econochlor Pentamycetin/hc Chloromycetin Sopamycetin/hc Ointment Chloroptic Dps 0.5% Minims Chloramphenicol 0.5% Novo-chlorocap Cap 250mg
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.
Categories	Alcohols Amphenicols Anti-Acne Preparations Anti-Acne Preparations for Topical Use Anti-Bacterial Agents Anti-Infective Agents Antibacterials for Systemic Use Antibiotics for Topical Use Antiinfectives for Systemic Use Antiinfectives for Treatment of Acne Benzene Derivatives Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 Inhibitors (strong) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A5 Inhibitors Cytochrome P-450 CYP3A5 Inhibitors (strength unknown) Cytochrome P-450 CYP3A7 Inhibitors Cytochrome P-450 CYP3A7 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inhibitors Dermatologicals Enzyme Inhibitors Genito Urinary System and Sex Hormones Glycols Gynecological Antiinfectives and Antiseptics Immunosuppressive Agents Myelosuppressive Agents Nitro Compounds Nitrobenzenes OAT1/SLC22A6 inhibitors Ophthalmological and Otological Preparations Ophthalmologicals Otologicals Propylene Glycols Protein Synthesis Inhibitors Sensory Organs
ATC-Code	D06AX02 S02AA01 D10AF03 S01AA01 G01AA05 J01BA01 S03AA08
CAS number	56-75-7

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
50S ribosomal protein L16	MLQPKRTKFRKMHKGRNRGLAQGTDVSFGSFGLKAVGRGRLTARQIEAAR...	unknown	inhibitor
Dr hemagglutinin structural subunit	MKKLAIMAAASMVFAVSSAHAGFTPSGTTGTTKLTVTEECQVRVGDLTVA...	unknown	antagonist
Complement decay-accelerating factor	MTVARPSVPAALPLLGELPRLLLLVLLCLPAVWGDCGLPPDVPNAQPALE...	unknown	other
Chloramphenicol acetyltransferase 3	MNYTKFDVKNWVRREHFEFYRHRLPCGFSLTSKIDITTLKKSLDDSAYKF...	unknown	substrate
Chloramphenicol acetyltransferase	MGNYFESPFRGKLLSEQVSNPNIRVGRYSYYSGYYHGHSFDDCARYLMPD...	unknown	substrate
Chloramphenicol 3-O phosphotransferase	MTTRMIILNGGSSAGKSGIVRCLQSVLPEPWLAFGVDSLIEAMPLKMQSA...	unknown	substrate
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	inhibitor
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	inhibitor
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	inhibitor
Solute carrier family 22 member 6	MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682