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Compound Summary

General Compound Information

Chloramphenicol

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Description

Chloramphenicol is an organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond and two alcohol functions. It has a role as an antimicrobial agent, an antibacterial drug, a protein synthesis inhibitor, an Escherichia coli metabolite and a Mycoplasma genitalium metabolite. It is an organochlorine compound, a diol, a C-nitro compound and a carboxamide.

Synonyms

chloramphenicol; 56-75-7; Chloromycetin; Chlornitromycin; Levomycetin;

Chloroamphenicol;Halomycetin;Levomicetina;Chlorocid;Globenicol;Alficetyn;Chloramex;Chlorocol;Detreomycin;Oleomycetin;Fenicol;Amphenicol;Aquamycetin;Chloramficin;Chloramfilin;Chloroptic;Cloramicol;D-Chloramphenicol;Econochlor;Enteromycetin;Juvamycetin;Leukomycin;Novomycetin;Ophthochlor;Sificetina;Amphicol;Mychel;Chloramphenicolum;Chloronitrin;Ciplamycetin;Detreomycine;Intramycetin;Laevomycetinum;Levomitsetin;Mediamycetine;Micochlorine;Novophenicol;Stanomycetin;Synthomycetin;Amseclor;Anacetin;Austracil;Austracol;Biocetin;Biophenicol;Chemicetin;Chemicetina;Chlomycol;Chloramsaar;Chlorasol;Chloricol;Chlorocaps;Chlorocide;Chlorovules;Cidocetine;Cloramficin;Cloramidina;Clorocyn;Cloromisan;Clorosintex;Comycetin;Cylphenicol;Doctamicina;Embacetin;Erbaplast;Farmicetina;Hortfenicol;Isicetin;Ismicetina;Isophenicol;Kemicetina;Kemicetine;Leukomyan;Loromisin;Mastiphen;Medichol;Micloretin;Micoclorina;Microcetina;Rivomycin;Ambofen;Catilan;Chlomin;Desphen;Emetren;Enicol;Ertilen;Glorous;Kamaver;Klorita;Isopto fenicol;Chlora-tabs;Chlorocidin C;Chloroject L;Normimycin V;Chlorocid S;Klorocid S;Mychel-Vet;Chloramfenikol;Cloramfenicol;Novochlorocap;Sintomicetina;Chloromax;Oftalent;Otachron;Pantovernil;Pentamycetin;Quemicetina;Romphenil;Ronphenil;Septicol;Chloro-25 vetag;Mycinol;Opclor;Otophen;Paraxin;Sintomicetine R;Sno-Phenicol;Chlorocidin C tetran;Chlorofair;Cloroamfenicolo;Optomycin;D-(-)-Chloramphenicol;Chloromycetny;Dextromycetin;Synthomycetine;Treomicetina;Tevcocin;Tifomycine;Unimycetin;Veticol;Viceton;Tiromycetin;Leukamycin;Loromisan;Tifomycin;D-(-)-threo-Chloramphenicol;Tega-Cetin;I 337A;2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide;U-6062;NCI-C55709;NSC 3069;D-threo-Chloramphenicol;D(-)-threo-Chloramphenicol;D-(-)-threo-1-p-Nitrophenyl-2-dichloroacetylamino-1,3-propanediol;CAF;Cloramfen;Chloramphenicol (Chloromycetin);2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide;Ak-chlor;CHEBI:17698;NSC3069;NSC-3069;D-(-)-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenylethyl)acetamide;D-(-)-threo-1-p-Nitrophenyl-2-dichloracetamido-1,3-propanediol;Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (R-(R,R))-;125440-98-4;Cloramfenicolo;Syntomycin;DTXSID7020265;D-(-)-threo-2-Dichloroacetamido-1-p-nitrophenyl-1,3-propanediol;D-(-)-threo-1-(4-Nitrophenyl)-2-dichloroacetamido-1,3-propanediol;D-threo-(1R,2R)-1-p-Nitrophenyl-2-dichloroacetamido-1,3-propanediol;Chloramphenicol-[ring-3,5-3H];Acetamide, 2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [R-(R,R)]-;66974FR9Q1;NCGC00091011-05;CAF (pharmaceutical);Chloramfenikol [Czech];Chloromycetny [Polish];Cloramfenicolo [DCIT];D-threo-N-(1,1'-Dihydroxy-1-p-nitrophenylisopropyl)dichloroacetamide;2,2-Dichloro-N-((1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide;Chlorbiotic (Veterinary);Chloramphenicol 100 microg/mL in Ethyl acetate;Cloroamfenicolo [Italian];Chloramphenicol crystalline;Elase-Chloromycetin;Gloveticol;Mycochlorin;Ocuphenicol;Sintomicetin;Tyfomycine;Chlorocin;Halcetin;Levocin;Levoplast;Levosin;Levovetin;Myclocin;Soluthor;DTXCID90265;Chloramphenicol, d-;Chloroptic S.O.P.;Cloramfenicol [INN-Spanish];Chloramphenicolum [INN-Latin];Ophtochlor;Synthomycine;Tevcosin;Opelor;D(-)-threo-2-Dichloroacetamido-1-p-nitrophenyl-1,3-propanediol;(-)-chloramphenicol;2,2-Dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)-2-propyl]acetamide;Acetamide, 2,2-dichloro-N-((1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-;Econochlor (TN);Amphicol (TN);Ophthocort (Salt/Mix);ACETAMIDE, 2,2-DICHLORO-N-[(1R,2R)-2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-NITROPHENYL)ETHYL]-;SMR000471851;Chloromyxin (Salt/Mix);Chloromycetin (TN);CCRIS 3922;HSDB 3027;SR-01000761450;EINECS 200-287-4;Elase-Chloromycetin (Salt/Mix);BRN 2225532;chioramphenicol;Chloramphenicole;AI3-25003;UNII-66974FR9Q1;CAS-56-75-7;NCGC00094620-01;Thiamphenicol,(S);2,2-DICHLORO-N-((1R,2R)-2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-NITROPHENYL)ETHYL)ACETAMIDE;2787-09-9;D-(-)-threo-2,2-Dichloro-N-(.beta.-hydroxy-.alpha.-(hydroxymethyl))-p-nitrophenethylacetamide;D-(-)-threo-2,2-Dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)]-p-nitrophenethylacetamide;Chloramphenicol [USP:INN:BAN:JAN];Chloramphenicol,(S);MFCD00078159;Prestwick3_000031;CHEMBL130;Epitope ID:114066;Pork muscle-Chloramphenicol;CHLORAMPHENICOL [MI];SCHEMBL16111;BSPBio_000121;CHLORAMPHENICOL [INN];CHLORAMPHENICOL [JAN];WLN: WNR DYQY1QMVYGG;4-13-00-02742 (Beilstein Handbook Reference);MLS001055372;MLS001066397;MLS001332385;MLS001332386;MLS002222155;BIDD:GT0145;CHLORAMPHENICOL [HSDB];CHLORAMPHENICOL [IARC];DivK1c_000544;CHLORAMPHENICOL [VANDF];BPBio1_000135;CHLORAMPHENICOL [MART.];CHLORAMPHENICOLUM [HPUS];CHLORAMPHENICOL [USP-RS];CHLORAMPHENICOL [WHO-DD];CHLORAMPHENICOL [WHO-IP];D-(-)-threo-1-(p-Nitrophenyl)-2-(dichloroacetylamino)-1,3-propanediol;D-(-)-threo-N-Dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol;BDBM23447;Chloramphenicol, gamma-irradiated;GTPL10901;HMS501L06;KBio1_000544;NINDS_000544;Chloramphenicol (JP17/USP/INN);HMS2090M15;HMS2095G03;HMS2269N06;HMS3712G03;ZINC113382;Chloramphenicol, >=98% (HPLC);Acetamide, 2,2-dichloro-N-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl)-, D-(-)-threo-;Acetamide, 2,2-dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]-, D-threo-(-)-;BCP12150;D-(-)-threo-2,2-Dichloro-N-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenyl-ethyl)acetamide;D-threo-N-Dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol;HY-B0239;RKL10087;CHLORAMPHENICOL [GREEN BOOK];Tox21_111306;Tox21_400061;CHLORAMPHENICOL [ORANGE BOOK];D-(-)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol;s1677;CHLORAMPHENICOL [EP MONOGRAPH];AKOS005111001;Chloramphenicol for peak identification;Porcine muscle-Chloramphenicol (blank);CCG-220031;CHLORAMPHENICOL [USP MONOGRAPH];DB00446;CHLORAMPHENICOLUM [WHO-IP LATIN];D-threo-(-)-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)acetamide;IDI1_000544;SMP1_000065;NCGC00091011-01;NCGC00091011-02;NCGC00091011-03;NCGC00091011-04;NCGC00091011-06;NCGC00091011-08;NCGC00091011-09;NCGC00091011-20;Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (theta-(theta,theta))-;Acetamide, 2,2-dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)-, D-(-)-threo-;AS-14683;NCI60_002620;OPHTHOCORT COMPONENT CHLORAMPHENICOL;Chloramphenicol, puriss., 98.0-102.0%;CHLOROMYXIN COMPONENT CHLORAMPHENICOL;AB00374860;Chloramphenicol 10 microg/mL in Acetonitrile;Chloramphenicol, tested according to Ph.Eur.;SW198497-2;CHLORAMPHENICOL COMPONENT OF OPHTHOCORT;C-3307;C00918;CHLORAMPHENICOL COMPONENT OF CHLOROMYXIN;D00104;AB00374860-13;AB00374860-14;AB00374860_15;Chloramphenicol, meets USP testing specifications;Q274515;Chloramphenicol, VETRANAL(TM), analytical standard;ELASE-CHLOROMYCETIN COMPONENT CHLORAMPHENICOL;SR-01000761450-2;SR-01000761450-3;SR-01000761450-5;BRD-K08111712-001-02-7;BRD-K08111712-001-16-7;CHLORAMPHENICOL COMPONENT OF ELASE-CHLOROMYCETIN;Chloramphenicol, Antibiotic for Culture Media Use Only;CHLOROPTIC-P S.O.P. COMPONENT CHLORAMPHENICOL;CHLORAMPHENICOL COMPONENT OF CHLOROPTIC-P S.O.P.;Z2065671241;Chloramphenicol, BioReagent, suitable for plant cell culture;Chloramphenicol, certified reference material, TraceCERT(R);CHLOROMYCETIN HYDROCORTISONE COMPONENT CHLORAMPHENICOL;CHLORAMPHENICOL COMPONENT OF CHLOROMYCETIN HYDROCORTISONE;Chloramphenicol, British Pharmacopoeia (BP) Reference Standard;Chloramphenicol, European Pharmacopoeia (EP) Reference Standard;Chloramphenicol, United States Pharmacopeia (USP) Reference Standard;D-threo-1-(p-Nitrophenyl)-2-(dichloroacetylamino)-1,3-propanediol;Acetamide,2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-;Acetamide,2-dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl];Chloramphenicol, Biotechnology Performance Certified, suitable for plant cell culture;D-(-)-2,2-Dichloro-N-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenyl-ethyl)acetamide;2,2-Dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(hydroxy(oxido)amino)phenyl)ethyl)acetamide, (1R, 2R)-;Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (R,R)-(+-)-;Acetamide,2-dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]-, D-threo-(-)-;Acetamide,2-dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]-,D-(-)-threo-;Acetamide,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [R-(R,R)]-;Chloramphenicol 10 microg/mL in Acetonitrile. Short expiry date due to chemical nature of component(s);D-(-)-threo-alpha, alpha-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)acetamide;D-THREO-(-)-2,2-DICHLORO-N-(.BETA.-HYDROXY-.ALPHA.-(HYDROXYMETHYL)-P-NITROPHENETHYL)ACETAMIDE;

FlavorDB ID

63

PUBCHEM ID

5959

Molecular Weight

323.13

Molecular Formula

C11H12Cl2N2O5

Openeye Can Smiles

C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]

IUPAC Inchikey

WIIZWVCIJKGZOK-RKDXNWHRSA-N

Network

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Similarity

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Compound Classification

Classification (Parent Nodes)

ClassyFire Ontology

Compound Quality

Quality information of this compound is not available!

Compound Toxicity and Food Additive Safety (OFAS)

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
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.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)

Receptors

Receptor	REFERENCE	EC50 [µM]	Effective Concentration [µM]
TAS2R1	details	Activated	100.00
TAS2R8	details	555.00	30.00
TAS2R10	details	Activated	100.00
TAS2R39	details	Activated	1000.00
TAS2R41	details	Activated	500.00
TAS2R43	details	Activated	100.00
TAS2R46	details	Activated	10.00

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental LCMS	view	LCMS_Positive	positive
Experimental LCMS	view	LCMS_Negative	negative