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Substance Name: Chloramphenicol [USP:INN:BAN:JAN]
RN: 56-75-7
UNII: 66974FR9Q1
InChIKey: WIIZWVCIJKGZOK-RKDXNWHRSA-N

Note

  • 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

  • C11-H12-Cl2-N2-O5

Molecular Weight

  • 323.1308
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Antirickettsial
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Fungicide, Bactericide, Wood Preservative
  • Human Data
  • Mutation Data
  • Natural Product
  • Protein Synthesis Inhibitors
  • Reproductive Effect
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 2A

Names and Synonyms

Name of Substance

  • Chloramphenicol
  • Chloramphenicol [USP:INN:BAN:JAN]

MeSH Heading

  • Chloramphenicol

Synonyms

  • 4-13-00-02742 (Beilstein Handbook Reference)
  • Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (R-(R*,R*))-
  • AI3-25003
  • Alficetyn
  • Ambofen
  • Amphenicol
  • Amphicol
  • Amseclor
  • Anacetin
  • Aquamycetin
  • Austracil
  • Austracol
  • Biocetin
  • Biophenicol
  • BRN 2225532
  • CAF
  • CAF (pharmaceutical)
  • CAM
  • CAP (ambiguous)
  • Catilan
  • CCRIS 3922
  • Chemicetin
  • Chemicetina
  • Chlomin
  • Chlomycol
  • Chlora-tabs
  • Chloramex
  • Chloramfenikol
  • Chloramfenikol [Czech]
  • Chloramficin
  • Chloramfilin
  • Chloramphenicol
  • Chloramphenicol crystalline
  • Chloramphenicol, d-
  • Chloramphenicolum
  • Chloramphenicolum [INN-Latin]
  • Chloramsaar
  • Chlorasol
  • Chlorbiotic (Veterinary)
  • Chloricol
  • Chlornitromycin
  • Chloro-25 vetag
  • Chloroamphenicol
  • Chlorocaps
  • Chlorocid
  • Chlorocid S
  • Chlorocide
  • Chlorocidin C
  • Chlorocidin C tetran
  • Chlorocol
  • Chlorofair
  • Chloroject L
  • Chloromax
  • Chloromycetin
  • Chloromycetny
  • Chloromycetny [Polish]
  • Chloronitrin
  • Chloroptic
  • Chloroptic S.O.P.
  • Chlorovules
  • Cidocetine
  • Ciplamycetin
  • Cloramfenicol
  • Cloramfenicol [INN-Spanish]
  • Cloramfenicolo
  • Cloramfenicolo [DCIT]
  • Cloramficin
  • Cloramicol
  • Cloramidina
  • Cloroamfenicolo
  • Cloroamfenicolo [Italian]
  • Clorocyn
  • Cloromisan
  • Clorosintex
  • Comycetin
  • CPh
  • Cylphenicol
  • D-(-)-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenylethyl)acetamide
  • D-(-)-Chloramphenicol
  • D-(-)-threo-1-(4-Nitrophenyl)-2-dichloroacetamido-1,3-propanediol
  • D-(-)-threo-1-p-Nitrophenyl-2-dichloracetamido-1,3-propanediol
  • D-(-)-threo-1-p-Nitrophenyl-2-dichloroacetylamino-1,3-propanediol
  • D-(-)-threo-2-Dichloroacetamido-1-p-nitrophenyl-1,3-propanediol
  • D-(-)-threo-Chloramphenicol
  • D-Chloramphenicol
  • D-threo-(-)-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)acetamide
  • D-threo-(1R,2R)-1-p-Nitrophenyl-2-dichloroacetamido-1,3-propanediol
  • Desphen
  • Detreomycin
  • Detreomycine
  • Dextromycetin
  • Doctamicina
  • Econochlor
  • EINECS 200-287-4
  • Embacetin
  • Emetren
  • Enicol
  • Enteromycetin
  • Erbaplast
  • Ertilen
  • Farmicetina
  • Fenicol
  • Globenicol
  • Glorous
  • Halomycetin
  • Hortfenicol
  • HSDB 3027
  • I 337A
  • Intramycetin
  • Isicetin
  • Ismicetina
  • Isophenicol
  • Isopto fenicol
  • Juvamycetin
  • Kamaver
  • Kemicetina
  • Kemicetine
  • Klorita
  • Klorocid S
  • Laevomycetinum
  • Leukomyan
  • Leukomycin
  • Levomicetina
  • Levomitsetin
  • Levomycetin
  • Loromisin
  • Mastiphen
  • Mediamycetine
  • Medichol
  • Micloretin
  • Micochlorine
  • Micoclorina
  • Microcetina
  • Mychel
  • Mychel-Vet
  • Mycinol
  • NCI-C55709
  • Normimycin V
  • Novochlorocap
  • Novomycetin
  • Novophenicol
  • NSC 16331
  • NSC 3069
  • Oftalent
  • Oleomycetin
  • Opclor
  • Ophthochlor
  • Optomycin
  • Otachron
  • Otophen
  • Pantovernil
  • Paraxin
  • Pentamycetin
  • Quemicetina
  • Rivomycin
  • Romphenil
  • Ronphenil
  • Septicol
  • Sificetina
  • Sintomicetina
  • Sintomicetine R
  • Sno-Phenicol
  • Stanomycetin
  • Synthomycetin
  • U-6062
  • UNII-66974FR9Q1

Systematic Names

  • Acetamide, 2,2-dichloro-N-((1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-
  • Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (R-(R*,R*))-
  • 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-
  • Chloramphenicol

Superlist Name

  • Chloramphenicol

Mixture Names

  • Chloromyxin
  • Elase-Chloromycetin
  • Ophthochlor
  • Ophthocort

Registry Numbers

CAS Registry Number

  • 56-75-7

FDA UNII

  • 66974FR9Q1

Other Registry Numbers

  • 137731-90-9
  • 15313-32-3
  • 55172-72-0
  • 59112-59-3
  • 85666-84-8

System Generated Number

  • 0000056757

Structure Descriptors

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

WIIZWVCIJKGZOK-RKDXNWHRSA-N

Smiles

c1cc(ccc1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo unreported 250mg/kg/10D (250mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

BLOOD: HEMORRHAGE

LIVER: OTHER CHANGES
Clinical Pediatrics Vol. 14, Pg. 499, 1975.
dog LD intramuscular > 101mg/kg (101mg/kg)   Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
dog LD oral > 300mg/kg (300mg/kg)   Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
dog LDLo intravenous 150mg/kg (150mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Bacteriology. Vol. 55, Pg. 425, 1948.
guinea pig LD50 intravenous 560mg/kg (560mg/kg)   Farmaco, Edizione Scientifica. Vol. 9, Pg. 21, 1954.
guinea pig LD50 oral 500mg/kg (500mg/kg)   Farmaco, Edizione Scientifica. Vol. 10, Pg. 3, 1955.
infant LDLo intravenous 30mg/kg/3D-I (30mg/kg) CARDIAC: CARDIAC OUTPUT

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Pediatrics. Vol. 103, Pg. 487, 1983.
infant LDLo unreported 200mg/kg/4D-I (200mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BLOOD: EOSINOPHILIA
Lancet. Vol. 1, Pg. 555, 1986.
infant TDLo intramuscular 250mg/kg/2D (250mg/kg) VASCULAR: CHANGE IN PLASMA OR BLOOD VALUME New England Journal of Medicine. Vol. 262, Pg. 787, 1960.
infant TDLo oral 440mg/kg (440mg/kg)   JAMA, Journal of the American Medical Association. Vol. 234, Pg. 149, 1975.
infant TDLo oral 440mg/kg (440mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES
JAMA, Journal of the American Medical Association. Vol. 234, Pg. 149, 1975.
mouse LD50 intraperitoneal 1100mg/kg (1100mg/kg)   Dissertationes Pharmaceuticae. Vol. 14, Pg. 21, 1962.
mouse LD50 intravenous 110mg/kg (110mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
mouse LD50 oral 1500mg/kg (1500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 1, 1955.
mouse LD50 subcutaneous 400mg/kg (400mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 493, 1978.
rabbit LD50 intravenous 117mg/kg (117mg/kg)   Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
rat LD50 intraperitoneal 1811mg/kg (1811mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 intravenous 171mg/kg (171mg/kg)   Journal of Clinical Investigation. Vol. 28, Pg. 943, 1949.
rat LD50 oral 2500mg/kg (2500mg/kg)   Farmaco, Edizione Scientifica. Vol. 10, Pg. 3, 1955.
rat LD50 subcutaneous 5gm/kg (5000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Toxicology and Applied Pharmacology. Vol. 9, Pg. 445, 1966.
women LDLo oral 400mg/kg (400mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

VASCULAR: SHOCK
JAMA, Journal of the American Medical Association. Vol. 234, Pg. 149, 1975.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 150.5 deg C   EXP
log P (octanol-water) 1.14 (none)   EXP
Water Solubility 2500 mg/L 25 EXP
Vapor Pressure 1.73E-12 mm Hg 25 EST
Henry's Law Constant 2.29E-18 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.10E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.