|
|
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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
* denotes mobile formatted website
Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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
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/s1InChIKey
WIIZWVCIJKGZOK-RKDXNWHRSA-NSmiles
OC[C@@H](NC(=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.