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Substance Name: Rifampin [USAN:USP]
RN: 13292-46-1
UNII: VJT6J7R4TR
InChIKey: JQXXHWHPUNPDRT-WLSIYKJHSA-N
Note
- A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160).
Molecular Formula
- C43-H58-N4-O12
Molecular Weight
- 822.9472
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterial
- Antibiotics, Antitubercular
- Antitubercular Agents
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2C19 Inducers
- Cytochrome P-450 CYP2C8 Inducers
- Cytochrome P-450 CYP2C9 Inducers
- Cytochrome P-450 CYP3A Inducers
- Drug / Therapeutic Agent
- Enzyme Inhibitors
- Human Data
- Leprostatic Agents
- Metabolic Side Effects of Drugs and Substances
- Mutation Data
- Nucleic Acid Synthesis Inhibitors
- Reproductive Effect
- Tumor Data
Superlist Classification Code
- Overall Carcinogenic Evaluation: Group 3
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NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
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Names and Synonyms
Name of Substance
- Rifampin
- Rifampin [USAN:USP]
MeSH Heading
- Rifampin
Synonyms
- 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV
- 3-(4-Methylpiperazinyliminomethyl)-rifamycin SV
- 5,6,9,17,19,21-Hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2H)-dione 21-acetate
- 8-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV
- 8-(4-Methylpiperazinyliminomethyl) rifamycin SV
- Archidyn
- Arficin
- Arzide
- Ba 41166/E
- Benemicin
- CCRIS 551
- Dione 21-acetate
- Doloresum
- EINECS 236-312-0
- Eremfat
- Fenampicin
- HSDB 3181
- L-5103 Lepetit
- NSC 113926
- R/AMP
- Ramp
- Rifa
- Rifadin
- Rifadin I.V.
- Rifagen
- Rifaldazin
- Rifaldazine
- Rifam
- Rifamor
- Rifampicin
- Rifampicin SV
- Rifampicin [INN:BAN:JAN]
- Rifampicina
- Rifampicina [INN-Spanish]
- Rifampicine
- Rifampicine [French]
- Rifampicinum
- Rifampicinum [INN-Latin]
- Rifampin
- Rifamycin AMP
- Rifamycin, 3-(((4-methyl-1-piperazinyl)imino)methyl)-
- Rifaprodin
- Rifcin
- Rifinah
- Rifobac
- Rifoldin
- Rifoldine
- Rifomycin SV, 8-(N-(4-methyl-1-piperazinyl)formidoyl)-
- Riforal
- Rimactan
- Rimactane
- Rimactazid
- Rimactizid
- Rimazid
- Sinerdol
- Tubocin
- UNII-VJT6J7R4TR
Systematic Names
- 2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2H)-dione, 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-, 21-acetate
- Rifampicin
- Rifamycin, 3-(((4-methyl-1-piperazinyl)imino)methyl)-
- Rifomycin SV, 8-(N-(4-methyl-1-piperazinyl)formidoyl)-
Superlist Names
- Rifampicin
- Rifampin
Mixture Name
- Rifater
Registry Numbers
CAS Registry Number
- 13292-46-1
FDA UNII
- VJT6J7R4TR
System Generated Number
- 0013292461
Structure Descriptors
InChI
InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1InChIKey
JQXXHWHPUNPDRT-WLSIYKJHSA-NSmiles
CO[C@H]1\C=C\O[C@@]2(C)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | intraperitoneal | 639mg/kg (639mg/kg) | Antibiotica et Chemotherapia Vol. 16, Pg. 316, 1970. | |
human | TDLo | oral | 180mg/kg (180mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" SENSE ORGANS AND SPECIAL SENSES: IRITIS: EYE SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE | British Medical Journal. Vol. 2, Pg. 1189, 1977. |
man | LDLo | oral | 857mg/kg (857mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" GASTROINTESTINAL: OTHER CHANGES GASTROINTESTINAL: NAUSEA OR VOMITING | JAMA, Journal of the American Medical Association. Vol. 240, Pg. 2283, 1978. |
man | TDLo | oral | 13mg/kg/2D (13mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE | British Medical Journal. Vol. 1, Pg. 199, 1976. |
man | TDLo | oral | 814mg/kg/15W- (814mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" KIDNEY, URETER, AND BLADDER: HEMATURIA | American Journal of Kidney Diseases. Vol. 32, Pg. 533, 1998. |
mouse | LD50 | intraperitoneal | 416mg/kg (416mg/kg) | Chemotherapia. Vol. 12, Pg. 155, 1967. | |
mouse | LD50 | intravenous | 260mg/kg (260mg/kg) | Antibiotica et Chemotherapia Vol. 16, Pg. 316, 1970. | |
mouse | LD50 | oral | 500mg/kg (500mg/kg) | Comptes Rendus des Seances de l'Academie des Sciences, Serie D: Sciences Naturelles. Vol. 269, Pg. 2147, 1969. | |
mouse | LD50 | subcutaneous | 621mg/kg (621mg/kg) | Japanese Journal of Antibiotics. Vol. 23, Pg. 242, 1970. | |
rabbit | LD50 | oral | 2120mg/kg (2120mg/kg) | Antibiotica et Chemotherapia Vol. 16, Pg. 316, 1970. | |
rat | LD50 | intraperitoneal | 511mg/kg (511mg/kg) | Japanese Journal of Antibiotics. Vol. 23, Pg. 257, 1970. | |
rat | LD50 | oral | 1570mg/kg (1570mg/kg) | Japanese Journal of Antibiotics. Vol. 23, Pg. 257, 1970. | |
rat | LD50 | subcutaneous | 534mg/kg (534mg/kg) | Japanese Journal of Antibiotics. Vol. 23, Pg. 242, 1970. | |
women | TDLo | oral | 315mg/kg/5W-I (315mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Journal of the American Academy of Dermatology. Vol. 17, Pg. 303, 1987. |
women | TDLo | oral | 504mg/kg/42D- (504mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BLOOD: APLASTIC ANEMIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | American Journal of Medicine. Vol. 87, Pg. 459, 1989. |
women | TDLo | oral | 744mg/kg/9W-I (744mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | American Journal of Kidney Diseases. Vol. 31, Pg. 108, 1998. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
log P (octanol-water) | 4.240 | (none) | EST | |
Water Solubility | 1400 | mg/L | 25 | EXP |
Atmospheric OH Rate Constant | 5.06E-10 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.