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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
 

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

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 (8CI)
  • 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

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/s1

InChIKey

JQXXHWHPUNPDRT-WLSIYKJHSA-N

Smiles

Cc1c(c2c3c4c1O[C@@](C4=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](/C=C/C=C(\C(=O)Nc(c2O)c(c3O)/C=N/N5CCN(CC5)C)/C)C)O)C)O)C)OC(=O)C)C)OC)C)O

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) SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SENSE ORGANS AND SPECIAL SENSES: IRITIS: 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) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: HEMATURIA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
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) BLOOD: APLASTIC ANEMIA

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
American Journal of Medicine. Vol. 87, Pg. 459, 1989.
women TDLo oral 744mg/kg/9W-I (744mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
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.