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Substance Name: Rifapentine [USAN:INN:BAN]
RN: 61379-65-5
UNII: XJM390A33U
InChIKey: WDZCUPBHRAEYDL-GZAUEHORSA-N

Note

  • Cyclopentyl derivative of rifampicin.

Molecular Formula

  • C47-H64-N4-O12

Molecular Weight

  • 877.0386
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Antibiotics, Antitubercular
  • Antitubercular Agents
  • Drug / Therapeutic Agent
  • Leprostatic Agents

Names and Synonyms

Name of Substance

  • Rifapentine
  • Rifapentine [USAN:INN:BAN]

Synonyms

  • 3-(((4-Cyclopentyl-1-piperazinyl)imino)methyl)rifamycin
  • 3-(4-Cyclopentyl-1-piperazinyl)iminomethylrifamycin SV
  • 3-(N-(4-Cyclopentyl-1-piperazinyl)formimidoyl)rifamycin
  • Antibiotic DL 473IT
  • Cyclopentylrifampicin
  • DL 473
  • DRG-0283
  • EINECS 262-743-9
  • KTC 1
  • MDL 473
  • Priftin
  • R 77-3
  • R-773
  • Rifamycin AF/ACPP
  • Rifamycin, 3-(((4-cyclopentyl-1-piperazinyl)imino)methyl)-
  • Rifapentina
  • Rifapentina [Spanish]
  • Rifapentine
  • Rifapentinum
  • Rifapentinum [Latin]
  • UNII-XJM390A33U

Systematic Names

  • Rifamycin, 3-(((4-cyclopentyl-1-piperazinyl)imino)methyl)-
  • Rifapentine

Registry Numbers

CAS Registry Number

  • 61379-65-5

FDA UNII

  • XJM390A33U

Other Registry Numbers

  • 71950-35-1
  • 773848-08-1

System Generated Number

  • 0061379655

Structure Descriptors

InChI

InChI=1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1

InChIKey

WDZCUPBHRAEYDL-GZAUEHORSA-N

Smiles

CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)\C(=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(=O)C)[C@@H]1C)\C)c(\C=N\N5CCN(CC5)C6CCCC6)c(O)c4c3C2=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 710mg/kg (710mg/kg)   Journal of Antibiotics. Vol. 34, Pg. 1026, 1981.
mouse LD50 oral 3300mg/kg (3300mg/kg)   Journal of Antibiotics. Vol. 34, Pg. 1026, 1981.
rat LD50 intraperitoneal > 2gm/kg (2000mg/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 242, 1992.
rat LD50 oral > 4gm/kg (4000mg/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 242, 1992.