Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Irinotecan [INN:BAN]
RN: 97682-44-5
UNII: 7673326042
InChIKey: UWKQSNNFCGGAFS-XIFFEERXSA-N

Note

  • NCI: Irinotecan hydrochloride [ irinotecan; irinotecan HCl] The hydrochloride salt of a semisynthetic derivative of camptothecin, a cytotoxic, quinoline-based alkaloid extracted from the Asian tree Camptotheca acuminata. Irinotecan, a prodrug, is converted to a biologically active metabolite 7-ethyl-10-hydroxy-camptothecin (SN-38) by a carboxylesterase-converting enzyme. One thousand-fold more potent than its parent compound irinotecan, SN-38 inhibits topoisomerase I activity by stabilizing the cleavable complex between topoisomerase I and DNA, resulting in DNA breaks that inhibit DNA replication and trigger apoptotic cell death. Because ongoing DNA synthesis is necessary for irinotecan to exert its cytotoxic effects, it is classified as an S-phase-specific agent. (NCI Thesaurus)

Molecular Formula

  • C33-H38-N4-O6

Molecular Weight

  • 586.6852
 

Classification Codes

  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Enzyme Inhibitors
  • Radiation-Sensitizing Agents
  • Topoisomerase I Inhibitors
  • Topoisomerase Inhibitors

Names and Synonyms

Name of Substance

  • Irinotecan [INN:BAN]

Synonyms

  • (+)-Irinotecan
  • Camptosar
  • HSDB 7607
  • Irinophore C
  • Irinotecan
  • Irinotecan lactone
  • Irinotecan mylan
  • Irinotecanum
  • Irinotecanum [INN-Latin]
  • UNII-7673326042

Systematic Name

  • (1,4'-Bipiperidine)-1'-carboxylic acid, 4,11-diethyl-3,4,12-14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinolin-9-yl ester, (S)-

Registry Numbers

CAS Registry Number

  • 97682-44-5

FDA UNII

  • 7673326042

System Generated Number

  • 0097682445

Structure Descriptors

InChI

1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1

InChIKey

UWKQSNNFCGGAFS-XIFFEERXSA-N

Smiles

CCc1c2cc(ccc2nc-3c1Cn4c3cc5c(c4=O)COC(=O)[C@@]5(CC)O)OC(=O)N6CCC(CC6)N7CCCCC7