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Substance Name: Irinotecan hydrochloride [USAN:JAN]
RN: 100286-90-6
UNII: 06X131E4OE
InChIKey: GURKHSYORGJETM-WAQYZQTGSA-N

Note

  • NK012 is a polymeric micellar preparation of SN-38.

    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.Cl-H

Molecular Weight

  • 623.1461
 

Classification Codes

  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Radiation-Sensitizing Agents
  • Reproductive Effect
  • Topoisomerase I Inhibitors
  • Topoisomerase Inhibitors

Names and Synonyms

Name of Substance

  • Irinotecan
  • Irinotecan hydrochloride [USAN:JAN]

Synonyms

  • 7-Ethyl-10-(4-(1-piperidino)-1-piperidino)carbonyloxy camptothecin hydrochloride
  • Campto
  • Camptosar
  • Camptothecin 11 hydrochloride
  • CPT 11
  • CPT-11
  • Irinotecan HCl
  • Irinotecan hydrochloride
  • Topotecin
  • U 101440E
  • UNII-06X131E4OE

Systematic Names

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

Registry Numbers

CAS Registry Number

  • 100286-90-6

FDA UNII

  • 06X131E4OE

Other Registry Number

  • 111348-33-5

System Generated Number

  • 0100286906

Molecular Formulas

Molecular Formula

  • C33-H38-N4-O6.Cl-H

Molecular Formula Fragments

  • C33-H38-N4-O6
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C33H38N4O6.ClH/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;1H/t33-;/m0./s1

InChIKey

GURKHSYORGJETM-WAQYZQTGSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 40mg/kg (40mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7185, 1990.
mouse LD50 intraperitoneal 177mg/kg (177mg/kg)   Cancer Research. Vol. 47, Pg. 5944, 1987.
mouse LD50 intravenous 132mg/kg (132mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7185, 1990.
mouse LD50 oral 765mg/kg (765mg/kg)   Cancer Research. Vol. 47, Pg. 5944, 1987.
rat LD50 intravenous 83600ug/kg (83.6mg/kg)   Cancer Research. Vol. 47, Pg. 5944, 1987.
rat LD50 oral 867mg/kg (867mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7185, 1990.