Irinotecan hydrochlorideProduct ingredient for Irinotecan

Name
Irinotecan hydrochloride
Drug Entry
Irinotecan

Irinotecan is an antineoplastic enzyme inhibitor primarily used in the treatment of colorectal cancer. It is a derivative of camptothecin that inhibits the action of topoisomerase I. Irinotecan prevents religation of the DNA strand by binding to topoisomerase I-DNA complex, and causes double-strand DNA breakage and cell death. It is a derivative of camptothecin. Irinotecan was approved for the treatment of advanced pancreatic cancer in October, 2015 (irinotecan liposome injection, trade name Onivyde).

Accession Number
DBSALT000103
Structure
Synonyms
Irinotecan HCl / Irinotecan hydrochloride anhydrous
UNII
06X131E4OE
CAS Number
100286-90-6
Weight
Average: 623.139
Monoisotopic: 622.255812707
Chemical Formula
C33H39ClN4O6
InChI Key
GURKHSYORGJETM-WAQYZQTGSA-N
InChI
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
IUPAC Name
(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-7-yl [1,4'-bipiperidine]-1'-carboxylate hydrochloride
SMILES
Cl.CCC1=C2C=C(OC(=O)N3CCC(CC3)N3CCCCC3)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O
KEGG Compound
C11294
PubChem Compound
74990
ChemSpider
67545
ChEBI
5971
ChEMBL
CHEMBL541887
Wikipedia
Irinotecan
Predicted Properties
PropertyValueSource
Water Solubility0.107 mg/mLALOGPS
logP3.94ALOGPS
logP2.78Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)11.71Chemaxon
pKa (Strongest Basic)9.47Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area112.51 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity161.33 m3·mol-1Chemaxon
Polarizability66.02 Å3Chemaxon
Number of Rings7Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon