ChemSpider 2D Image | Irinotecan | C33H38N4O6

Irinotecan

  • Molecular FormulaC33H38N4O6
  • Average mass586.678 Da
  • Monoisotopic mass586.279114 Da
  • ChemSpider ID54825
  • defined stereocentres - 1 of 1 defined stereocentres


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Featured data source



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(+)-Irinotecan
(4S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]chinolin-9-yl-1,4'-bipiperidin-1'-carboxylat [German] [ACD/IUPAC Name]
(4S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl 1,4'-bipiperidine-1'-carboxylate [ACD/IUPAC Name]
[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 [ACD/Index Name]
1,4'-Bipipéridine-1'-carboxylate de (4S)-4,11-diéthyl-4-hydroxy-3,14-dioxo-3,4,12,14-tétrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoléin-9-yle [French] [ACD/IUPAC Name]
6694
7673326042
97682-44-5 [RN]
Campto [Trade name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS108177 [DBID]
AIDS-108177 [DBID]
CPT-11 [DBID]
NCI60_005051 [DBID]
PubChem Substance ID 24891849 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      L01XX19 Wikidata Q412197
      Safety glasses. Oxford University Chemical Safety Data (No longer updated) More details
    • Chemical Class:

      A member of the class of pyranoindolizinoquinolines that is the carbamate ester obtained by formal condensation of the carboxy group of [1,4'-bipiperidine]-1'-carboxylic acid with the phenolic hydroxy group of (4<stereo>S</stereo>)-4,11-diethyl-4,9-dihydroxy-1<element>H</element>-pyrano[3',4':6,7]indolizino[1,2- hydrochloride]quinoline-3,14-dione. Used (in the form of its hydrochloride salt trihyd rate) in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabine-based therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active. ChEBI CHEBI:80630
    • Bio Activity:

      Antineoplastic agent; Zerenex Molecular [ZBioX-0049]
      Cell Cycle/DNA Damage MedChem Express HY-16562
      Cell Cycle/DNA Damage; MedChem Express HY-16562
      Irinotecan(CPT-11) prevents DNA from unwinding by inhibition of topoisomerase 1.; IC50 Value: 15.8 ?M(LoVo cells); 5.17 ?M(HT-29 cells); Target: Topoisomerase I; in vitro: Irinotecan is activated to SN-38 by carboxylesterases to become able to interact with its target, topoisomerase I. MedChem Express HY-16562
      Topoisomerase MedChem Express HY-16562

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.4±0.1 g/cm3
Boiling Point: 873.4±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization: 133.0±3.0 kJ/mol
Flash Point: 482.0±34.3 °C
Index of Refraction: 1.689
Molar Refractivity: 159.1±0.4 cm3
#H bond acceptors: 10
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 2
ACD/LogP: 4.35
ACD/LogD (pH 5.5): 0.68
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.18
ACD/LogD (pH 7.4): 2.14
ACD/BCF (pH 7.4): 10.17
ACD/KOC (pH 7.4): 63.00
Polar Surface Area: 113 Å2
Polarizability: 63.1±0.5 10-24cm3
Surface Tension: 74.2±5.0 dyne/cm
Molar Volume: 416.8±5.0 cm3

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