irrinotecan (CHEM045629)

Record Information
Version1.0
Creation Date2016-06-03 13:31:30 UTC
Update Date2026-08-22 11:10:01 UTC
Accession NumberCHEM045629
Identification
Common Nameirrinotecan
ClassSmall Molecule
Description
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 (4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2- hydrochloride]quinoline-3,14-dione. Used (in the form of its hydrochloride salt trihydrate) 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-IrinotecanChEBI
HSDB 7607ChEBI
Irinophore CChEBI
Irinotecan lactoneChEBI
Irinotecan mylanChEBI
IrinotecanumChEBI
BiotecanKegg
Irinotecan hydrochloride trihydrateHMDB
CPT-11HMDB
sn38 CPDHMDB
7-Ethyl-10-hydroxycamptothecinHMDB
CamptosarHMDB
IrrinotecanHMDB
Camptothecin-11HMDB
Irinotecan hydrochlorideHMDB
NK012 CompoundHMDB
sn-38HMDB
CPT 11HMDB
sn 38HMDB
7 Ethyl 10 hydroxycamptothecinHMDB
CPT11HMDB
Camptothecin 11HMDB
Chemical FormulaC33H38N4O6
Average Molecular Mass586.678 g/mol
Monoisotopic Mass586.279 g/mol
CAS Registry Number97682-44-5
IUPAC Name(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate
Traditional Nameirinotecan
SMILESCCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2
InChI IdentifierInChI=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
InChI KeyUWKQSNNFCGGAFS-XIFFEERXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCamptothecins
Sub ClassNot Available
Direct ParentCamptothecins
Alternative Parents
Substituents
  • Camptothecin
  • Pyranopyridine
  • Quinoline
  • Piperidinecarboxylic acid
  • 4-aminopiperidine
  • Pyridinone
  • Piperidine
  • Pyridine
  • Benzenoid
  • Carbamic acid ester
  • Tertiary alcohol
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Lactam
  • Lactone
  • Carbonic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity161.33 m³·mol⁻¹ChemAxon
Polarizability65.27 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00762
HMDB IDHMDB0014900
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00052324
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDCP0
Wikipedia LinkIrinotecan
Chemspider ID54825
ChEBI ID80630
PubChem Compound ID60838
Kegg Compound IDC16641
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=26081596
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=26352218
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26381420
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26487578
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26503200
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26526067
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26541586
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26574999
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26580826
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26739304
11. Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59.
12. Innocenti F, Undevia SD, Iyer L, Chen PX, Das S, Kocherginsky M, Karrison T, Janisch L, Ramirez J, Rudin CM, Vokes EE, Ratain MJ: Genetic variants in the UDP-glucuronosyltransferase 1A1 gene predict the risk of severe neutropenia of irinotecan. J Clin Oncol. 2004 Apr 15;22(8):1382-8. Epub 2004 Mar 8.
13. O'Dwyer PJ, Catalano RB: Uridine diphosphate glucuronosyltransferase (UGT) 1A1 and irinotecan: practical pharmacogenomics arrives in cancer therapy. J Clin Oncol. 2006 Oct 1;24(28):4534-8.
14. Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345.
15. FDA label