Irinotecan hydrochloride (CHEM018663)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:25:37 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018663
Identification
Common NameIrinotecan hydrochloride
ClassSmall Molecule
DescriptionA hydrochloride obtained by combining irinotecan with one molar equivalent of hydrochloric acid. Used (in the form of its 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
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7-Ethyl-10-(4-(1-piperidino)-1-piperidino)carbonyloxy camptothecin hydrochlorideChEBI
Camptothecin 11 hydrochlorideChEBI
CPT 11ChEBI
CPT-11ChEBI
Irinotecan HCLChEBI
Irinotecan hydrochlorideChEBI
Irinotecan monohydrochlorideChEBI
U 101440EChEBI
7-Ethyl-10-hydroxycamptothecinMeSH
NK012 CompoundMeSH
CPT11MeSH
CamptosarMeSH
Camptothecin-11MeSH
IrinotecanMeSH
sn-38MeSH
IrrinotecanMeSH
7 Ethyl 10 hydroxycamptothecinMeSH
Camptothecin 11MeSH
sn 38MeSH
sn38 CPDMeSH
Chemical FormulaC33H39ClN4O6
Average Molecular Mass623.139 g/mol
Monoisotopic Mass622.256 g/mol
CAS Registry Number100286-90-6
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(11),3,5,7,9,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate hydrochloride
Traditional Nameirinotecan hydrochloride
SMILESCl.CCC1=C2C=C(OC(=O)N3CCC(CC3)N3CCCCC3)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O
InChI IdentifierInChI=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
InChI KeyGURKHSYORGJETM-WAQYZQTGSA-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
  • Heteroaromatic compound
  • Tertiary alcohol
  • Carbamic acid ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactam
  • Lactone
  • Carbonic acid derivative
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organopnictogen compound
  • Hydrochloride
  • Organic oxide
  • Organic oxygen compound
  • 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
Polarizability66.02 ųChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000009000-a291f0f267a7041ca065Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000009000-a291f0f267a7041ca065Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0000009000-a291f0f267a7041ca065Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000009000-4bb7cf00e10c9cfab6c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000009000-4bb7cf00e10c9cfab6c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0000009000-4bb7cf00e10c9cfab6c1Spectrum
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
DrugBank IDDBSALT000103
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIrinotecan
Chemspider IDNot Available
ChEBI ID5971
PubChem Compound ID74990
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24474168
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25142792
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25233635
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25512111
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25750295
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26309154
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26352218
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26422291
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26526067
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26540095
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=26604633