Irinotecan hydrochlorideProduct ingredient for Irinotecan
- Name
- Irinotecan hydrochloride
- Drug Entry
- Irinotecan
Irinotecan is a topoisomerase inhibitor used for chemotherapy. It is a water-soluble analogue of camptothecin, which is extracted from the Chinese tree Camptotheca acuminate.5 The bis-piperidine side chain in the structure of irinotecan bestows enhanced water solubility.6 As an anticancer drug, irinotecan was first commercially available in Japan in 1994 to treat various cancers such as lung, cervical and ovarian cancer.5 Approved by the FDA in 1996,3 irinotecan is used to treat colorectal cancer and pancreatic adenocarcinoma.7,8,10 Irinotecan liposome was approved by the FDA in February 2024.8
The active metabolite SN-38 is also a potent inhibitor of DNA topoisomerase I. Both irinotecan and SN-38 mediate antitumor activity by forming a complex with topoisomerase I and blocking its enzymatic activity, thereby interfering with DNA synthesis. This leads to the arrest of the cell cycle in the S-G2 phase and cancer cell death.5
- Accession Number
- DBSALT000103
- Structure
Structure for Irinotecan hydrochloride (DBSALT000103)
- 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
- External Links
- KEGG Compound
- C11294
- PubChem Compound
- 74990
- ChemSpider
- 67545
- ChEBI
- 5971
- ChEMBL
- CHEMBL541887
- Wikipedia
- Irinotecan
- Predicted Properties
Property Value Source Water Solubility 0.107 mg/mL ALOGPS logP 3.94 ALOGPS logP 2.78 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 11.71 Chemaxon pKa (Strongest Basic) 9.47 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 112.51 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 161.33 m3·mol-1 Chemaxon Polarizability 66.02 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon