Irinotecan sucrosofateProduct ingredient for Irinotecan
- Name
- Irinotecan sucrosofate
- 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
- DBSALT002617
- Structure
- Synonyms
- Not Available
- External IDs
- MM 398 / MM-398 / PEP 02 / PEP-02
- UNII
- OL741S3N8B
- CAS Number
- 1361317-83-0
- Weight
- Average: 3329.51
Monoisotopic: 3326.887271639 - Chemical Formula
- C144H174N16O59S8
- InChI Key
- BCPSLKYBXGKPIW-RTXWKGGWSA-N
- InChI
- InChI=1S/4C33H38N4O6.C12H22O35S8/c4*1-3-22-23-16-21(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;13-48(14,15)37-1-4-6(43-51(22,23)24)8(45-53(28,29)30)9(46-54(31,32)33)11(40-4)42-12(3-39-50(19,20)21)10(47-55(34,35)36)7(44-52(25,26)27)5(41-12)2-38-49(16,17)18/h4*8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3;4-11H,1-3H2,(H,13,14,15)(H,16,17,18)(H,19,20,21)(H,22,23,24)(H,25,26,27)(H,28,29,30)(H,31,32,33)(H,34,35,36)/t4*33-;4-,5-,6-,7-,8+,9-,10+,11-,12+/m00001/s1
- IUPAC Name
- tetrakis((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),2,4(9),5,7,10,15(20)-heptaen-7-yl [1,4'-bipiperidine]-1'-carboxylate); [(2S,3S,4R,5R)-4-(sulfooxy)-2,5-bis[(sulfooxy)methyl]-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris(sulfooxy)-6-[(sulfooxy)methyl]oxan-2-yl]oxy}oxolan-3-yl]oxidanesulfonic acid
- SMILES
- CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2.CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2.CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2.CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2.OS(=O)(=O)OC[C@H]1O[C@@](COS(O)(=O)=O)(O[C@H]2O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]2OS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@@H]1OS(O)(=O)=O
- External Links
- ChemSpider
- 34992843
- Predicted Properties
Property Value Source Water Solubility 1.45 mg/mL ALOGPS logP -1.8 ALOGPS logP -4.1 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) -3.4 Chemaxon Physiological Charge -8 Chemaxon Hydrogen Acceptor Count 27 Chemaxon Hydrogen Donor Count 8 Chemaxon Polar Surface Area 536.49 Å2 Chemaxon Rotatable Bond Count 41 Chemaxon Refractivity 148.71 m3·mol-1 Chemaxon Polarizability 73.55 Å3 Chemaxon Number of Rings 30 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon