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
ChemSpider
34992843
Predicted Properties
PropertyValueSource
Water Solubility1.45 mg/mLALOGPS
logP-1.8ALOGPS
logP-4.1Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)-3.4Chemaxon
Physiological Charge-8Chemaxon
Hydrogen Acceptor Count27Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area536.49 Å2Chemaxon
Rotatable Bond Count41Chemaxon
Refractivity148.71 m3·mol-1Chemaxon
Polarizability73.55 Å3Chemaxon
Number of Rings30Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon