| Stereochemistry | ABSOLUTE |
| Molecular Formula | 4C33H38N4O6.C12H22O35S8 |
| Molecular Weight | 3329.514 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 13 / 13 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC1=C2C=C(OC(=O)N3CCC(CC3)N4CCCCC4)C=CC2=NC5=C1CN6C5=CC7=C(COC(=O)[C@]7(O)CC)C6=O.CCC8=C9C=C(OC(=O)N%10CCC(CC%10)N%11CCCCC%11)C=CC9=NC%12=C8CN%13C%12=CC%14=C(COC(=O)[C@]%14(O)CC)C%13=O.CCC%15=C%16C=C(OC(=O)N%17CCC(CC%17)N%18CCCCC%18)C=CC%16=NC%19=C%15CN%20C%19=CC%21=C(COC(=O)[C@]%21(O)CC)C%20=O.CCC%22=C%23C=C(OC(=O)N%24CCC(CC%24)N%25CCCCC%25)C=CC%23=NC%26=C%22CN%27C%26=CC%28=C(COC(=O)[C@]%28(O)CC)C%27=O.OS(=O)(=O)OC[C@H]%29O[C@@](COS(O)(=O)=O)(O[C@H]%30O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]%30OS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@@H]%29OS(O)(=O)=O
InChI
InChIKey=BCPSLKYBXGKPIW-RTXWKGGWSA-N
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
| Molecular Formula | C33H38N4O6 |
| Molecular Weight | 586.678 |
| Charge | 0 |
| Count |
MOL RATIO
4 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C12H22O35S8 |
| Molecular Weight | 982.802 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Irinotecan is an antineoplastic enzyme inhibitor primarily used in the treatment of colorectal cancer. Irinotecan is sold under the brand name Camptosar among others. CAMPTOSAR is a topoisomerase inhibitor indicated for:
• First-line therapy in combination with 5-fluorouracil and leucovorin for
patients with metastatic carcinoma of the colon or rectum.
• Patients with metastatic carcinoma of the colon or rectum whose disease
has recurred or progressed following initial fluorouracil-based therapy.
Irinotecan is a derivative of camptothecin. Camptothecins interact specifically with the enzyme
topoisomerase I, which relieves torsional strain in DNA by inducing reversible single-strand
breaks. Irinotecan and its active metabolite SN-38 bind to the topoisomerase I-DNA complex
and prevent religation of these single-strand breaks. Current research suggests that the
cytotoxicity of irinotecan is due to double-strand DNA damage produced during DNA synthesis
when replication enzymes interact with the ternary complex formed by topoisomerase I, DNA,
and either irinotecan or SN-38. Mammalian cells cannot efficiently repair these double-strand
breaks.
CNS Activity
Originator
Approval Year
Doses
AEs
Sourcing
Sample Use Guides
Usual Adult Dose for Colorectal Cancer
Either as a single agent or in combination with fluorouracil and leucovorin:
125 mg/m2 intravenously over 90 minutes once a week for four doses
or
as a single agent:
350 mg/m2 intravenously over 90 minutes every three weeks
or
in combination with fluorouracil and leucovorin:
180 mg/m2 intravenously over 90 minutes every other week for three doses.
Route of Administration:
Intravenous
The sensitivity to CPT-11 (Irinotecan) alone, of 5 human colon-cancer cell lines, expressed as IC50 values, varied between 2.5 and 6.1uM. The anti-proliferative effectsof the active metabolite SN-38 showed IC50 values between 5.6 and 38 nM, 130 to 570 times lower than those measured for CPT-11 alone. The sensitivity to SN-38 was highest in LS174T and COLO320 cells, intermediate in SW1398 cells and lowest in COLO 205 and WiDr cells.
