Irinotecan

Irinotecan, sold under the brand name Camptosar among others, is an anti-cancer medication used to treat colon cancer and small cell lung cancer. For colon cancer it is used either alone or with fluorouracil. For small cell lung cancer it is used with cisplatin. It is given intravenously.

Irinotecan
Clinical data
Trade namesCamptosar, Campto, Onivyde, others
AHFS/Drugs.comMonograph
MedlinePlusa608043
License data
Pregnancy
category
  • AU: D
Routes of
administration
Intravenous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityNA
MetabolismLiver glucuronidation
Elimination half-life6 to 12 hours
ExcretionBile duct and kidney
Identifiers
  • (S)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-
    3,14-dioxo1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinolin-
    9-yl-[1,4'bipiperidine]-1'-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.219.260
Chemical and physical data
FormulaC33H38N4O6
Molar mass586.689 g·mol−1
3D model (JSmol)
SMILES
  • O=C7OCC=6C(=O)N2C(\c1nc5c(c(c1C2)CC)cc(OC(=O)N4CCC(N3CCCCC3)CC4)cc5)=C/C=6[C@@]7(O)CC
  • InChI=1S/C33H38N4O6/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/t33-/m0/s1 Y
  • Key:UWKQSNNFCGGAFS-XIFFEERXSA-N Y
 NY (what is this?)  (verify)

Common side effects include diarrhea, vomiting, bone marrow suppression, hair loss, shortness of breath, and fever. Other severe side effects include blood clots, colon inflammation, and allergic reactions. Those with two copies of the UGT1A1*28 gene variant are at higher risk for side effects. Use during pregnancy can result in harm to the baby. Irinotecan is a topoisomerase inhibitor—it blocks the topoisomerase I enzyme, resulting in DNA damage and cell death.

Irinotecan was approved for medical use in the United States in 1996. It is on the World Health Organization's List of Essential Medicines. It is made from the natural compound camptothecin which is found in the Chinese ornamental tree Camptotheca acuminata.

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