Irinotecan

Irinotecan

Clinical data
Trade names	Camptosar (US), Campto (EU), Onivyde (liposomal)
AHFS/Drugs.com	Monograph
MedlinePlus	a608043
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	Intravenous
ATC code	L01XX19 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	NA
Metabolism	Liver glucuronidation
Biological half-life	6 to 12 hours
Excretion	Biliary and kidney
Identifiers
IUPAC name (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	97682-44-5 N
PubChem CID	60838
IUPHAR/BPS	6823
DrugBank	DB00762 Y
ChemSpider	54825 Y
UNII	7673326042
KEGG	D08086 Y
ChEBI	CHEBI:80630 N
ChEMBL	CHEMBL481 Y
ECHA InfoCard	100.127.784
Chemical and physical data
Formula	C33H38N4O6
Molar mass	586.678 g/mol (irinotecan) 623.139 g/mol (irinotecan hydrochloride) 677.185 g/mol (irinotecan hydrochloride trihydrate)
3D model (Jmol)	Interactive image
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 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?)

Irinotecan, sold under the brand name Camptosar among others, is a 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 by slow injection into a vein.

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 in topoisomerase inhibitor family of medication. It works by blocking topoisomerase 1 which results 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, the most effective and safe medicines needed in a health system. In the United Kingdom it is available as a generic medication and costs the NHS about 114.00 pounds per 100 mg. It is made from the natural compound camptothecin.