Irinotecan

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
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 Edit this at Wikidata
Chemical and physical data
FormulaC33H38N4O6
Molar mass586.689 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:UWKQSNNFCGGAFS-XIFFEERXSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Irinotecan, sold under the brand name Camptosar among others, is an anti-cancer medication used to treat colon cancer and small cell lung cancer.[8] For colon cancer it is used either alone or with fluorouracil.[8] For small cell lung cancer it is used with cisplatin.[8] It is given intravenously.[8]

Common side effects include diarrhea, vomiting, bone marrow suppression, hair loss, shortness of breath, and fever.[8] Other severe side effects include blood clots, colon inflammation, and allergic reactions.[8] Those with two copies of the UGT1A1*28 gene variant are at higher risk for side effects.[8] Use during pregnancy can result in harm to the baby.[8] Irinotecan is a topoisomerase inhibitor[9]—it blocks the topoisomerase I enzyme, resulting in DNA damage and cell death.[8]

Irinotecan was approved for medical use in the United States in 1996.[8] It is on the World Health Organization's List of Essential Medicines.[10] It is made from the natural compound camptothecin which is found in the Chinese ornamental tree Camptotheca acuminata.[8][11]

  1. ^ "Prescription medicines: registration of new chemical entities in Australia, 2016". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
  2. ^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.
  3. ^ "Cancer therapies". Health Canada. 8 May 2018. Retrieved 13 April 2024.
  4. ^ "Onivyde pegylated liposomal 4.3 mg/ml concentrate for solution for infusion – Summary of Product Characteristics (SmPC)". (emc). 18 February 2020. Retrieved 25 May 2020.
  5. ^ Cite error: The named reference Camptosar FDA label was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Onivyde FDA label was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference Onivyde EPAR was invoked but never defined (see the help page).
  8. ^ a b c d e f g h i j k "Irinotecan Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 22 December 2016. Retrieved 8 December 2016.
  9. ^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 624. ISBN 9780857111562.
  10. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  11. ^ Heinrich M, Barnes J, Gibbons S, Williamson EM (2012). Fundamentals of pharmacognosy and phytotherapy (2nd ed.). Edinburgh: Elsevier. p. 130. ISBN 978-0-7020-5231-6. OCLC 802051297.