Structure via PubChem · Public domain (PubChem)
irinotecan
Sign in to saveAlso known as (+)-irinotecan, biotecan, Irinotecan lactone, HSDB 7607, Irinotecan mylan, Irinophore C, Biotecan
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.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 477494806
- Drug.image
- irinotecan.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 240
- Drug.image2
- Irinotecan ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Camptosar, Campto, Onivyde, others
- Drug.MedlinePlus
- a608043
- Drug.DailyMedID
- Irinotecan
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- Intravenous
- Drug.ATC_prefix
- L01
- Drug.ATC_suffix
- CE02
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
via Wikipedia infobox
Chemical data
- Formula
- C33H38N4O6
- Molecular weight
- 586.7 g/mol
- IUPAC name
- [(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-piperidin-1-ylpiperidine-1-carboxylate
- SMILES
- CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)N7CCCCC7
- InChIKey
- UWKQSNNFCGGAFS-XIFFEERXSA-N
- XLogP
- 3
- Polar surface area
- 113 Ų
- H-bond donors
- 1
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Research
14,702 papers- Liposomal irinotecan (Onivyde): Exemplifying the benefits of nanotherapeutic drugs.Cancer science · 2022
- Irinotecan-Still an Important Player in Cancer Chemotherapy: A Comprehensive Overview.International journal of molecular sciences · 2020
- Individualization of Irinotecan Treatment: A Review of Pharmacokinetics, Pharmacodynamics, and Pharmacogenetics.Clinical pharmacokinetics · 2018
- Irinotecan dose schedule for the treatment of Ewing sarcoma.Pediatric blood & cancer · 2023
- Irinotecan pharmacogenomics.Pharmacogenomics · 2010
via PubMed
Wikidata facts
- Mass
- 586.279
Show 5 more facts
- chemical formula
- C₃₃H₃₈N₄O₆
- Commons category
- Irinotecan
- canonical SMILES
- CCC1=C2C=C(C=CC2=NC3=C1CN4C3=CC5=C(C4=O)COC(=O)C5(CC)O)OC(=O)N6CCC(CC6)N7CCCCC7
- isomeric SMILES
- CCC1=C2C=C(C=CC2=NC3=C1CN4C3=CC5=C(C4=O)COC(=O)[C@@]5(CC)O)OC(=O)N6CCC(CC6)N7CCCCC7
- World Health Organisation international non-proprietary name
- irinotecan
via Wikidata · CC0
~11 min read
Article
25 sectionsContents
- Medical uses
- Side effects
- Diarrhea
- Immunosuppression
- Mechanism of action
- Interactive pathway
- Pharmacokinetics
- Administration
- Distribution
- Metabolism
- Activation by carboxylesterases and butyrylcholinesteras
- Inactivation by uridine diphosphate glucuronosyltransferases
- De-conjugation by β-glucuronidases
- Metabolism by cytochrome P450 enzymes
- Transport to bile
- Elimination
- Pharmacogenomics
- *28 variant patients
- History
- Society and culture
- Legal status
- Names
- References
- Further reading
- External links
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.
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.