Structure via PubChem · Public domain (PubChem)
capecitabine
Sign in to saveAlso known as Ro-09-1978-000, Ro-091978000, Xeloda®, (1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl ester, pentyl 1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate, Pentyl [1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate, Capecitabin, Capecitabina
Capecitabine, sold under the brand name Xeloda among others, is an anticancer medication used to treat breast cancer, gastric cancer and colorectal cancer. For breast cancer it is often used together with docetaxel. It is taken by mouth.
Chemical data
- Formula
- C15H22FN3O6
- Molecular weight
- 359.35 g/mol
- IUPAC name
- pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate
- SMILES
- CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@H]2[C@@H]([C@@H]([C@H](O2)C)O)O
- InChIKey
- GAGWJHPBXLXJQN-UORFTKCHSA-N
- XLogP
- 0.6
- Polar surface area
- 121 Ų
- H-bond donors
- 3
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 359.149264
- Has use
- medication
Show 11 more facts
- chemical formula
- C₁₅H₂₂FN₃O₆
- route of administration
- oral administration
- Commons category
- Capecitabine
- canonical SMILES
- CCCCCOC(=O)NC1=NC(=O)N(C=C1F)C2C(C(C(O2)C)O)O
- isomeric SMILES
- CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@H]2[C@@H]([C@@H]([C@H](O2)C)O)O
- World Health Organisation international non-proprietary name
- capecitabine
- subject has role
- essential medicine
- facet of
- breast cancer
- physically interacts with
- Thymidylate synthetase
- legal status (medicine)
- boxed warning
- significant drug interaction
- acenocoumarol
Sources (6)
via Wikidata · CC0
~6 min read
Encyclopedic overview
12 sectionsContents
- Medical uses
- Adverse effects
- Contraindications
- Drug interactions
- Pharmacogenetics
- Mechanism of action
- Drug synthesis
- Overdose
- Society and culture
- Brand names
- References
- Further reading
Capecitabine, sold under the brand name Xeloda among others, is an anticancer medication used to treat breast cancer, gastric cancer and colorectal cancer. For breast cancer it is often used together with docetaxel. It is taken by mouth.
Common side effects include abdominal pain, vomiting, diarrhea, weakness, and rashes. Other severe side effects include blood clotting problems, allergic reactions, heart problems such as cardiomyopathy, and low blood cell counts. Use during pregnancy may result in harm to the fetus. Capecitabine, inside the body, is converted to 5-fluorouracil (5-FU) through which it acts. It belongs to the class of medications known as fluoropyrimidines, which also includes 5-FU and tegafur.
Excerpted from Wikipedia’s “capecitabine” article, available under the CC BY-SA 4.0 licence.