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F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
Capecitabine Pronunciation Trade names Xeloda, Xitabin, Kapetral, others AHFS /Drugs.com Monograph MedlinePlus a699003 Pregnancy
Routes of By mouth Drug class Antineoplastic agent ATC code Legal status
AU S4 (Prescription only)
CA ℞-only
UK POM (Prescription only)
US WARNING [1]
EU [2]
Bioavailability Extensive Protein binding < 60% Metabolism liver, to 5'-DFCR, 5'-DFUR (inactive); neoplastic tissue, 5'-DFUR to active fluorouracil Elimination half-life 38–45 minutes Excretion kidney (95.5%), faecal (2.6%)
Pentyl [1-(3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1H
CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.112.980 Formula C 15 H 22 F N 3 O 6 Molar mass −1 3D model (JSmol )
FC=1\C(=N/C(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](O )[C@H]2O)C)\NC(=O)OCCCCC
InChI=1S/C15H22FN3O6/c1-3-4-5-6-24-15(23 )18-12-9(16 )7-19(14(22 )17-12)13-11(21 )10(20 )8(2 )25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10-,11-,13-/m1/s1 Y
Key:GAGWJHPBXLXJQN-UORFTKCHSA-N Y
(verify)
Capecitabine , sold under the brand name Xeloda among others, is a anticancer medication used to treat breast cancer , gastric cancer and colorectal cancer .[3] docetaxel .[4] by mouth .[4]
Common side effects include abdominal pain, vomiting, diarrhea , weakness, and rashes.[4] allergic reactions , heart problems such as cardiomyopathy , and low blood cell counts .[4] pregnancy may result in harm to the fetus.[4] 5-fluorouracil (5-FU) through which it acts.[4] fluoropyrimidines , which also includes 5-FU and tegafur .[5]
Capecitabine was patented in 1992 and approved for medical use in 1998.[6] World Health Organization's List of Essential Medicines .[7]
Medical uses
[ edit ]
Capecitabine is indicated for
adjuvant treatment of people with Stage III colon cancer as a single agent or as a component of a combination chemotherapy regimen;[8]
perioperative treatment of adults with locally advanced rectal cancer as a component of chemoradiotherapy;[8]
treatment of people with unresectable or metastatic colorectal cancer as a single agent or as a component of a combination chemotherapy regimen;[8]
treatment of people with advanced or metastatic breast cancer as a single agent if an anthracycline- or taxane-containing chemotherapy is not indicated;[8]
treatment of people with advanced or metastatic breast cancer in combination with docetaxel after disease progression on prior anthracycline-containing chemotherapy;[8]
treatment of adults with unresectable or metastatic gastric, esophageal, or gastroesophageal junction cancer as a component of a combination chemotherapy regimen;[8]
treatment of adults with HER2-overexpressing metastatic gastric or gastroesophageal junction adenocarcinoma who have not received prior treatment for metastatic disease as a component of a combination regimen;[8]
adjuvant treatment of adults with pancreatic adenocarcinoma as a component of a combination chemotherapy regimen.[8]
Adverse effects
[ edit ]
Adverse effects by frequency:[9] [10] [11] [12]
Very common (>10% frequency)
Diarrhea
Vomiting
Nausea
Stomatitis
Abdominal pain
Fatigue
Weakness
Hand-foot syndrome [13]
Oedema
Fever
Pain
Headache
Hair loss
Dermatitis
Indigestion
Shortness of breath
Eye irritation
Myelosuppression[Note 1]
Notes on adverse effects:
Contraindications
[ edit ]
Contraindications include:[11]
Drug interactions
[ edit ]
Drugs it is known to interact with include:[11]
Sorivudine or its analogues, such as, brivudine .
CYP2C9 substrates, including, warfarin and other coumarin-derivatives anticoagulants
Phenytoin , as it increases the plasma concentrations of phenytoin.
Calcium folinate may enhance the therapeutic effects of capecitabine by means of synergising with its metabolite, 5-FU. It may also induce more severe diarrhoea by means of this synergy.[14]
Pharmacogenetics
[ edit ]
The dihydropyrimidine dehydrogenase (DPD) enzyme is responsible for the detoxifying metabolism of fluoropyrimidines, a class of drugs that includes capecitabine, 5-fluorouracil and tegafur .[5] Genetic variations within the DPD gene (DPYD ) can lead to reduced or absent DPD activity, and individuals who are heterozygous or homozygous for these variations may have partial or complete DPD deficiency ; an estimated 0.2% of individuals have complete DPD deficiency .[5] [15] myelosuppression , neurotoxicity and hand-foot syndrome .[5] [15]
Mechanism of action
[ edit ]
Click on genes, proteins and metabolites below to link to respective articles. [§ 1]
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|alt=Fluorouracil (5-FU) Activity edit ]]
Fluorouracil (5-FU) Activity edit
Capecitabine is metabolised to 5-FU which in turn is a thymidylate synthase inhibitor, hence inhibiting the synthesis of thymidine monophosphate (ThMP), the active form of thymidine which is required for the de novo synthesis of DNA.[16]
Drug synthesis
[ edit ]
Society and culture
[ edit ]
Brand names
[ edit ]
One of the brand names is Xeloda, marketed by Genentech .
Others include Xitabin, Capcibin, Kapetral and Pecaset by Eurolab .
References
[ edit ]
^ "Xeloda EPAR" . European Medicines Agency . 2 February 2001. Retrieved 2 July 2024 .
^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 585, 588. ISBN 9780857111562
^ a b c d e f "Capecitabine" . The American Society of Health-System Pharmacists. Archived from the original on 15 April 2016. Retrieved 8 December 2016 .
^ a b c d Caudle KE, Thorn CF, Klein TE, Swen JJ, McLeod HL, Diasio RB, et al. (December 2013). "Clinical Pharmacogenetics Implementation Consortium guidelines for dihydropyrimidine dehydrogenase genotype and fluoropyrimidine dosing" . Clinical Pharmacology and Therapeutics . 94 6 ): 640–645. doi :10.1038/clpt.2013.172 . PMC 3831181 PMID 23988873 .
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery ISBN 9783527607495 Archived from the original on 12 January 2023. Retrieved 30 August 2017 .
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019 . Geneva: World Health Organization. hdl :10665/325771
^ a b c d e f g h "FDA approves updated drug labeling including new indications and dosing regimens for capecitabine tablets under Project Renewal" . U.S. Food and Drug Administration . 15 December 2022. Archived from the original on 27 January 2023. Retrieved 26 January 2023 .public domain .
^ "XELODA (capecitabine) tablet, film coated [Genentech, Inc.]" . DailyMed . Genentech, Inc. December 2013. Archived from the original on 1 February 2014. Retrieved 25 January 2014 .
^ "Capecitabine Teva : EPAR – Product Information" (PDF) . European Medicines Agency . Teva Pharma B.V. 10 January 2014. Archived (PDF) from the original on 4 February 2014. Retrieved 25 January 2014 .
^ a b c "Capecitabine 150mg – Summary of Product Characteristics (SPC)" . electronic Medicines Compendium . Zentiva. 23 December 2013. Archived from the original on 1 February 2014. Retrieved 25 January 2014 .
^ "NAME OF THE MEDICINE XELODA® Capecitabine" (PDF) . TGA eBusiness Services . Roche Products Pty Limited. 5 December 2013. Archived from the original on 11 September 2017. Retrieved 25 January 2014 .
^ Reddening, swelling, numbness and desquamation on palms and soles
^ Rossi S, ed. (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. ISBN 978-0-9805790-9-3
^ a b Amstutz U, Froehlich TK, Largiadèr CR (September 2011). "Dihydropyrimidine dehydrogenase gene as a major predictor of severe 5-fluorouracil toxicity". Pharmacogenomics . 12 9 ): 1321–1336. doi :10.2217/pgs.11.72 . PMID 21919607 .
^ "Xeloda (capecitabine) dosing, indications, interactions, adverse effects, and more" . Medscape Reference . WebMD. 25 January 2014. Archived from the original on 2 February 2014.
Further reading
[ edit ]
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Capecitabine&oldid=1232142630 " C a t e g o r i e s : ● C a r b a m a t e s ● F l u o r o p y r i m i d i n e s ● D r u g s d e v e l o p e d b y G e n e n t e c h ● D r u g s d e v e l o p e d b y H o f f m a n n - L a R o c h e ● O r g a n o f l u o r i d e s ● P r o d r u g s ● P y r i m i d i n e a n t a g o n i s t s ● P y r i m i d o n e s ● S p e c i a l t y d r u g s ● W o r l d H e a l t h O r g a n i z a t i o n e s s e n t i a l m e d i c i n e s H i d d e n c a t e g o r i e s : ● S o u r c e a t t r i b u t i o n ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● U s e d m y d a t e s f r o m J a n u a r y 2 0 2 3 ● D r u g s w i t h n o n - s t a n d a r d l e g a l s t a t u s ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● D r u g b o x e s w h i c h c o n t a i n c h a n g e s t o w a t c h e d f i e l d s ● A r t i c l e s n e e d i n g a d d i t i o n a l r e f e r e n c e s f r o m A u g u s t 2 0 2 0 ● A l l a r t i c l e s n e e d i n g a d d i t i o n a l r e f e r e n c e s ● W i k i p e d i a m e d i c i n e a r t i c l e s r e a d y t o t r a n s l a t e
● T h i s p a g e w a s l a s t e d i t e d o n 2 J u l y 2 0 2 4 , a t 0 5 : 1 6 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
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