capecitabine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
nucleosides antiviral or antineoplastic agents, cytarabine or azacitidine derivatives	480	154361-50-9

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: capecitabine capecitibine capecytabine capiibine captabin xeloda	A deoxycytidine derivative and fluorouracil PRODRUG that is used as an ANTINEOPLASTIC ANTIMETABOLITE in the treatment of COLON CANCER; BREAST CANCER and GASTRIC CANCER. Molecular weight: 359.35 Formula: C15H22FN3O6 CLOGP: 0.84 LIPINSKI: 0 HAC: 9 HDO: 3 TPSA: 120.69 ALOGS: -3.16 ROTB: 7 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

capecitabine
capecitibine
capecytabine
capiibine
captabin
xeloda

A deoxycytidine derivative and fluorouracil PRODRUG that is used as an ANTINEOPLASTIC ANTIMETABOLITE in the treatment of COLON CANCER; BREAST CANCER and GASTRIC CANCER.

Molecular weight: 359.35
Formula: C15H22FN3O6
CLOGP: 0.84
LIPINSKI: 0
HAC: 9
HDO: 3
TPSA: 120.69
ALOGS: -3.16
ROTB: 7

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	3 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	26 mg/mL	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	171.93 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

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Date	Agency	Company
April 16, 2003	PMDA	CHUGAI PHARMACEUTICAL CO., LTD.
April 30, 1998	FDA	HOFFMANN LA ROCHE
Nov. 19, 2012	EMA	medac Gesellschaft für klinische Spezialpräparate mbH

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FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Palmar-plantar erythrodysaesthesia syndrome	8018.66	13.54	2544	110902	20471	63355105
Disease progression	3732.96	13.54	2462	110984	120296	63255280
Diarrhoea	2558.45	13.54	4554	108892	710812	62664764
Malignant neoplasm progression	2393.09	13.54	1606	111840	80515	63295061
Metastases to liver	1636.21	13.54	813	112633	22826	63352750
Metastases to bone	1390.06	13.54	701	112745	20318	63355258
Death	1261.37	13.54	2332	111114	372049	63003527
Mucosal inflammation	1124.62	13.54	815	112631	46113	63329463
Metastases to central nervous system	854.34	13.54	433	113013	12672	63362904
Metastases to lung	815.82	13.54	416	113030	12334	63363242

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Palmar-plantar erythrodysaesthesia syndrome	2434.82	14.46	929	52707	15866	34887429
Diarrhoea	1383.32	14.46	2271	51365	387641	34515654
Disease progression	1220.83	14.46	1134	52502	106943	34796352
Death	589.70	14.46	1629	52007	396420	34506875
Arteriospasm coronary	485.22	14.46	186	53450	3196	34900099
Neuropathy peripheral	398.58	14.46	561	53075	82702	34820593
Mucosal inflammation	388.22	14.46	381	53255	38241	34865054
Vomiting	260.38	14.46	902	52734	246719	34656576
Stomatitis	256.36	14.46	321	53315	42193	34861102
Dehydration	255.22	14.46	594	53042	129375	34773920

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Palmar-plantar erythrodysaesthesia syndrome	7642.36	12.86	2609	124613	30525	79586641
Disease progression	3274.06	12.86	2551	124671	181811	79435355
Diarrhoea	2852.81	12.86	5037	122185	875452	78741714
Malignant neoplasm progression	1258.15	12.86	1305	125917	134685	79482481
Mucosal inflammation	1132.18	12.86	949	126273	74631	79542535
Metastases to liver	1055.66	12.86	622	126600	27692	79589474
Neuropathy peripheral	884.76	12.86	1108	126114	140197	79476969
Metastases to bone	818.27	12.86	501	126721	23926	79593240
Arteriospasm coronary	757.70	12.86	314	126908	6402	79610764
Metastases to lung	703.26	12.86	409	126813	17754	79599412

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01BC06	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ANTIMETABOLITES Pyrimidine analogues
CHEBI has role	CHEBI:35221	antimetabolite
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:50266	Prodrugs
FDA EPC	N0000175595	Nucleoside Metabolic Inhibitor
FDA MoA	N0000000233	Nucleic Acid Synthesis Inhibitors
MeSH PA	D000963	Antimetabolites
MeSH PA	D000964	Antimetabolites, Antineoplastic
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D009676	Noxae

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Metastasis from malignant tumor of colon	indication	314998002
Malignant tumor of stomach	indication	363349007	DOID:10534
Metastatic Breast Carcinoma	indication
Lymph Node Positive Colorectal Carcinoma	indication
Malignant tumor of ovary	off-label use	363443007	DOID:2394
Adenocarcinoma of pancreas	off-label use	700423003	DOID:4074
Pancreatic Neuroendocrine Tumor	off-label use	717919005
Necrotizing enterocolitis in fetus OR newborn	contraindication	2707005
Hyperbilirubinemia	contraindication	14783006	DOID:2741
Infectious disease	contraindication	40733004

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	12.3	acidic
pKa2	12.91	acidic
pKa3	13.46	acidic
pKa4	0.75	Basic

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Orange Book patent data (new drug applications)

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Orange Book exclusivity data (new drug applications)

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Thymidylate synthase	Enzyme	P04818	TYSY_HUMAN	INHIBITOR				WOMBAT-PK	CHEMBL

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External reference:

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ID	Source
007533	NDDF
108761006	SNOMEDCT_US
11693	MMSL
194000	RXNORM
210675	MMSL
386906001	SNOMEDCT_US
4021099	VUID
4021099	VANDF
4344	MMSL
60953	PUBCHEM_CID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Capecitabine	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0271	TABLET, FILM COATED	150 mg	ORAL	ANDA	31 sections
Capecitabine	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0271	TABLET, FILM COATED	150 mg	ORAL	ANDA	31 sections
Capecitabine	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0271	TABLET, FILM COATED	150 mg	ORAL	ANDA	31 sections
Capecitabine	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0271	TABLET, FILM COATED	150 mg	ORAL	ANDA	31 sections
Capecitabine	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0272	TABLET, FILM COATED	500 mg	ORAL	ANDA	31 sections
Capecitabine	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0272	TABLET, FILM COATED	500 mg	ORAL	ANDA	31 sections
Capecitabine	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0272	TABLET, FILM COATED	500 mg	ORAL	ANDA	31 sections
Capecitabine	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0272	TABLET, FILM COATED	500 mg	ORAL	ANDA	31 sections
Capecitabine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-7473	TABLET, FILM COATED	150 mg	ORAL	ANDA	29 sections
Capecitabine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-7473	TABLET, FILM COATED	150 mg	ORAL	ANDA	29 sections

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