capecitabine indications/contra

Stem definitionDrug idCAS RN
nucleosides antiviral or antineoplastic agents, cytarabine or azacitidine derivatives 480 154361-50-9

Description:

MoleculeDescription

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

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
April 30, 1998 FDA HOFFMANN LA ROCHE

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Diarrhoea 10147.70 40.54 3733 18348 100615 3263163
Palmar-plantar erythrodysaesthesia syndrome 9739.79 40.54 2023 20058 4509 3359269
Disease progression 6497.54 40.54 2015 20066 30244 3333534
Death 4467.55 40.54 2370 19711 149954 3213824
Vomiting 4129.42 40.54 1902 20179 87629 3276149
Nausea 3447.08 40.54 1897 20184 127748 3236030
Mucosal inflammation 3001.24 40.54 815 21266 7168 3356610
Neutropenia 2636.21 40.54 1044 21037 32342 3331436
Dehydration 2378.16 40.54 972 21109 32677 3331101
Malignant neoplasm progression 2210.33 40.54 777 21304 17016 3346762
Decreased appetite 1936.74 40.54 895 21186 40595 3323183
Fatigue 1907.07 40.54 1217 20864 106023 3257755
Stomatitis 1783.40 40.54 598 21483 11254 3352524
Thrombocytopenia 1635.42 40.54 758 21323 34510 3329268
Neuropathy peripheral 1460.46 40.54 565 21516 16242 3347536
Febrile neutropenia 1294.76 40.54 536 21545 18439 3345339
Asthenia 1261.01 40.54 785 21296 64880 3298898
Abdominal pain 1235.71 40.54 685 21396 45540 3318238
Anaemia 1208.45 40.54 714 21367 53619 3310159
Metastases to liver 1173.63 40.54 337 21744 3659 3360119
Pyrexia 1137.74 40.54 797 21284 80318 3283460
Leukopenia 1051.91 40.54 439 21642 15384 3348394
Pulmonary embolism 894.02 40.54 467 21614 27421 3336357
Sepsis 834.09 40.54 469 21612 31904 3331874
Breast cancer metastatic 794.45 40.54 210 21871 1623 3362155
General physical health deterioration 785.52 40.54 388 21693 20201 3343577
Gastrointestinal toxicity 753.49 40.54 181 21900 896 3362882
Constipation 696.22 40.54 410 21671 30402 3333376
Dyspnoea 690.67 40.54 659 21422 102275 3261503
Dysphagia 631.71 40.54 330 21751 19321 3344457

Pharmacologic Action:

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SourceCodeDescription
ATC L01BC06 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Pyrimidine analogues
FDA MoA N0000000233 Nucleic Acid Synthesis Inhibitors
FDA EPC N0000175595 Nucleoside Metabolic Inhibitor
MeSH PA D000963 Antimetabolites
MeSH PA D000964 Antimetabolites, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D009676 Noxae
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:35610 antineoplastic agent

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
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
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005 DOID:8677
Hyperbilirubinemia contraindication 14783006 DOID:2741
Infectious disease contraindication 40733004
Conduction disorder of the heart contraindication 44808001
Acute nephropathy contraindication 58574008
Stomatitis contraindication 61170000 DOID:9637
Dihydrouracil dehydrogenase (NADP^+^) deficiency contraindication 77365006 DOID:14218
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Severe diarrhea contraindication 409587002
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Palmar-Plantar Erythrodysesthesia contraindication
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

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.3 acidic
pKa2 12.91 acidic
pKa3 13.46 acidic
pKa4 0.75 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Thymidylate synthase Enzyme INHIBITOR WOMBAT-PK CHEMBL

External reference:

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IDSource
4021099 VUID
N0000148555 NUI
C0671970 UMLSCUI
6799 IUPHAR_LIGAND_ID
D01223 KEGG_DRUG
6804DJ8Z9U UNII
7317 INN_ID
DB01101 DRUGBANK_ID
d04311 MMSL
4344 MMSL
194000 RXNORM
108761006 SNOMEDCT_US
386906001 SNOMEDCT_US
4021099 VANDF
N0000148555 NDFRT
N0000005958 NDFRT
007533 NDDF
210675 MMSL
60953 PUBCHEM_CID
CHEMBL1773 ChEMBL_ID
DB00544 DRUGBANK_ID
D000069287 MESH_DESCRIPTOR_UI
CHEBI:31348 CHEBI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Xeloda HUMAN PRESCRIPTION DRUG LABEL 1 0004-1100 TABLET, FILM COATED 150 mg ORAL NDA 21 sections
Xeloda HUMAN PRESCRIPTION DRUG LABEL 1 0004-1101 TABLET, FILM COATED 500 mg ORAL NDA 21 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 0054-0271 TABLET, FILM COATED 150 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 0054-0272 TABLET, FILM COATED 500 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 0093-7473 TABLET, FILM COATED 150 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 0093-7474 TABLET, FILM COATED 500 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 0179-0149 TABLET, FILM COATED 500 mg ORAL ANDA 18 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 0179-0195 TABLET, FILM COATED 500 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 0179-0229 TABLET 500 mg ORAL ANDA 19 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 0378-2511 TABLET, FILM COATED 150 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 0378-2512 TABLET, FILM COATED 500 mg ORAL ANDA 20 sections
CAPECITABINE HUMAN PRESCRIPTION DRUG LABEL 1 16714-467 TABLET, FILM COATED 150 mg ORAL ANDA 21 sections
CAPECITABINE HUMAN PRESCRIPTION DRUG LABEL 1 16714-468 TABLET, FILM COATED 500 mg ORAL ANDA 21 sections
CAPECITABINE HUMAN PRESCRIPTION DRUG LABEL 1 16729-072 TABLET, FILM COATED 150 mg ORAL ANDA 21 sections
CAPECITABINE HUMAN PRESCRIPTION DRUG LABEL 1 16729-073 TABLET, FILM COATED 500 mg ORAL ANDA 21 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 42291-167 TABLET 500 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 42291-190 TABLET, FILM COATED 150 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 42291-191 TABLET, FILM COATED 500 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 51079-510 TABLET, FILM COATED 500 mg ORAL ANDA 20 sections
Xeloda HUMAN PRESCRIPTION DRUG LABEL 1 53808-0411 TABLET, FILM COATED 500 mg ORAL NDA 14 sections
Xeloda HUMAN PRESCRIPTION DRUG LABEL 1 54868-4143 TABLET, FILM COATED 150 mg ORAL NDA 20 sections
Xeloda HUMAN PRESCRIPTION DRUG LABEL 1 54868-5260 TABLET, FILM COATED 500 mg ORAL NDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 60687-149 TABLET, FILM COATED 500 mg ORAL ANDA 21 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 63759-3001 TABLET, FILM COATED 500 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 64980-276 TABLET, FILM COATED 150 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 64980-277 TABLET, FILM COATED 500 mg ORAL ANDA 20 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 65162-843 TABLET 150 mg ORAL ANDA 19 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 65162-844 TABLET 500 mg ORAL ANDA 19 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 67877-458 TABLET, FILM COATED 150 mg ORAL ANDA 19 sections
Capecitabine HUMAN PRESCRIPTION DRUG LABEL 1 67877-459 TABLET, FILM COATED 500 mg ORAL ANDA 19 sections