Capecitabine
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1998
- First approval year
- 1998
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Capecitabine
- Molecular weight
- 359.35
- Structure (SMILES)
- CCCCCOC(=O)Nc1nc(=O)n([C@@H]2O[C@H](C)[C@@H](O)[C@H]2O)cc1F
- capecitabine
- Capecitabine
- capecitabine accord
- Capecitabine accord
- Capecitabine component of xeliri capecitibine
- capecitabine component of xeliri capecitibine
- capecitabine component of xelox
- Capecitabine component of xelox
- capecitabine medac
- Capecitabine medac
- capecitabine sun
- Capecitabine sun
- capecitabine teva
- Capecitabine teva
- Ecansya (previously capecitabine krka)
- ecansya previously capecitabine krka
- xeloda
- Xeloda
- "Capecitabine"
- capecitabina
- Capecitabina
- capecitabine
- Capecitabine
- CAPECITABINE
- Capecitabine (Xeloda) Pharmacogenetic Test Reagents
- CAPECITABINE [EMA EPAR]
- CAPECITABINE [EP MONOGRAPH]
- CAPECITABINE [HSDB]
- capecitabine [INN]
- CAPECITABINE [JAN]
- CAPECITABINE [MART.]
- CAPECITABINE [MI]
- CAPECITABINE [ORANGE BOOK]
- CAPECITABINE [USAN]
- CAPECITABINE [USP IMPURITY]
- CAPECITABINE [USP MONOGRAPH]
- CAPECITABINE [USP-RS]
- CAPECITABINE [VANDF]
- Capecitabine [WHO-DD]
- Capecitabine 150Mg Oral Tablet
- Capecitabine 500 MG
- Capecitabine 500mg
- Capecitabine 500Mg Oral Tablet
And 57 more, listed on the interactive page.
- ATC classification codes
- L01BC06
Sources for recorded values
- CAS registry numbers
- 154361-50-9
- ChEMBL ID
- CHEMBL1773
- InChIKey
- GAGWJHPBXLXJQN-UORFTKCHSA-N
- PubChem compound IDs
- 60953
- RxNorm IDs (RxCUI)
- 194000
- FDA ingredient codes (UNII)
- 6804DJ8Z9U
- Applicant
- CHEPLAPHARM
- Approval date
- 30 Apr 1998
- Application number
- NDA020896
- Status
- Authorised
- Status date
- 2 Feb 2001
- Authorisation date
- 2 Feb 2001
- Approved indications
- Xeloda is indicated for the adjuvant treatment of patients following surgery of stage III (Dukes' stage C) colon cancer. Xeloda is indicated for the treatment of metastatic colorectal cancer. Xeloda is indicated for first-line treatment of advanced gastric cancer in combination with a platinum-based regimen. Xeloda in combination with docetaxel is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of cytotoxic chemotherapy. Previous therapy should have included an anthracycline. Xeloda is also indicated as monotherapy for the treatment of patients with locally advanced or metastatic breast cancer after failure of taxanes and an anthracycline-containing chemotherapy regimen or for whom further anthracycline therapy is not indicated.
- Product number
- EMEA/H/C/000316
- Authorisation holder
- CHEPLAPHARM Arzneimittel GmbH
- Priority medicines scheme
- No
- Generic
- No
- Biosimilar
- No
- Generic medicines
- 4
- Biosimilar medicines
- 0
- Advanced therapy
- No
- Conditional approval
- No
- Additional monitoring
- No
- Accelerated assessment
- No
- Exceptional circumstances
- No
Therapeutic areas
- Breast Neoplasms
- Colonic Neoplasms
- Colorectal Neoplasms
- Stomach Neoplasms
European medicines record
- Patents
- 0
- Designations
- 2
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- Yes
- Orphan exclusivity
- No
- Accelerated approval
- Yes
- Availability
- Prescription only
- Boxed warning
- Yes
- Pharmacology name
- capecitabine
- Type
- Synthetic organic
- Drug name stem
- -citabine
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- Action
- Inhibition
- Action type
- Inhibitor
- Target
- thymidylate synthetase
- Gene symbol
- TYMS
- Protein identifier
- P04818
- Primary target
- Yes
- Mechanism
- DNA inhibitor
- Action type
- Inhibitor
- Target
- DNA
- Mechanism
- RNA inhibitor
- Action type
- Inhibitor
- Target
- RNA
- Mechanism
- Thymidylate synthase inhibitor
- Action type
- Inhibitor
- Target
- Thymidylate synthase
- Protein identifier
- P04818
Open Targets mechanisms
- Mechanism
- Thymidylate synthase inhibitor
- Action type
- Inhibitor
- Target
- Thymidylate synthase
DrugCentral mechanisms
- Action type
- Inhibitor
- Gene symbol
- TYMS
- Protein identifier
- P04818
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Stomach Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000178
- Subject identifier
- D013274
- Condition
- Carcinoma, Squamous Cell
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000181
- Subject identifier
- D002294
- Condition
- Carcinoma, Hepatocellular
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000182
- Subject identifier
- D006528
- Condition
- Adenocarcinoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000228
- Subject identifier
- D000230
- Condition
- Breast Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000305
- Subject identifier
- D001943
- Condition
- Carcinoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000313
- Subject identifier
- D002277
- Condition
- Colorectal Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000365
- Subject identifier
- D015179
- Condition
- Stomach Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000503
- Subject identifier
- D013274
- Condition
- Glioblastoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000519
- Subject identifier
- D005909
- Condition
- Mesothelioma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000588
- Subject identifier
- D008654
- Condition
- Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000616
- Subject identifier
- D009369
- Condition
- Carcinoma, Renal Cell
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000681
- Subject identifier
- D002292
- Condition
- Carcinoma, Squamous Cell
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000707
- Subject identifier
- D002294
- Condition
- Melanoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000756
- Subject identifier
- D008545
- Condition
- Ovarian Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0001075
- Subject identifier
- D010051
- Condition
- Melanoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0002617
- Subject identifier
- D008545
- Condition
- Pancreatic Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0002618
- Subject identifier
- D010190
- Condition
- Esophageal Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0002916
- Subject identifier
- D004938
- Condition
- Hypopharyngeal Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0002938
- Subject identifier
- D007012
- Condition
- Carcinoma, Non-Small-Cell Lung
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003060
- Subject identifier
- D002289
- Condition
- Brain Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0003833
- Subject identifier
- D001932
- Condition
- Pancreatic Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003860
- Subject identifier
- D010190
- Condition
- Kidney Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0003865
- Subject identifier
- D007680
- Condition
- Breast Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003869
- Subject identifier
- D001943
- Condition
- Biliary Tract Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003891
- Subject identifier
- D001661
And 65 more, listed on the interactive page.
- Condition identifier
- EFO_0000178
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000181
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000182
- Condition identifier
- EFO_0000228
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000305
- Condition identifier
- EFO_0000313
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000365
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000478
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000503
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000519
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000588
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000616
- Condition identifier
- EFO_0000681
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000707
- Highest recorded phase
- 3
- Condition identifier
- EFO_0002618
- Highest recorded phase
- 3
- Condition identifier
- EFO_0002916
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003060
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003860
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003863
- Highest recorded phase
- 2
- Condition identifier
- EFO_0003869
- Condition identifier
- EFO_0003891
- Highest recorded phase
- 2
- Condition identifier
- EFO_0003897
- Condition identifier
- EFO_0004142
- Condition identifier
- EFO_0004252
- Highest recorded phase
- 3
- Condition identifier
- EFO_0004284
- Highest recorded phase
- 2
And 165 more, listed on the interactive page.
Warnings
- Warning
- Black Box Warning
Open Targets warnings
- Warning
- Black Box Warning
- Country
- United States
- Event
- arteriospasm coronary
- Reports
- 339
- Reporting signal score
- 798.323
- Event
- bone marrow failure
- Reports
- 532
- Reporting signal score
- 638.101
- Event
- breast cancer metastatic
- Reports
- 328
- Reporting signal score
- 724.097
- Event
- decreased appetite
- Reports
- 1,106
- Reporting signal score
- 544.299
- Event
- dehydration
- Reports
- 1,065
- Reporting signal score
- 646.489
- Event
- diarrhoea
- Reports
- 5,243
- Reporting signal score
- 4,105.95
- Event
- disease progression
- Reports
- 2,243
- Reporting signal score
- 3,298.45
- Event
- febrile neutropenia
- Reports
- 702
- Reporting signal score
- 467.139
- Event
- gastrointestinal toxicity
- Reports
- 293
- Reporting signal score
- 656.619
- Event
- haematotoxicity
- Reports
- 291
- Reporting signal score
- 439.607
- Event
- leukopenia
- Reports
- 683
- Reporting signal score
- 513.003
- Event
- malignant neoplasm progression
- Reports
- 1,201
- Reporting signal score
- 1,488.66
- Event
- metastases to bone
- Reports
- 474
- Reporting signal score
- 859.856
- Event
- metastases to central nervous system
- Reports
- 291
- Reporting signal score
- 463.122
- Event
- metastases to liver
- Reports
- 625
- Reporting signal score
- 1,309.31
- Event
- metastases to lung
- Reports
- 322
- Reporting signal score
- 594.552
- Event
- mucosal inflammation
- Reports
- 1,065
- Reporting signal score
- 1,831.02
- Event
- myelosuppression
- Reports
- 291
- Reporting signal score
- 431.594
- Event
- nausea
- Reports
- 3,117
- Reporting signal score
- 807.57
- Event
- neuropathy peripheral
- Reports
- 1,012
- Reporting signal score
- 768.749
- Event
- neurotoxicity
- Reports
- 471
- Reporting signal score
- 632.863
- Event
- neutropenia
- Reports
- 1,664
- Reporting signal score
- 1,240.81
- Event
- palmar-plantar erythrodysaesthesia syndrome
- Reports
- 2,928
- Reporting signal score
- 8,486.48
- Event
- skin toxicity
- Reports
- 234
- Reporting signal score
- 412.832
- Event
- stomatitis
- Reports
- 1,049
- Reporting signal score
- 1,363.03
And 2 more, listed on the interactive page.
- NCT00003704
- NCT00003867
- NCT00010023
- NCT00082433
- NCT00083525
- NCT00119171
- NCT00177255
- NCT00177307
- NCT00249977
- NCT00277069
- NCT00278902
- NCT00327743
- NCT00329329
- NCT00613145
- NCT00637702
- NCT00660426
- NCT00707278
- NCT00710736
- NCT00798252
- NCT00833326
- NCT00849550
- NCT01013740
- NCT01079702
- NCT01213238
- NCT01332604
And 1,144 more, listed on the interactive page.
- Dose
- 1250mg/m2
- Route
- Oral
- How often
- Twice daily for the first 14 days of each 21-day cycle
Conditions of use
- Maximum of 8 cycles
- Hydrogen bond acceptors
- 8
- Hydrogen bond donors
- 3
- Polar surface area
- 122.91
- Calculated partition coefficient (ALogP)
- 0.76
- Calculated partition coefficient (XLogP)
- 0.6
- Prodrug
- Yes
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 6
- Heavy atoms
- 25
- Molecular formula
- C15H22FN3O6
- Monoisotopic mass
- 359.14926359
- Natural product
- No
- 0093-7473
- 0093-7474
- 16729-072
- 16729-073
- 31722-774
- 31722-775
- 51407-639
- 51407-640
- 55111-496
- 55111-497
- 59651-204
- 59651-205
- 60687-149
- 61269-475
- 62756-238
- 62756-239
- 67877-458
- 67877-459
- 68001-487
- 68001-488
- 68001-643
- 68001-644
- 69097-948
- 69097-949
- 70756-815
And 11 more, listed on the interactive page.
- Recorded assays
- 956
- Active assays
- 8
- Confirmatory
- Other
- Screening
- Antimetabolites, Antineoplastic
Related records
Trials (1,845)
- "Phase II Study of PET Guided Neoadjuvant Chemotherapy (NAC) and Oncotype Guided Hormonal Therapy of Breast Cancer"
- 177Lutethium - Peptide Receptor Radionuclide Therapy (Lu-PRRT) Plus Capecitabine Versus Lu-PRRT in FDG Positive, Gastro-entero-pancreatic Neuroendocrine Tumors
- 1st or 2nd Line MBC (Metastatic Breast Cancer) With Previous Avastin (Bevacizumab) Therapy
- 1stline Study Capecitabine Administered on Continuous Way Plus Oxaliplatin&Bevacizumab Every 2weeks in Metastatic CCR.
- 2-arm Trial of Paclitaxel Plus Bevacizumab vs. Capecitabine Plus Bevacizumab
- 5-FU Based Maintenance Therapy in RAS Wild Type Metastatic Colorectal Cancer After Induction With FOLFOX Plus Panitumumab
- 6-TG, Capecitabine and Celecoxib Plus TMZ or CCNU for Anaplastic Glioma Patients
- 8 Continuous vs 8 Intermittent Cycles in First and Second Line in HER2/Neu Neg Metastatic Breast Cancer
- A Bioequivalence Study of Capecitabine Tablets
- A Bioequivalence Study of Capecitabine Tablets 500 mg in Adult Cancer Patients Under Fed Condition
- A Clinical Study Conducted in Multiple Centers Evaluating Escalating Doses of Veliparib in Combination With Capecitabine and Radiation in Patients With Locally Advanced Rectal Cancer
- A Clinical Study of Boserolimab (MK-5890) With Pembrolizumab and Chemotherapy in People With Early Triple-Negative Breast Cancer (MK-5890-003)
- A Clinical Study of JS105 in Combination With Other Anti-tumor Therapies in Patients With Solid Tumors
- A Clinical Study of Patritumab Deruxtecan to Treat Breast Cancer (MK-1022-016)
- A Clinical Study of PD-L1 Antibody ZKAB001 Combined With Capecitabine in Resected Biliary Tract Cancer
- A Clinical Study of Sacituzumab Tirumotecan (Sac-TMT, MK-2870) in People With Breast Cancer (MK-2870-032)
- A Clinical Study of SH006 Injection in Combination Therapy Versus Regorafenib in the Treatment of Advanced Hepatocellular Carcinoma
- A Clinical Study of the Efficacy and Safety of Chidamide in Combination With Camrelizumab and Carboplatin or Capecitabine in the Second and Third Line Treatment of Relapsed/Metastatic Triple-negative Breast Cancer
- A Clinical Study of TQB2930 Injection and Chemotherapy With or Without Bevacizumab in the Treatment of Advanced Colorectal Cancer
- A Clinical Study To Evaluate Camrelizumab (SHR-1210) Plus Capecitabine and Oxaliplatin Followed by Sequential Treatment With Camrelizumab Plus Apatinib Mesylate in Advanced or Metastatic Gastric Cancer (GC) or Gastroesophageal Junction Cancer (GEJ) Without Prior Systemic Therapy
Approved for (17)
- Breast cancer
- Breast carcinoma
- Breast neoplasm
- Cancer
- Colon carcinoma
- Colonic neoplasm
- Colorectal adenocarcinoma
- Colorectal cancer
- Colorectal carcinoma
- Colorectal neoplasm
- Gastric adenocarcinoma
- Gastric cancer
- Gastric carcinoma
- Gastric neoplasm
- HER2 positive breast carcinoma
- Malignant colon neoplasm
- Neoplasm
In development for (75)
- Adenocarcinoma Phase 3
- Adult hepatocellular carcinoma Phase 3
- Anus cancer Phase 2
- Bile duct cancer Phase 2
- Bile duct carcinoma Phase 2
- Biliary tract cancer Phase 3
- Biliary tract neoplasm Phase 3
- Brain cancer Phase 2
- Brain disorder Phase 3
- Brain neoplasm Phase 2
- Carcinoma Phase 3
- Carcinoma of esophagus Phase 3
- Central nervous system neoplasm Phase 1
- Cervical cancer Phase 2
- Cholangiocarcinoma Phase 3
- Colon adenocarcinoma Phase 3
- Cutaneous neuroendocrine carcinoma Phase 1
- Esophageal adenocarcinoma Phase 2
- Esophageal cancer Phase 3
- Esophageal squamous cell carcinoma Phase 3
Targets (1)
- TYMS Thymidylate synthase inhibitor