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Atlas / Drug / Capecitabine

Capecitabine

drug
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Also known as CapecitabinaCapecitabine accordCapecitabine component of xeloxCapecitabine medacCapecitabine sunCapecitabine tevaCapecitibineCapecytabineCapiibineCaptabinEcansyaEcansya (previously capecitabine krka)NSC-759853RO-091978000XelodaSID144205751SID174006945SID170464779CapecitabineÊ

Summary

Capecitabine (CHEMBL1773) is an approved small-molecule antineoplastic agent (ATC L01BC06) targeting TYMS; indicated across 90 conditions including breast carcinoma and colorectal adenocarcinoma; with CIViC clinical evidence for 17 variant-indication associations (e.g. ERBB2 Amplification in her2-receptor positive breast cancer).

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: L01BC06
  • Targets: 1 (TYMS)
  • Indications: 90 conditions
  • Clinical trials: 1,659
  • Precision-oncology evidence (CIViC): 17 variant–indication associations
  • Chemistry: 359.35 Da · C15H22FN3O6

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1773
NameCapecitabine
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID60953
ChEBICHEBI:31348
ATCL01BC06
Molecular formulaC15H22FN3O6
Molecular weight359.35
InChIKeyGAGWJHPBXLXJQN-UORFTKCHSA-N

SMILES: CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@H]2[C@@H]([C@@H]([C@H](O2)C)O)O

IUPAC name: pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate

ChEBI definition: A carbamate ester that is cytidine in which the hydrogen at position 5 is replaced by fluorine and in which the amino group attached to position 4 is converted into its N-(penyloxy)carbonyl derivative. Capecitabine is a antineoplastic agent used in the treatment of cancers.

Pharmacological roles (ChEBI): antineoplastic agent, prodrug.

Other ChEBI roles (chemical / environmental): antimetabolite.

Also known as: Capecitabina, Capecitabine, Capecitabine accord, Capecitabine component of xelox, Capecitabine medac, Capecitabine sun, Capecitabine teva, Capecitibine, Capecytabine, Capiibine, Captabin, Ecansya

Patent coverage: 29,582 distinct patent families (118,696 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
TYMSthymidylate synthetaseInhibition50.8%P04818

Bioactivity

No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).

Target pathways

Aggregated over 1 target gene(s): TYMS.

Top Reactome pathways

2 total, by targets touching each:

PathwayTargetsGenes
Interconversion of nucleotide di- and triphosphates1TYMS
G1/S-Specific Transcription1TYMS

Dominant GO biological processes

GO termTargets
dTMP biosynthetic process1
dTTP biosynthetic process1
negative regulation of translation1
methylation1
tetrahydrofolate interconversion1
DNA biosynthetic process1
one-carbon metabolic process1
nucleotide biosynthetic process1
tetrahydrofolate metabolic process1

Indications & clinical

Indications

90 indications (17 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
breast carcinoma4MONDO:0004989EFO:0000305
colorectal adenocarcinoma4MONDO:0005008EFO:0000365
gastric carcinoma4MONDO:0004950EFO:0000178
neoplasm4MONDO:0005070EFO:0000616
gastric neoplasm4MONDO:0021085EFO:0003897
colonic neoplasm4MONDO:0005401EFO:0004288
breast neoplasm4MONDO:0021100EFO:0003869
gastric adenocarcinoma4MONDO:0005036EFO:0000503
colorectal neoplasm4MONDO:0005335EFO:0004142
colorectal carcinoma4MONDO:0024331EFO:1001951
HER2 positive breast carcinoma4MONDO:0006244EFO:1000294
colon carcinoma4MONDO:0002032EFO:1001950
carcinoma of esophagus3MONDO:0019086EFO:0002916
exocrine pancreatic carcinoma3MONDO:0005192EFO:0002618
squamous cell carcinoma3MONDO:0005096EFO:0000707
nasopharyngeal neoplasm3MONDO:0005375EFO:0004252
renal cell carcinoma3MONDO:0005086EFO:0000681
biliary tract neoplasm3MONDO:0005304EFO:0003891
cholangiocarcinoma3MONDO:0019087EFO:0005221
rectal cancer3MONDO:0006519EFO:1000657
head and neck squamous cell carcinoma3MONDO:0010150EFO:0000181
adenocarcinoma3MONDO:0004970EFO:0000228
carcinoma3MONDO:0004993EFO:0000313
non-small cell lung carcinoma3MONDO:0005233EFO:0003060
pancreatic neoplasm3MONDO:0021040EFO:0003860
brain disorder3MONDO:0005560EFO:0005774
pancreatic neuroendocrine tumor3MONDO:0019954EFO:1000045
neuroendocrine neoplasm3MONDO:0019496EFO:1001901
triple-negative breast carcinoma3MONDO:0005494EFO:0005537
esophageal squamous cell carcinoma3MONDO:0005580EFO:0005922
colon adenocarcinoma3MONDO:0002271EFO:1001949
intrahepatic cholangiocarcinoma3MONDO:0003210EFO:1001961
rectal neoplasm3MONDO:0002165MONDO:0002165
gallbladder neoplasm3MONDO:0021253MONDO:0005411
hand-foot syndrome3MONDO:0700048EFO:1001893
gallbladder carcinoma3MONDO:0003220EFO:1001956
pancreatic ductal adenocarcinoma3MONDO:0005184MONDO:0005184
nasopharyngeal carcinoma3MONDO:0015459MONDO:0015459
hepatocellular carcinoma2MONDO:0007256EFO:0000182
male breast carcinoma2MONDO:0005628EFO:0006861
mesothelioma2MONDO:0005065EFO:0000588
glioblastoma2MONDO:0018177EFO:0000519
kidney neoplasm2MONDO:0021163EFO:0003865
head and neck cancer2MONDO:0005627EFO:0006859
upper aerodigestive tract neoplasm2MONDO:0005398EFO:0004284
inflammatory breast carcinoma2MONDO:0006804EFO:1000984
hypopharyngeal carcinoma2MONDO:0005216EFO:0002938
pancreatic endocrine carcinoma2MONDO:0005893EFO:0007416
brain cancer2MONDO:0001657MONDO:0001657
anus neoplasm2MONDO:0003046MONDO:0001879
peritoneal neoplasm2MONDO:0006901MONDO:0002087
neuroendocrine carcinoma2MONDO:0002120MONDO:0002120
fallopian tube neoplasm2MONDO:0021092MONDO:0002158
kidney cancer2MONDO:0002367MONDO:0002367
ovarian cancer2MONDO:0008170MONDO:0008170
lung neoplasm2MONDO:0021117MONDO:0008903
oropharynx cancer2MONDO:0004608MONDO:0044926
ovarian carcinoma2MONDO:0005140EFO:0001075
laryngeal squamous cell carcinoma2MONDO:0005595EFO:0006352
fallopian tube carcinoma2MONDO:0006206EFO:1000251
glioma2MONDO:0021042MONDO:0100342
skin carcinoma2MONDO:0002656EFO:0009259
skin neoplasm2MONDO:0002531MONDO:0002898
pseudomyxoma peritonei2MONDO:0017048EFO:0007456
bile duct carcinoma2MONDO:0005496EFO:0005540
brain neoplasm2MONDO:0021211EFO:0003833
paraganglioma2MONDO:0000448EFO:1000453
bile duct neoplasm2MONDO:0021662MONDO:0003059
melanoma1MONDO:0005105EFO:0000756
cutaneous neuroendocrine carcinoma1MONDO:0019210EFO:1001471
urothelial carcinoma1MONDO:0040679EFO:0008528
non-Hodgkin lymphoma1MONDO:0018908EFO:0005952
central nervous system neoplasm1MONDO:0006130EFO:1000158
metastatic melanoma1MONDO:0005191EFO:0002617

16 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 1,659.

Phase distribution

(phase/status distribution below is over 1,600 sampled trials of the 1,659 total).

PhaseTrials
PHASE2817
PHASE3337
PHASE1200
PHASE1/PHASE2155
PHASE2/PHASE349
PHASE423
Not specified15
EARLY_PHASE14

Top trials by phase / activity

NCTPhaseStatusTitle
NCT06090994PHASE4RECRUITINGPrevention of Recurrence and Metastasis of Colorectal Cancer by Comparing Huaier With Capecitabine Monotherapy
NCT06217185PHASE4RECRUITINGThe Efficacy and Safety of Pyrotinib, Trastuzumab Combined With Taxanes in the Treatment of Trastuzumab-treated HER2+ Advanced Breast Cancer (ABC).
NCT06387368PHASE4NOT_YET_RECRUITINGClinical Study of Huaier Granule in the Treatment of Unresectable Pancreatic Cancer
NCT07094893PHASE4NOT_YET_RECRUITINGAnti-EGFR Agents in Patients With Right-sided Advanced Colorectal Cancer With Wild-type RAS and AREG/EREG High Status
NCT07158164PHASE4RECRUITINGDPYD Pharmacogenomics and Fluoropyrimidine (FP) Dose-Adjustment
NCT07483060PHASE4NOT_YET_RECRUITINGNext Generation STAR-TREC (NG-ST) - Organ Preservation in Early Rectal Cancer
NCT00087620PHASE4TERMINATEDA Study of Capecitabine In Combination With Docetaxel vs Capecitabine Followed by Docetaxel As First-Line Treatment For Metastatic Breast Cancer
NCT00121836PHASE4COMPLETEDA Study of Xeloda (Capecitabine) in Women With HER2-Negative Metastatic Breast Cancer
NCT00127933PHASE4COMPLETEDXeNA Study - A Study of Xeloda (Capecitabine) in Patients With Invasive Breast Cancer
NCT00216424PHASE4TERMINATEDCapecitabine (Xeloda) and Radiation for Patients With Rectosigmoid Carcinoma
NCT00220168PHASE4COMPLETEDPhase II Trial Evaluating Irinotecan and Capecitabine Relapsed/Refractory Upper GI Tumours
NCT00502671PHASE4COMPLETEDA Study of Xeloda (Capecitabine) as Adjuvant Monotherapy in Patients With Colon Cancer.
NCT00559676PHASE4COMPLETEDStudy of Biomarkers in Patients Undergoing Chemotherapy for Metastatic Colorectal Cancer
NCT00577031PHASE4COMPLETEDOBELIX Study: A Study of Avastin (Bevacizumab) in Combination With XELOX in Patients With Metastatic Cancer of the Colon or Rectum.
NCT00812864PHASE4COMPLETEDPharmacokinetic Study of Capecitabine in Elderly Cancer Patient (≥ 75 Years)
NCT00854477PHASE4COMPLETEDPharmacokinetic Study of Adjuvant Capecitabine After Resection of Pancreatic Adenocarcinoma
NCT00871273PHASE4TERMINATEDPharmacokinetic Study of Capecitabine After Total Gastrectomy for Stomach Adenocarcinoma
NCT01588990PHASE4COMPLETEDA Translational Study of Bevacizumab in Participants With Metastatic Colorectal Cancer
NCT02248571PHASE4COMPLETEDPatient Preference for Everolimus in Combination With Exemestane or Capecitabine in Combination With Bevacizumab
NCT02567331PHASE4COMPLETEDA Study of Capecitabine (Xeloda) in Patients With Metastatic Colorectal Cancer
NCT02581423PHASE4COMPLETEDA Study of Capecitabine (Xeloda) in the Adjuvant Treatment of Participants With Resected Colon Cancer
NCT03465202PHASE4UNKNOWNAssociation of Capecitabine Pharmacokinetics and Toxicity With Aging
NCT04480268PHASE4UNKNOWNPAXG Out in the Country
NCT01081262PHASE3ACTIVE_NOT_RECRUITINGCarboplatin and Paclitaxel or Oxaliplatin and Capecitabine With or Without Bevacizumab as First-Line Therapy in Treating Patients With Newly Diagnosed Stage II-IV or Recurrent Stage I Epithelial Ovarian or Fallopian Tube Cancer
NCT01917552PHASE3RECRUITINGAdjuvant Capecitabine Versus Observation Alone in Curatively Resected Stage IB Gastric Cancer((KCSG ST14-05): CATALYSIS
NCT01918527PHASE3ACTIVE_NOT_RECRUITINGNeoadjuvant Chemotherapy Versus Standard Treatment in Patients With Locally Advanced Colon Cancer
NCT01935778PHASE3RECRUITINGCompare Adjuvant Chemotherapy of Docetaxel/Capecitabine/Oxliplatin Versus Capecitabine/Oxaliplatin in Advanced Gastric Cancer at Stage IIIb and IV(KCSG ST15-08): TRIUMPH
NCT02170090PHASE3ACTIVE_NOT_RECRUITINGAdjuvant Chemotherapy With Gemcitabine and Cisplatin Compared to Standard of Care After Curative Intent Resection of Biliary Tract Cancer
NCT02344472PHASE3ACTIVE_NOT_RECRUITINGDetect V / CHEVENDO (Chemo vs. Endo)
NCT02445391PHASE3ACTIVE_NOT_RECRUITINGPlatinum in Treating Patients With Residual Triple-Negative Breast Cancer Following Neoadjuvant Chemotherapy
NCT02505750PHASE3ACTIVE_NOT_RECRUITINGSafety of a Boost (CXB or EBRT) in Combination With Neoadjuvant Chemoradiotherapy for Early Rectal Adenocarcinoma
NCT03399110PHASE3ACTIVE_NOT_RECRUITINGXELOX for 4 Months Versus 6 Months in Gastric Cancer (LOMAC)
NCT03503136PHASE3NOT_YET_RECRUITINGNedaplatin Versus Cisplatin and Capecitabine Versus Fluorouracil in IC + CCRT for Locoregionally Advanced NPC
NCT03561740PHASE3RECRUITINGA Study of the Addition of Metronomic Capecitabine to Standard Adjuvant Therapy in High Risk HER2+ BC paTients
NCT03653507PHASE3ACTIVE_NOT_RECRUITINGA Study of Zolbetuximab (IMAB362) Plus CAPOX Compared With Placebo Plus CAPOX as First-line Treatment of Subjects With Claudin (CLDN) 18.2-positive, HER2-negative, Locally Advanced Unresectable or Metastatic Gastric or Gastroesophageal Junction (GEJ) Adenocarcinoma (GLOW).
NCT03734029PHASE3ACTIVE_NOT_RECRUITINGTrastuzumab Deruxtecan (DS-8201a) Versus Investigator’s Choice for HER2-low Breast Cancer That Has Spread or Cannot be Surgically Removed [DESTINY-Breast04]
NCT03801876PHASE3RECRUITINGComparing Proton Therapy to Photon Radiation Therapy for Esophageal Cancer
NCT03869892PHASE3ACTIVE_NOT_RECRUITINGPhase III Study in First-line Treatment of Patients With Metastatic Colorectal Cancer Who Are Not Candidate for Intensive Therapy.
NCT04068103PHASE2/PHASE3ACTIVE_NOT_RECRUITINGCirculating Tumor DNA Testing in Predicting Treatment for Patients With Stage IIA Colon Cancer After Surgery
NCT04089631PHASE3RECRUITINGCirculating Tumour DNA Based Decision for Adjuvant Treatment in Colon Cancer Stage II Evaluation

Clinical evidence (CIViC)

Variant × indication × effect (17 predictive associations from 18 curated evidence items):

VariantIndicationEffectTherapyLevelCIViC
ERBB2 AmplificationHer2-receptor Positive Breast CancerSensitivity/ResponseCapecitabine + NeratinibCIViC AEID8048 +1
ERBB2 AmplificationBreast CancerSensitivity/ResponseCapecitabine + LapatinibCIViC AEID11247
ERBB2 AmplificationBreast CancerSensitivity/ResponseTrastuzumab + Tucatinib + CapecitabineCIViC AEID11250
DPYD DPYD*13 HOMOZYGOSITYCancerAdverse ResponseCapecitabine + Fluorouracil + TegafurCIViC AEID1801
DPYD DPYD*2A HOMOZYGOSITYCancerAdverse ResponseTegafur + Capecitabine + FluorouracilCIViC AEID1800
DPYD RS67376798 HOMOZYGOSITYCancerAdverse ResponseTegafur + Fluorouracil + CapecitabineCIViC AEID1803
ERBB2 AmplificationHer2-receptor Positive Breast CancerSensitivity/ResponseCapecitabine + LapatinibCIViC BEID1132
ERBB2 AmplificationHer2-receptor Positive Breast CancerSensitivity/ResponseCapecitabine + TrastuzumabCIViC BEID1133
ERBB2 OverexpressionPancreatic CancerSensitivity/ResponseTrastuzumab + CapecitabineCIViC BEID5955
TP53 WildtypeColorectal CancerSensitivity/ResponseCapecitabine + Oxaliplatin + CetuximabCIViC BEID875
BRAF V600EColorectal CancerResistanceBevacizumab + Capecitabine + OxaliplatinCIViC BEID2121
BRAF V600EColorectal CancerResistanceOxaliplatin + Capecitabine + Bevacizumab + CetuximabCIViC BEID8646
ERBB2 AmplificationColorectal CancerResistanceOxaliplatin + Cetuximab + CapecitabineCIViC BEID895
PIK3CA MutationHer2-receptor Positive Breast CancerResistanceCapecitabine + LapatinibCIViC BEID8705
ERBB2 L755STriple-receptor Negative Breast CancerSensitivity/ResponseCapecitabine + NeratinibCIViC CEID8055
ERBB2 OverexpressionSalivary Gland CancerSensitivity/ResponseTrastuzumab + Capecitabine + Zoledronic AcidCIViC CEID6171
BRAF V600EColorectal CancerSensitivity/ResponseCapecitabine + Vemurafenib + BevacizumabCIViC DEID98

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (5) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

GuidelineSourceGene(s)DosingRecommendation
Annotation of DPWG Guideline for capecitabine and DPYDDPWGDPYDyesyes
Annotation of CPIC Guideline for capecitabine and DPYDCPICDPYDyesyes
Annotation of RNPGx Guideline for capecitabine, fluorouracil and DPYDRNPGxDPYDyesyes
Annotation of SEFF/SEOM Guideline for capecitabine, fluorouracil, tegaSEFF/SEOMDPYDyesyes
Annotation of AIOM Guideline for capecitabine, fluorouracil, tegafur aAIOMDPYDyesyes

PharmGKB also curates 70 clinical and 548 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

9 molecules share ≥1 primary target. Top 9 by shared-target count:

MoleculeSourceStatusShared targets
FOLIC ACIDChEMBL + PubChemPhase 4 (approved)TYMS
METHOTREXATEChEMBL + PubChemPhase 4 (approved)TYMS
PEMETREXEDChEMBL + PubChemPhase 4 (approved)TYMS
PEMETREXED DISODIUMChEMBL + PubChemPhase 4 (approved)TYMS
PHENOLPHTHALEINChEMBLPhase 4 (approved)TYMS
RALTITREXEDChEMBLPhase 4 (approved)TYMS
NOLATREXEDChEMBLPhase 3TYMS
METESINDChEMBLPhase 2TYMS
OSI-7904ChEMBLPhase 2TYMS

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot