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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1773
CHEMBL1773
Compound Name CAPECITABINE
ChEMBL Synonyms CAPECITABINE | XELODA | RO 09-1978/000
Max Phase 4 (Approved)
Trade Names XELODA | CAPECITABINE
Molecular Formula C15H22FN3O6

Additional synonyms for CHEMBL1773 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@@H]2O[C@H](C)[C@@H](O)[C@H]2 ...
Download SMILES
Standard InChI InChI=1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14( ...
Download InChI
Standard InChI Key GAGWJHPBXLXJQN-UORFTKCHSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1773

Molecule Features

CHEMBL1773 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA inhibitor DNA DailyMed PubMed
RNA inhibitor RNA DailyMed PubMed
Thymidylate synthase inhibitor Thymidylate synthase DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Carcinoma, Pancreatic DuctalD021441EFO:0002517pancreatic ductal adenocarcinoma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Stomach NeoplasmsD013274EFO:0003897stomach neoplasm3ClinicalTrials
Thyroid NeoplasmsD013964EFO:0002892thyroid carcinoma2ClinicalTrials
Anus NeoplasmsD001005EFO:0003835anal neoplasm2ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma3ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma3ClinicalTrials
Neuroendocrine TumorsD018358EFO:1001901neuroendocrine neoplasm2ClinicalTrials
AdenocarcinomaD000230EFO:0000228adenocarcinoma3ClinicalTrials
Brain DiseasesD001927EFO:0005774brain disease3ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm4ClinicalTrials
Colonic NeoplasmsD003110EFO:0004288colonic neoplasm4ClinicalTrials
DailyMed
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NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma3ClinicalTrials
Stomach NeoplasmsD013274EFO:0000503gastric adenocarcinoma3ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma2ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma3ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma3ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma3ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer2ClinicalTrials
MelanomaD008545EFO:0000756melanoma1ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma4ClinicalTrials
Colorectal NeoplasmsD015179EFO:0005842colorectal cancer3ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma2ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia2ClinicalTrials
Kidney NeoplasmsD007680EFO:0003865kidney neoplasm2ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000181head and neck squamous cell carcinoma3ClinicalTrials
CholangiocarcinomaD018281EFO:0005221cholangiocarcinoma3ClinicalTrials
Colorectal NeoplasmsD015179EFO:0000365colorectal adenocarcinoma3ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma1ClinicalTrials
MesotheliomaD008654EFO:0000588mesothelioma2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer3ClinicalTrials
Carcinoma, Merkel CellD015266EFO:1001471Merkel cell skin cancer1ClinicalTrials
Colonic NeoplasmsD003110EFO:1001950colon carcinoma4ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma2ClinicalTrials
Neuroendocrine TumorsD018358EFO:1000045pancreatic neuroendocrine tumor2ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma3ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0003860pancreatic neoplasm3ClinicalTrials
Biliary Tract NeoplasmsD001661EFO:0003891biliary tract neoplasm2ClinicalTrials
Colorectal NeoplasmsD015179EFO:0004142colorectal neoplasm3ClinicalTrials
GliomaD005910EFO:0005543glioma2ClinicalTrials
Nasopharyngeal NeoplasmsD009303EFO:0004252nasopharyngeal neoplasm3ClinicalTrials

Clinical Data

ClinicalTrials.gov CAPECITABINE
The Cochrane Collaboration CAPECITABINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1773. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 0.995
CHEMBL226 Adenosine A1 receptor Homo sapiens 0.744
CHEMBL276 Muscarinic acetylcholine receptor M1 Rattus norvegicus 0.723
CHEMBL256 Adenosine A3 receptor Homo sapiens 0.685

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 0.991
CHEMBL256 Adenosine A3 receptor Homo sapiens 0.908
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 0.697
CHEMBL226 Adenosine A1 receptor Homo sapiens 0.617
CHEMBL276 Muscarinic acetylcholine receptor M1 Rattus norvegicus 0.606
CHEMBL251 Adenosine A2a receptor Homo sapiens 0.239

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
359.4 359.1493 0.76 6 122.91 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
8 3 0 9 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
5.41 1.75 1.04 -.6 1 25 0.64

Structural Alerts

There are 4 structural alerts for CHEMBL1773. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01B - ANTIMETABOLITES
L01BC - Pyrimidine analogues
L01BC06 - capecitabine

ChemSpider ChemSpider:GAGWJHPBXLXJQN-UORFTKCHSA-N
DailyMed capecitabine
PubChem SID: 144205751 SID: 170464779
Wikipedia Capecitabine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1773



ACToR 154361-50-9
Brenda 38000 148223
ChEBI 31348
ChemicalBook CB1324457
DrugBank DB01101
DrugCentral 480
eMolecules 6719200
EPA CompTox Dashboard DTXSID3046451
FDA SRS 6804DJ8Z9U
Guide to Pharmacology 6799
Human Metabolome Database HMDB0015233
IBM Patent System 6F8086BDD9C1CD3F7F7F7782F1286F96
KEGG Ligand C12650
LINCS LSM-5705
Mcule MCULE-2851259722
MolPort MolPort-005-938-254
Nikkaji J949.163E
PharmGKB PA448771
PubChem 60953
PubChem: Drugs of the Future 12014895
PubChem: Thomson Pharma 14925873 14828191
Selleck Capecitabine(Xeloda)
SureChEMBL SCHEMBL8153
ZINC ZINC000003806413

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/GAGWJHPBXLXJQN-UORFTKCHSA-N spacer
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