Drug Details

General Information of the Drug (ID: DR8297)
Name
Capecitabine
Synonyms
Capecitabin; Capecitabina; Capecitabinum; Capecitibine; Capiibine; Caxeta; Xabine; Xeloda; Capecitabine [USAN]; R340; R-340; RG-340; Ro 09-1978; Xeloda (TN); Ro 09-1978/000; Ro-09-1978; Xeloda, Captabin, Capecitabine; Capecitabine (JAN/USAN/INN); Ro-09-1978/000; N(4)-Pentyloxycarbonyl-5'-deoxy-5-fluorocytidine; Pentyl 1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate; Pentyl [1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate; Carbamic acid, (1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-, pentyl ester; Pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate; (1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl ester; 5'-Deoxy-5-fluoro-N-((pentyloxy)carbonyl)cytidine; 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine; Capecitabine (Fluoropyrimidine)
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Molecular Type
Small molecule
Disease Colorectal cancer [ICD-11: 2B91] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C15H22FN3O6
PubChem CID
60953
Canonical SMILES
CCCCCOC(=O)NC1=NC(=O)N(C=C1F)C2C(C(C(O2)C)O)O
InChI
1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14(22)17-12)13-11(21)10(20)8(2)25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10-,11-,13-/m1/s1
InChIKey
GAGWJHPBXLXJQN-UORFTKCHSA-N
CAS Number
CAS 154361-50-9
ChEBI ID
CHEBI:31348
TTD Drug ID
D00HCQ
DrugBank ID
DB01101
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Curcumin      Hellenia speciosa     Click to Show/Hide the Molecular Data of This NP
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Expression CXCR4  Molecule Info 
Pathway MAP
Down-regulation Expression ICAM1  Molecule Info 
Pathway MAP
Down-regulation Expression MMP-9  Molecule Info 
Pathway MAP
Down-regulation Expression MYC  Molecule Info 
Pathway MAP
Down-regulation Expression p105  Molecule Info 
Pathway MAP
Down-regulation Expression PECAM1  Molecule Info 
Pathway MAP
Down-regulation Expression VEGFA  Molecule Info 
Pathway MAP
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
HT-29 CVCL_0320 Colon adenocarcinoma Homo sapiens
SW620 CVCL_0547 Colon adenocarcinoma Homo sapiens
                    In-vivo Model A total of 2*105 HCT 116 cells in 20 uL PBS were injected into the cecum of male athymic nu/nu mice.
                    Experimental
                    Result(s)		 Curcumin sensitizes CRC to the antitumor and antimetastatic effects of capecitabine by suppressing NF-kappaB cell signaling pathway.
          Ginsenoside Rg3      Panax ginseng     Click to Show/Hide the Molecular Data of This NP
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression CD34  Molecule Info 
Pathway MAP
Down-regulation Expression VEGFA  Molecule Info 
Pathway MAP
                    In-vivo Model 4T1 cells (1*106) were suspended in 0.1 mL of PBS and injected into the mammary fat pad in the right flank of each BALB/c mice.
                    Experimental
                    Result(s)		 The study demonstrates the feasibility of delivering capecitabine and gensinoside Rg3 in a metronomic chemotherapy regimen, which is proved to be safe, effective, and potentially applicable to clinical treatment.
          Ursolic acid      Potentilla indica     Click to Show/Hide the Molecular Data of This NP
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-xL  Molecule Info 
Pathway MAP
Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
Down-regulation Expression CFLAR  Molecule Info 
Pathway MAP
Down-regulation Expression CTNNB1  Molecule Info 
Pathway MAP
Down-regulation Expression EGFR  Molecule Info 
Pathway MAP
Down-regulation Expression ICAM1  Molecule Info 
Pathway MAP
Down-regulation Expression MMP-9  Molecule Info 
Pathway MAP
Down-regulation Expression p105  Molecule Info 
Pathway MAP
Down-regulation Expression PECAM1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation STAT3  Molecule Info 
Pathway MAP
Up-regulation Expression TP53  Molecule Info 
Pathway MAP
Down-regulation Expression VEGFA  Molecule Info 
Pathway MAP
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
HT-29 CVCL_0320 Colon adenocarcinoma Homo sapiens
Caco-2 CVCL_0025 Colon adenocarcinoma Homo sapiens
                    In-vivo Model HCT116 cells (1.5*106 cells) in 50 mL of PBS were injected into the cecum of athymic nu/nu mice (4 weeks old) using a 30-gauge needle.
                    Experimental
                    Result(s)		 Ursolic acid can inhibit the growth and metastasis of CRC and further enhance the therapeutic effects of capecitabine through the suppression of multiple biomarkers linked to inflammation, proliferation, invasion, angiogenesis, and metastasis.
Target and Pathway
Target(s) Candida thymidylate synthase (Candi TMP1)  Molecule Info  [5]
BioCyc Pyrimidine deoxyribonucleotides biosynthesis from CTP Click to Show/Hide
2 Pyrimidine deoxyribonucleotides de novo biosynthesis
3 Superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis
4 Superpathway of pyrimidine deoxyribonucleoside salvage
5 DTMP de novo biosynthesis (mitochondrial)
6 Pyrimidine deoxyribonucleosides salvage
KEGG Pathway Pyrimidine metabolism Click to Show/Hide
2 One carbon pool by folate
3 Metabolic pathways
Panther Pathway De novo pyrimidine deoxyribonucleotide biosynthesis Click to Show/Hide
2 Formyltetrahydroformate biosynthesis
Pathwhiz Pathway Pyrimidine Metabolism Click to Show/Hide
Pathway Interaction Database E2F transcription factor network Click to Show/Hide
Reactome E2F mediated regulation of DNA replication Click to Show/Hide
2 Pyrimidine biosynthesis
3 G1/S-Specific Transcription
WikiPathways Trans-sulfuration and one carbon metabolism Click to Show/Hide
2 Retinoblastoma (RB) in Cancer
3 One Carbon Metabolism
4 Integrated Pancreatic Cancer Pathway
5 miR-targeted genes in muscle cell - TarBase
6 miR-targeted genes in lymphocytes - TarBase
7 miR-targeted genes in leukocytes - TarBase
8 miR-targeted genes in epithelium - TarBase
9 Metabolism of nucleotides
10 Fluoropyrimidine Activity
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6799).
Reference 2 Curcumin sensitizes human colorectal cancer to capecitabine by modulation of cyclin D1, COX-2, MMP-9, VEGF and CXCR4 expression in an orthotopic mouse model. Int J Cancer. 2009 Nov 1;125(9):2187-97.
Reference 3 Antiangiogenic effect of capecitabine combined with ginsenoside Rg3 on breast cancer in mice. Cancer Biother Radiopharm. 2008 Oct;23(5):647-53.
Reference 4 Ursolic acid inhibits growth and metastasis of human colorectal cancer in an orthotopic nude mouse model by targeting multiple cell signaling pathways: chemosensitization with capecitabine. Clin Cancer Res. 2012 Sep 15;18(18):4942-53.
Reference 5 UGT1A7 and UGT1A9 polymorphisms predict response and toxicity in colorectal cancer patients treated with capecitabine/irinotecan. Clin Cancer Res. 2005 Feb 1;11(3):1226-36.
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