Details of the Drug

General Information of Drug (ID: DMTS85L)

Drug 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)

Indication

Disease Entry	ICD 11	Status	REF
Colorectal cancer	2B91.Z	Approved	[1], [2]
Breast cancer	2C60-2C65	Phase 3	[1], [2]

Therapeutic Class

Anticancer Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

359.35

Topological Polar Surface Area (xlogp)

0.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Bioavailability: The bioavailability of drug is 70% [4]
Elimination: 3% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 45 - 60 minutes [5]
Metabolism: The drug is metabolized via thymidine phosphorylase to fluoruracil [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 171.9326 micromolar/kg/day [6]
Water Solubility: The ability of drug to dissolve in water is measured as 26 mg/mL [3]

Chemical Identifiers

Formula: C15H22FN3O6
IUPAC Name: pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate
Canonical SMILES: CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@H]2[C@@H]([C@@H]([C@H](O2)C)O)O
InChI: 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

Cross-matching ID

PubChem CID: 60953
ChEBI ID: CHEBI:31348
CAS Number: 154361-50-9
DrugBank ID: DB01101
TTD ID: D00HCQ
VARIDT ID: DR00380
INTEDE ID: DR0266
ACDINA ID: D00095

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Candida Thymidylate synthase (Candi TMP1)	TTU6BFZ	TYSY_CANAL	Inhibitor	[7]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytidine aminohydrolase (CDA)	DEKEDRC	CDD_HUMAN	Substrate	[8]
Thymidine phosphorylase (TYMP)	DE4HCYL	TYPH_HUMAN	Substrate	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Capecitabine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Roflumilast	DMPGHY8	Moderate	Additive immunosuppressive effects by the combination of Capecitabine and Roflumilast.	Asthma [CA23]	[28]
Ofloxacin	DM0VQN3	Minor	Decreased absorption of Capecitabine due to intestinal mucosa variation caused by Ofloxacin.	Bacterial infection [1A00-1C4Z]	[29]
Sparfloxacin	DMB4HCT	Minor	Decreased absorption of Capecitabine due to intestinal mucosa variation caused by Sparfloxacin.	Bacterial infection [1A00-1C4Z]	[29]
Gemifloxacin	DMHT34O	Minor	Decreased absorption of Capecitabine due to intestinal mucosa variation caused by Gemifloxacin.	Bacterial infection [1A00-1C4Z]	[29]
ABT-492	DMJFD2I	Minor	Decreased absorption of Capecitabine due to intestinal mucosa variation caused by ABT-492.	Bacterial infection [1A00-1C4Z]	[29]
Levofloxacin	DMS60RB	Minor	Decreased absorption of Capecitabine due to intestinal mucosa variation caused by Levofloxacin.	Bacterial infection [1A00-1C4Z]	[29]
Nefazodone	DM4ZS8M	Moderate	Decreased metabolism of Capecitabine caused by Nefazodone mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[30]
Teriflunomide	DMQ2FKJ	Major	Additive myelosuppressive effects by the combination of Capecitabine and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[31]
Denosumab	DMNI0KO	Moderate	Additive myelosuppressive effects by the combination of Capecitabine and Denosumab.	Low bone mass disorder [FB83]	[32]
Tecfidera	DM2OVDT	Moderate	Additive immunosuppressive effects by the combination of Capecitabine and Tecfidera.	Multiple sclerosis [8A40]	[33]
Fingolimod	DM5JVAN	Major	Additive immunosuppressive effects by the combination of Capecitabine and Fingolimod.	Multiple sclerosis [8A40]	[34]
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Capecitabine and Ocrelizumab.	Multiple sclerosis [8A40]	[35]
Ozanimod	DMT6AM2	Major	Additive immunosuppressive effects by the combination of Capecitabine and Ozanimod.	Multiple sclerosis [8A40]	[28]
Omacetaxine mepesuccinate	DMPU2WX	Moderate	Additive immunosuppressive effects by the combination of Capecitabine and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[36]
Canakinumab	DM8HLO5	Moderate	Additive immunosuppressive effects by the combination of Capecitabine and Canakinumab.	Rheumatoid arthritis [FA20]	[37]
Rilonacept	DMGLUQS	Moderate	Additive immunosuppressive effects by the combination of Capecitabine and Rilonacept.	Rheumatoid arthritis [FA20]	[37]
Golimumab	DMHZV7X	Major	Additive immunosuppressive effects by the combination of Capecitabine and Golimumab.	Rheumatoid arthritis [FA20]	[38]
Anthrax vaccine	DM9GSWY	Moderate	Antagonize the effect of Capecitabine when combined with Anthrax vaccine.	Sepsis [1G40-1G41]	[39]
Valganciclovir	DMS2IUH	Moderate	Additive myelosuppressive effects by the combination of Capecitabine and Valganciclovir.	Virus infection [1A24-1D9Z]	[40]
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⏷ Show the Full List of 19 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Carmellose sodium	E00625	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Hypromellose	E00634	Not Available	Coating agent
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 1000	E00647	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
Water	E00035	962	Solvent
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⏷ Show the Full List of 14 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Capecitabine 150 mg tablet	150 mg	Oral Tablet	Oral
Capecitabine 500 mg tablet	500 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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9	Induction of thymidine phosphorylase in both irradiated and shielded, contralateral human U87MG glioma xenografts: implications for a dual modality treatment using capecitabine and irradiation. Mol Cancer Ther. 2002 Oct;1(12):1139-45.
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13	Tracking decitabine incorporation into malignant myeloid cell DNA in vitro and in vivo by LC-MS/MS with enzymatic digestion. Sci Rep. 2019 Mar 14;9(1):4558.
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22	DNA damage and homologous recombination signaling induced by thymidylate deprivation. Biochem Pharmacol. 2008 Oct 15;76(8):987-96.
23	Antisense down-regulation of thymidylate synthase to suppress growth and enhance cytotoxicity of 5-FUdR, 5-FU and Tomudex in HeLa cells. Br J Pharmacol. 1999 Aug;127(8):1777-86.
24	Decreased levels of UMP kinase as a mechanism of fluoropyrimidine resistance. Mol Cancer Ther. 2009 May;8(5):1037-44.
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27	Cooperative inhibition of human thymidylate synthase by mixtures of active site binding and allosteric inhibitors. Biochemistry. 2007 Mar 13;46(10):2823-30.
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30	Product Information. Serzone (nefazodone). Bristol-Myers Squibb, Princeton, NJ.
31	Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.
32	Product Information. Prolia (denosumab). Amgen USA, Thousand Oaks, CA.
33	Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA.
34	Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
35	Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
36	Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
37	Product Information. Arcalyst (rilonacept). Regeneron Pharmaceuticals Inc, Tarrytown, NY.
38	Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA.
39	CDC. Centers for Disease Control and Prevention/ "Recommendations of the advisory committtee on immunization practices (ACIP): use of vaccines and immune globulins in persons with altered immunocompetence." MMWR Morb Mortal Wkly Rep 42(RR-04) (1993): 1-18. [PMID: 20300058]
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