Capecitabine (CED0001420)

Record Information

Version

1.0

Creation Date

2009-07-30 17:58:54 UTC

Update Date

2026-05-14 16:57:50 UTC

SynCED ID

CED0001420

Secondary Accession Numbers

CHEM002517
T3D3507

Identification

Common Name

Capecitabine

Class

Small Molecule

Description

Capecitabine is an exogenous organic compound with the formula C15H22FN3O6 and an average molecular weight of 359.35 g/mol. It exists as a solid at room temperature. Capecitabine belongs to the 5'-deoxyribonucleosides, a class of nucleosides, nucleotides, and analogues within the organic compounds. It is used as an antineoplastic agent and functions as a prodrug and biological antimetabolite. The recorded exposure route for this compound is oral. It has been found in healthcare, pharmaceuticals and veterinary products (antineoplastic agents), electrical and electronic equipment (power cables and electrically stimulated smoking devices), and household cleaning and consumer products (non electric simulated smoking devices). As a prodrug, capecitabine is selectively tumour-activated to its cytotoxic moiety, fluorouracil, by thymidine phosphorylase. Fluorouracil is further metabolized within normal and tumour cells to two active metabolites: 5-fluorouridine triphosphate (FUTP) and 5-fluoro-2-deoxyuridine monophosphate (FdUMP). FUTP inhibits protein and RNA synthesis by competing with uridine triphosphate, while FdUMP inhibits DNA synthesis by reducing normal thymidine production. Recorded protein targets include Dihydropyrimidine dehydrogenase [NADP(+)] (DPYD) and Thymidylate synthase (TYMS), for which capecitabine acts as an inhibitor of Thymidylate synthase (TMP1).

Contaminant Type

Amine
Antimetabolite
Antimetabolite, Antineoplastic
Antineoplastic Agent
Drug
Ester
Ether
Human Neurotoxin
Metabolite
Organic Compound
Organofluoride
Prodrug
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl ester	ChEBI
Capecitabin	ChEBI
Capecitabina	ChEBI
Capecitabinum	ChEBI
Pentyl 1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate	ChEBI
Pentyl [1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate	ChEBI
Xeloda	ChEBI
(1-(5-Deoxy-b-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamate pentyl ester	Generator
(1-(5-Deoxy-b-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl ester	Generator
(1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamate pentyl ester	Generator
(1-(5-Deoxy-β-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamate pentyl ester	Generator
(1-(5-Deoxy-β-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl ester	Generator
Pentyl 1-(5-deoxy-b-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate	Generator
Pentyl 1-(5-deoxy-b-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamic acid	Generator
Pentyl 1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamic acid	Generator
Pentyl 1-(5-deoxy-β-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate	Generator
Pentyl 1-(5-deoxy-β-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamic acid	Generator
Pentyl [1-(5-deoxy-b-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate	Generator
Pentyl [1-(5-deoxy-b-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamic acid	Generator
Pentyl [1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamic acid	Generator
Pentyl [1-(5-deoxy-β-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate	Generator
Pentyl [1-(5-deoxy-β-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamic acid	Generator
R340	HMDB
N(4)-Pentyloxycarbonyl-5'-deoxy-5-fluorocytidine	HMDB

Chemical Formula

C₁₅H₂₂FN₃O₆

Average Molecular Mass

359.350 g/mol

Monoisotopic Mass

359.149 g/mol

CAS Registry Number

154361-50-9

IUPAC Name

pentyl N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate

Traditional Name

capecitabine

SMILES

CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@@H]1O[C@H](C)[C@@H](O)[C@H]1O

InChI Identifier

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

InChI Key

GAGWJHPBXLXJQN-UORFTKCHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5'-deoxyribonucleosides. These are nucleosides in which the oxygen atom at the 5'position of the ribose moiety has been replaced by another atom. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

5'-deoxyribonucleosides

Sub Class

Not Available

Direct Parent

5'-deoxyribonucleosides

Alternative Parents

Substituents

5'-deoxyribonucleoside
Glycosyl compound
N-glycosyl compound
Halopyrimidine
Pyrimidone
Aryl fluoride
Aryl halide
Pyrimidine
Hydropyrimidine
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Organopnictogen compound
Organohalogen compound
Organofluoride
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:31348 )
carbamate ester (CHEBI:31348 )
cytidines (CHEBI:31348 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

antimetabolite (PMC9165247 )?A chemical that inhibits the use of a metabolite, which is another chemical that is part of normal metabolism
prodrug (PMC12121898 , PMC3397678 )?
antineoplastic agent (PMC7380718 )?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	110-121°C
Boiling Point	Not Available
Solubility	26 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.77	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.23	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	120.69 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	82.75 m³·mol⁻¹	ChemAxon
Polarizability	35.81 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0ab9-9112000000-35a3e944454fc6eca103	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0079-9502500000-bb4d3c6463fb0a87a997	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0109000000-c0c4de3c4233af3f34d4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0901000000-676f6925c6c255f4dd24	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-236cb917e50b215b9bd1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-1900000000-f06b7309e7a2ebfb3bde	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ufr-3900000000-6bb1981f61b4205a9991	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0kdi-6900000000-ac9a56401938b72ae4f1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0309000000-feac9f5163221adf2a7d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udj-0912000000-258b837e7c98d16aafbf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-db3e2d6a5526611d6a6e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-b792e6750d1eaccca7aa	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0pb9-0609000000-cd05885e7f4f8d1853ec	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0090000000-8029f6bc09ef7062240e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006x-0590000000-8cea6a9f156f58ccb593	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00e9-0920000000-e942daf2b25f1829bec1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0089-0900000000-2a5dcf8bb6ff7ae6d72f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-460a3e3f1f8b25687c86	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0090000000-6105bf5c619fbe72100a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-af842efa254483370f53	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-1900000000-61c84595e7254f9493c9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-25912e0277815dec7dfc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-f992985efa9f7da2dbba	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0090000000-6ec0fa0ed4f779ff959a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0090000000-3be9f054ad6d351dfcda	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-007o-0960000000-eeaa7c678c405b7f7e1f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0912000000-be45a1fa8c22b36a6c60	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-5e93922774dd269cf218	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0109000000-ff9395434207210d1694	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-c7a3925ff6235bc70416	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0090000000-75be93b6d98e065948a6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006x-0590000000-8cea6a9f156f58ccb593	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0089-0900000000-ee8d83cc7a0bb466949c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00e9-0920000000-3e79c1a44fafdca630ad	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-be8d28ce79156e7077ef	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0090000000-697882779d5d2e581742	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-007o-0960000000-a5afd133d5ad6a4d6ea9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0109000000-8ff7496a20ae8c8dc7ba	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-1900000000-da2f22c77e17b085111b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0090000000-7fe9f3c6b8aeb0249328	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ufr-3900000000-e4d8de17496da9bfc7af	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udj-0912000000-258b837e7c98d16aafbf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0309000000-feac9f5163221adf2a7d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0pb9-0609000000-d19b0a9e32c67579452c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-4e770954bc6b3311a5ec	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-b792e6750d1eaccca7aa	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-db3e2d6a5526611d6a6e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0901000000-5bdf57459c9182f5560a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-f64ccb69437fbc037e3b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-2090000000-4b8cf489e15586dfdae8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-5390000000-679252cae00158da4c5a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0096-9250000000-13f9259c8bd82a744463	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006y-2792000000-3a1107d332a241bc2b9d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f6x-3691000000-15dcc8cfd9d6e268fa7e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0076-7950000000-99f8f0926e3b4607c61b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0191000000-c7667e326d5d3d120fd2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-1931000000-ae681a3f65c2e431c6e7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a5c-4930000000-f4af491edf1508725146	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0319000000-53ef230fdcdaff5a98b2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-1931000000-5369ff2bd32dfd8be11e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004l-5930000000-ec9e61270c86d4df55ab	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2563.0 Log mg/kg [1400:4600]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Capecitabine is a prodrug that is selectively tumour-activated to its cytotoxic moiety, fluorouracil, by thymidine phosphorylase. Fluorouracil is further metabolized to two active metabolites, 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP), within normal and tumour cells. FdUMP inhibits DNA synthesis by reducing normal thymidine production, while FUTP inhibits RNA and protein synthesis by competing with uridine triphosphate.3 The active moiety of capecitabine, fluorouracil, is cell cycle phase-specific (Sphase). Both normal and tumor cells metabolize 5-FU to 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP). These metabolites cause cell injury by two different mechanisms. First, FdUMP and the folate cofactor, N5-10-methylenetetrahydrofolate, bind to thymidylate synthase (TS) to form a covalently bound ternary complex. This binding inhibits the formation of thymidylate from 2'-deaxyuridylate. Thymidylate is the necessary precursor of thymidine triphosphate, which is essential for the synthesis of DNA, so that a deficiency of this compound can inhibit cell division. Second nuclear transcriptional enzymes can mistakenly incorporate FUTP in place of uridine triphosphate (UTP) during the synthesis of RNA. This metabolic error can interfere with RNA processing and protein synthesis.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
cancer	Not Available	Not Available	Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. Possible signs and symptoms include a lump, abnormal bleeding, prolonged cough, unexplained weight loss, and a change in bowel movements. There are over 100 types of cancers affect humans. The risk of developing certain cancers can be reduced by not smoking, maintaining a healthy weight, not drinking too much alcohol, eating plenty of vegetables, fruits and whole grains, vaccination against certain infectious diseases, not eating too much processed and red meat and avoiding too much sunlight exposure. Cancer is often treated with some combination of radiation therapy, surgery, chemotherapy and targeted therapy. The majority of cancers, some 90–95% of cases, are due to genetic mutations from environmental and lifestyle factors. The remaining 5–10% are due to inherited genetics.	PMC7248840 , PMC12580929
breast cancer	Not Available	Not Available	A breast cancer that has material basis in abnormally proliferating cells derives from epithelial cells. (DO)	PMC13319688 , PMC3897212
ovarian cancer	Not Available	Not Available	A female reproductive organ cancer that is located in the ovary. (DO)	PMC12067445
breast	Not Available	Not Available	Not Available	PMC12430546
pancreatic cancer	Not Available	Not Available	An endocrine gland cancer located in the pancreas. (DO)	PMC12430546 , PMC8399040
metastatic neoplasm	Associated With?	Not Available	Not Available	PMC8091793
bilirubin metabolic disorder	Associated With?	increase	Not Available	PMC7123643
small cell lung carcinoma	Not Available	Not Available	Not Available	PMC12067445

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000181	Ballast water?Ballast water, taken on by ships to maintain stability and balance, often contains a diverse array of microorganisms, including bacteria, viruses, and plankton.	Marine, shipping & aquaculture	PubChem
CEDs000182	Bilge water?Bilge water is a byproduct generated from the accumulation of water in the lowest part of a ship's hull, which may include a mixture of seawater, oil, fuel residues, and various contaminants.	Marine, shipping & aquaculture	PubChem
CEDs000358	Antineoplastic agents?Antineoplastic agents are a class of synthetic chemicals used primarily in the treatment of cancer.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000529	Power Cables?Power cables are used to transmit electrical energy and are typically composed of conductive materials, insulation, and protective coatings.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000561	Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.	Household cleaning & consumer products	PubChem
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
CEDs000667	Gaseous Fire Fighting?Gaseous fire fighting systems utilize synthetic chemicals, such as halocarbons and inert gases, to suppress fires through chemical and physical processes.	Fire suppression systems & agents	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000673	Unmanned Aerial Vehicles?Unmanned Aerial Vehicles (UAVs), commonly known as drones, utilize various synthetic chemicals in their manufacturing, operation, and maintenance processes.	Aviation & Aerospace	PubChem
CEDs000684	Cements?Cements are a composite material primarily used as a binding agent in construction applications, formed by the calcination of limestone and clay minerals at high temperatures.	Building & Construction	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000688	Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.	Building & Construction	PubChem
CEDs000692	Silica Free Oxide Glass?Silica Free Oxide Glass is a type of glass that is produced using alternative materials to traditional silica-based formulations.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000732	Spectacle Cases?Spectacle cases can serve as a source of synthetic chemical contamination due to the materials used in their production, such as polycarbonate, PVC, and various plastics, which may leach harmful substances over time.	Healthcare, pharmaceuticals & veterinary products	PubChem
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem
CEDs02255	Water	Aquatic systems & sediments	PMC10579118
CEDs03079	Secondary Effluent	Wastewater, sanitation & biosolids	PMC9412706

Pathways

6 pathwaysPathway Source: PathBank

Capecitabine Action Pathway

Capecitabine Metabolism Pathway

Fluorouracil Metabolism

Capecitabine Action Pathway (New)

Capecitabine Drug Metabolism Action Pathway

Capecitabine Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytidine deaminase	P0ABF6	Escherichia coli (strain K12)	Known	Not Available
Click to view 3D structure	Thymidine phosphorylase	P07650	Escherichia coli (strain K12)	Known	Not Available
Click to view 3D structure	Thymidine kinase	P0C0E6	HHV-3	Predicted (SEA)	Prediction Confidence Score 0.321 Applicability Domain 0.321 Statistical Significance 3.00e-05 Supporting Reference Compounds 1 E-value 0.233548
Click to view 3D structure	Cell division protein FtsZ	P9WN95	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	Prediction Confidence Score 0.289 Applicability Domain 0.289 Low confidence Statistical Significance 1.80e-04 Supporting Reference Compounds 1 E-value 1.40129
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	Prediction Confidence Score 0.277 Applicability Domain 0.3 Statistical Significance 0.0493 Supporting Reference Compounds 391 E-value 383.719
Click to view 3D structure	Adenosine receptor A2a	P30543	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.273 Applicability Domain 0.3 Statistical Significance 0.0244 Supporting Reference Compounds 174 E-value 190.03
Click to view 3D structure	Adenosine receptor A3	P28647	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.268 Applicability Domain 0.3 Statistical Significance 0.0119 Supporting Reference Compounds 71 E-value 92.7184
Click to view 3D structure	Genome polyprotein	P03300	Poliovirus type 1 (strain Mahoney)	Predicted (SEA)	Prediction Confidence Score 0.267 Applicability Domain 0.267 Low confidence Statistical Significance 0.0017 Supporting Reference Compounds 1 E-value 13.0787
Click to view 3D structure	2-oxoglutarate receptor 1	Q6Y1R5	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.266 Applicability Domain 0.296 Low confidence Statistical Significance 0.0049 Supporting Reference Compounds 11 E-value 38.1461
Click to view 3D structure	Adenosine receptor A1	P25099	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.263 Applicability Domain 0.296 Low confidence Statistical Significance 0.0367 Supporting Reference Compounds 221 E-value 285.473
Click to view 3D structure	Long-chain-fatty-acid--AMP ligase FadD28	P9WQ59	Mycobacterium tuberculosis	Predicted (SEA)	Prediction Confidence Score 0.257 Applicability Domain 0.278 Low confidence Statistical Significance 0.005 Supporting Reference Compounds 2 E-value 38.6132
Click to view 3D structure	Adenosine receptor A2a	P29274	Humans	Predicted (SEA)	Prediction Confidence Score 0.256 Applicability Domain 0.271 Low confidence Statistical Significance 0.0804 Supporting Reference Compounds 303 E-value 625.752
Click to view 3D structure	Adenosine receptor A1	P30542	Humans	Predicted (SEA)	Prediction Confidence Score 0.256 Applicability Domain 0.271 Low confidence Statistical Significance 0.0688 Supporting Reference Compounds 302 E-value 535.447
Click to view 3D structure	4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	P62615	Escherichia coli (strain K12)	Predicted (SEA)	Prediction Confidence Score 0.253 Applicability Domain 0.253 Low confidence Statistical Significance 0.0013 Supporting Reference Compounds 1 E-value 10.3539
Click to view 3D structure	Medium/long-chain-fatty-acid--CoA/3-oxocholest-4-en-26-oate--CoA ligase	P9WQ51	Mycobacterium tuberculosis	Predicted (SEA)	Prediction Confidence Score 0.251 Applicability Domain 0.278 Low confidence Statistical Significance 0.005 Supporting Reference Compounds 2 E-value 39.236
Click to view 3D structure	Tyrosine--tRNA ligase	P0AGJ9	Escherichia coli (strain K12)	Predicted (SEA)	Prediction Confidence Score 0.25 Applicability Domain 0.25 Low confidence Statistical Significance 0.0023 Supporting Reference Compounds 1 E-value 17.7496
Click to view 3D structure	Endoplasmin	Q29092	Sus scrofa	Predicted (SEA)	Prediction Confidence Score 0.25 Applicability Domain 0.25 Low confidence Statistical Significance 0.0054 Supporting Reference Compounds 1 E-value 41.7272
Click to view 3D structure	Acid ceramidase	Q6P7S1	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.249 Applicability Domain 0.282 Low confidence Statistical Significance 0.0024 Supporting Reference Compounds 10 E-value 18.606
Click to view 3D structure	Histamine H3 receptor	Q9QYN8	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.248 Applicability Domain 0.267 Low confidence Statistical Significance 0.037 Supporting Reference Compounds 80 E-value 287.886
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.247 Applicability Domain 0.271 Low confidence Statistical Significance 0.3269 Supporting Reference Compounds 955 E-value 2544.74
Click to view 3D structure	UDP-3-O-acyl-N-acetylglucosamine deacetylase	O67648	Aquifex aeolicus (strain VF5)	Predicted (SEA)	Prediction Confidence Score 0.246 Applicability Domain 0.246 Low confidence Statistical Significance 0.0147 Supporting Reference Compounds 1 E-value 114.127
Click to view 3D structure	P2Y purinoceptor 6	Q15077	Humans	Predicted (SEA)	Prediction Confidence Score 0.244 Applicability Domain 0.282 Low confidence Statistical Significance 0.0048 Supporting Reference Compounds 38 E-value 37.3676
Click to view 3D structure	Histamine H2 receptor	P47747	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.244 Applicability Domain 0.26 Low confidence Statistical Significance 0.0136 Supporting Reference Compounds 45 E-value 106.264
Click to view 3D structure	Fatty-acid amide hydrolase 1	P97612	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.242 Applicability Domain 0.282 Low confidence Statistical Significance 0.0689 Supporting Reference Compounds 102 E-value 536.693
Click to view 3D structure	P-selectin	Q01102	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.241 Applicability Domain 0.241 Low confidence Statistical Significance 7.50e-04 Supporting Reference Compounds 3 E-value 5.83869
Click to view 3D structure	E-selectin	Q00690	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.241 Applicability Domain 0.241 Low confidence Statistical Significance 7.50e-04 Supporting Reference Compounds 1 E-value 5.83869
Click to view 3D structure	L-selectin	P18337	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.241 Applicability Domain 0.241 Low confidence Statistical Significance 7.50e-04 Supporting Reference Compounds 2 E-value 5.83869
Click to view 3D structure	Dihydropyrimidine dehydrogenase [NADP(+)]	Q12882	Humans	Known	Capecitabine is a prodrug that is selectively tumour-activated to its cytotoxic moiety, fluorouracil, by thymidine phosphorylase. Fluorouracil is further metabolized to two active metabolites, 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP), within normal and tumour cells. FdUMP inhibits DNA synthesis by reducing normal thymidine production, while FUTP inhibits RNA and protein synthesis by competing with uridine triphosphate.3 The active moiety of capecitabine, fluorouracil, is cell cycle phase-specific (Sphase). Both normal and tumor cells metabolize 5-FU to 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP). These metabolites cause cell injury by two different mechanisms. First, FdUMP and the folate cofactor, N5-10-methylenetetrahydrofolate, bind to thymidylate synthase (TS) to form a covalently bound ternary complex. This binding inhibits the formation of thymidylate from 2'-deaxyuridylate. Thymidylate is the necessary precursor of thymidine triphosphate, which is essential for the synthesis of DNA, so that a deficiency of this compound can inhibit cell division. Second nuclear transcriptional enzymes can mistakenly incorporate FUTP in place of uridine triphosphate (UTP) during the synthesis of RNA. This metabolic error can interfere with RNA processing and protein synthesis.
Click to view 3D structure	Thymidylate synthase	P04818	Humans	Known	Capecitabine is a prodrug that is selectively tumour-activated to its cytotoxic moiety, fluorouracil, by thymidine phosphorylase. Fluorouracil is further metabolized to two active metabolites, 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP), within normal and tumour cells. FdUMP inhibits DNA synthesis by reducing normal thymidine production, while FUTP inhibits RNA and protein synthesis by competing with uridine triphosphate.3 The active moiety of capecitabine, fluorouracil, is cell cycle phase-specific (Sphase). Both normal and tumor cells metabolize 5-FU to 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP). These metabolites cause cell injury by two different mechanisms. First, FdUMP and the folate cofactor, N5-10-methylenetetrahydrofolate, bind to thymidylate synthase (TS) to form a covalently bound ternary complex. This binding inhibits the formation of thymidylate from 2'-deaxyuridylate. Thymidylate is the necessary precursor of thymidine triphosphate, which is essential for the synthesis of DNA, so that a deficiency of this compound can inhibit cell division. Second nuclear transcriptional enzymes can mistakenly incorporate FUTP in place of uridine triphosphate (UTP) during the synthesis of RNA. This metabolic error can interfere with RNA processing and protein synthesis.

Concentrations

Not Available

External Links

DrugBank ID

DB01101

HMDB ID

HMDB0015233

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

DrugSyn.org

MSDS

Not Available

General References

de Bono JS, Twelves CJ: The oral fluorinated pyrimidines. Invest New Drugs. 2001;19(1):41-59. [PubMed: 11291832]
Walko CM, Lindley C: Capecitabine: a review. Clin Ther. 2005 Jan;27(1):23-44. [PubMed: 15763604]
Wagstaff AJ, Ibbotson T, Goa KL: Capecitabine: a review of its pharmacology and therapeutic efficacy in the management of advanced breast cancer. Drugs. 2003;63(2):217-36. [PubMed: 12515569]
Koukourakis GV, Kouloulias V, Koukourakis MJ, Zacharias GA, Zabatis H, Kouvaris J: Efficacy of the oral fluorouracil pro-drug capecitabine in cancer treatment: a review. Molecules. 2008 Aug 27;13(8):1897-922. [PubMed: 18794792]
Twelves C: Vision of the future: capecitabine. Oncologist. 2001;6 Suppl 4:35-9. [PubMed: 11585973]
Milano G, Ferrero JM, Francois E: Comparative pharmacology of oral fluoropyrimidines: a focus on pharmacokinetics, pharmacodynamics and pharmacomodulation. Br J Cancer. 2004 Aug 16;91(4):613-7. [PubMed: 15280932]
Drugs.com - http://www.drugs.com/cons/Capecitabine.html

Capecitabine (CED0001420)

Structure for CHEM002517: Capecitabine

Structure