5'-DEOXY-5-FLUOROCYTIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H12FN3O4
Molecular Weight	245.2077
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=C(F)C(N)=NC2=O

InChI

InChIKey=YSNABXSEHNLERR-ZIYNGMLESA-N

InChI=1S/C9H12FN3O4/c1-3-5(14)6(15)8(17-3)13-2-4(10)7(11)12-9(13)16/h2-3,5-6,8,14-15H,1H3,(H2,11,12,16)/t3-,5-,6-,8-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C9H12FN3O4
Molecular Weight	245.2077
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/xeloda-drug.htm https://www.drugs.com/mtm/capecitabine.html

Capecitabine is a fluoropyrimidine carbamate with antineoplastic activity. It is an orally administered systemic prodrug which is converted to 5-fluorouracil (5-FU). 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’-deoxyuridylate. 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. Most common adverse reactions (≥30%) were diarrhea, hand-and-foot syndrome, nausea, vomiting, abdominal pain, fatigue/weakness, and hyperbilirubinemia. The concentration of 5-fluorouracil is increased and its toxicity may be enhanced by leucovorin.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thymidylate synthase 33 Target ID: CHEMBL1952 Sources: http://www.drugbank.ca/drugs/DB01101 \| http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/16178783 \| https://www.ncbi.nlm.nih.gov/pubmed/1704999 \| https://www.ncbi.nlm.nih.gov/pubmed/25634241 \| https://www.ncbi.nlm.nih.gov/pubmed/8996166	Inhibitor 8504
RNA 19 Target ID: CHEMBL2311222 Sources: http://www.drugbank.ca/drugs/DB01101 \| http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	Interacts 323
Cytidine deaminase 5 Target ID: CHEMBL4502 Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/xeloda-epar-scientific-discussion_en.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/18562256	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Colorectal cancer 102 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	Primary		Approved 8583	XELODA Approved Use Capecitabine tablets, USP are a nucleoside metabolic inhibitor with antineoplastic activity indicated for: • Adjuvant Colon Cancer (1.1) oPatients with Dukes’ C colon cancer • Metastatic Colorectal Cancer (1.1) oFirst-line as monotherapy when treatment with fluoropyrimidine therapy alone is preferred • Metastatic Breast Cancer (1.2) oIn combination with docetaxel after failure of prior anthracycline-containing therapy oAs monotherapy in patients resistant to both paclitaxel and an anthracycline-containing regimen 1.1 Colorectal Cancer •Capecitabine tablets, USP are indicated as a single agent for adjuvant treatment in patients with Dukes’ C colon cancer who have undergone complete resection of the primary tumor when treatment with fluoropyrimidine therapy alone is preferred. Capecitabine was non-inferior to 5-fluorouracil and leucovorin (5-FU/LV) for disease-free survival (DFS). Physicians should consider results of combination chemotherapy trials, which have shown improvement in DFS and OS, when prescribing single-agent capecitabine in the adjuvant treatment of Dukes’ C colon cancer. •Capecitabine tablets are indicated as first-line treatment of patients with metastatic colorectal carcinoma when treatment with fluoropyrimidine therapy alone is preferred. Combination chemotherapy has shown a survival benefit compared to 5-FU/LV alone. A survival benefit over 5-FU/LV has not been demonstrated with capecitabine monotherapy. Use of capecitabine instead of 5-FU/LV in combinations has not been adequately studied to assure safety or preservation of the survival advantage. 1.2 Breast Cancer •Capecitabine tablets, USP in combination with docetaxel are indicated for the treatment of patients with metastatic breast cancer after failure of prior anthracycline-containing chemotherapy. •Capecitabine tablets monotherapy is also indicated for the treatment of patients with metastatic breast cancer resistant to both paclitaxel and an anthracycline-containing chemotherapy regimen or resistant to paclitaxel and for whom further anthracycline therapy is not indicated (e.g., patients who have received cumulative doses of 400 mg/m2 of doxorubicin or doxorubicin equivalents). Resistance is defined as progressive disease while on treatment, with or without an initial response, or relapse within 6 months of completing treatment with an anthracycline-containing adjuvant regimen. Launch Date 1998
Breast cancer 432 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	Primary		Approved 8583	XELODA Approved Use Capecitabine tablets, USP are a nucleoside metabolic inhibitor with antineoplastic activity indicated for: • Adjuvant Colon Cancer (1.1) oPatients with Dukes’ C colon cancer • Metastatic Colorectal Cancer (1.1) oFirst-line as monotherapy when treatment with fluoropyrimidine therapy alone is preferred • Metastatic Breast Cancer (1.2) oIn combination with docetaxel after failure of prior anthracycline-containing therapy oAs monotherapy in patients resistant to both paclitaxel and an anthracycline-containing regimen 1.1 Colorectal Cancer •Capecitabine tablets, USP are indicated as a single agent for adjuvant treatment in patients with Dukes’ C colon cancer who have undergone complete resection of the primary tumor when treatment with fluoropyrimidine therapy alone is preferred. Capecitabine was non-inferior to 5-fluorouracil and leucovorin (5-FU/LV) for disease-free survival (DFS). Physicians should consider results of combination chemotherapy trials, which have shown improvement in DFS and OS, when prescribing single-agent capecitabine in the adjuvant treatment of Dukes’ C colon cancer. •Capecitabine tablets are indicated as first-line treatment of patients with metastatic colorectal carcinoma when treatment with fluoropyrimidine therapy alone is preferred. Combination chemotherapy has shown a survival benefit compared to 5-FU/LV alone. A survival benefit over 5-FU/LV has not been demonstrated with capecitabine monotherapy. Use of capecitabine instead of 5-FU/LV in combinations has not been adequately studied to assure safety or preservation of the survival advantage. 1.2 Breast Cancer •Capecitabine tablets, USP in combination with docetaxel are indicated for the treatment of patients with metastatic breast cancer after failure of prior anthracycline-containing chemotherapy. •Capecitabine tablets monotherapy is also indicated for the treatment of patients with metastatic breast cancer resistant to both paclitaxel and an anthracycline-containing chemotherapy regimen or resistant to paclitaxel and for whom further anthracycline therapy is not indicated (e.g., patients who have received cumulative doses of 400 mg/m2 of doxorubicin or doxorubicin equivalents). Resistance is defined as progressive disease while on treatment, with or without an initial response, or relapse within 6 months of completing treatment with an anthracycline-containing adjuvant regimen. Launch Date 1998

C_max

Value	Dose	Analyte	Population
9105 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022189	1000 mg/m² 2 times / day multiple, oral dose: 1000 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	CAPECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3515 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29948022	1250 mg/m² 2 times / day multiple, oral dose: 1250 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	.ALPHA.-FLUORO-.BETA.-ALANINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
3035 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022189	1000 mg/m² 2 times / day multiple, oral dose: 1000 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	CAPECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
10238 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022189	1000 mg/m² 2 times / day multiple, oral dose: 1000 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	CAPECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
45027 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29948022	1250 mg/m² 2 times / day multiple, oral dose: 1250 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	.ALPHA.-FLUORO-.BETA.-ALANINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
4098 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022189	1000 mg/m² 2 times / day multiple, oral dose: 1000 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	CAPECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
0.75 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	1250 mg/m² 2 times / day multiple, oral dose: 1250 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	CAPECITABINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
0.78 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022189	1000 mg/m² 2 times / day multiple, oral dose: 1000 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	CAPECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
0.74 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24022189	1000 mg/m² 2 times / day multiple, oral dose: 1000 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	CAPECITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
40% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	1250 mg/m² 2 times / day multiple, oral dose: 1250 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:		CAPECITABINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2500 mg 2 times / day multiple, oral Highest studied dose Dose: 2500 mg, 2 times / day Route: oral Route: multiple Dose: 2500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18398145	unhealthy, 34-68 Health Status: unhealthy Age Group: 34-68 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/18398145	DLT: Hand-and-foot syndrome, Diarrhea... Dose limiting toxicities: Hand-and-foot syndrome (grade 3, 28.6%) Diarrhea (grade 3, 14.29%) Sources: https://pubmed.ncbi.nlm.nih.gov/18398145
2000 mg 2 times / day multiple, oral MTD Dose: 2000 mg, 2 times / day Route: oral Route: multiple Dose: 2000 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18398145	unhealthy, 41-53 Health Status: unhealthy Age Group: 41-53 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/18398145	DLT: Hand-and-foot syndrome... Dose limiting toxicities: Hand-and-foot syndrome (grade 3, 14.29%) Sources: https://pubmed.ncbi.nlm.nih.gov/18398145
1250 mg/m2 2 times / day multiple, oral Recommended Dose: 1250 mg/m2, 2 times / day Route: oral Route: multiple Dose: 1250 mg/m2, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	Disc. AE: Coagulopathy, Diarrhea... AEs leading to discontinuation/dose reduction: Coagulopathy Diarrhea Cardiotoxicity Dehydration Renal failure Fetal damage Mucocutaneous disorder (severe) Stevens Johnson syndrome Toxic epidermal necrolysis Hyperbilirubinemia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf

AEs

AE	Significance	Dose	Population
Diarrhea	grade 3, 14.29% DLT	2500 mg 2 times / day multiple, oral Highest studied dose Dose: 2500 mg, 2 times / day Route: oral Route: multiple Dose: 2500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18398145	unhealthy, 34-68 Health Status: unhealthy Age Group: 34-68 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/18398145
Hand-and-foot syndrome	grade 3, 28.6% DLT	2500 mg 2 times / day multiple, oral Highest studied dose Dose: 2500 mg, 2 times / day Route: oral Route: multiple Dose: 2500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18398145	unhealthy, 34-68 Health Status: unhealthy Age Group: 34-68 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/18398145
Hand-and-foot syndrome	grade 3, 14.29% DLT	2000 mg 2 times / day multiple, oral MTD Dose: 2000 mg, 2 times / day Route: oral Route: multiple Dose: 2000 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18398145	unhealthy, 41-53 Health Status: unhealthy Age Group: 41-53 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/18398145
Cardiotoxicity	Disc. AE	1250 mg/m2 2 times / day multiple, oral Recommended Dose: 1250 mg/m2, 2 times / day Route: oral Route: multiple Dose: 1250 mg/m2, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf
Coagulopathy	Disc. AE	1250 mg/m2 2 times / day multiple, oral Recommended Dose: 1250 mg/m2, 2 times / day Route: oral Route: multiple Dose: 1250 mg/m2, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf
Dehydration	Disc. AE	1250 mg/m2 2 times / day multiple, oral Recommended Dose: 1250 mg/m2, 2 times / day Route: oral Route: multiple Dose: 1250 mg/m2, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf
Diarrhea	Disc. AE	1250 mg/m2 2 times / day multiple, oral Recommended Dose: 1250 mg/m2, 2 times / day Route: oral Route: multiple Dose: 1250 mg/m2, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf
Fetal damage	Disc. AE	1250 mg/m2 2 times / day multiple, oral Recommended Dose: 1250 mg/m2, 2 times / day Route: oral Route: multiple Dose: 1250 mg/m2, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf
Hyperbilirubinemia	Disc. AE	1250 mg/m2 2 times / day multiple, oral Recommended Dose: 1250 mg/m2, 2 times / day Route: oral Route: multiple Dose: 1250 mg/m2, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf
Renal failure	Disc. AE	1250 mg/m2 2 times / day multiple, oral Recommended Dose: 1250 mg/m2, 2 times / day Route: oral Route: multiple Dose: 1250 mg/m2, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf
Stevens Johnson syndrome	Disc. AE	1250 mg/m2 2 times / day multiple, oral Recommended Dose: 1250 mg/m2, 2 times / day Route: oral Route: multiple Dose: 1250 mg/m2, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf
Toxic epidermal necrolysis	Disc. AE	1250 mg/m2 2 times / day multiple, oral Recommended Dose: 1250 mg/m2, 2 times / day Route: oral Route: multiple Dose: 1250 mg/m2, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf
Mucocutaneous disorder	severe Disc. AE	1250 mg/m2 2 times / day multiple, oral Recommended Dose: 1250 mg/m2, 2 times / day Route: oral Route: multiple Dose: 1250 mg/m2, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf

PubMed

Title	Date	PubMed
Gene expression predicts differential capecitabine metabolism, impacting on both pharmacokinetics and antitumour activity.	2008-01	18077151
Hydrolysis of capecitabine to 5'-deoxy-5-fluorocytidine by human carboxylesterases and inhibition by loperamide.	2005-06	15687373
Gene expression profiling revealed novel mechanism of action of Taxotere and Furtulon in prostate cancer cells.	2005-01-18	15656911
Capecitabine (Xeloda).	2002-03-20	11899401
Dear doctor: we really are not sure what dose of capecitabine you should prescribe for your patient.	2002-03-15	11896086
Drug combination approved for advanced breast cancer.	2002-03-08	11881602
Xeloda. Warning: drug interaction increase bleeding risks.	2002-03	11902039
The effect of adjuvant 5'-deoxy-5-fluorouridine in early stage breast cancer patients: results from a multicenter randomized controlled trial.	2002-03	11836563
An evolving role for oral fluoropyrimidine drugs.	2002-02-15	11844808
Treatment of patients with superficial bladder cancer by intravesical instillation of anticancer drugs plus oral chemotherapy following TUR-Bt: a randomized controlled trial.	2002-02-12	11836593
Prediction of the response of colorectal cancer to systemic therapy.	2002-02	11902527
Recent development of anti-cancer drugs for treatment of GI malignancies in Japan.	2002-02	11890118
Future treatment options with capecitabine in solid tumours.	2002-02	11841932
Capecitabine as first-line treatment in colorectal cancer. Pooled data from two large, phase III trials.	2002-02	11841931
Clinical experience of capecitabine in metastatic breast cancer.	2002-02	11841930
Rational development of capecitabine.	2002-02	11841929
[The new chemotherapy of colorectal cancers].	2002-01-26	11859739
Dose-escalating study of capecitabine plus gemcitabine combination therapy in patients with advanced cancer.	2002-01-15	11786589
Phase II study of oral capecitabine in patients with advanced or metastatic pancreatic cancer.	2002-01-01	11773165
Taxanes and capecitabine in combination: rationale and clinical results.	2002-01	11899360
Immunohistochemical variation of human equilibrative nucleoside transporter 1 protein in primary breast cancers.	2002-01	11801546
Capecitabine in the treatment of metastatic renal cell carcinoma failing immunotherapy.	2002-01	11774101
Incidence and severity of hand-foot syndrome in colorectal cancer patients treated with capecitabine: a single-institution experience.	2002	11853000
Hand-foot syndrome associated with short infusions of combination chemotherapy with gemcitabine and vinorelbine.	2001-12	11843256
Capecitabine and oxaliplatin in advanced colorectal cancer: a dose-finding study.	2001-12	11843252
Phase I trial of capecitabine in combination with interferon alpha in patients with metastatic renal cancer: toxicity and pharmacokinetics.	2001-12	11800031
Combination chemotherapy of the taxanes and antimetabolites: its use and limitations.	2001-12	11720823
Clinical picture: leopard-like vitiligo with capecitabine.	2001-11-10	11716883
From the Food and Drug Administration.	2001-11-07	11694130
Oral capecitabine compared with intravenous fluorouracil plus leucovorin in patients with metastatic colorectal cancer: results of a large phase III study.	2001-11-01	11689577
Oral versus intravenous fluoropyrimidines for advanced colorectal cancer: by either route, it's all the same.	2001-11-01	11689576
An EORTC phase I study of epirubicin in combination with fixed doses of cyclophosphamide and infusional 5-fu (CEF-infu) as primary treatment of large operable or locally advanced/inflammatory breast cancer.	2001-11	11768362
Acquisition of human concentrative nucleoside transporter 2 (hcnt2) activity by gene transfer confers sensitivity to fluoropyrimidine nucleosides in drug-resistant leukemia cells.	2001-11	11641443
Mucositis as a treatment-limiting side effect in the use of capecitabine for the treatment of metastatic breast cancer.	2001-11	11606938
[New therapeutic options in chemotherapy of advanced colorectal cancer].	2001-10-15	11715331
[Coronary insufficiency after an oral intake of capecitabine].	2001-10-13	11598548
Multicenter, Phase II study of capecitabine in taxane-pretreated metastatic breast carcinoma patients.	2001-10-01	11745247
Nonsurgical treatment of hepatocellular carcinoma.	2001-10	11685743
Recent advances in the use of radiosensitizing nucleosides.	2001-10	11677652
[Recent aspects of palliative treatment of metastasized colorectal carcinoma].	2001-09-15	11603115
Randomized, open-label, phase II trial of oral capecitabine (Xeloda) vs. a reference arm of intravenous CMF (cyclophosphamide, methotrexate and 5-fluorouracil) as first-line therapy for advanced/metastatic breast cancer.	2001-09	11697835
Capecitabine: a novel agent for the treatment of solid tumors.	2001-09	11604550
Capecitabine monotherapy in metastatic colorectal cancer.	2001-07	11905733
Capecitabine in breast cancer: current status.	2001-01	11899351
Investigation of 5-FU disposition after oral administration of capecitabine, a triple-prodrug of 5-FU, using a physiologically based pharmacokinetic model in a human cancer xenograft model: comparison of the simulated 5-FU exposures in the tumour tissue between human and xenograft model.	2001-01	11745902
Use of capecitabine as first-line therapy in patients with metastatic breast cancer relapsing after high-dose chemotherapy and autologous stem cell support.	2001	11824880
Capecitabine: a review of its use in the treatment of advanced or metastatic colorectal cancer.	2001	11772141
Oral fluoropyrimidines: are they the equivalent of parenteral infusional 5-fluorouracil?	2001	11768039
Dose scheduling--Herceptin.	2001	11694785
Disease management considerations: disease management considerations.	2001	11693464

Patents

Sample Use Guides

In Vivo Use Guide

Take XELODA with water within 30 min after a meal. Monotherapy: 1250 mg/m2 twice daily orally for 2 weeks followed by a one week rest period in 3-week cycles.

Route of Administration: Oral

In Vitro Use Guide

After 48 hours treatment of MCF7 cell line with capecitabine, in the concentration of 1147.9 μg/ml 50% of cells have been inhibited. After 72 hours treatment of the cells with capecitabine, at the concentration of 921 μg/ml 50% of cells have been inhibited.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:33:37 GMT 2025` Edited by `admin` on `Mon Mar 31 21:33:37 GMT 2025`
Record UNII	8RWB05I6ON
Record Status	`Validated (UNII)`
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Name

Type

Language

5'-DEOXY-5-FLUOROCYTIDINE

Systematic Name

English

CAPECITABINE RELATED COMPOUND A

Preferred Name

English

CAPECITABINE RELATED COMPOUND A [USP IMPURITY]

Common Name

English

CYTIDINE, 5'-DEOXY-5-FLUORO-

Systematic Name

English

5'-DFCR

Common Name

English

CYTIDINE, 5'-DEOXY-5-FLUORO

Common Name

English

CAPECITABINE RELATED COMPOUND A [USP-RS]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID00216543