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 32 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 8297
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 101 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	Primary		Approved 8429	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 434 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf	Primary		Approved 8429	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	Co-administered	Analyte	Population
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 blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
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 blood	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
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 blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
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 blood	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
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 blood	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
65% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf			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 Page: p.1799	unhealthy, 34-68 n = 7 Health Status: unhealthy Condition: Breast cancer Age Group: 34-68 Sex: F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/18398145 Page: p.1799	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 Page: p.1799
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 Page: p.1799	unhealthy, 41-53 n = 7 Health Status: unhealthy Condition: Breast cancer Age Group: 41-53 Sex: F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/18398145 Page: p.1799	DLT: Hand-and-foot syndrome... Dose limiting toxicities: Hand-and-foot syndrome (grade 3, 14.29%) Sources: https://pubmed.ncbi.nlm.nih.gov/18398145 Page: p.1799
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Adjuv ant Colon Cancer\|Metastatic Colorectal Cancer\|Metastatic Breast Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf Page: p.1	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 Page: p.1

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 Page: p.1799	unhealthy, 34-68 n = 7 Health Status: unhealthy Condition: Breast cancer Age Group: 34-68 Sex: F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/18398145 Page: p.1799
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 Page: p.1799	unhealthy, 34-68 n = 7 Health Status: unhealthy Condition: Breast cancer Age Group: 34-68 Sex: F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/18398145 Page: p.1799
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 Page: p.1799	unhealthy, 41-53 n = 7 Health Status: unhealthy Condition: Breast cancer Age Group: 41-53 Sex: F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/18398145 Page: p.1799
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Adjuv ant Colon Cancer\|Metastatic Colorectal Cancer\|Metastatic Breast Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Adjuv ant Colon Cancer\|Metastatic Colorectal Cancer\|Metastatic Breast Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Adjuv ant Colon Cancer\|Metastatic Colorectal Cancer\|Metastatic Breast Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Adjuv ant Colon Cancer\|Metastatic Colorectal Cancer\|Metastatic Breast Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Adjuv ant Colon Cancer\|Metastatic Colorectal Cancer\|Metastatic Breast Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Adjuv ant Colon Cancer\|Metastatic Colorectal Cancer\|Metastatic Breast Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Adjuv ant Colon Cancer\|Metastatic Colorectal Cancer\|Metastatic Breast Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Adjuv ant Colon Cancer\|Metastatic Colorectal Cancer\|Metastatic Breast Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Adjuv ant Colon Cancer\|Metastatic Colorectal Cancer\|Metastatic Breast Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Adjuv ant Colon Cancer\|Metastatic Colorectal Cancer\|Metastatic Breast Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020896s037lbl.pdf Page: p.1

PubMed

Title	Date	PubMed
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
Improving chemoradiotherapy in rectal cancer.	2001	11585972
Integrating oxaliplatin into the management of colorectal cancer.	2001	11585971
Optimizing the use of irinotecan in colorectal cancer.	2001	11585970
Answering patients' needs: oral alternatives to intravenous therapy.	2001	11585969
The evolution of fluoropyrimidine therapy: from intravenous to oral.	2001	11585968
Thymidine phosphorylase (TP) activation: convenience through innovation.	2001	11585967
[Capecitabine (Ro09-1978) for therapy of advanced and recurrent gastric cancer].	2001 Apr	11424414
Metastatic breast cancer: understanding current management options.	2001 Apr	11338758
A physiologically based pharmacokinetic analysis of capecitabine, a triple prodrug of 5-FU, in humans: the mechanism for tumor-selective accumulation of 5-FU.	2001 Aug	11587492
Capecitabine for 5-fluorouracil-resistant brain metastases from breast cancer.	2001 Aug	11474279
[Coronary insufficiency after an oral intake of capecitabine].	2001 Aug-Sep	11598548
Capecitabine and oxaliplatin in advanced colorectal cancer: a dose-finding study.	2001 Dec	11843252
Combination chemotherapy of the taxanes and antimetabolites: its use and limitations.	2001 Dec	11720823
Capecitabine in breast cancer: current status.	2001 Jan	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 Jan	11745902
Capecitabine (Xeloda).	2001 Jan-Feb	11899401
Capecitabine monotherapy in metastatic colorectal cancer.	2001 Jul	11905733
New chemotherapy approaches in colorectal cancer.	2001 Jul	11429486
Thymidine phosphorylase expression and effect of doxifluridine: a phase II study.	2001 Jul-Aug	11410777
[Tumoral levels of thymidine phosphorylase and dihydropyrimidine dehydrogenase in elderly colorectal cancer patients].	2001 Jun	11432349
Role of the human concentrative nucleoside transporter (hCNT1) in the cytotoxic action of 5[Prime]-deoxy-5-fluorouridine, an active intermediate metabolite of capecitabine, a novel oral anticancer drug.	2001 Jun	11353816
A phase I and pharmacologic study of capecitabine and paclitaxel in breast cancer patients.	2001 May	11432617
Acute cardiotoxicity during capecitabine treatment: a case report.	2001 May-Jun	11504378
Mucositis as a treatment-limiting side effect in the use of capecitabine for the treatment of metastatic breast cancer.	2001 Nov	11606938
Clinical picture: leopard-like vitiligo with capecitabine.	2001 Nov 10	11716883
From the Food and Drug Administration.	2001 Nov 7	11694130
Recent advances in the use of radiosensitizing nucleosides.	2001 Oct	11677652
Multicenter, Phase II study of capecitabine in taxane-pretreated metastatic breast carcinoma patients.	2001 Oct 1	11745247
[New therapeutic options in chemotherapy of advanced colorectal cancer].	2001 Oct 15	11715331
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 Sep	11697835
Capecitabine: a novel agent for the treatment of solid tumors.	2001 Sep	11604550
Onychomadesis and onycholysis associated with capecitabine.	2001 Sep	11531857
Role of thymidine phosphorylase in biomodulation of fluoropyrimidines.	2001 Sep	11530879
A randomized study comparing oral and standard regimens for metastatic breast cancer.	2001 Sep-Oct	11496318
Incidence and severity of hand-foot syndrome in colorectal cancer patients treated with capecitabine: a single-institution experience.	2002	11853000
Prediction of the response of colorectal cancer to systemic therapy.	2002 Feb	11902527
Recent development of anti-cancer drugs for treatment of GI malignancies in Japan.	2002 Feb	11890118
Capecitabine as first-line treatment in colorectal cancer. Pooled data from two large, phase III trials.	2002 Feb	11841931
Clinical experience of capecitabine in metastatic breast cancer.	2002 Feb	11841930
Rational development of capecitabine.	2002 Feb	11841929
An evolving role for oral fluoropyrimidine drugs.	2002 Feb 15	11844808
Taxanes and capecitabine in combination: rationale and clinical results.	2002 Jan	11899360
Immunohistochemical variation of human equilibrative nucleoside transporter 1 protein in primary breast cancers.	2002 Jan	11801546
Xeloda. Warning: drug interaction increase bleeding risks.	2002 Mar	11902039
The effect of adjuvant 5'-deoxy-5-fluorouridine in early stage breast cancer patients: results from a multicenter randomized controlled trial.	2002 Mar	11836563
Dear doctor: we really are not sure what dose of capecitabine you should prescribe for your patient.	2002 Mar 15	11896086
Treatment of patients with superficial bladder cancer by intravesical instillation of anticancer drugs plus oral chemotherapy following TUR-Bt: a randomized controlled trial.	2002 Mar-Apr	11836593

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 `Sat Dec 16 05:50:24 GMT 2023` Edited by `admin` on `Sat Dec 16 05:50:24 GMT 2023`
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 [USP IMPURITY]

Common Name

English

CYTIDINE, 5'-DEOXY-5-FLUORO-

Systematic Name

English

5'-DFCR

Common Name

English

CAPECITABINE RELATED COMPOUND A

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