Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H22FN3O6 |
Molecular Weight | 359.3501 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@@H]2O[C@H](C)[C@@H](O)[C@H]2O
InChI
InChIKey=GAGWJHPBXLXJQN-UORFTKCHSA-N
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
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.rxlist.com/xeloda-drug.htm
https://www.drugs.com/mtm/capecitabine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25547867
Curator's Comment: The CNS penetration of 5-FU (Capecitabine is a prodrug that is enzymatically converted to 5-fluorouracil (5-FU) in the body) in human was predicted based on the penetration in preclinical brain tumor, CSF, and human PK and the predicted free CNS concentration was below the antiproliferative potency.
Originator
Sources: https://www.google.com/patents/US5472949
Curator's Comment: # Hoffmann-La Roche Inc.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1952 |
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Target ID: CHEMBL2311222 |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | XELODA Approved UseCapecitabine 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 Date1998 |
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Primary | XELODA Approved UseCapecitabine 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 Date1998 |
Cmax
Value | Dose | Co-administered | 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 |
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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 | Co-administered | 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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.75 h |
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 |
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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 |
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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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40% |
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: |
unhealthy, 34-68 |
DLT: Hand-and-foot syndrome, Diarrhea... Dose limiting toxicities: Hand-and-foot syndrome (grade 3, 28.6%) Sources: Diarrhea (grade 3, 14.29%) |
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: |
unhealthy, 41-53 |
DLT: Hand-and-foot syndrome... Dose limiting toxicities: Hand-and-foot syndrome (grade 3, 14.29%) Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Coagulopathy, Diarrhea... AEs leading to discontinuation/dose reduction: Coagulopathy Sources: Diarrhea Cardiotoxicity Dehydration Renal failure Fetal damage Mucocutaneous disorder (severe) Stevens Johnson syndrome Toxic epidermal necrolysis Hyperbilirubinemia |
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: |
unhealthy, 34-68 |
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: |
unhealthy, 34-68 |
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: |
unhealthy, 41-53 |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
[The potential of capecitabine (Xeloda) in the treatment of disseminated solid tumors]. | 2001 |
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Chemotherapy of metastatic breast cancer: what to expect in 2001 and beyond. | 2001 |
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The oral fluorinated pyrimidines. | 2001 |
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The role of capecitabine, an oral, enzymatically activated fluoropyrimidine, in the treatment of metastatic breast cancer. | 2001 |
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New options for outpatient chemotherapy--the role of oral fluoropyrimidines. | 2001 Aug |
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Capecitabine and oxaliplatin in advanced colorectal cancer: a dose-finding study. | 2001 Dec |
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Combination chemotherapy of the taxanes and antimetabolites: its use and limitations. | 2001 Dec |
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Capecitabine in breast cancer: current status. | 2001 Jan |
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Capecitabine in colorectal cancer. | 2001 Jan |
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[Capecitabine in the treatment of colorectal cancer]. | 2001 Jan-Feb |
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The significance of thymidine phosphorylase expression in colorectal cancer. | 2001 Jan-Feb |
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Xeloda in colorectal cancer. | 2001 Jun |
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Integrating the oral fluoropyrimidines into the management of advanced colorectal cancer. | 2001 May |
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Enhancement of sensitivity to capecitabine in human renal carcinoma cells transfected with thymidine phosphorylase cDNA. | 2001 May 1 |
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Oral versus intravenous fluoropyrimidines for advanced colorectal cancer: by either route, it's all the same. | 2001 Nov 1 |
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From the Food and Drug Administration. | 2001 Nov 7 |
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Role of thymidine phosphorylase in biomodulation of fluoropyrimidines. | 2001 Sep |
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[Recent aspects of palliative treatment of metastasized colorectal carcinoma]. | 2001 Sep 15 |
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Incidence and severity of hand-foot syndrome in colorectal cancer patients treated with capecitabine: a single-institution experience. | 2002 |
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Future treatment options with capecitabine in solid tumours. | 2002 Feb |
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Capecitabine as first-line treatment in colorectal cancer. Pooled data from two large, phase III trials. | 2002 Feb |
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An evolving role for oral fluoropyrimidine drugs. | 2002 Feb 15 |
Sample Use Guides
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
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Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
CAPECITABINE ACCORD (AUTHORIZED: COLONIC NEOPLASMS, BREAST NEOPLASMS, COLORECTAL NEOPLASMS, STOMACH NEOPLASMS)
Created by
admin on Mon Mar 31 18:01:20 GMT 2025 , Edited by admin on Mon Mar 31 18:01:20 GMT 2025
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EMA ASSESSMENT REPORTS |
CAPECITABINE MEDAC (AUTHORIZED: COLORECTAL NEOPLASMS)
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admin on Mon Mar 31 18:01:20 GMT 2025 , Edited by admin on Mon Mar 31 18:01:20 GMT 2025
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EMA ASSESSMENT REPORTS |
CAPECITABINE ACCORD (AUTHORIZED: STOMACH NEOPLASMS)
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EMA ASSESSMENT REPORTS |
CAPECITABINE SUN (AUTHORIZED: STOMACH NEOPLASMS)
Created by
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EMA ASSESSMENT REPORTS |
CAPECITABINE SUN (AUTHORIZED: COLONIC NEOPLASMS)
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EMA ASSESSMENT REPORTS |
ECANSYA (AUTHORIZED: COLONIC NEOPLASMS)
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EMA ASSESSMENT REPORTS |
ECANSYA (AUTHORIZED: COLORECTAL NEOPLASMS)
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NDF-RT |
N0000000233
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EMA ASSESSMENT REPORTS |
XELODA (AUTHRIZED: STOMACH NEOPLASMS)
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EMA ASSESSMENT REPORTS |
CAPECITABINE TEVA (AUTHORIZED: COLONIC NEOPLASMS)
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EMA ASSESSMENT REPORTS |
XELODA (AUTHORIZED: COLORECTAL NEOPLASMS)
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EMA ASSESSMENT REPORTS |
CAPECITABINE TEVA (AUTHORIZED: COLORECTAL NEOPLASMS)
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NCI_THESAURUS |
C1557
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WHO-VATC |
QL01BC06
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EMA ASSESSMENT REPORTS |
CAPECITABINE TEVA (AUTHORIZED: STOMACH NEOPLASMS)
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LIVERTOX |
NBK547986
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EMA ASSESSMENT REPORTS |
ECANSYA (AUTHORIZED: STOMACH NEOPLAMS)
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EMA ASSESSMENT REPORTS |
CAPECITABINE SUN (AUTHORIZED: COLORECTAL NEOPLASMS)
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EMA ASSESSMENT REPORTS |
CAPECITABINE ACCORD (AUTHORIZED: COLORECTAL NEOPLASMS)
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NDF-RT |
N0000175595
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WHO-ATC |
L01BC06
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EMA ASSESSMENT REPORTS |
XELODA (AUTHORIZED: COLONIC NEOPLASMS)
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Capecitabine
Created by
admin on Mon Mar 31 18:01:20 GMT 2025 , Edited by admin on Mon Mar 31 18:01:20 GMT 2025
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HH-37
Created by
admin on Mon Mar 31 18:01:20 GMT 2025 , Edited by admin on Mon Mar 31 18:01:20 GMT 2025
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6804DJ8Z9U
Created by
admin on Mon Mar 31 18:01:20 GMT 2025 , Edited by admin on Mon Mar 31 18:01:20 GMT 2025
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PRODRUG)
SUBSTANCE RECORD