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Chemistry

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Also known as: 154361-50-9, Xeloda, Capiibine, Capecitibine, Captabin, Capecytabine
Molecular Formula
C15H22FN3O6
Molecular Weight
359.35  g/mol
InChI Key
GAGWJHPBXLXJQN-UORFTKCHSA-N
FDA UNII
6804DJ8Z9U

Capecitabine
A deoxycytidine derivative and fluorouracil PRODRUG that is used as an ANTINEOPLASTIC ANTIMETABOLITE in the treatment of COLON CANCER; BREAST CANCER and GASTRIC CANCER.
Capecitabine is a Nucleoside Metabolic Inhibitor. The mechanism of action of capecitabine is as a Nucleic Acid Synthesis Inhibitor.
1 2D Structure

Capecitabine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate
2.1.2 InChI
InChI=1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14(22)17-12)13-11(21)10(20)8(2)25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10-,11-,13-/m1/s1
2.1.3 InChI Key
GAGWJHPBXLXJQN-UORFTKCHSA-N
2.1.4 Canonical SMILES
CCCCCOC(=O)NC1=NC(=O)N(C=C1F)C2C(C(C(O2)C)O)O
2.1.5 Isomeric SMILES
CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@H]2[C@@H]([C@@H]([C@H](O2)C)O)O
2.2 Other Identifiers
2.2.1 UNII
6804DJ8Z9U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. N(4)-pentyloxycarbonyl-5'-deoxy-5-fluorocytidine

2. Xeloda

2.3.2 Depositor-Supplied Synonyms

1. 154361-50-9

2. Xeloda

3. Capiibine

4. Capecitibine

5. Captabin

6. Capecytabine

7. 5'-deoxy-5-fluoro-n-[(pentyloxy)carbonyl]cytidine

8. Ro 09-1978

9. Capecitabine Sun

10. Capecitabine Teva

11. Capecitabine Medac

12. Capecitabine Accord

13. Ro 09-1978/000

14. Ecansya

15. Pentyl (1-((2r,3r,4s,5r)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

16. Cytidine, 5'-deoxy-5-fluoro-n-[(pentyloxy)carbonyl]-

17. Pentyl 1-(5-deoxy-beta-d-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate

18. Pentyl N-[1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate

19. 5'-deoxy-5-fluoro-n-((pentyloxy)carbonyl)cytidine

20. Ro-091978000

21. Chebi:31348

22. 6804dj8z9u

23. Nsc-759853

24. (1-(5-deoxy-beta-d-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic Acid Pentyl Ester

25. Pentyl N-{1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate

26. Capecitabin

27. Caxeta

28. Xabine

29. Capecitabine [usan]

30. Ro-09-1978000

31. Dsstox_cid_26451

32. Dsstox_rid_81625

33. Pentyl [1-(5-deoxy-beta-d-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate

34. Dsstox_gsid_46451

35. Pentyl 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-ylcarbamate

36. Cytidine, 5'-deoxy-5-fluoro-n-((pentyloxy)carbonyl)-

37. Capecitabina

38. Capecitabinum

39. C15h22fn3o6

40. Capecitabine (xeloda)

41. Smr002530052

42. Xeloda (tn)

43. Cas-154361-50-9

44. N(4)-pentyloxycarbonyl-5'-deoxy-5-fluorocytidine

45. Cpecitabine

46. R340

47. Unii-6804dj8z9u

48. Hsdb 7656

49. Ncgc00164569-01

50. Capecitabine [usan:usp:inn:ban]

51. Rg-340

52. Capecitabine- Bio-x

53. Carbamic Acid, (1-(5-deoxy-beta-d-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-, Pentyl Ester

54. Ro-09-1978

55. Capecitabine [mi]

56. R-340

57. Capecitabine [inn]

58. Capecitabine [jan]

59. Capecitabine [hsdb]

60. Schembl8153

61. Capecitabine [vandf]

62. Chembl1773

63. Capecitabine [mart.]

64. Mls003915642

65. Mls004774137

66. Capecitabine [usp-rs]

67. Capecitabine [who-dd]

68. Capecitabine (jan/usp/inn)

69. Gtpl6799

70. Capecitabine [ema Epar]

71. Dtxsid3046451

72. Capecitabine, Analytical Standard

73. Capecitabine, >=98% (hplc)

74. Ex-a835

75. Bcpp000300

76. Capecitabine [orange Book]

77. Capecitabine [ep Monograph]

78. Capecitabine [usp Impurity]

79. Hy-b0016

80. Xeliri Component Capecitibine

81. Zinc3806413

82. Capecitabine [usp Monograph]

83. Tox21_112198

84. Mfcd00930626

85. S1156

86. Akos015920130

87. Tox21_112198_1

88. Am84502

89. Bcp9000483

90. Bs-1000

91. Ccg-264841

92. Cs-0768

93. Db01101

94. Nsc 759853

95. Ncgc00164569-02

96. Ncgc00164569-05

97. Bc164277

98. 3-(2-hydroxyethyl)thiazoliumbromide

99. Ro-9-1978

100. Ro-09-1978-000

101. D01223

102. N4-pentyloxycarbonyl-5'-deoxy-5-fluorocytidine

103. Ab01274776-01

104. Ab01274776-02

105. Ab01274776_04

106. 361c509

107. 5'-deoxy-5-fluoro-n4-(pentyloxycarbonyl)cytidine

108. 5-deoxy-5-fluoro-n-[(pentyloxy)carbonyl]cytidine

109. Q420207

110. Sr-01000931255

111. 5-deoxy-5-fluoro-n4-[(pentyloxy)carbonyl]cytidine

112. J-700154

113. Q-200788

114. Sr-01000931255-3

115. Brd-k61192372-001-08-9

116. Z1741971721

117. Capecitabine, European Pharmacopoeia (ep) Reference Standard

118. Capecitabine, United States Pharmacopeia (usp) Reference Standard

119. Capecitabine, Pharmaceutical Secondary Standard; Certified Reference Material

120. 958887-39-3

121. Carbamic Acid, (1-(5-deoxy-.beta.-d-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-, Pentyl Ester

122. Pentyl 1-(5-deoxy-.beta.-d-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 359.35 g/mol
Molecular Formula C15H22FN3O6
XLogP30.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Exact Mass359.14926359 g/mol
Monoisotopic Mass359.14926359 g/mol
Topological Polar Surface Area121 Ų
Heavy Atom Count25
Formal Charge0
Complexity582
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameCapecitabine
PubMed HealthCapecitabine (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelXELODA (capecitabine) is a fluoropyrimidine carbamate with antineoplastic activity. It is an orally administered systemic prodrug of 5'-deoxy-5-fluorouridine (5'-DFUR) which is converted to 5-fluorouracil.The chemical name for capecitabine is 5&
Active IngredientCapecitabine
Dosage FormTablet
RouteOral
Strength150mg; 500mg
Market StatusPrescription
CompanyMylan Pharms; Teva Pharms Usa

2 of 4  
Drug NameXeloda
PubMed HealthCapecitabine (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelXELODA (capecitabine) is a fluoropyrimidine carbamate with antineoplastic activity. It is an orally administered systemic prodrug of 5'-deoxy-5-fluorouridine (5'-DFUR) which is converted to 5-fluorouracil.The chemical name for capecitabine is 5&
Active IngredientCapecitabine
Dosage FormTablet
RouteOral
Strength150mg; 500mg
Market StatusPrescription
CompanyHoffmann La Roche

3 of 4  
Drug NameCapecitabine
PubMed HealthCapecitabine (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelXELODA (capecitabine) is a fluoropyrimidine carbamate with antineoplastic activity. It is an orally administered systemic prodrug of 5'-deoxy-5-fluorouridine (5'-DFUR) which is converted to 5-fluorouracil.The chemical name for capecitabine is 5&
Active IngredientCapecitabine
Dosage FormTablet
RouteOral
Strength150mg; 500mg
Market StatusPrescription
CompanyMylan Pharms; Teva Pharms Usa

4 of 4  
Drug NameXeloda
PubMed HealthCapecitabine (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelXELODA (capecitabine) is a fluoropyrimidine carbamate with antineoplastic activity. It is an orally administered systemic prodrug of 5'-deoxy-5-fluorouridine (5'-DFUR) which is converted to 5-fluorouracil.The chemical name for capecitabine is 5&
Active IngredientCapecitabine
Dosage FormTablet
RouteOral
Strength150mg; 500mg
Market StatusPrescription
CompanyHoffmann La Roche

4.2 Therapeutic Uses

Antimetabolites, Antineoplastic Agent

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Capecitabine is 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). Although neither Capecitabine nor combination chemotherapy prolongs overall survival (OS), combination chemotherapy has been demonstrated to improve disease-free survival compared to 5-FU/LV. Physicians should consider these results when prescribing single-agent capecitabine in the adjuvant treatment of Dukes' C colon cancer. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Xeloda (Capecitabine) (June 2006). Available from, as of Nov. 17, 2008: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=630


Capecitabine is 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. /Included in US product label/.

US Natl Inst Health; DailyMed. Current Medication Information for Xeloda (Capecitabine) (June 2006). Available from, as of Nov. 17, 2008: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=630


Capecitabine in combination with docetaxel is indicated for the treatment of patients with metastatic breast cancer after failure of prior anthracycline-containing chemotherapy. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Xeloda (Capecitabine) (June 2006). Available from, as of Nov. 17, 2008: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=630


Capecitabine 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, eg, patients who have received cumulative doses of 400 mg/sq m 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. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Xeloda (Capecitabine) (June 2006). Available from, as of Nov. 17, 2008: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=630


4.3 Drug Warning

Diarrhea, a dose-limiting and common adverse effect of capecitabine, occurs in 55-67% of patients receiving the drug for metastatic breast cancer or metastatic colorectal cancer, and is severe or life-threatening in 15% of patients. Nausea and vomiting occur in 43-53% and 27-37%, respectively, of patients receiving capecitabine for metastatic breast cancer or metastatic colorectal cancer. Among patients with metastatic breast cancer who developed severe nausea and/or vomiting associated with capecitabine monotherapy, onset of these adverse GI effects was early, usually occurring during the first month of treatment.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 959


Among patients receiving capecitabine alone as adjuvant therapy for stage III colon cancer, diarrhea occurred in 47% of patients and was severe or life-threatening (grade 3 or 4) in 12%; nausea occurred in 34%, and vomiting in 15%, of patients.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 959


Severe adverse GI effects associated with capecitabine may occur more frequently in geriatric patients. Among 21 patients aged 80 years or older receiving capecitabine monotherapy for metastatic breast cancer or metastatic colorectal cancer in clinical trials, severe or life-threatening (grade 3 or 4) diarrhea, nausea, or vomiting occurred in 29, 14, or 10%, respectively. Among 10 patients aged 70-80 years receiving capecitabine in combination with docetaxel for metastatic breast cancer, grade 3 or 4 diarrhea and stomatitis each occurred in 30%.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 959


Capecitabine-induced diarrhea may respond to standard antidiarrheal therapy (eg, loperamide). Patients with severe diarrhea should be closely monitored and given fluid and electrolyte replacement for dehydration as indicated.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 959


For more Drug Warnings (Complete) data for CAPECITABINE (38 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment of patients with metastatic breast cancer resistant to both paclitaxel and an anthracycline-containing chemotherapy regimen. May also be used in combination with docetaxel for the treatment of metastatic breast cancer in patients who have failed to respond to, or recurred or relasped during or following anthracycline-containing chemotherapy. Capecitabine is used alone as an adjuvant therapy following the complete resection of primary tumor in patients with stage III colon cancer when monotherapy with fluroprymidine is preferred. The use or capecitabine in combination regimens for advanced gastric cancer is currently being investigated.


FDA Label


Capecitabine Medac is indicated for the adjuvant treatment of patients following surgery of stage-III (Dukes stage-C) colon cancer .

Capecitabine Medac is indicated for the treatment of metastatic colorectal cancer .

Capecitabine Medac is indicated for first-line treatment of advanced gastric cancer in combination with a platinum-based regimen.

Capecitabine Medac in combination with docetaxel is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of cytotoxic chemotherapy. Previous therapy should have included an anthracycline.

Capecitabine Medac is also indicated as monotherapy for the treatment of patients with locally advanced or metastatic breast cancer after failure of taxanes and an anthracycline-containing chemotherapy regimen or for whom further anthracycline therapy is not indicated.


Capecitabine Accord is indicated for the adjuvant treatment of patients following surgery of stage-III (Dukes stage-C) colon cancer .

Capecitabine Accord is indicated for the treatment of metastatic colorectal cancer .

Capecitabine Accord is indicated for first-line treatment of advanced gastric cancer in combination with a platinum-based regimen.

Capecitabine Accord in combination with docetaxel is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of cytotoxic chemotherapy. Previous therapy should have included an anthracycline.

Capecitabine Accord is also indicated as monotherapy for the treatment of patients with locally advanced or metastatic breast cancer after failure of taxanes and an anthracycline containing chemotherapy regimen or for whom further anthracycline therapy is not indicated.


Ecansya is indicated for the adjuvant treatment of patients following surgery of stage-III (Dukes stage-C) colon cancer .

Ecansya is indicated for the treatment of metastatic colorectal cancer .

Ecansya is indicated for first-line treatment of advanced gastric cancer in combination with a platinum-based regimen.

Ecansya in combination with docetaxel is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of cytotoxic chemotherapy. Previous therapy should have included an anthracycline. Ecansya is also indicated as monotherapy for the treatment of patients with locally advanced or metastatic breast cancer after failure of taxanes and an anthracycline containing chemotherapy regimen or for whom further anthracycline therapy is not indicated.


Capecitabine Teva is indicated for the adjuvant treatment of patients following surgery of stage III (Dukes stage C) colon cancer .

Capecitabine Teva is indicated for the treatment of metastatic colorectal cancer .

Capecitabine Teva is indicated for firstline treatment of advanced gastric cancer in combination with a platinumbased regimen.

Capecitabine Teva in combination with docetaxel is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of cytotoxic chemotherapy. Previous therapy should have included an anthracycline. Capecitabine Teva is also indicated as monotherapy for the treatment of patients with locally advanced or metastatic breast cancer after failure of taxanes and an anthracycline containing chemotherapy regimen or for whom further anthracycline therapy is not indicated.


- Xeloda is indicated for the adjuvant treatment of patients following surgery of stage III (Dukes' stage C) colon cancer .

- Xeloda is indicated for the treatment of metastatic colorectal cancer .

- Xeloda is indicated for first-line treatment of advanced gastric cancer in combination with a platinum-based regimen.

- Xeloda in combination with docetaxel is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of cytotoxic chemotherapy. Previous therapy should have included an anthracycline. Xeloda is also indicated as monotherapy for the treatment of patients with locally advanced or metastatic breast cancer after failure of taxanes and an anthracycline-containing chemotherapy regimen or for whom further anthracycline therapy is not indicated.


Capecitabine is indicated for the adjuvant treatment of patients following surgery of stage-III (Dukes stage-C) colon cancer .

Capecitabine is indicated for the treatment of metastatic colorectal cancer .

Capecitabine is indicated for first-line treatment of advanced gastric cancer in combination with a platinum-based regimen.

Capecitabine in combination with docetaxel is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of cytotoxic chemotherapy. Previous therapy should have included an anthracycline. Capecitabine is also indicated as monotherapy for the treatment of patients with locally advanced or metastatic breast cancer after failure of taxanes and an anthracycline-containing chemotherapy regimen or for whom further anthracycline therapy is not indicated.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Capecitabine is a fluoropyrimidine carbamate with antineoplastic activity indicated for the treatment of metastatic breast cancer and colon cancer. It is an orally administered systemic prodrug that has little pharmacologic activity until it is converted to fluorouracil by enzymes that are expressed in higher concentrations in many tumors. Fluorouracil it then metabolized both normal and tumor cells to 5-fluoro-2-deoxyuridine 5-monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP).


5.2 MeSH Pharmacological Classification

Antimetabolites, Antineoplastic

Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CAPECITABINE
5.3.2 FDA UNII
6804DJ8Z9U
5.3.3 Pharmacological Classes
Nucleoside Metabolic Inhibitor [EPC]; Nucleic Acid Synthesis Inhibitors [MoA]
5.4 ATC Code

L01BC06


L01BC06


L01BC06


L01BC06


L01BC06


L01BC06


L01BC06

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01B - Antimetabolites

L01BC - Pyrimidine analogues

L01BC06 - Capecitabine


5.5 Absorption, Distribution and Excretion

Absorption

Readily absorbed through the GI tract (~70%)


Route of Elimination

Capecitabine and its metabolites are predominantly excreted in urine; 95.5% of administered capecitabine dose is recovered in urine. Fecal excretion is minimal (2.6%). The major metabolite excreted in urine is FBAL which represents 57% of the administered dose.About 3% of the administered dose is excreted in urine as unchanged drug.


Capecitabine is readily absorbed from the GI tract; on average, at least 70% of an oral dose of the drug is absorbed. Although in vitro studies have shown that capecitabine is unstable under highly acidic conditions, the drug appears to be absorbed intact immediately upon dissolution without degradation secondary to the acidic pH of the stomach.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 963


According to the manufacturer, peak plasma concentrations of capecitabine occur in about 1.5 hours, and peak plasma concentrations of fluorouracil, its active drug, occur slightly later at 2 hours.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 963


In adults with cancer who received a capecitabine dosage of 2510 mg/sq m daily in 2 divided doses, administered approximately 12 hours apart within 30 minutes following the end of a meal, blood samples drawn on day 1 of the treatment cycle showed that peak plasma concentrations of 3.93 and 0.66 ug/mL for capecitabine and fluorouracil, respectively, were achieved in about 2 hours.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 963


Considerable interindividual variations (ie, exceeding 85%) in peak plasma concentrations and areas under the concentration-time curves (AUCs) have been reported following oral administration of capecitabine.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 963


For more Absorption, Distribution and Excretion (Complete) data for CAPECITABINE (12 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Metabolized by thymidine phosphorylase to fluoruracil.


Capecitabine, an anticancer prodrug, is thought to be biotransformed into active 5-fluorouracil (5-FU) by three enzymes. After oral administration, capecitabine is first metabolized to 5'-deoxy-5-fluorocytidine (5'-DFCR) by carboxylesterase (CES), then 5'-DFCR is converted to 5'-deoxy-5-fluorouridine (5'-DFUR) by cytidine deaminase. 5'-DFUR is activated to 5-FU by thymidine phosphorylase. Although high activities of drug metabolizing enzymes are expressed in human liver, the involvement of the liver in capecitabine metabolism is not fully understood. In this study, the metabolism of capecitabine in human liver was investigated in vitro. 5'-DFCR, 5'-DFUR, and 5-FU formation from capecitabine were investigated in human liver S9, microsomes, and cytosol in the presence of the inhibitor of dihydropyrimidine dehydrogenase, 5-chloro-2,4-dihydroxypyridine. 5'-DFCR, 5'-DFUR, and 5-FU were formed from capecitabine in cytosol and in the combination of microsomes and cytosol. Only 5'-DFCR formation was detected in microsomes. The apparent K(m) and V(max) values of 5-FU formation catalyzed by cytosol alone and in combination with microsomes were 8.1 mM and 106.5 pmol/min/mg protein, and 4.0 mM and 64.0 pmol/min/mg protein, respectively. The interindividual variability in 5'-DFCR formation in microsomes and cytosol among 14 human liver samples was 8.3- and 12.3-fold, respectively. Capecitabine seems to be metabolized to 5-FU in human liver. 5'-DFCR formation was exhibited in cytosol with large interindividual variability, although CES is located in microsomes in human liver. In the present study, it has been clarified that the cytosolic enzyme would be important in 5'-DFCR formation, as is CES.

PMID:15205393 Tabata T et al; Drug Metab Dispos 32 (7): 762-7 (2004)


Capecitabine (Xeloda; CAP) is a recently developed oral antineoplastic prodrug of 5-fluorouracil (5-FU) with enhanced tumor selectivity. Previous studies have shown that CAP activation follows a pathway with three enzymatic steps and two intermediary metabolites, 5'-deoxy-5-fluorocytidine (5'-DFCR) and 5'-deoxy-5-fluorouridine (5'-DFUR), to form 5-FU preferentially in tumor tissues. In the present work, all fluorinated compounds present in liver, bile, and perfusate medium of isolated perfused rat liver (IPRL) and in liver, plasma, kidneys, bile, and urine of healthy rats /were investigated/. Moreover, data obtained from rat urine were compared with those from mice and human urine. According to a low cytidine deaminase activity in rats, 5'-DFCR was by far the main product in perfusate medium from IPRL and plasma and urine from rats. Liver and circulating 5'-DFCR in perfusate and plasma equilibrated at the same concentration value in the range 25 to 400 microM, which supports the involvement of es-type nucleoside transporter in the liver. 5'-DFUR and alpha-fluoro-beta-ureidopropionic acid (FUPA) + alpha-fluoro-beta-alanine (FBAL) were the main products in urine of mice, making up 23 to 30% of the administered dose versus 3 to 4% in rat. In human urine, FUPA + FBAL represented 50% of the administered dose, 5'-DFCR 10%, and 5'-DFUR 7%. Since fluorine-19 nuclear magnetic resonance spectroscopy gives an overview of all the fluorinated compounds present in a sample, we observed the following unreported metabolites of CAP: 1) 5-fluorocytosine and its hydroxylated metabolite, 5-fluoro-6-hydroxycytosine, 2) fluoride ion, 3) 2-fluoro-3-hydroxypropionic acid and fluoroacetate, and 4) a glucuroconjugate of 5'-DFCR.

PMID:12386128 Desmoulin F et al; Drug Metab Dispos 30 (11): 1221-9 (2002)


Fluorouracil is catabolized to dihydrofluorouracil (FUH2), a much less toxic metabolite, by dihydropyrimidine dehydrogenase. Dihydropyrimidinase cleaves the pyrimidine ring of dihydrofluorouracil, yielding 5-fluoro-ureido-propionic acid (FUPA), which is then cleaved by beta-ureido-propionase to form alpha-fluoro-beta-alanine (FBAL).

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 963


5.7 Biological Half-Life

45-60 minutes for capecitabine and its metabolites.


The plasma elimination half-life of capecitabine and its metabolites, including the active drug, fluorouracil, is about 45-60 minutes, except for alpha-fluoro-beta-alanine (FBAL), a catabolite of fluorouracil, which has an initial half-life of about 3 hours.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 963


5.8 Mechanism of Action

Capecitabine is a prodrug that is selectively tumour-activated to its cytotoxic moiety, fluorouracil, by thymidine phosphorylase, an enzyme found in higher concentrations in many tumors compared to normal tissues or plasma. Fluorouracil is further metabolized to two active metabolites, 5-fluoro-2'-deoxyuridine 5'-monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP), within normal and tumour cells. 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, therefore a deficiency of this compound can inhibit cell division. Secondly, 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 through the production of fraudulent RNA.


Capecitabine is a prodrug and has little pharmacologic activity until it is converted to fluorouracil, an antimetabolite. Because capecitabine is converted to fluorouracil by enzymes that are expressed at higher concentrations in many tumors than in adjacent normal tissues or plasma, it is thought that high tumor concentrations of the active drug may be achieved with less systemic toxicity. Fluorouracil is metabolized in both normal and tumor cells to 5-fluoro-2'-deoxyuridine 5'-monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP). Although the precise mechanisms of action of fluorouracil have not been fully elucidated, the main mechanism is thought to be the binding of the deoxyribonucleotide of the drug (FdUMP) and the folate cofactor (N5-10-methylenetetrahydrofolate) to thymidylate synthase (TS) to form a covalently bound ternary complex, which inhibits the formation of thymidylate from 2'-deoxyuridylate, thereby interfering with DNA synthesis. In addition, FUTP can be incorporated into RNA in place of uridine triphosphate (UTP), producing a fraudulent RNA and interfering with RNA processing and protein synthesis. Capecitabine has been shown to be active in xenograft tumors that are resistant to fluorouracil indicating incomplete cross-resistance between the drugs.

American Society of Health System Pharmacists. AHFS Drug Information 2008. Bethesda, Maryland 2008, p. 963


In this report, /the authors/ investigated whether apoptosis induced by capecitabine was mediated by the Fas/FasL system. To achieve this goal, a specific in vitro coculture model mixing hepatoma and human colorectal cell line was used. A bystander effect was observed between HepG2 and LS174T cells treated with capecitabine. Besides this, Xeloda showed a 7-fold higher cytotoxicity and markedly stronger apoptotic potential in thymidine phosphorylase (TP)-transfected LS174T-c2 cells. The striking enhancement of thymidylate synthase inhibition that we observed in cells with high TP activity was most probably at the origin of the potentiation of capecitabine antiproliferative efficacy. In addition, this increase of sensitivity was accompanied by a strong overexpression of the CD95-Fas receptor on the cell surface. Both Fas and FasL mRNA expression were triggered after exposing TP+ cells to the drug. This implication of Fas in Xeloda-induced apoptosis was next confirmed by using antagonistic anti-Fas and anti-FasL antibodies that proved to reverse capecitabine antiproliferative activity, thus highlighting the key role that Fas could play in the optimization of an antitumor response to fluoropyrimidine drugs. /The/ data, therefore, show that TP plays a key role in the capecitabine activity and that the Fas/FasL system could be considered as a new determinant for Xeloda efficacy.

PMID:12481413 Ciccolini J et al; Mol Cancer Ther 1 (11): 923-7 (2002)


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12-Jan-2021
29-Aug-2024
KGS
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