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  • 154361-50-9 , Capecitabine, 卡培他滨, CAS: 154361-50-9
  • 154361-50-9 , Capecitabine, 卡培他滨, CAS: 154361-50-9
154361-50-9 , Capecitabine, 卡培他滨, CAS: 154361-50-9 154361-50-9 , Capecitabine, 卡培他滨, CAS: 154361-50-9

154361-50-9 , Capecitabine, 卡培他滨, CAS: 154361-50-9

154361-50-9 , Capecitabine,
卡培他滨,
CAS: 154361-50-9
C15H22FN3O6 / 359.35
MFCD00930626

Capecitabine, 卡培他滨

Pro-drug of 5-FU; anti-cancer agent.

Capecitabine is a prodrug of 5-fluorouracil (5-FU;). It is converted to 5-FU via several enzymatic steps beginning in the liver and ending with conversion in tumor tissue by thymidine phosphorylase, an enzyme that is more concentrated in tumor tissue compared with normal tissue. Capecitabine is cytotoxic only at high concentrations in Scaber, SIHA, and MKN45 cells (IC50s = 97, 578, and 994 µM, respectively) and is inactive in a variety of cancer cell lines, including COLO205, HCT116, and MCF-7 cells (IC50s = >1,000 µM).

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Capecitabine is an orally administered drug belonging to the class of fluoropyrimidine carbamates. It converts into 5-fluorouracil (5-FU) at the tumor tissues by exploiting the high intratumoral concentrations of thymidine phosphorylase.

Capecitabine is a fluoropyrimidine carbamate belonging to the class of antineoplastic agents called antimetabolites. As a prodrug, capecitabine is selectively activated by tumor cells to its cytotoxic moiety, 5-fluorouracil (5-FU); subsequently, 5-FU is metabolized to two active metabolites, 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP) by both tumor cells and normal cells. FdUMP inhibits DNA synthesis and cell division by reducing normal thymidine production, while FUTP inhibits RNA and protein synthesis by competing with uridine triphosphate for incorporation into the RNA strand. (NCI04)

Capecitabine is a pyrimidine analogue used as an antineoplastic agent to treat metastatic and advanced forms of breast and colon cancer, often in combination with other agents. Capecitabine is associated with a low rate of transient serum aminotransferase elevations during therapy but has been only rarely implicated in cases of clinically apparent acute liver injury.

Capecitabine, also known as xeloda or ro 09-1978/000, belongs to the class of organic compounds known as 5'-deoxyribonucleosides. These are nucleosides in which the oxygen atom at the 5'position of the ribose moiety has been replaced by another atom. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives. Capecitabine is a drug which is used 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. Capecitabine exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Capecitabine has been detected in multiple biofluids, such as urine and blood. Within the cell, capecitabine is primarily located in the cytoplasm and membrane (predicted from logP). Capecitabine can be converted into 5'-deoxy-5-fluorouridine and meprobamate; which is mediated by the enzymes liver carboxylesterase 1 and cytidine deaminase. In humans, capecitabine is involved in the capecitabine action pathway and the capecitabine metabolism pathway. Capecitabine is a potentially toxic compound.

Title: Capecitabine

CAS Registry Number: 154361-50-9

CAS Name: 5'-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine

Additional Names: [1-(5-deoxy-b-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl]carbamic acid pentyl ester; pentyl 1-(5-deoxy-b-D-ribofuranosyl)-5-fluoro-1,2-dihyro-2-oxo-4-pyrimidinecarbamate

Manufacturers' Codes: Ro-9-1978

Trademarks: Xeloda (Roche)

Molecular Formula: C15H22FN3O6

Molecular Weight: 359.35

Percent Composition: C 50.14%, H 6.17%, F 5.29%, N 11.69%, O 26.71%

Literature References: Orally active fluoropyrimidine. Prodrug of doxifluridine, q.v., designed to be metabolized to 5-fluorouracil, q.v., at the tumor site. Prepn: M. Arasaki et al., EP 602454; eidem, US 5472949 (1994, 1995 both to Hoffmann-La Roche). Metabolism by tumor enzymes: T. Ishikawa et al., Cancer Res. 58, 685 (1998). Clinical comparison with i.v. fluorouracil in colorectal cancer: P. M. Hoff et al., J. Clin. Oncol. 19, 2282 (2001); E. Van Cutsem et al., ibid. 4097. Review of pharmacology and clinical experience: J. K. McGavin, K. L. Goa, Drugs 61, 2309-2326 (2001).

Properties: Crystals from ethyl acetate, mp 110-121°. Soly in water (20°): 26 mg/ml.

Melting point: mp 110-121°

Therap-Cat: Antineoplastic.

Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs.

CAS Number

154361-50-9

Product Name

Capecitabine

IUPAC Name

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

Molecular Formula

C15H22FN3O6

Molecular Weight

359.35 g/mol

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

InChI Key

GAGWJHPBXLXJQN-UORFTKCHSA-N

SMILES

CCCCCOC(=O)NC1=NC(=O)N(C=C1F)C2C(C(C(O2)C)O)O

Solubility

26 mg/mL
In water, 26 mg/mL at 20 °C
2.48e-01 g/L

Synonyms

Ro 091978000; Ro-091978000; Ro091978000; Capecitabine; Abbreviation: CAPE. US brand name: Xeloda.

Canonical SMILES

CCCCCOC(=O)NC1=NC(=O)N(C=C1F)C2C(C(C(O2)C)O)O

Isomeric SMILES

CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@H]2[C@@H]([C@@H]([C@H](O2)C)O)O


CAS No: 154361-50-9 Synonyms: 5'-Deoxy-5-fluoro-N4-(pentyloxycarbonyl)cytidine[1-(5-Deoxy-b-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl] carbamic acid pentyl ester5-Fluoro-N4-(pentyloxycarbonyl)-5'-deoxycytidineXeloda MDL No: MFCD00930626 Chemical Formula: C15H22FN3O6 Molecular Weight: 359.35

COA:

Product name: Capecitabine           

CAS:154361-50-9      M.F.: C15H22O6N3F     M.W.: 359.35   

Items

Specifications

Results

Appearance

A white or off white crystalline

Complies

Identification

HPLC and IR

Positive

Specific rotation [α]D20

+96o ~ +100 o

+98.2 o

Water

Min.0.5%

0.1%

Residue on ignition

Min.0.1%

0.05%

Heavy metals

Min.20ppm

Complies

Single impurity

Min.0.5%

Complies

Assay (HPLC)

≥98.0%

99.2%

References:

1. Xiangshu F, et.al.,, Nucl. Med. Biol., 2004, 31, p1033

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