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G-4177 Gemcitabine, Hydrochloride Salt, >99%       Prices Reduced (December 2011)

[dFdC] [Gamcitabine] [Gemcitera] [Gemsar] [Gemzar] [LY-188011] [LY 188011] [LY188011]

M.W. 299.66

C9H11F2N3O4•HCl

[122111-03-9]

M.I. 14:  4386

Storage:  Store at or below -20 ºC.  Solubility:  Soluble in DMSO at 12.5 mg/mL with slight warming; very poorly soluble in ethanol; soluble in water at 25 mg/mL with slight warming; buffers, serum, or other additives may increase or decrease the aqueous solubility.  Disposal:  A

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• Gemcitabine is a nucleoside analog of deoxycytidine used as chemotherapy to treat patients with various types of cancer.

• After passage through the cell membrane via nucleoside transporters, gemcitabine undergoes complex intracellular conversion to gemcitabine diphosphate (dFdCDP) and triphosphate (dFdCTP).  dFdCTP inhibits DNA polymerase by competing with deoxycytidine triphosphate (dCTP).  dFdCDP inhibits ribonucleoside reductase and DNA synthesis by causing depletion of deoxyribonucleotide pools, and thus potentiating the effects of dFdCTP.  Gemcitabine can be inactivated to 2,2'-difluorodeoxyuridine, mainly by deoxycytidine deaminase.  Also, 5'-nucleotidase catalyses the conversion of nucleotides to nucleosides and inhibits nucleoside kinases.  Mini, E., et al.  "Cellular pharmacology of gemcitabine."  Ann. Oncol. 17:  v7-v12 (2006).

• Gemcitabine remains the current standard of care for pancreatic cancer as a single agent.  Combinations with biological agents or other chemotherapeutic drugs (including capecitabine, platinum compounds, erlotinib, and monoclonal antibodies cetuximab and bevacizumab) have shown limited improvement.  Cartwright, T., et al.  "Cancer of the pancreas: are we making progress? A review of studies in the US Oncology Research Network."  Cancer Control 15:  308-313 (2008).

• Gemcitabine inhibited DNA synthesis in a concentration-dependent manner in human lymphoblastoid CEM cells.  The apparent Ki values of gemcitabine triphosphate (dFdCTP) were 11.2 µM for DNA polymerase α and 14.4 µM for polymerase ε.  Huang, P., et al.  "Action of 2',2'-difluorodeoxycytidine on DNA synthesis."  Cancer Res. 51:  6110-6117 (1991).

• Gemcitabine inhibited DNA synthesis.  However, the cytotoxicity of gemcitabine on proliferating cells was not specific for cells initially in S phase.  The kinetics of cell recycling from a first gemcitabine treatment have a strong effect on the outcome of a second treatment with either gemcitabine itself or cisplatin.  Cappella, P., et al.  "Cell cycle effects of gemcitabine."  Int. J. Cancer 93:  401-408 (2001).

• Gemcitabine increases DNA ligase I levels severalfold in different types of tumor cell lines, including MiaPaCa, NGP and SK-N-BE.  However, DNA ligases III and IV either remained unchanged or decreased with treatment.  Sun, D., et al.  "Enhancement of DNA ligase I level by gemcitabine in human cancer cells."  Clin. Cancer Res. 8:  1189-1195 (2002).

• Gemcitabine is the active ingredient in the drug sold under the trade name Gemzar®.  This drug has been approved in at least one country for use in patients with various carcinomas: non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.  NOTE:  THE GEMCITABINE, HYDROCHLORIDE SALT RESEARCH COMPOUND SOLD BY LC LABORATORIES IS NOT GEMZAR® AND IS NOT FOR HUMAN USE.

• Our gemcitabine product is the hydrochloride salt, whose CAS number is given above.  The CAS number of the free base is 95058-81-4.

• Sold for laboratory or manufacturing purposes only; not for human, medical, veterinary, food, or household use.

• This product is offered for R&D use in accordance with (i) 35 USC 271(e)+A13(1) in the U.S.; (ii) Section 69.1 of Japanese Patent Law in Japan; (iii) Section 11, No. 2 of the German Patent Act of 1981 in Germany; (iv) Section 60, Paragraph 5b of the U.K. Patents Act of 1977 in the U.K.; (v) Sections 55.2(1) and 55.2(6) and other common law exemptions of Canadian patent law; (vi) Section 68B of the Patents Act of 1953 in New Zealand together with the amendment of same by the Statutes Amendment Bill of 2002; (vii) such related legislation and/or case law as may be or become applicable in the aforementioned countries; and (viii) such similar laws and rules as may apply in various other countries.

• Not available in some countries; not available to some institutions; not available for some uses.