122111-03-9 Gemcitabine HCl AKSci J10060
 
 
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  J10060    AKSci Reference Standard
Gemcitabine HCl, 99% (HPLC), powder
 
2'-Deoxy-2',2'-difluorocytidine
IDENTITY
CAS Number:122111-03-9
MDL Number:MFCD01735988
MF:C9H11F2N3O4.HCl
MW:299.66
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:99% (HPLC), powder
Physical Form (at 20°C):Solid
Melting Point:258-278°C
Optical Rotation:+43 °- +50° (c=1, water)
Long-Term Storage:Store long-term in a cool, dry place
DOT/IATA TRANSPORT INFORMATION
Not hazardous material

BIOLOGICAL INFO
Solubility:DMSO: <1mg/mL; H2O: >=10mg/mL; EtOH: <1mg/mL
Application(s):ribonucleotide reductase (RNR) inhibitor; DNA synthesis inhibitor
Form:HCl salt

REVIEW
 Gemcitabine inhibits thymidylate synthetase, leading to inhibition of DNA synthesis and cell death. Gemcitabine is a prodrug so activity occurs as a result of intracellular conversion to two active metabolites, gemcitabine diphosphate and gemcitabine triphosphate by deoxycitidine kinase. Gemcitabine diphosphate also inhibits ribonucleotide reductase, the enzyme responsible for catalyzing synthesis of deoxynucleoside triphosphates required for DNA synthesis. Finally, Gemcitabine triphosphate (diflurorodeoxycytidine triphosphate) competes with endogenous deoxynucleoside triphosphates for incorporation into DNA.

REFERENCES
[1]N. M. F. S. A. Cerqueira, P. A. Fernandes, M. J. Ramos (2007). Understanding ribonucleotide reductase inactivation by gemcitabine. Chemistry: A European Journal 13 (30): 8507-15. doi:10.1002/chem.200700260. PMID 17636467.
[2] 'Chu E., DeVita V. T., Physicians'' Cancer Chemotherapy Drug Manual, 2007, Jones & Bartlett, 2007.'
[3] Oettle H, Post S, Neuhaus P, et al. (January 2007). Adjuvant chemotherapy with gemcitabine vs observation in patients undergoing curative-intent resection of pancreatic cancer: a randomized controlled trial. JAMA 297 (3): 267-77. doi:10.1001/jama.297.3.267. PMID 17227978.
[4] Von Der Maase, H; Hansen, SW; Roberts, JT; Dogliotti, L; Oliver, T; Moore, MJ; Bodrogi, I; Albers, P et al. (2000). Gemcitabine and cisplatin versus methotrexate, vinblastine, doxorubicin, and cisplatin in advanced or metastatic bladder cancer: results of a large, randomized, multinational, multicenter, phase III study.. J Clin Oncol 18 (17): 3068. PMID 11001674.

GLOBALLY HARMONIZED SYSTEM (GHS)

Pictograms

Signal Word
Danger

Hazard Statements
H360

Precautionary Statements
P201; P202; P281; P308+P313; P405; P501

RELATED PRODUCTS
F287Gemcitabine hydrochloride
K723Gemcitabine

Current as of May 15, 2024

AKSci Reference Standards are high-purity, low-impurity compounds suitable for use as standards.


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CATEGORIES
 APIs and Bioactives > Chemotherapeutics


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