Gemcitabine is a 2’-deoxycytidine analog antimetabolite that inhibits ribonucleotide reductase and DNA synthesis. Gemcitabine exhibits anticancer chemotherapeutic and antiviral activities. In pancreatic cancer cells, gemcitabine induces cell death via mitochondrial complexation of MST1 and cyclophilin D. Additionally, this compound is active against strains of HIV-1 and feline leukemia virus (FeLV/FeLuk).
| Cas No. | 122111-03-9 |
|---|---|
| Purity | ≥98% |
| Formula | C9H11F2N3O4 • HCl |
| Formula Wt. | 299.66 |
| Chemical Name | 2'-deoxy-2',2'-difluorocytidine monohydrochloride ((beta)-isomer) |
| IUPAC Name | 4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride |
| Synonym | Gemzar |
| Melting Point | 287-292°C |
| Solubility | Soluble in water. Slightly soluble in methanol, acetone, DMSO. |
| Appearance | White Crystal Powder |
| Store Temp | Ambient |
|---|---|
| Ship Temp | Ambient |
| MSDS | G1745 MSDS PDF |
|---|---|
| Info Sheet | G1745 Info Sheet PDF |
Chen SH, Li DL, Yang F, et al. Gemcitabine-induced pancreatic cancer cell death is associated with MST1/Cyclophilin D mitochondrial complexation. Biochimie. 2014 Apr 13. Epub ahead of print]. PMID: 24732633.
Su CH, Chu WC, Lan KH, et al. Gemcitabine causes telomere attrition by stabilizing TRF2. Eur J Cancer. 2012 Dec;48(18):3465-74. PMID: 22704123.
Greggs WM 3rd, Clouser CL, Patterson SE, et al. Discovery of drugs that possess activity against feline leukemia virus. J Gen Virol. 2012 Apr;93(Pt 4):900-5. PMID: 22258856.
Cerqueira NM, Fernandes PA, Ramos MJ. Understanding ribonucleotide reductase inactivation by gemcitabine. Chemistry. 2007;13(30):8507-15. PMID: 17636467.
Blackwood E, Epler J, Yen I, et al. Combination drug scheduling defines a “window of opportunity” for chemopotentiation of gemcitabine by an orally bioavailable, selective ChK1 inhibitor, GNE-900. Mol Cancer Ther. 2013 Oct;12(10):1968-1980. PMID: 23873850.
Reconstituted gemcitabine as the hydrochloride salt in the original vials is chemically stable at room temperature for 35 days but may develop crystals when stored at 4 degrees C. The crystals do not redissolve upon warming. Gemcitabine prepared as intravenous admixtures of 0.1 and 10 mg/mL as the hydrochloride salt in 5% dextrose injection and 0.9% sodium chloride injection in PVC bags and as a solution of 38 mg/mL in 0.9% sodium chloride injection packaged in plastic syringes is physically and chemically stable for at least 35 days at 4 degrees C and 23 degrees C. Gemcitabine as the hydrochloride salt is stable for at least 7 days at concentrations of 0.1, 10, and 38 mg/mL in 5% dextrose injection and 0.9% sodium chloride injection stored at 32 degrees C during simulated ambulatory infusion.
