Gemcitabine

Title: Gemcitabine
CAS Registry Number: 95058-81-4
CAS Name: 2¢-Deoxy-2¢,2¢-difluorocytidine
Additional Names: 1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose; dFdC; dFdCyd
Manufacturers' Codes: LY-188011
Trademarks: Gemzar (Lilly)
Molecular Formula: C9H11F2N3O4
Molecular Weight: 263.20
Percent Composition: C 41.07%, H 4.21%, F 14.44%, N 15.97%, O 24.32%
Literature References: Prepn: L. W. Hertel, GB 2136425; idem, US 4808614 (1984, 1989 both to Lilly); L. W. Hertel et al., J. Org. Chem. 53, 2406 (1988); T. S. Chou et al., Synthesis 1992, 565. Antitumor activity: L. W. Hertel et al., Cancer Res. 50, 4417 (1990). Mode of action study: V. W. T. Ruiz et al., Biochem. Pharmacol. 46, 762 (1993). Clinical pharmacokinetics and toxicity: J. L. Abbruzzese et al., J. Clin. Oncol. 9, 491 (1991). Review of clinical studies: B. Lund et al., Cancer Treat. Rev. 19, 45-55 (1993).
Properties: Crystals from water, pH 8.5. [a]365 +425.36°; [a]D +71.51° (c = 0.96 in methanol). uv max (ethanol): 234, 268 (e 7810, 8560). LD10 i.v. in rats: 200 mg/m2 (Abbruzzese).
Optical Rotation: [a]365 +425.36°; [a]D +71.51°
Absorption maximum: uv max (ethanol): 234, 268 (e 7810, 8560)
Toxicity data: LD10 i.v. in rats: 200 mg/m2 (Abbruzzese)
Derivative Type: Hydrochloride
CAS Registry Number: 122111-03-9
Molecular Formula: C9H11F2N3O4.HCl
Molecular Weight: 299.66
Percent Composition: C 36.07%, H 4.04%, F 12.68%, N 14.02%, O 21.36%, Cl 11.83%
Properties: Crystals from water-acetone, mp 287-292° (dec). [a]D +48°; [a]365 +257.9° (c = 1.0 in deuterated water). uv max (water): 232, 268 nm (e 7960, 9360).
Melting point: mp 287-292° (dec)
Optical Rotation: [a]D +48°; [a]365 +257.9° (c = 1.0 in deuterated water)
Absorption maximum: uv max (water): 232, 268 nm (e 7960, 9360)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs.
Gemeprost Gemfibrozil Gemifloxacin Gemtuzumab Ozogamicin Genite?

Gemcitabine
Gemcitabine.svg
Gemcitabine-hydrochloride-from-xtal-3D-balls.png
Systematic (IUPAC) name
4-amino-1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-on
Clinical data
Trade names Gemzar
AHFS/Drugs.com monograph
Pregnancy cat. D (US)
Legal status  ?
Routes Oral, intravenous
Pharmacokinetic data
Protein binding <10%
Half-life Short infusions 32-94 minutes
for long infusions 245-638 minutes
Identifiers
CAS number 95058-81-4 YesY
ATC code L01BC05
PubChem CID 60750
DrugBank DB00441
ChemSpider 54753 YesY
UNII B76N6SBZ8R YesY
KEGG D02368 YesY
ChEBI CHEBI:175901 YesY
ChEMBL CHEMBL888 YesY
Chemical data
Formula C9H11F2N3O4 
Mol. mass 263.198 g/mol
 YesY (what is this?)  (verify)

Gemcitabine (pronunciation: jem-SITE-a-been) is a nucleoside analog used as chemotherapy. It is marketed as Gemzar by Eli Lilly and Company.