Gemcitabine

Gemcitabine
Clinical data


Pronunciation	jem-SEYE-tə-been
Trade names	Gemzar, others
AHFS/Drugs.com	Monograph
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	Intravenous
ATC code	L01BC05 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	<10%
Biological half-life	Short infusions: 32–94 minutes Long infusions: 245–638 minutes
Identifiers
IUPAC name 4-Amino-1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-on
CAS Number	95058-81-4^Y
PubChem CID	60750
IUPHAR/BPS	4793
DrugBank	DB00441^Y
ChemSpider	54753^Y
UNII	B76N6SBZ8R
KEGG	D02368^Y
ChEBI	CHEBI:175901^Y
ChEMBL	CHEMBL888^Y
ECHA InfoCard	100.124.343
Chemical and physical data
Formula	C₉H₁₁F₂N₃O₄
Molar mass	263.198 g/mol
3D model (Jmol)	Interactive image
SMILES c1cn(c(=O)nc1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
InChI InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1^Y Key:SDUQYLNIPVEERB-QPPQHZFASA-N^Y

Gemcitabine, sold under the brand name Gemzar among others, is a chemotherapy medication used to treat a number of types of cancer. This includes breast cancer, non-small cell lung cancer, pancreatic cancer, bladder cancer, and biliary tract cancer. It is used by injection into a vein.

Common side effects include bone marrow suppression, liver problems, nausea, fever, rash, shortness of breath, and hair loss. Other severe side effects include kidney problems and allergic reactions. Use during pregnancy will likely result in harm to the baby. Gemcitabine is in the nucleoside analog family of medication. It works by blocking the creation of new DNA.

Gemcitabine was patented in 1983 and was approved for medical use in 1995. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 24.41 to 316.99 USD per gm vial. In the United Kingdom a gm vial costs the NHS about 155.00 pounds.

Gemcitabine is used in various carcinomas: non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer. It is being investigated for use in esophageal cancer, and is used experimentally in lymphomas and various other tumor types.

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Wikipedia