Article: Gemcitabine

Gemcitabine
Systematic (IUPAC) name
4-amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-pyrimidin- 2-one
Identifiers
CAS number	95058-81-4
ATC code	L01BC05
PubChem	60750
DrugBank	APRD00201
Chemical data
Formula	C9H11F2N3O4
Mol. weight	263.198 g/mol
Pharmacokinetic data
Bioavailability	?
Protein binding	<10%
Metabolism	?
Half life	Short infusions 32-94 minutes for long infusions 245-638 minutes
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	Oral, intravenous

Gemcitabine is a nucleoside used as chemotherapy. It is marketed as Gemzar® by Eli Lilly and Company.

Pharmacology

Chemically gemcitabine is a nucleoside in which the hydrogens on the 2' carbon of deoxycytidine are replaced by fluorides.

As with fluorouracil and other analogues of pyrimidines, the drug replaces one of the building blocks of nucleic acids, in this case cytidine, during DNA replication. The process arrests tumor growth, as new nucleosides cannot be attached to the "faulty" nucleoside, resulting in apoptosis (cellular "suicide").

Indications

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