Gemcitabine

Gemcitabine
Clinical data
Pronunciation/dʒɛmˈsaɪtəbiːn/
Trade namesGemzar, others[1]
Other names2', 2'-difluoro 2'deoxycytidine, dFdC
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: D
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding<10%
Elimination half-lifeShort infusions: 32–94 minutes
Long infusions: 245–638 minutes
Identifiers
  • 4-Amino-1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-on
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.124.343 Edit this at Wikidata
Chemical and physical data
FormulaC9H11F2N3O4
Molar mass263.201 g·mol−1
3D model (JSmol)
  • c1cn(c(=O)nc1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
  • 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 checkY
  • Key:SDUQYLNIPVEERB-QPPQHZFASA-N checkY
  (verify)

Gemcitabine, sold under the brand name Gemzar, among others,[1] is a chemotherapy medication used to treat cancers.[2] It is used to treat testicular cancer,[3] breast cancer, ovarian cancer, non-small cell lung cancer, pancreatic cancer, and bladder cancer.[2][4] It is administered by intravenous infusion.[2] It acts against neoplastic growth, and it inhibits the replication of Orthohepevirus A, the causative agent of Hepatitis E, through upregulation of interferon signaling.[5]

Common side effects include bone marrow suppression, liver and kidney problems, nausea, fever, rash, shortness of breath, mouth sores, diarrhea, neuropathy, and hair loss.[2] Use during pregnancy will likely result in fetal harm.[2] Gemcitabine is in the nucleoside analog family of medication.[2] It works by blocking the creation of new DNA, which results in cell death.[2]

Gemcitabine was patented in 1983 and was approved for medical use in 1995.[6] Generic versions were introduced in Europe in 2009 and in the US in 2010.[7][8] It is on the WHO Model List of Essential Medicines.[9]

  1. ^ a b Cite error: The named reference brands was invoked but never defined (see the help page).
  2. ^ a b c d e f g "Gemcitabine Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 2 February 2017. Retrieved 8 December 2016.
  3. ^ "Drug Formulary/Drugs/ gemcitabine - Provider Monograph". Cancer Care Ontario. Retrieved 6 December 2020.
  4. ^ "FDA Approval for Gemcitabine Hydrochloride". National Cancer Institute. 2006-10-05. Archived from the original on 5 April 2017. Retrieved 22 April 2017.
  5. ^ Li Y, Li P, Li Y, Zhang R, Yu P, Ma Z, et al. (December 2020). "Drug screening identified gemcitabine inhibiting hepatitis E virus by inducing interferon-like response via activation of STAT1 phosphorylation". Antiviral Research. 184: 104967. doi:10.1016/j.antiviral.2020.104967. hdl:1765/133780. PMID 33137361.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 511. ISBN 9783527607495.
  7. ^ Myers C (13 March 2009). "Gemcitabine from Actavis launched on patent expiry in EU markets". FierceBiotech. Archived from the original on 11 September 2017.
  8. ^ "Press release: Hospira launches two-gram vial of gemcitabine hydrochloride for injection". Hospira via News-Medical.Net. 16 November 2010. Archived from the original on 2 October 2015.
  9. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.