Gemcitabine

Gemcitabine
Clinical data
Pronunciation	/dʒɛmˈsaɪtəbiːn/
Trade names	Gemzar, others
Other names	2', 2'-difluoro 2'deoxycytidine, dFdC
AHFS/Drugs.com	Monograph
Pregnancy; category	AU: D;
Routes of; administration	Intravenous
ATC code	L01BC05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	<10%
Elimination 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 ;
PubChem CID	60750;
IUPHAR/BPS	4793;
DrugBank	DB00441 ;
ChemSpider	54753 ;
UNII	B76N6SBZ8R;
KEGG	D02368 ;
ChEBI	CHEBI:175901 ;
ChEMBL	ChEMBL888 ;
CompTox Dashboard (EPA)	DTXSID3040487 ;
ECHA InfoCard	100.124.343
Chemical and physical data
Formula	C9H11F2N3O4
Molar mass	263.201 g·mol−1
3D model (JSmol)	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 ; Key:SDUQYLNIPVEERB-QPPQHZFASA-N ;
	(verify)

Gemcitabine, sold under the brand name Gemzar, among others,^[1] is a chemotherapy medication used to treat cancers.^[3] It is used to treat testicular cancer,^[4] breast cancer, ovarian cancer, non-small cell lung cancer, pancreatic cancer, and bladder cancer.^[3]^[5] It is administered by intravenous infusion.^[3] It acts against neoplastic growth, and it inhibits the replication of Orthohepevirus A, the causative agent of Hepatitis E, through upregulation of interferon signaling.^[6]

Common side effects include bone marrow suppression, liver and kidney problems, nausea, fever, rash, shortness of breath, mouth sores, diarrhea, neuropathy, and hair loss.^[3] Use during pregnancy will likely result in fetal harm.^[3] Gemcitabine is in the nucleoside analog family of medication.^[3] It works by blocking the creation of new DNA, which results in cell death.^[3]

Gemcitabine was patented in 1983 and was approved for medical use in 1995.^[7] Generic versions were introduced in Europe in 2009 and in the US in 2010.^[8]^[9] It is on the WHO Model List of Essential Medicines.^[10]

^ ^a ^b Cite error: The named reference brands was invoked but never defined (see the help page).
^ "Gemzar Product information". Health Canada. 11 March 2015. Retrieved 17 February 2025.
^ ^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.
^ "Drug Formulary/Drugs/ gemcitabine - Provider Monograph". Cancer Care Ontario. Retrieved 6 December 2020.
^ "FDA Approval for Gemcitabine Hydrochloride". National Cancer Institute. 5 October 2006. Archived from the original on 5 April 2017. Retrieved 22 April 2017.
^ 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.{{cite journal}}: CS1 maint: overridden setting (link)
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 511. ISBN 9783527607495.
^ Myers C (13 March 2009). "Gemcitabine from Actavis launched on patent expiry in EU markets". FierceBiotech. Archived from the original on 11 September 2017.
^ "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.
^ 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.

[brands-1] Cite error: The named reference brands was invoked but never defined (see the help page).

[2] "Gemzar Product information". Health Canada. 11 March 2015. Retrieved 17 February 2025.

[AHFS2016-3] ^ ^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.

[4] "Drug Formulary/Drugs/ gemcitabine - Provider Monograph". Cancer Care Ontario. Retrieved 6 December 2020.

[NCI2017-5] "FDA Approval for Gemcitabine Hydrochloride". National Cancer Institute. 5 October 2006. Archived from the original on 5 April 2017. Retrieved 22 April 2017.

[6] 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.{{cite journal}}: CS1 maint: overridden setting (link)

[Fis2006-7] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 511. ISBN 9783527607495.

[My2009-8] Myers C (13 March 2009). "Gemcitabine from Actavis launched on patent expiry in EU markets". FierceBiotech. Archived from the original on 11 September 2017.

[Press2010-9] "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.

[WHO23rd-10] 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.

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