Structure via PubChem · Public domain (PubChem)
gemcitabine
Sign in to saveAlso known as gemcitabine hydrochloride, Gemzar®, 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one, 4-amino-1-((2R,4R,5R)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one, Gemcitabinum, Gemcitabina, 2',2'-Difluorodeoxycytidine
Gemcitabine, sold under the brand name Gemzar, among others, is a chemotherapy medication used to treat cancers. It is used to treat testicular cancer, breast cancer, ovarian cancer, non-small cell lung cancer, pancreatic cancer, and bladder cancer. It is administered by intravenous infusion. It acts against neoplastic growth, and it inhibits the replication of Orthohepevirus A, the causative agent of hepatitis E, through upregulation of interferon signaling.
Key facts
- Drug.protein_bound
- <10%
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 461119246
- Drug.image
- Gemcitabine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 155
- Drug.image2
- Gemcitabine-hydrochloride-from-xtal-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Gemzar, others
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- Intravenous
- Drug.ATC_prefix
- L01
- Drug.ATC_suffix
- BC05
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.legal_status
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C9H11F2N3O4
- Molecular weight
- 263.2 g/mol
- IUPAC name
- 4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
- SMILES
- C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
- InChIKey
- SDUQYLNIPVEERB-QPPQHZFASA-N
- XLogP
- -1.5
- Polar surface area
- 108 Ų
- H-bond donors
- 3
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
24,774 papers- Barriers and opportunities for gemcitabine in pancreatic cancer therapy.American journal of physiology. Cell physiology · 2023
- Targeting UBE2T Potentiates Gemcitabine Efficacy in Pancreatic Cancer by Regulating Pyrimidine Metabolism and Replication Stress.Gastroenterology · 2023
- Randomized phase II study of gemcitabine and docetaxel compared with gemcitabine alone in patients with metastatic soft tissue sarcomas: results of sarcoma alliance for research through collaboration study 002 [corrected].Journal of clinical oncology : official journal of the American Society of Clinical Oncology · 2007
- Randomized phase III study of gemcitabine plus S-1, S-1 alone, or gemcitabine alone in patients with locally advanced and metastatic pancreatic cancer in Japan and Taiwan: GEST study.Journal of clinical oncology : official journal of the American Society of Clinical Oncology · 2013
- m6A eraser FTO impairs gemcitabine resistance in pancreatic cancer through influencing NEDD4 mRNA stability by regulating the PTEN/PI3K/AKT pathway.Journal of experimental & clinical cancer research : CR · 2023
via PubMed
Wikidata facts
- Mass
- 263.072
Show 4 more facts
- chemical formula
- C₉H₁₁F₂N₃O₄
- Commons category
- Gemcitabine
- canonical SMILES
- C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)(F)F
- isomeric SMILES
- C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
via Wikidata · CC0
~10 min read
Article
9 sectionsContents
- Medical uses
- Contraindications and interactions
- Adverse effects
- Pharmacology
- Chemistry
- History
- Society and culture
- Research
- References
Gemcitabine, sold under the brand name Gemzar, among others, is a chemotherapy medication used to treat cancers. It is used to treat testicular cancer, breast cancer, ovarian cancer, non-small cell lung cancer, pancreatic cancer, and bladder cancer. It is administered by intravenous infusion. It acts against neoplastic growth, and it inhibits the replication of Orthohepevirus A, the causative agent of hepatitis E, through upregulation of interferon signaling.
Common side effects include bone marrow suppression, liver and kidney problems, nausea, fever, rash, shortness of breath, mouth sores, diarrhea, neuropathy, and hair loss. Use during pregnancy will likely result in fetal harm. Gemcitabine is in the nucleoside analog family of medication. It works by blocking the creation of new DNA, which results in cell death.