Gemcitabine hydrochlorideProduct ingredient for Gemcitabine
- Name
- Gemcitabine hydrochloride
- Drug Entry
- Gemcitabine
Gemcitabine is a nucleoside analog and a chemotherapeutic agent. It was originally investigated for its antiviral effects, but it is now used as an anticancer therapy for various cancers.1 Gemcitabine is a cytidine analog with two fluorine atoms replacing the hydroxyl on the ribose.3 As a prodrug, gemcitabine is transformed into its active metabolites that work by replacing the building blocks of nucleic acids during DNA elongation, arresting tumour growth and promoting apoptosis of malignant cells.6 The structure, metabolism, and mechanism of action of gemcitabine are similar to cytarabine, but gemcitabine has a wider spectrum of antitumour activity.2
Gemcitabine is marketed as Gemzar and it is available as intravenous injection. It is approved by the FDA to treat advanced ovarian cancer in combination with carboplatin, metastatic breast cancer in combination with paclitaxel, non-small cell lung cancer in combination with cisplatin, and pancreatic cancer as monotherapy.4 It is also being investigated in other cancer and tumour types.
- Accession Number
- DBSALT000092
- Structure
- Synonyms
- Gemcitabine HCl
- UNII
- U347PV74IL
- CAS Number
- 122111-03-9
- Weight
- Average: 299.659
Monoisotopic: 299.048440004 - Chemical Formula
- C9H12ClF2N3O4
- InChI Key
- OKKDEIYWILRZIA-OSZBKLCCSA-N
- InChI
- InChI=1S/C9H11F2N3O4.ClH/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);1H/t4-,6-,7-;/m1./s1
- IUPAC Name
- 1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-ol hydrochloride
- SMILES
- Cl.[H][C@]1(CO)O[C@@]([H])(N2C=CC(=N)N=C2O)C(F)(F)[C@]1([H])O
- External Links
- PubChem Compound
- 60749
- ChemSpider
- 54752
- BindingDB
- 50247964
- ChEBI
- 31647
- ChEMBL
- CHEMBL1637
- Wikipedia
- Gemcitabine
- Predicted Properties
Property Value Source Water Solubility 0.824 mg/mL ALOGPS logP 0.28 ALOGPS logP -0.49 Chemaxon logS -2.5 ALOGPS pKa (Strongest Acidic) 5.38 Chemaxon pKa (Strongest Basic) 2.34 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 109.37 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 64.66 m3·mol-1 Chemaxon Polarizability 21.77 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon