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
PubChem Compound
60749
ChemSpider
54752
ChEBI
31647
ChEMBL
CHEMBL1637
Wikipedia
Gemcitabine
Predicted Properties
PropertyValueSource
Water Solubility0.824 mg/mLALOGPS
logP0.28ALOGPS
logP-0.49ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)5.38ChemAxon
pKa (Strongest Basic)2.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area109.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.66 m3·mol-1ChemAxon
Polarizability21.77 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon