Stereochemistry | ABSOLUTE |
Molecular Formula | C9H11F2N3O4.ClH |
Molecular Weight | 299.659 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)C2(F)F
InChI
InChIKey=OKKDEIYWILRZIA-OSZBKLCCSA-N
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
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C9H11F2N3O4 |
Molecular Weight | 263.1981 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Gemcitabine is a nucleoside analog used as chemotherapy. It is marketed as Gemzar® by Eli Lilly and Company. Gemcitabine inhibits thymidylate synthetase, leading to inhibition of DNA synthesis and cell death. Gemcitabine is a prodrug so activity occurs as a result of intracellular conversion to two active metabolites, gemcitabine diphosphate and gemcitabine triphosphate by deoxycitidine kinase. Gemcitabine diphosphate also inhibits ribonucleotide reductase, the enzyme responsible for catalyzing synthesis of deoxynucleoside triphosphates required for DNA synthesis. Finally, Gemcitabine triphosphate (diflurorodeoxycytidine triphosphate) competes with endogenous deoxynucleoside triphosphates for incorporation into DNA. Gemcitabine is indicated for the treatment of advanced ovarian cancer that has relapsed at least 6 months after completion of platinum-based therapy; metastatic ovarian cancer; inoperable, locally advanced (Stage IIIA or IIIB), or metastatic (Stage IV) non-small cell lung cancer; and locally advanced (nonresectable Stage II or Stage III) or metastatic (Stage IV) adenocarcinoma of the pancreas.
CNS Activity
Originator
Approval Year
Cmax
AUC
Doses
AEs
Sourcing
Sample Use Guides
For intravenous use only.
• Ovarian Cancer: 1000 mg/m2 over 30 minutes on Days 1 and 8 of
each 21-day cycle. (2.1)
• Breast Cancer: 1250 mg/m2
over 30 minutes on Days 1 and 8 of
each 21-day cycle. (2.2)
• Non-Small Cell Lung Cancer: 1000 mg/m2
over 30 minutes on
Days 1, 8, and 15 of each 28-day cycle or 1250 mg/m2
over 30
minutes on Days 1 and 8 of each 21-day cycle. (2.3)
• Pancreatic Cancer: 1000 mg/m2
over 30 minutes once weekly for
the first 7 weeks, then one week rest, then once weekly for 3
weeks of each 28-day cycle
Route of Administration:
Intravenous