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Details

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
Structure of GEMCITABINE HYDROCHLORIDE

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

HIDE SMILES / InChI

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

Description

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

Targets

Primary TargetPharmacologyConditionPotency
3.0 nM [IC50]
30.0 nM [IC50]
10.0 nM [IC50]
7.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Gemzar
Primary
Gemzar
Primary
Gemzar
Primary
Gemzar

Cmax

ValueDoseCo-administeredAnalytePopulation
229 nM
75 mg/m² 1 times / week multiple, intravenous
GEMCITABINE blood
Homo sapiens
263.6 nM
135 mg/m² 1 times / week multiple, intravenous
GEMCITABINE blood
Homo sapiens
292.5 nM
180 mg/m² 1 times / week multiple, intravenous
GEMCITABINE blood
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3526.4 nM × h
75 mg/m² 1 times / week multiple, intravenous
GEMCITABINE blood
Homo sapiens
4818.5 nM × h
135 mg/m² 1 times / week multiple, intravenous
GEMCITABINE blood
Homo sapiens
4863.4 nM × h
180 mg/m² 1 times / week multiple, intravenous
GEMCITABINE blood
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
Treatment of PANC-1 cells with gemcitabine (10 nM) increased the percentage of cells in S phase to 60.1±6.0% and reduced the percentage in the G0/G1 phase to 28.7±4.2%
Substance Class Chemical
Record UNII
U347PV74IL
Record Status Validated (UNII)
Record Version