U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11F2N3O4.ClH
Molecular Weight 299.6594
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GEMCITABINE HYDROCHLORIDE

SMILES

c1cn([C@@]2([H])C([C@@]([H])([C@@]([H])(CO)O2)O)(F)F)c(nc1=N)O.Cl

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 C9H11F2N3O4
Molecular Weight 263.1985
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment:: modest penetration of gemcitabine into the CSF after i.v. administration in nonhuman primates was shown, also can partially cross the BBB in humans https://www.ncbi.nlm.nih.gov/pubmed/17538177

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Primary
Primary
Gemzar

Approved Use

Gemzar is a nucleoside metabolic inhibitor indicated: • in combination with carboplatin, for the treatment of advanced ovarian cancer that has relapsed at least 6 months after completion of platinum- based therapy. • in combination with paclitaxel, for first-line treatment of metastatic breast cancer after failure of prior anthracycline-containing adjuvant chemotherapy, unless anthracyclines were clinically contraindicated. • in combination with cisplatin for the treatment of non-small cell lung cancer. • as a single agent for the treatment of pancreatic cancer.

Launch Date

832032000000
Primary
Gemzar

Approved Use

Gemzar is a nucleoside metabolic inhibitor indicated: • in combination with carboplatin, for the treatment of advanced ovarian cancer that has relapsed at least 6 months after completion of platinum- based therapy. • in combination with paclitaxel, for first-line treatment of metastatic breast cancer after failure of prior anthracycline-containing adjuvant chemotherapy, unless anthracyclines were clinically contraindicated. • in combination with cisplatin for the treatment of non-small cell lung cancer. • as a single agent for the treatment of pancreatic cancer.

Launch Date

832032000000
Primary
Gemzar

Approved Use

Gemzar is a nucleoside metabolic inhibitor indicated: • in combination with carboplatin, for the treatment of advanced ovarian cancer that has relapsed at least 6 months after completion of platinum- based therapy. • in combination with paclitaxel, for first-line treatment of metastatic breast cancer after failure of prior anthracycline-containing adjuvant chemotherapy, unless anthracyclines were clinically contraindicated. • in combination with cisplatin for the treatment of non-small cell lung cancer. • as a single agent for the treatment of pancreatic cancer.

Launch Date

832032000000
Primary
Gemzar

Approved Use

Gemzar is a nucleoside metabolic inhibitor indicated: • in combination with carboplatin, for the treatment of advanced ovarian cancer that has relapsed at least 6 months after completion of platinum- based therapy. • in combination with paclitaxel, for first-line treatment of metastatic breast cancer after failure of prior anthracycline-containing adjuvant chemotherapy, unless anthracyclines were clinically contraindicated. • in combination with cisplatin for the treatment of non-small cell lung cancer. • as a single agent for the treatment of pancreatic cancer.

Launch Date

832032000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
229 nM
75 mg/m² 1 times / week multiple, intravenous
dose: 75 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
GEMCITABINE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
263.6 nM
135 mg/m² 1 times / week multiple, intravenous
dose: 135 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
GEMCITABINE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
292.5 nM
180 mg/m² 1 times / week multiple, intravenous
dose: 180 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
GEMCITABINE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3526.4 nM × h
75 mg/m² 1 times / week multiple, intravenous
dose: 75 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
GEMCITABINE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4818.5 nM × h
135 mg/m² 1 times / week multiple, intravenous
dose: 135 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
GEMCITABINE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4863.4 nM × h
180 mg/m² 1 times / week multiple, intravenous
dose: 180 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
GEMCITABINE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5700 mg/m2 1 times / 2 weeks multiple, intravenous
MTD
Dose: 5700 mg/m2, 1 times / 2 weeks
Route: intravenous
Route: multiple
Dose: 5700 mg/m2, 1 times / 2 weeks
Sources:
unhealthy, 55 years (range: 34-71 years)
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Sources:
Other AEs: Myelosuppression, Paresthesia...
2200 mg/m2 3 times / 4 weeks multiple, intravenous
MTD
Dose: 2200 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 2200 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
Other AEs: Neutropenia, AST increased...
Other AEs:
Neutropenia (grade 2, 1 patient)
AST increased (grade 2, 1 patient)
ALT increased (grade 2, 1 patient)
Sources:
2800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 2800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 2800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
DLT: Hepatotoxicity, Neutropenic infection...
Dose limiting toxicities:
Hepatotoxicity (grade 3, 2 patients)
Neutropenic infection (grade 4, 1 patient)
Sources:
1000 mg/m2 3 times / 4 weeks multiple, intravenous
Recommended
Dose: 1000 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 1000 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, 74 years
Health Status: unhealthy
Age Group: 74 years
Sex: M
Sources:
Disc. AE: Necrosis skin...
AEs leading to
discontinuation/dose reduction:
Necrosis skin (1 patient)
Sources:
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Disc. AE: Myocardial infarction, Cerebrovascular accident...
AEs leading to
discontinuation/dose reduction:
Myocardial infarction (2%)
Cerebrovascular accident (2%)
Arrhythmia (2%)
Hypertension (2%)
Anemia (<1%)
Thrombocytopenia (<1%)
Hepatic dysfunction NOS (<1%)
Kidney dysfunction (<1%)
Nausea (<1%)
Vomiting (<1%)
Fever (<1%)
Rash (<1%)
Dyspnea (<1%)
Hemorrhage (<1%)
Infection (<1%)
Stomatitis (<1%)
Somnolence (<1%)
Flu syndrome (<1%)
Edema (<1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Myelosuppression
5700 mg/m2 1 times / 2 weeks multiple, intravenous
MTD
Dose: 5700 mg/m2, 1 times / 2 weeks
Route: intravenous
Route: multiple
Dose: 5700 mg/m2, 1 times / 2 weeks
Sources:
unhealthy, 55 years (range: 34-71 years)
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Sources:
Paresthesia
5700 mg/m2 1 times / 2 weeks multiple, intravenous
MTD
Dose: 5700 mg/m2, 1 times / 2 weeks
Route: intravenous
Route: multiple
Dose: 5700 mg/m2, 1 times / 2 weeks
Sources:
unhealthy, 55 years (range: 34-71 years)
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Sources:
Rash severe
5700 mg/m2 1 times / 2 weeks multiple, intravenous
MTD
Dose: 5700 mg/m2, 1 times / 2 weeks
Route: intravenous
Route: multiple
Dose: 5700 mg/m2, 1 times / 2 weeks
Sources:
unhealthy, 55 years (range: 34-71 years)
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Sources:
ALT increased grade 2, 1 patient
2200 mg/m2 3 times / 4 weeks multiple, intravenous
MTD
Dose: 2200 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 2200 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
AST increased grade 2, 1 patient
2200 mg/m2 3 times / 4 weeks multiple, intravenous
MTD
Dose: 2200 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 2200 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
Neutropenia grade 2, 1 patient
2200 mg/m2 3 times / 4 weeks multiple, intravenous
MTD
Dose: 2200 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 2200 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
Hepatotoxicity grade 3, 2 patients
DLT
2800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 2800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 2800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
Neutropenic infection grade 4, 1 patient
DLT
2800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 2800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 2800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
Necrosis skin 1 patient
Disc. AE
1000 mg/m2 3 times / 4 weeks multiple, intravenous
Recommended
Dose: 1000 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 1000 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, 74 years
Health Status: unhealthy
Age Group: 74 years
Sex: M
Sources:
Arrhythmia 2%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Cerebrovascular accident 2%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Hypertension 2%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Myocardial infarction 2%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Anemia <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Dyspnea <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Edema <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Fever <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Flu syndrome <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Hemorrhage <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Hepatic dysfunction NOS <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Infection <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Kidney dysfunction <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Nausea <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Rash <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Somnolence <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Stomatitis <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Thrombocytopenia <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Vomiting <1%
Disc. AE
800 mg/m2 3 times / 4 weeks multiple, intravenous
Dose: 800 mg/m2, 3 times / 4 weeks
Route: intravenous
Route: multiple
Dose: 800 mg/m2, 3 times / 4 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as victim
PubMed

PubMed

TitleDatePubMed
Treatment of classical Kaposi's sarcoma with gemcitabine.
2001
Noncardiogenic pulmonary edema: an unusual and serious complication of anticancer therapy.
2001
Chemotherapy of metastatic breast cancer: what to expect in 2001 and beyond.
2001
Achievement of complete remission in refractory Hodgkin's disease with prolonged infusion of gemcitabine.
2001
Treatment of extensive stage small cell lung cancer.
2001
Lung cancer: therapeutic options for stage IV and recurrent NSCLC.
2001
Chemoradiation in locally advanced non-small cell lung cancer.
2001
Options in advanced non-small cell lung cancer: a review and report on a phase II study of vinorelbine plus gemcitabine.
2001
2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentofuranosylcytosine: a novel anticancer nucleoside analog that causes both DNA strand breaks and G(2) arrest.
2001 Apr
Gemcitabine following radiotherapy with concurrent 5-fluorouracil for nonmetastatic adenocarcinoma of the pancreas.
2001 Apr 20
Phase II trial of two-weekly gemcitabine in patients with advanced biliary tract cancer.
2001 Feb
[Medical treatment of pulmonary neoplasms].
2001 Feb
Challenging the platinum combinations: docetaxel (Taxotere) combined with gemcitabine or vinorelbine in non-small cell lung cancer.
2001 Feb
The gemcitabine/epirubicin/paclitaxel trials in advanced breast cancer.
2001 Feb
Gemcitabine, paclitaxel, and trastuzumab in metastatic breast cancer.
2001 Feb
Gemcitabine and Pemetrexed disodium in treating breast cancer.
2001 Feb
Gemcitabine plus cisplatin in breast cancer.
2001 Feb
Gemcitabine and paclitaxel as salvage therapy in metastatic breast cancer.
2001 Feb
Docetaxel/gemcitabine: salvage chemotherapy in anthracycline-pretreated patients with advanced breast cancer.
2001 Feb
Effects of gemcitabine on cisplatin-induced nephrotoxicity in rats: schedule-dependent study.
2001 Feb
Syntheses and antitumor activities of potent inhibitors of ribonucleotide reductase: 3-amino-4-methylpyridine-2-carboxaldehyde-thiosemicarba-zone (3-AMP), 3-amino-pyridine-2-carboxaldehyde-thiosemicarbazone (3-AP) and its water-soluble prodrugs.
2001 Feb
Radiation concurrent with gemcitabine for locally advanced head and neck cancer: a phase I trial and intracellular drug incorporation study.
2001 Feb 1
End-joining deficiency and radiosensitization induced by gemcitabine.
2001 Feb 15
Gemcitabine for malignant mesothelioma: A phase II trial by the Cancer and Leukemia Group B.
2001 Feb-Mar
Activity and toxicity of gemcitabine and gemcitabine + vinorelbine in advanced non-small-cell lung cancer elderly patients: Phase II data from the Multicenter Italian Lung Cancer in the Elderly Study (MILES) randomized trial.
2001 Feb-Mar
Decreased myelotoxicity of gemcitabine and cisplatin in advanced non-small cell lung cancer (NSCLC) with cisplatin infusion on day 15.
2001 Feb-Mar
Cisplatin and vinorelbine as second-line chemotherapy in patients with advanced non-small cell lung cancer (NSCLC) resistant to taxol plus gemcitabine.
2001 Feb-Mar
Second-line chemotherapy for non-small-cell lung cancer with monthly docetaxel and weekly gemcitabine: a phase II trial.
2001 Jan
High-dose thiotepa and melphalan with hemopoietic progenitor support following induction therapy with epirubicin-paclitaxel-containing regimens in metastatic breast cancer (MBC).
2001 Jan
Docetaxel followed by gemcitabine and irinotecan in solid tumors.
2001 Jan
Irinotecan in combined-modality therapy for locally advanced non-small-cell lung cancer.
2001 Jan
[Refractory non-small-cell lung cancer responding to combination chemotherapy with docetaxel, gemcitabine and cisplatin].
2001 Jan
Preclinical in vivo antitumor efficacy of nedaplatin with gemcitabine against human lung cancer.
2001 Jan
Fatal pulmonary veno-occlusive disease possibly related to gemcitabine.
2001 Jan
Preirradiation gemcitabine chemotherapy for newly diagnosed glioblastoma. A phase II study.
2001 Jan 15
Novel approaches in the treatment of non-small-cell lung cancer.
2001 Mar
Treatment of elderly patients with non-small-cell lung cancer.
2001 Mar
Optimizing chemoradiation in locally advanced non-small-cell lung cancer.
2001 Mar
Gemcitabine and cisplatin combination in early-stage non-small-cell lung cancer.
2001 Mar
Gemcitabine and nonplatinum combinations in non-small-cell lung cancer.
2001 Mar
Gemcitabine in combination with new platinum compounds: an update.
2001 Mar
Unexpected severe myelotoxicity of gemcitabine in pretreated breast cancer patients.
2001 Mar
Neoadjuvant chemoradiotherapy for adenocarcinoma of the pancreas: treatment variables and survival duration.
2001 Mar
Optimizing chemoradiation therapy approaches to unresectable stage III non--small cell lung cancer.
2001 Mar
Predictive molecular markers in non-small cell lung cancer.
2001 Mar
Combined radiochemotherapy of locally advanced unresectable pancreatic adenocarcinoma with mitomycin C plus 24-hour continuous infusional gemcitabine.
2001 Mar 1
Phase I study of stealth liposomal doxorubicin in combination with gemcitabine in the treatment of patients with metastatic breast cancer.
2001 Mar 15
Cotton-wool spots associated with pancreatic carcinoma.
2001 Mar 26
Antiproliferative activity, mechanism of action and oral antitumor activity of CP-4126, a fatty acid derivative of gemcitabine, in in vitro and in vivo tumor models.
2011 Jun
Metabolism and accumulation of the lipophilic deoxynucleoside analogs elacytarabine and CP-4126.
2012 Oct
Patents

Sample Use Guides

In phase 2 study against pancreatic cancer, the drug was administered intravenously at 1250 mg/m2/d on day 1, 8 and 15 of each 4-week cycle.
Route of Administration: Intravenous
The in vitro experiments were performed in cell lines of leukemia and solid tumor origin, both sensitive and resistant to gemcitabine. All populations were cultured at 37°C in a humidified atmosphere of 95% air and 5% CO2. Sensitivity to drugs was defined by the concentration of the drug causing a growth inhibition of 50% (IC50) after 72 h drug exposure of the cells. The cells were plated in 24-well plates in different densities, depending on their doubling times, to enable log-linear growth for 72 h. Drugs were added directly after plating the cells. Final concentrations of the drugs in the wells ranged from 2.10−10 to 10−3 M.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:56:25 UTC 2021
Edited
by admin
on Fri Jun 25 20:56:25 UTC 2021
Record UNII
U347PV74IL
Record Status Validated (UNII)
Record Version
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Name Type Language
GEMCITABINE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
GEMCITABINE HYDROCHLORIDE [MI]
Common Name English
GEMCITABINE HYDROCHLORIDE [VANDF]
Common Name English
GEMCITABINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
GEMCITABINE HYDROCHLORIDE [WHO-DD]
Common Name English
INFUGEM
Brand Name English
4-AMINO-1-((2R,4R,5R)-3,3-DIFLUORO-4-HYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL)PYRIMIDIN-2-ONE HYDROCHLORIDE
Systematic Name English
GEMCITABINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
GEMCITABINE HYDROCHLORIDE [USP-RS]
Common Name English
GEMCITABINE HYDROCHLORIDE [MART.]
Common Name English
GEMCITABINE HYDROCHLORIDE [JAN]
Common Name English
LY-188011 HYDROCHLORIDE
Code English
GEMZAR
Brand Name English
CYTIDINE, 2'-DEOXY-2',2'-DIFLUORO-, MONOHYDROCHLORIDE
Common Name English
2'-DEOXY-2',2'-DIFLUOROCYTIDINE MONOHYDROCHLORIDE (.BETA.-ISOMER)
Common Name English
GEMCITABINE HYDROCHLORIDE [USAN]
Common Name English
LY188011 HYDROCHLORIDE
Code English
GEMCITABINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
GEMCITABINE HCL
Common Name English
GEMCITABINE (AS HYDROCHLORIDE)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1557
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
NCI_THESAURUS C2150
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
Code System Code Type Description
RXCUI
236234
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
PRIMARY RxNorm
FDA UNII
U347PV74IL
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
PRIMARY
EVMPD
SUB02324MIG
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
PRIMARY
CAS
122111-03-9
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
PRIMARY
ChEMBL
CHEMBL888
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
PRIMARY
DRUG BANK
DBSALT000092
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
PRIMARY
MERCK INDEX
M5690
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
PRIMARY Merck Index
PUBCHEM
60749
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
PRIMARY
EPA CompTox
122111-03-9
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
PRIMARY
USP_CATALOG
1288463
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
PRIMARY USP-RS
NCI_THESAURUS
C961
Created by admin on Fri Jun 25 20:56:25 UTC 2021 , Edited by admin on Fri Jun 25 20:56:25 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY