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
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020509s075lbl.pdf

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
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
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

8.3203201E11
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

8.3203201E11
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

8.3203201E11
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

8.3203201E11
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)
n = 4
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Population Size: 4
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)
n = 6
Health Status: unhealthy
Condition: Non-Small-Cell Lung Cancer
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Population Size: 6
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)
n = 5
Health Status: unhealthy
Condition: Non-Small-Cell Lung Cancer
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Population Size: 5
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
n = 1
Health Status: unhealthy
Age Group: 74 years
Sex: M
Population Size: 1
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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)
n = 4
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Population Size: 4
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)
n = 4
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Population Size: 4
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)
n = 4
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Population Size: 4
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)
n = 6
Health Status: unhealthy
Condition: Non-Small-Cell Lung Cancer
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Population Size: 6
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)
n = 6
Health Status: unhealthy
Condition: Non-Small-Cell Lung Cancer
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Population Size: 6
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)
n = 6
Health Status: unhealthy
Condition: Non-Small-Cell Lung Cancer
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Population Size: 6
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)
n = 5
Health Status: unhealthy
Condition: Non-Small-Cell Lung Cancer
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Population Size: 5
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)
n = 5
Health Status: unhealthy
Condition: Non-Small-Cell Lung Cancer
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Population Size: 5
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
n = 1
Health Status: unhealthy
Age Group: 74 years
Sex: M
Population Size: 1
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as victim
PubMed

PubMed

TitleDatePubMed
Acute myocardial infarction following gemcitabine therapy--a case report.
1999 Dec
Activity of standard and investigational cytotoxic drugs in primary cultures of tumor cells from patients with kidney and urinary bladder carcinomas.
1999 Dec
Cardiotoxicity of epirubicin/paclitaxel-containing regimens: role of cardiac risk factors.
1999 Nov
Severe non-haematological toxicity after treatment with gemcitabine.
1999 Nov
Effects of gemcitabine on cell proliferation and apoptosis in non-small-cell lung cancer (NSCLC) cell lines.
2000
Phase I study of paclitaxel and day 1/day 8 gemcitabine in patients with solid malignancies.
2000 Aug
Paclitaxel-induced stomal neuropathy: a unique cause of pain in a patient with ileal conduit.
2000 Dec 20
A dose-finding study of gemcitabine and vinorelbine in advanced previously treated malignancies.
2000 Jan
Differential transport of cytosine-containing nucleosides by recombinant human concentrative nucleoside transporter protein hCNT1.
2000 Jan-Feb
Malignant pleural mesothelioma.
2001
Treatment of extensive stage small cell lung cancer.
2001
Lung cancer: therapeutic options for stage IV and recurrent NSCLC.
2001
Induction chemotherapy followed by concomitant chemoradiotherapy for non-small cell lung cancer.
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
[Palliative therapy of pancreatic adenocarcinoma].
2001 Feb
Biweekly gemcitabine, doxorubicin, and paclitaxel as first-line treatment in metastatic breast cancer. Final results from a phase II trial.
2001 Feb
The gemcitabine/epirubicin/paclitaxel trials in advanced breast cancer.
2001 Feb
Gemcitabine, paclitaxel, and trastuzumab in metastatic breast cancer.
2001 Feb
Treatment of advanced breast cancer with gemcitabine and vinorelbine.
2001 Feb
Chemotherapy agents in transitional cell carcinoma: the old and the new.
2001 Feb
Effects of gemcitabine on cisplatin-induced nephrotoxicity in rats: schedule-dependent study.
2001 Feb
The clinical implications of gemcitabine radiosensitization.
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
Gemcitabine and cisplatin for advanced, metastatic bladder cancer.
2001 Feb 15
Phase II trial of paclitaxel plus gemcitabine in patients with locally advanced or metastatic non-small-cell lung cancer.
2001 Feb 15
Gemcitabine for malignant mesothelioma: A phase II trial by the Cancer and Leukemia Group B.
2001 Feb-Mar
Gemcitabine-associated posterior reversible encephalopathy syndrome: MR imaging and MR spectroscopy findings.
2001 Jan
Phase I trial of gemcitabine in patients with advanced pancreatic cancer.
2001 Jan
Second-line chemotherapy for non-small-cell lung cancer with monthly docetaxel and weekly gemcitabine: a phase II trial.
2001 Jan
Treatment of pancreatic cancer with a combination of docetaxel, gemcitabine and granulocyte colony-stimulating factor: a phase II study of the Greek Cooperative Group for Pancreatic Cancer.
2001 Jan
Development of cyclin-dependent kinase modulators as novel therapeutic approaches for hematological malignancies.
2001 Jan
Irinotecan in combined-modality therapy for locally advanced non-small-cell lung cancer.
2001 Jan
Treatment of non-small-cell lung cancer in North America: the emerging role of irinotecan.
2001 Jan
Anticancer drug-induced kidney disorders.
2001 Jan
Preclinical in vivo antitumor efficacy of nedaplatin with gemcitabine against human lung cancer.
2001 Jan
Preirradiation gemcitabine chemotherapy for newly diagnosed glioblastoma. A phase II study.
2001 Jan 15
Gemcitabine and cisplatin combination in early-stage non-small-cell lung cancer.
2001 Mar
Triplet combination chemotherapy and targeted therapy regimens.
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
[A case of primary malignant hemangiopericytoma of the lung with marked response to combination chemotherapy with cisplatin, ifosfamide and gemcitabine].
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
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
Human cytosolic 5'-nucleotidase I: characterization and role in nucleoside analog resistance.
2001 Mar 30
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