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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

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

CNS Penetrant
2588
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

Originator

Eli Lilly|University of Innsbruck
2
Curator's Comment: # Eli Lilly; University of Innsbruck

Approval Year

1996
224
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Inhibitor
8504
T-24
2
Target ID: CHEMBL614774
Inhibitor
8504
 3.0 nM [IC50]
CAKI-1
3
Target ID: CHEMBL614067
Inhibitor
8504
 30.0 nM [IC50]
PANC-1
5
Target ID: CHEMBL614139
Inhibitor
8504
 10.0 nM [IC50]
Inhibitor
8504
 7.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
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

1996
Primary
Approved
8583
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

1996
Primary
Approved
8583
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

1996
Primary
Approved
8583
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

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
229 nM
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/19556122
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/19556122
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/19556122
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/19556122
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/19556122
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/19556122
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/17434832
unhealthy, 55 years (range: 34-71 years)
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/17434832
Other AEs: Myelosuppression, Paresthesia...
Other AEs:
Myelosuppression
Paresthesia
Rash (severe)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/17434832
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:
https://pubmed.ncbi.nlm.nih.gov/8996158
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8996158
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:
https://pubmed.ncbi.nlm.nih.gov/8996158
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:
https://pubmed.ncbi.nlm.nih.gov/8996158
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8996158
DLT: Hepatotoxicity, Neutropenic infection...
Dose limiting toxicities:
Hepatotoxicity (grade 3, 2 patients)
Neutropenic infection (grade 4, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8996158
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:
https://pubmed.ncbi.nlm.nih.gov/30397477
unhealthy, 74 years
Health Status: unhealthy
Age Group: 74 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/30397477
Disc. AE: Necrosis skin...
AEs leading to
discontinuation/dose reduction:
Necrosis skin (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/30397477
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/17434832
unhealthy, 55 years (range: 34-71 years)
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/17434832
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/17434832
unhealthy, 55 years (range: 34-71 years)
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/17434832
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/17434832
unhealthy, 55 years (range: 34-71 years)
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/17434832
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:
https://pubmed.ncbi.nlm.nih.gov/8996158
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8996158
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:
https://pubmed.ncbi.nlm.nih.gov/8996158
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8996158
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:
https://pubmed.ncbi.nlm.nih.gov/8996158
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8996158
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:
https://pubmed.ncbi.nlm.nih.gov/8996158
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8996158
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:
https://pubmed.ncbi.nlm.nih.gov/8996158
unhealthy, 58 years (range: 40-77 years)
Health Status: unhealthy
Age Group: 58 years (range: 40-77 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8996158
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:
https://pubmed.ncbi.nlm.nih.gov/30397477
unhealthy, 74 years
Health Status: unhealthy
Age Group: 74 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/30397477
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
TK2
3

hCNT1
2

hCNT2
2

hCNT3
2

MRP5
41
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
MRP5
41
 yes
TK2
3
 yes
hCNT1
2
 yes
hCNT2
2
 yes
hCNT3
2
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:175901
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:175901
ChemicalBook
CB4438054
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4438054
MolPort
MolPort-003-987-478
https://www.molport.com/shop/molecule-link/MolPort-003-987-478
Selleck Chemicals
Gemcitabine(Gemzar)
http://www.selleckchem.com/products/Gemcitabine(Gemzar).html
ZINC
ZINC000018279854
http://zinc15.docking.org/substances/ZINC000018279854
PubMed

PubMed

TitleDatePubMed
Haemolytic uraemic syndrome after gemcitabine treatment for pancreatic carcinoma.
1999 Oct
Gemcitabine plus vinorelbine in nonsmall cell lung carcinoma patients age 70 years or older or patients who cannot receive cisplatin. Oncopaz Cooperative Group.
1999 Oct 15
Membranoproliferative glomerulonephritis following gemcitabine and vinorelbine chemotherapy for peritoneal mesothelioma.
1999 Oct 20
Phase I study of paclitaxel and day 1/day 8 gemcitabine in patients with solid malignancies.
2000 Aug
[A 42-year-old patient with the hemolytic-uremic syndrome under gemcitabine therapy for an adenocarcinoma of the liver. The hemolytic-uremic syndrome and gemcitabine].
2000 Jul
Second-line chemotherapy with paclitaxel, cisplatin and gemcitabine in pre-treated sensitive cisplatin-based patients with advanced non-small cell lung cancer.
2000 May-Jun
Treatment of classical Kaposi's sarcoma with gemcitabine.
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
Lung cancer: therapeutic options for stage IV and recurrent NSCLC.
2001
Induction chemotherapy followed by concomitant chemoradiotherapy for 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
Neoadjuvant, adjuvant, and palliative treatment of pancreatic cancer.
2001 Apr
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 and paclitaxel as salvage therapy in metastatic breast cancer.
2001 Feb
Treatment of advanced breast cancer with gemcitabine and vinorelbine.
2001 Feb
The role of apoptosis in 2',2'-difluoro-2'-deoxycytidine (gemcitabine)-mediated radiosensitization.
2001 Feb
The clinical implications of gemcitabine radiosensitization.
2001 Feb
P53 modulates the effect of loss of DNA mismatch repair on the sensitivity of human colon cancer cells to the cytotoxic and mutagenic effects of cisplatin.
2001 Feb 15
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
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
Triplet combination chemotherapy and targeted therapy regimens.
2001 Mar
Latent hematopoietic stem cell toxicity associated with protracted drug administration.
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
Cotton-wool spots associated with pancreatic carcinoma.
2001 Mar 26
Akt, MAPK (Erk1/2), and p38 act in concert to promote apoptosis in response to ErbB receptor family inhibition.
2001 May 4
Patents

Patents

JP2004518776A
9
JP2006502184A
41
JP2006523607A
9
JP2007518822A
8
JP2007533670A
6
JP2008510795A
76
JP2008533019A
34
JP2009531296A
19
JP2011501962A
8
JP2011528275A
456
JP2012500104A
108
JP2013231029A
2
JP4397691B2
21

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%
Name Type Language
INFUGEM
Preferred Name English
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
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 Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
NCI_THESAURUS C2150
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
Code System Code Type Description
RXCUI
236234
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY RxNorm
FDA UNII
U347PV74IL
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
SMS_ID
100000089809
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
EVMPD
SUB02324MIG
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
CAS
122111-03-9
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL888
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
DRUG BANK
DBSALT000092
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
RS_ITEM_NUM
1288463
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
MERCK INDEX
m5690
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY Merck Index
PUBCHEM
60749
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID3047849
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
DAILYMED
U347PV74IL
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
USAN
CC-15
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
NCI_THESAURUS
C961
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
CHEBI
31647
Created by admin on Mon Mar 31 17:50:15 GMT 2025 , Edited by admin on Mon Mar 31 17:50:15 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of GEMCITABINE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
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