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

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11F2N3O4
Molecular Weight 263.1985
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GEMCITABINE

SMILES

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

InChI

InChIKey=SDUQYLNIPVEERB-QPPQHZFASA-N
InChI=1S/C9H11F2N3O4/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)/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

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
2344
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

Approval Year

1996
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7728
Inhibitor
7728
Target ID: DNA
Inhibitor
7728
T-24
3
Target ID: CHEMBL614774
Inhibitor
7728
 3.0 nM [IC50]
CAKI-1
4
Target ID: CHEMBL614067
Inhibitor
7728
 30.0 nM [IC50]
PANC-1
6
Target ID: CHEMBL614139
Inhibitor
7728
 10.0 nM [IC50]
Inhibitor
7728
 7.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1101
Unknown

Approved Use

Unknown
Primary
Phase I
409
Unknown

Approved Use

Unknown
Primary
Approved
8043
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
Approved
8043
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
Approved
8043
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
Approved
8043
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
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)
n = 4
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Population Size: 4
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)
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:
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)
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:
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
n = 1
Health Status: unhealthy
Age Group: 74 years
Sex: M
Population Size: 1
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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)
n = 4
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Population Size: 4
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)
n = 4
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Population Size: 4
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)
n = 4
Health Status: unhealthy
Age Group: 55 years (range: 34-71 years)
Sex: M+F
Population Size: 4
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)
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:
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)
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:
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)
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:
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)
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:
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)
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:
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
n = 1
Health Status: unhealthy
Age Group: 74 years
Sex: M
Population Size: 1
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
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
n = 979
Health Status: unhealthy
Condition: malignancies
Age Group: adult
Sex: M+F
Population Size: 979
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
TK2
4

hCNT1
3

hCNT2
3

hCNT3
3

MRP5
39
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
MRP5
39
 yes
TK2
4
 yes
hCNT1
3
 yes
hCNT2
3
 yes
hCNT3
3
 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
Activity of standard and investigational cytotoxic drugs in primary cultures of tumor cells from patients with kidney and urinary bladder carcinomas.
1999 Dec
Severe non-haematological toxicity after treatment with gemcitabine.
1999 Nov
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 dose-finding study of gemcitabine and vinorelbine in advanced previously treated malignancies.
2000 Jan
Treatment of classical Kaposi's sarcoma with gemcitabine.
2001
Noncardiogenic pulmonary edema: an unusual and serious complication of anticancer therapy.
2001
Recent advances in bladder cancer chemotherapy.
2001
Malignant pleural mesothelioma.
2001
Treatment of extensive stage small cell lung cancer.
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
Activity of gemcitabine and continuous infusion fluorouracil in advanced pancreatic cancer.
2001
Gemcitabine, paclitaxel, and trastuzumab in metastatic 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
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
Radiation concurrent with gemcitabine for locally advanced head and neck cancer: a phase I trial and intracellular drug incorporation study.
2001 Feb 1
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
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
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
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
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
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
Irinotecan in combined-modality therapy for locally advanced non-small-cell lung cancer.
2001 Jan
Preirradiation gemcitabine chemotherapy for newly diagnosed glioblastoma. A phase II study.
2001 Jan 15
Optimizing chemoradiation in locally advanced non-small-cell lung cancer.
2001 Mar
Gemcitabine and nonplatinum combinations in non-small-cell lung cancer.
2001 Mar
Latent hematopoietic stem cell toxicity associated with protracted drug administration.
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
Steroids affect collateral sensitivity to gemcitabine of multidrug-resistant human lung cancer cells.
2001 Mar 23
Human cytosolic 5'-nucleotidase I: characterization and role in nucleoside analog resistance.
2001 Mar 30
Akt, MAPK (Erk1/2), and p38 act in concert to promote apoptosis in response to ErbB receptor family inhibition.
2001 May 4
Metabolism and accumulation of the lipophilic deoxynucleoside analogs elacytarabine and CP-4126.
2012 Oct
Patents

Patents

20100279966
3
20100279977
3
20130116207
3
JP2004518776A
8
JP2006502184A
39
JP2006523607A
9
JP2007518822A
9
JP2007533670A
7
JP2008510795A
65
JP2008533019A
33
JP2009531296A
20
JP2011501962A
9
JP2011528275A
417
JP2012500104A
106
JP2013231029A
3
JP4397691B2
22

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Sat Jun 26 03:34:51 UTC 2021
Edited
by admin
on Sat Jun 26 03:34:51 UTC 2021
Record UNII
B76N6SBZ8R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GEMCITABINE
HSDB   INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
GEMCITABINE [USAN]
Common Name English
LY188011
Code English
GEMCITABINE [MI]
Common Name English
GEMCITABINE [HSDB]
Common Name English
GEMCITABINE [WHO-DD]
Common Name English
CYTIDINE, 2'-DEOXY-2',2'-DIFLUORO-
Systematic Name English
LY-188011
Code English
NSC-613327
Code English
GEMCITABINE [VANDF]
Common Name English
2'-DEOXY-2',2'-DIFLUOROCYTIDINE
Systematic Name English
GEMCITABINE [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QL01BC05
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
WHO-ATC L01BC05
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
FDA ORPHAN DRUG 477015
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
NCI_THESAURUS C2150
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
FDA ORPHAN DRUG 504815
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
FDA ORPHAN DRUG 620917
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
NDF-RT N0000000233
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
NCI_THESAURUS C1557
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
FDA ORPHAN DRUG 476915
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
NDF-RT N0000175595
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
LIVERTOX 451
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
FDA ORPHAN DRUG 737820
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
FDA ORPHAN DRUG 502015
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
Code System Code Type Description
EVMPD
SUB07892MIG
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
HSDB
7567
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
WIKIPEDIA
GEMCITABINE
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
RXCUI
12574
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M5690
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY Merck Index
CAS
95058-81-4
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
FDA UNII
B76N6SBZ8R
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
DRUG BANK
DB00441
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
INN
6515
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
LACTMED
Gemcitabine
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
PUBCHEM
60750
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
DRUG CENTRAL
1283
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
NCI_THESAURUS
C66876
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
EPA CompTox
95058-81-4
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
ChEMBL
CHEMBL888
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
MESH
C056507
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
IUPHAR
4793
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
PRIMARY
CAS
103882-84-4
Created by admin on Sat Jun 26 03:34:51 UTC 2021 , Edited by admin on Sat Jun 26 03:34:51 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
Related Record Type Details
DEOXYCYTIDINE KINASE
METABOLIC ENZYME -> SUBSTRATE
Km
Structure of GEMCITABINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
EQUILIBRATIVE NUCLEOSIDE TRANSPORTER 1
TRANSPORTER -> SUBSTRATE
kcat
DEOXYCYTIDINE KINASE
METABOLIC ENZYME -> SUBSTRATE
kcat
Related Record Type Details
Structure of LY-2334737
PRODRUG -> METABOLITE ACTIVE
Structure of GEMCITABINE TRIPHOSPHATE
METABOLITE ACTIVE -> PARENT
Structure of GEMCITABINE 5'-MONOPHOSPHATE
METABOLITE ACTIVE -> PARENT
Structure of GEMCITABINE TRIPHOSPHATE
METABOLITE ACTIVE -> PARENT
can be extracted from peripheral blood mononuclear cells.
Structure of 2',2'-DIFLUORODEOXYURIDINE
METABOLITE INACTIVE -> PARENT
PLASMA; URINE
Structure of 2'-DEOXY-2',2'-DIFLUORO-5'-URIDYLIC ACID
METABOLITE -> PARENT
Structure of FOSGEMCITABINE PALABENAMIDE
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of GEMCITABINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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