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
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
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 |
DescriptionSources: http://adisinsight.springer.com/drugs/800025123 | https://www.ncbi.nlm.nih.gov/pubmed/20066470 | https://www.ncbi.nlm.nih.gov/pubmed/22002019http://www.drugbank.ca/drugs/DB00441Curator's Comment:: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020509s075lbl.pdf
Sources: http://adisinsight.springer.com/drugs/800025123 | https://www.ncbi.nlm.nih.gov/pubmed/20066470 | https://www.ncbi.nlm.nih.gov/pubmed/22002019http://www.drugbank.ca/drugs/DB00441
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11391856
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
Sources: http://adisinsight.springer.com/drugs/800025123http://adisinsight.springer.com/drugs/800000811
Curator's Comment:: # Eli Lilly; University of Innsbruck
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: map03030 |
|||
Target ID: CHEMBL1830 Sources: http://www.drugbank.ca/drugs/DB00441 |
|||
Target ID: DNA Sources: http://www.drugbank.ca/drugs/DB00441 |
|||
Target ID: CHEMBL614774 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833690 |
3.0 nM [IC50] | ||
Target ID: CHEMBL614067 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833690 |
30.0 nM [IC50] | ||
Target ID: CHEMBL614139 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25517919 |
10.0 nM [IC50] | ||
Target ID: CHEMBL614725 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25517919 |
7.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Gemzar Approved UseGemzar 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 Date8.3203201E11 |
|||
Primary | Gemzar Approved UseGemzar 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 Date8.3203201E11 |
|||
Primary | Gemzar Approved UseGemzar 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 Date8.3203201E11 |
|||
Primary | Gemzar Approved UseGemzar 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 Date8.3203201E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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... Other AEs: Myelosuppression Sources: Paresthesia Rash (severe) |
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) Sources: AST increased (grade 2, 1 patient) ALT increased (grade 2, 1 patient) |
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) Sources: Neutropenic infection (grade 4, 1 patient) |
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%) Sources: 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%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.nature.com/articles/6601011/ Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00913198
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20066470
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
Edited
Fri Jun 25 20:56:25 UTC 2021
by
admin
on
Fri Jun 25 20:56:25 UTC 2021
|
Record UNII |
U347PV74IL
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 |