Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H10F2N2O5 |
| Molecular Weight | 264.1829 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@@H](N2C=CC(=O)NC2=O)C(F)(F)[C@@H]1O
InChI
InChIKey=FIRDBEQIJQERSE-QPPQHZFASA-N
InChI=1S/C9H10F2N2O5/c10-9(11)6(16)4(3-14)18-7(9)13-2-1-5(15)12-8(13)17/h1-2,4,6-7,14,16H,3H2,(H,12,15,17)/t4-,6-,7-/m1/s1
| Molecular Formula | C9H10F2N2O5 |
| Molecular Weight | 264.1829 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Ecotoxicity and genotoxicity assessment of cytotoxic antineoplastic drugs and their metabolites. | 2010-09 |
|
| Population pharmacokinetics of gemcitabine and its metabolite in Japanese cancer patients: impact of genetic polymorphisms. | 2010-08 |
|
| Gemcitabine-loaded PEGylated unilamellar liposomes vs GEMZAR: biodistribution, pharmacokinetic features and in vivo antitumor activity. | 2010-06-01 |
|
| Gemcitabine and epirubicin plasma concentration-related excretion in saliva in patients with non-small cell lung cancer. | 2010-06 |
|
| Pharmacokinetics of gemcitabine in non-small-cell lung cancer patients: impact of the 79A>C cytidine deaminase polymorphism. | 2010-06 |
|
| Systemic absorption and pharmacokinetics of single-dose intravesical gemcitabine after transurethral resection of the bladder in non-muscle-invasive bladder cancer. | 2009-11 |
|
| Simultaneous quantification of 2',2'-difluorodeoxycytidine and 2',2'-difluorodeoxyuridine nucleosides and nucleotides in white blood cells using porous graphitic carbon chromatography coupled with tandem mass spectrometry. | 2009-10 |
|
| Mass flows of X-ray contrast media and cytostatics in hospital wastewater. | 2009-07-01 |
|
| Retention studies of 2'-2'-difluorodeoxycytidine and 2'-2'-difluorodeoxyuridine nucleosides and nucleotides on porous graphitic carbon: development of a liquid chromatography-tandem mass spectrometry method. | 2009-04-10 |
|
| Challenge of high polarity and low concentrations in analysis of cytostatics and metabolites in wastewater by hydrophilic interaction chromatography/tandem mass spectrometry. | 2009-02-13 |
|
| A phase I pharmacokinetic study of hypoxic abdominal stop-flow perfusion with gemcitabine in patients with advanced pancreatic cancer and refractory malignant ascites. | 2009-01 |
|
| Does saturable formation of gemcitabine triphosphate occur in patients? | 2008-12 |
|
| New insights into the pharmacology and cytotoxicity of gemcitabine and 2',2'-difluorodeoxyuridine. | 2008-08 |
|
| Extensive metabolism and hepatic accumulation of gemcitabine after multiple oral and intravenous administration in mice. | 2008-08 |
|
| A pharmacodynamic model for the time course of tumor shrinkage by gemcitabine + carboplatin in non-small cell lung cancer patients. | 2008-07-01 |
|
| Phase I clinical trial of intrathecal gemcitabine in patients with neoplastic meningitis. | 2008-07 |
|
| Oral administration of gemcitabine in patients with refractory tumors: a clinical and pharmacologic study. | 2008-06-01 |
|
| Prolonged versus standard gemcitabine infusion: translation of molecular pharmacology to new treatment strategy. | 2008-03 |
|
| Measurement of plasma concentration of gemcitabine and its metabolite dFdU in hemodialysis patients with advanced urothelial cancer. | 2008-03 |
|
| Simultaneous determination of gemcitabine and its main metabolite, dFdU, in plasma of patients with advanced non-small-cell lung cancer by high-performance liquid chromatography-tandem mass spectrometry. | 2008-02 |
|
| Pharmacokinetics and toxicity of an early single intravesical instillation of gemcitabine after endoscopic resection of superficial bladder cancer. | 2007-05-01 |
|
| Phase II study with the combination of gemcitabine and DTIC in patients with advanced soft tissue sarcomas. | 2007-02 |
|
| Pharmacokinetics of gemcitabine in Japanese cancer patients: the impact of a cytidine deaminase polymorphism. | 2007-01-01 |
|
| Validated assay for the simultaneous determination of the anti-cancer agent gemcitabine and its metabolite 2',2'-difluorodeoxyuridine in human plasma by high-performance liquid chromatography with tandem mass spectrometry. | 2007 |
|
| Characterization of lipophilic gemcitabine prodrug-liposomal membrane interaction by differential scanning calorimetry. | 2006-12-05 |
|
| Quantitative analysis of gemcitabine triphosphate in human peripheral blood mononuclear cells using weak anion-exchange liquid chromatography coupled with tandem mass spectrometry. | 2006-12 |
|
| Phase I/II trial of doxorubicin and fixed dose-rate infusion gemcitabine in advanced soft tissue sarcomas: a GEIS study. | 2006-06-19 |
|
| High-performance liquid chromatographic method for the determination of gemcitabine and 2',2'-difluorodeoxyuridine in plasma and tissue culture media. | 2006-05-01 |
|
| Pharmacokinetics of gemcitabine and its primary metabolite in dogs after intravenous infusion. | 2006-04 |
|
| Pharmacokinetics of gemcitabine and its primary metabolite in dogs after intravenous bolus dosing and its in vitro pharmacodynamics. | 2006-04 |
|
| Gemcitabine and atrial fibrillation: a rare manifestation of chemotherapy toxicity. | 2006-03 |
|
| Micro-array analysis of resistance for gemcitabine results in increased expression of ribonucleotide reductase subunits. | 2006 |
|
| Intravesical gemcitabine in superficial bladder cancer: a phase II safety, efficacy and pharmacokinetic study. | 2005-08-06 |
|
| Severe drug toxicity associated with a single-nucleotide polymorphism of the cytidine deaminase gene in a Japanese cancer patient treated with gemcitabine plus cisplatin. | 2005-04-01 |
|
| Comparative pharmacokinetics and metabolic pathway of gemcitabine during intravenous and intra-arterial delivery in unresectable pancreatic cancer patients. | 2005 |
|
| Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing lipophilic gemcitabine prodrugs. | 2004-12-10 |
|
| Phase I clinical trial of fixed-dose rate infusional gemcitabine and dacarbazine in the treatment of advanced soft tissue sarcoma, with assessment of gemcitabine triphosphate accumulation. | 2004-11-15 |
|
| Investigation of the pharmacokinetics of gemcitabine and 2',2'-difluorodeoxyuridine in human plasma by liquid chromatography. | 2004-09-15 |
|
| Phase I trial and pharmacokinetics of gemcitabine in children with advanced solid tumors. | 2004-06-15 |
|
| Intravesical administration of gemcitabine in superficial bladder cancer: a phase I study with pharmacodynamic evaluation. | 2004-03 |
|
| Validated procedure for simultaneous trace level determination of the anti-cancer agent gemcitabine and its metabolite in human urine by high-performance liquid chromatography with tandem mass spectrometry. | 2004 |
|
| An expedient assay for determination of gemcitabine and its metabolite in human plasma using isocratic ion-pair reversed-phase high-performance liquid chromatography. | 2003-10 |
|
| Pharmacokinetics of gemcitabine in a patient with end-stage renal disease: effective clearance of its main metabolite by standard hemodialysis treatment. | 2003-03 |
|
| Measurement of the anti-cancer agent gemcitabine in human plasma by high-performance liquid chromatography. | 2003-02-25 |
|
| Intravesical gemcitabine therapy for superficial transitional cell carcinoma of the bladder: a phase I and pharmacokinetic study. | 2003-02-15 |
|
| In vitro studies on the immunosuppressive effect of 2',2'-difluorodeoxycytidine (dFdC) and its metabolite 2',2'-difluorodeoxyuridine (dFdU). | 2003 |
|
| Phase I-II and pharmacokinetic study of gemcitabine combined with oxaliplatin in patients with advanced non-small-cell lung cancer and ovarian carcinoma. | 2002-09 |
|
| Pharmacokinetics of intrathecal gemcitabine in nonhuman primates. | 2002-07 |
|
| Gemcitabine, epirubicin and paclitaxel: pharmacokinetic and pharmacodynamic interactions in advanced breast cancer. | 2002-06 |
|
| Drug distribution and pharmacokinetic/pharmacodynamic relationship of paclitaxel and gemcitabine in patients with non-small-cell lung cancer. | 2001-11 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:43:12 GMT 2025
by
admin
on
Mon Mar 31 22:43:12 GMT 2025
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| Record UNII |
Y30D8SIL1I
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| Record Status |
Validated (UNII)
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| Record Version |
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9871558
Created by
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114248-23-6
Created by
admin on Mon Mar 31 22:43:12 GMT 2025 , Edited by admin on Mon Mar 31 22:43:12 GMT 2025
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DTXSID50891460
Created by
admin on Mon Mar 31 22:43:12 GMT 2025 , Edited by admin on Mon Mar 31 22:43:12 GMT 2025
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Y30D8SIL1I
Created by
admin on Mon Mar 31 22:43:12 GMT 2025 , Edited by admin on Mon Mar 31 22:43:12 GMT 2025
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PARENT -> METABOLITE INACTIVE |
PLASMA; URINE
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