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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
Structure of 2′,2′-Difluorodeoxyuridine

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

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
Drug distribution and pharmacokinetic/pharmacodynamic relationship of paclitaxel and gemcitabine in patients with non-small-cell lung cancer.
2001 Nov
Pharmacokinetics of intrathecal gemcitabine in nonhuman primates.
2002 Jul
Gemcitabine, epirubicin and paclitaxel: pharmacokinetic and pharmacodynamic interactions in advanced breast cancer.
2002 Jun
Phase I-II and pharmacokinetic study of gemcitabine combined with oxaliplatin in patients with advanced non-small-cell lung cancer and ovarian carcinoma.
2002 Sep
In vitro studies on the immunosuppressive effect of 2',2'-difluorodeoxycytidine (dFdC) and its metabolite 2',2'-difluorodeoxyuridine (dFdU).
2003
Intravesical gemcitabine therapy for superficial transitional cell carcinoma of the bladder: a phase I and pharmacokinetic study.
2003 Feb 15
Measurement of the anti-cancer agent gemcitabine in human plasma by high-performance liquid chromatography.
2003 Feb 25
Pharmacokinetics of gemcitabine in a patient with end-stage renal disease: effective clearance of its main metabolite by standard hemodialysis treatment.
2003 Mar
An expedient assay for determination of gemcitabine and its metabolite in human plasma using isocratic ion-pair reversed-phase high-performance liquid chromatography.
2003 Oct
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
Intravesical administration of gemcitabine in superficial bladder cancer: a phase I study with pharmacodynamic evaluation.
2004 Mar
Comparative pharmacokinetics and metabolic pathway of gemcitabine during intravenous and intra-arterial delivery in unresectable pancreatic cancer patients.
2005
Intravesical gemcitabine in superficial bladder cancer: a phase II safety, efficacy and pharmacokinetic study.
2005 May-Jun
Micro-array analysis of resistance for gemcitabine results in increased expression of ribonucleotide reductase subunits.
2006
Quantitative analysis of gemcitabine triphosphate in human peripheral blood mononuclear cells using weak anion-exchange liquid chromatography coupled with tandem mass spectrometry.
2006 Dec
Gemcitabine and atrial fibrillation: a rare manifestation of chemotherapy toxicity.
2006 Mar
High-performance liquid chromatographic method for the determination of gemcitabine and 2',2'-difluorodeoxyuridine in plasma and tissue culture media.
2006 May 1
Characterization of lipophilic gemcitabine prodrug-liposomal membrane interaction by differential scanning calorimetry.
2006 Nov-Dec
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
Pharmacokinetics of gemcitabine in Japanese cancer patients: the impact of a cytidine deaminase polymorphism.
2007 Jan 1
Pharmacokinetics and toxicity of an early single intravesical instillation of gemcitabine after endoscopic resection of superficial bladder cancer.
2007 Mar-Apr
New insights into the pharmacology and cytotoxicity of gemcitabine and 2',2'-difluorodeoxyuridine.
2008 Aug
Extensive metabolism and hepatic accumulation of gemcitabine after multiple oral and intravenous administration in mice.
2008 Aug
Does saturable formation of gemcitabine triphosphate occur in patients?
2008 Dec
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 Feb
Phase I clinical trial of intrathecal gemcitabine in patients with neoplastic meningitis.
2008 Jul
Prolonged versus standard gemcitabine infusion: translation of molecular pharmacology to new treatment strategy.
2008 Mar
Measurement of plasma concentration of gemcitabine and its metabolite dFdU in hemodialysis patients with advanced urothelial cancer.
2008 Mar
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 Apr 10
Mass flows of X-ray contrast media and cytostatics in hospital wastewater.
2009 Jul 1
Systemic absorption and pharmacokinetics of single-dose intravesical gemcitabine after transurethral resection of the bladder in non-muscle-invasive bladder cancer.
2009 Nov
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 Oct
Population pharmacokinetics of gemcitabine and its metabolite in Japanese cancer patients: impact of genetic polymorphisms.
2010 Aug
Gemcitabine and epirubicin plasma concentration-related excretion in saliva in patients with non-small cell lung cancer.
2010 Jun
Pharmacokinetics of gemcitabine in non-small-cell lung cancer patients: impact of the 79A>C cytidine deaminase polymorphism.
2010 Jun
Gemcitabine-loaded PEGylated unilamellar liposomes vs GEMZAR: biodistribution, pharmacokinetic features and in vivo antitumor activity.
2010 Jun 1
Ecotoxicity and genotoxicity assessment of cytotoxic antineoplastic drugs and their metabolites.
2010 Sep
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:33:15 UTC 2023
Edited
by admin
on Sat Dec 16 09:33:15 UTC 2023
Record UNII
Y30D8SIL1I
Record Status Validated (UNII)
Record Version
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Name Type Language
2′,2′-Difluorodeoxyuridine
Systematic Name English
GEMCITABINE HYDROCHLORIDE IMPURITY C [ EP IMPURITY]
Common Name English
1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin-2,4(1H,3H)-dione
Systematic Name English
2′-deoxy-2′,2′-difluorouridine
Common Name English
Code System Code Type Description
PUBCHEM
9871558
Created by admin on Sat Dec 16 09:33:15 UTC 2023 , Edited by admin on Sat Dec 16 09:33:15 UTC 2023
PRIMARY
CAS
114248-23-6
Created by admin on Sat Dec 16 09:33:15 UTC 2023 , Edited by admin on Sat Dec 16 09:33:15 UTC 2023
PRIMARY
EPA CompTox
DTXSID50891460
Created by admin on Sat Dec 16 09:33:15 UTC 2023 , Edited by admin on Sat Dec 16 09:33:15 UTC 2023
PRIMARY
FDA UNII
Y30D8SIL1I
Created by admin on Sat Dec 16 09:33:15 UTC 2023 , Edited by admin on Sat Dec 16 09:33:15 UTC 2023
PRIMARY
Related Record Type Details
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