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18771-50-1,MFCD00063468
Catalog No.:AA0038TU

18771-50-1 | Tetrahydrouridine

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10mg
≥95%
in stock  
$233.00   $163.00
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25mg
≥95%
in stock  
$493.00   $345.00
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50mg
≥95%
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$928.00   $649.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0038TU
Chemical Name:
Tetrahydrouridine
CAS Number:
18771-50-1
Molecular Formula:
C9H16N2O6
Molecular Weight:
248.2331
MDL Number:
MFCD00063468
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1CCC(NC1=O)O
Properties
Computed Properties
 
Complexity:
301  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
5  
Rotatable Bond Count:
2  
Undefined Atom Stereocenter Count:
1  
XLogP3:
-2.4  

Downstream Synthesis Route

[1]CurrentPatentAssignee:PFIZERINC-US4017606,1977,A

[1]CurrentPatentAssignee:PFIZERINC-US4017606,1977,A

84-53-7    18771-50-1   
4-hydroxy-1-β-D-ribofuranosyl-tetrahydro-2(1H)-pyrimidinone3'-phosphate 

[1]CurrentPatentAssignee:PFIZERINC-US4017606,1977,A

Literature

Title: Epigenetic regulation by decitabine of melanoma differentiation in vitro and in vivo.

Journal: International journal of cancer 20120701

Title: Effects of tetrahydrouridine on pharmacokinetics and pharmacodynamics of oral decitabine.

Journal: Blood 20120202

Title: Tetrahydrouridine inhibits cell proliferation through cell cycle regulation regardless of cytidine deaminase expression levels.

Journal: PloS one 20120101

Title: Comparison of in vitro metabolic conversion of capecitabine to 5-FU in rats, mice, monkeys and humans--toxicological implications.

Journal: The Journal of toxicological sciences 20110801

Title: Plasma pharmacokinetics and oral bioavailability of the 3,4,5,6-tetrahydrouridine (THU) prodrug, triacetyl-THU (taTHU), in mice.

Journal: Cancer chemotherapy and pharmacology 20110201

Title: An APCI LC-MS/MS method for routine determination of capecitabine and its metabolites in human plasma.

Journal: Journal of mass spectrometry : JMS 20100601

Title: Stability of 5-fluoro-2'-deoxycytidine and tetrahydrouridine in combination.

Journal: AAPS PharmSciTech 20100301

Title: Is the resistance of gemcitabine for pancreatic cancer settled only by overexpression of deoxycytidine kinase?

Journal: Oncology reports 20100201

Title: Synthesis of deoxytetrahydrouridine.

Journal: The Journal of organic chemistry 20090306

Title: Plasma pharmacokinetics and oral bioavailability of 3,4,5,6-tetrahydrouridine, a cytidine deaminase inhibitor, in mice.

Journal: Cancer chemotherapy and pharmacology 20080801

Title: Concentrations of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine (FdCyd) and its cytotoxic metabolites in plasma of patients treated with FdCyd and tetrahydrouridine (THU).

Journal: Cancer chemotherapy and pharmacology 20080701

Title: Optimized blood sampling with cytidine deaminase inhibitor for improved analysis of capecitabine metabolites.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080701

Title: Modulation of gemcitabine (2',2'-difluoro-2'-deoxycytidine) pharmacokinetics, metabolism, and bioavailability in mice by 3,4,5,6-tetrahydrouridine.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080601

Title: Quantitative determination of the cytidine deaminase inhibitor tetrahydrouridine (THU) in mouse plasma by liquid chromatography/electrospray ionization tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20070101

Title: The 1.48 A resolution crystal structure of the homotetrameric cytidine deaminase from mouse.

Journal: Biochemistry 20060627

Title: Relatively small increases in the steady-state levels of nucleobase deamination products in DNA from human TK6 cells exposed to toxic levels of nitric oxide.

Journal: Chemical research in toxicology 20060101

Title: Structure of human cytidine deaminase bound to a potent inhibitor.

Journal: Journal of medicinal chemistry 20050210

Title: Molecular characterization of thymidine kinase from Ureaplasma urealyticum: nucleoside analogues as potent inhibitors of mycoplasma growth.

Journal: Molecular microbiology 20031101

Title: Epimer interconversion, isomerization, and hydrolysis of tetrahydrouridine: implications for cytidine deaminase inhibition.

Journal: Journal of pharmaceutical sciences 20031001

Title: Analytical and pharmacokinetic studies with 5-chloro-2'-deoxycytidine.

Journal: Biochemical pharmacology 20021115

Title: Five-chlorodeoxycytidine, a tumor-selective enzyme-driven radiosensitizer, effectively controls five advanced human tumors in nude mice.

Journal: International journal of radiation oncology, biology, physics 20011101

Title: Regulatory effects of deoxyribonucleosides on the activity of 5-methoxymethyl-2'-deoxycytidine: modulation of antiherpes activity by deoxyguanosine and tetrahydrodeoxyuridine.

Journal: Antiviral research 19910501

Title: Antiherpes virus activity and effect on deoxyribonucleoside triphosphate pools of (E)-5-(2-bromovinyl)-2'-deoxycytidine in combination with deaminase inhibitors.

Journal: Antiviral research 19900301

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