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MedKoo Cat#: 206568 | Name: Tetrahydrouridine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tetrahydrouridine is a synthetic pyrimidine nucleoside analogue with biomodulating activity. Tetrahydrouridine increases the efficacy of the radiosensitizer cytochlor (5-chloro-2'-deoxycytidine) by inhibiting the enzyme deoxycytidine monophosphate (dCMP) deaminase and preventing the premature deamination of the cytochlor metabolite 5-chloro-2'-deoxycytidine monophosphate (CldCMP) to 5-chloro-2'-deoxyuridine monophosphate (CldUMP); in turn, this increases tumor concentrations of CldUMP which is then further anabolized and incorporated selectively into tumor DNA as CldU (5-chloro-2'-deoxyuridine).

Chemical Structure

Tetrahydrouridine
Tetrahydrouridine
CAS#18771-50-1

Theoretical Analysis

MedKoo Cat#: 206568

Name: Tetrahydrouridine

CAS#: 18771-50-1

Chemical Formula: C9H16N2O6

Exact Mass: 248.1008

Molecular Weight: 248.24

Elemental Analysis: C, 43.55; H, 6.50; N, 11.29; O, 38.67

Price and Availability

Size Price Availability Quantity
25mg USD 550.00 2 Weeks
50mg USD 950.00 2 Weeks
100mg USD 1,650.00 2 Weeks
200mg USD 2,650.00 2 Weeks
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Related CAS #
No Data
Synonym
Tetrahydrouridine, NSC 112907; NSC-112907; NSC112907.
IUPAC/Chemical Name
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-hydroxytetrahydropyrimidin-2(1H)-one
InChi Key
UCKYOOZPSJFJIZ-XVKVHKPRSA-N
InChi Code
InChI=1S/C9H16N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4-8,12-15H,1-3H2,(H,10,16)/t4-,5?,6-,7-,8-/m1/s1
SMILES Code
C1CN(C(=O)NC1O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 248.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Morfouace M, Nimmervoll B, Boulos N, Patel YT, Shelat A, Freeman BB 3rd, Robinson GW, Wright K, Gajjar A, Stewart CF, Gilbertson RJ, Roussel MF. Preclinical studies of 5-fluoro-2'-deoxycytidine and tetrahydrouridine in pediatric brain tumors. J Neurooncol. 2015 Oct 30. [Epub ahead of print] PubMed PMID: 26518542. 2: Mano Y, Sakamaki K, Ueno T, Kita K, Ishii T, Hotta K, Kusano K. Validation of a hydrophilic interaction ultra-performance liquid chromatography-tandem mass spectrometry method for the determination of gemcitabine in human plasma with tetrahydrouridine. Biomed Chromatogr. 2015 Sep;29(9):1343-9. doi: 10.1002/bmc.3429. Epub 2015 Feb 2. PubMed PMID: 25641274. 3: Newman EM, Morgan RJ, Kummar S, Beumer JH, Blanchard MS, Ruel C, El-Khoueiry AB, Carroll MI, Hou JM, Li C, Lenz HJ, Eiseman JL, Doroshow JH. A phase I, pharmacokinetic, and pharmacodynamic evaluation of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine, administered with tetrahydrouridine. Cancer Chemother Pharmacol. 2015 Mar;75(3):537-46. doi: 10.1007/s00280-014-2674-7. Epub 2015 Jan 8. PubMed PMID: 25567350; PubMed Central PMCID: PMC4344391. 4: Terse P, Engelke K, Chan K, Ling Y, Sharpnack D, Saunthararajah Y, Covey JM. Subchronic oral toxicity study of decitabine in combination with tetrahydrouridine in CD-1 mice. Int J Toxicol. 2014 Mar-Apr;33(2):75-85. doi: 10.1177/1091581814524994. Epub 2014 Mar 17. PubMed PMID: 24639139; PubMed Central PMCID: PMC4001115. 5: Ferraris D, Duvall B, Delahanty G, Mistry B, Alt J, Rojas C, Rowbottom C, Sanders K, Schuck E, Huang KC, Redkar S, Slusher BB, Tsukamoto T. Design, synthesis, and pharmacological evaluation of fluorinated tetrahydrouridine derivatives as inhibitors of cytidine deaminase. J Med Chem. 2014 Mar 27;57(6):2582-8. doi: 10.1021/jm401856k. Epub 2014 Feb 24. PubMed PMID: 24520856. 6: Funamizu N, Lacy CR, Fujita K, Furukawa K, Misawa T, Yanaga K, Manome Y. Tetrahydrouridine inhibits cell proliferation through cell cycle regulation regardless of cytidine deaminase expression levels. PLoS One. 2012;7(5):e37424. doi: 10.1371/journal.pone.0037424. Epub 2012 May 16. PubMed PMID: 22616006; PubMed Central PMCID: PMC3353937. 7: Lavelle D, Vaitkus K, Ling Y, Ruiz MA, Mahfouz R, Ng KP, Negrotto S, Smith N, Terse P, Engelke KJ, Covey J, Chan KK, Desimone J, Saunthararajah Y. Effects of tetrahydrouridine on pharmacokinetics and pharmacodynamics of oral decitabine. Blood. 2012 Feb 2;119(5):1240-7. doi: 10.1182/blood-2011-08-371690. Epub 2011 Dec 7. PubMed PMID: 22160381; PubMed Central PMCID: PMC3277356. 8: Beumer JH, Eiseman JL, Gilbert JA, Holleran JL, Yellow-Duke AE, Clausen DM, D'Argenio DZ, Ames MM, Hershberger PA, Parise RA, Bai L, Covey JM, Egorin MJ. Plasma pharmacokinetics and oral bioavailability of the 3,4,5,6-tetrahydrouridine (THU) prodrug, triacetyl-THU (taTHU), in mice. Cancer Chemother Pharmacol. 2011 Feb;67(2):421-30. doi: 10.1007/s00280-010-1337-6. Epub 2010 May 5. PubMed PMID: 20443002; PubMed Central PMCID: PMC2954253. 9: Guo D, Myrdal PB, Karlage KL, O'Connell SP, Wissinger TJ, Tabibi SE, Yalkowsky SH. Stability of 5-fluoro-2'-deoxycytidine and tetrahydrouridine in combination. AAPS PharmSciTech. 2010 Mar;11(1):247-52. doi: 10.1208/s12249-010-9383-2. Epub 2010 Feb 12. PubMed PMID: 20151336; PubMed Central PMCID: PMC2850501. 10: Beumer JH, Eiseman JL, Parise RA, Joseph E, Covey JM, Egorin MJ. Modulation of gemcitabine (2',2'-difluoro-2'-deoxycytidine) pharmacokinetics, metabolism, and bioavailability in mice by 3,4,5,6-tetrahydrouridine. Clin Cancer Res. 2008 Jun 1;14(11):3529-35. doi: 10.1158/1078-0432.CCR-07-4885. PubMed PMID: 18519786. 11: Beumer JH, Eiseman JL, Parise RA, Florian JA Jr, Joseph E, D'Argenio DZ, Parker RS, Kay B, Covey JM, Egorin MJ. Plasma pharmacokinetics and oral bioavailability of 3,4,5,6-tetrahydrouridine, a cytidine deaminase inhibitor, in mice. Cancer Chemother Pharmacol. 2008 Aug;62(3):457-64. Epub 2007 Nov 15. PubMed PMID: 18008070; PubMed Central PMCID: PMC2677692. 12: Beumer JH, Parise RA, Newman EM, Doroshow JH, Synold TW, Lenz HJ, Egorin MJ. 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). Cancer Chemother Pharmacol. 2008 Jul;62(2):363-8. Epub 2007 Sep 26. PubMed PMID: 17899082. 13: Parise RA, Egorin MJ, Eiseman JL, Joseph E, Covey JM, Beumer JH. Quantitative determination of the cytidine deaminase inhibitor tetrahydrouridine (THU) in mouse plasma by liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(13):1991-7. PubMed PMID: 17526067. 14: Xiang TX, Niemi R, Bummer P, Anderson BD. Epimer interconversion, isomerization, and hydrolysis of tetrahydrouridine: implications for cytidine deaminase inhibition. J Pharm Sci. 2003 Oct;92(10):2027-39. PubMed PMID: 14502542. 15: Marsh JH, Kreis W, Barile B, Akerman S, Schulman P, Allen SL, DeMarco LC, Schuster MW, Budman DR. Therapy of refractory/relapsed acute myeloid leukemia and blast crisis of chronic myeloid leukemia with the combination of cytosine arabinoside, tetrahydrouridine, and carboplatin. Cancer Chemother Pharmacol. 1993;31(6):481-4. PubMed PMID: 8453688. 16: Riva C, Barra Y, Carcassonne Y, Cano JP, Rustum Y. Effect of tetrahydrouridine on metabolism and transport of 1-beta-D-arabinofuranosylcytosine in human cells. Chemotherapy. 1992;38(5):358-66. PubMed PMID: 1286578. 17: Kreis W, Budman DR, Chan K, Allen SL, Schulman P, Lichtman S, Weiselberg L, Schuster M, Freeman J, Akerman S, et al. Therapy of refractory/relapsed acute leukemia with cytosine arabinoside plus tetrahydrouridine (an inhibitor of cytidine deaminase)--a pilot study. Leukemia. 1991 Nov;5(11):991-8. PubMed PMID: 1961042. 18: Grant S, Bhalla K, McCrady C. Effect of tetrahydrouridine and deoxytetrahydrouridine on the interaction between 2'-deoxycytidine and 1-beta-D-arabinofuranosylcytosine in human leukemia cells. Leuk Res. 1991;15(4):205-13. PubMed PMID: 2030601. 19: Lawrence TS, Davis MA. Selective radiosensitization and cytotoxicity of human melanoma cells using halogenated deoxycytidines and tetrahydrouridine. Int J Radiat Oncol Biol Phys. 1989 May;16(5):1243-6. PubMed PMID: 2715074. 20: Kreis W, Chan K, Budman DR, Schulman P, Allen S, Weiselberg L, Lichtman S, Henderson V, Freeman J, Deere M, et al. Effect of tetrahydrouridine on the clinical pharmacology of 1-beta-D-arabinofuranosylcytosine when both drugs are coinfused over three hours. Cancer Res. 1988 Mar 1;48(5):1337-42. PubMed PMID: 3342412.

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