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584223

Sigma-Aldrich

Tetrahydrouridine

≥90% (TLC), liquid, Cytidine deaminase inhibitor, Calbiochem®

Synonym(s):

InSolution Tetrahydrouridine, THU, H4U, 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-hydroxytetrahydropyrimidin-2(1H)-one, dihydrate

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About This Item

Empirical Formula (Hill Notation):
C9H16N2O6 · 2H2O
CAS Number:
18771-50-1
Molecular Weight:
284.26
MDL number:
MFCD00063468
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Tetrahydrouridine, InSolution, ≥90%, competitive inhibitor of cytidine deaminase

Quality Level

100

Assay

≥90% (TLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
avoid repeated freeze/thaw cycles
protect from light

shipped in

dry ice

storage temp.

−70°C

SMILES string

OC1CCN([C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2)C(N1)=O

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

InChI key

UCKYOOZPSJFJIZ-XVKVHKPRSA-N

General description

A potent competitive inhibitor of cytidine deaminase. Used in combination with cytosine arabinoside (Ara-C) to assess the anti-leukemic activity and anti-tumor activity of Ara-C in in vitro studies. The solid form of this compound (Cat. No. 584222) is also available.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
cytidine deaminase
Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Physical form

A 100 mM (25 mg/879 µL) solution of Tetrahydrouridine (Cat. No. 584222) in H₂O.

Reconstitution

Following initial thaw, aliquot and freeze (-70°C). Aliquots are stable for up to 6 months at -70°C.

Other Notes

Yusa, K., et al. 1995. Biochem. Biophys. Res. Commun.206, 486.

Bouffard, D.Y., et al. 1993. Biochem Pharmacol.45, 1857.
Laliberte, J., et al. 1992. Cancer Chemotherap. Pharmacol.30, 7.
Riva, C., et al. 1992. Chemotherapy38, 358.
Yusa, K., et al. 1992. J. Biol. Chem.267, 16848.
Hanze, A.R. 1967. J. Am. Chem. Soc.89, 6720.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

12 - Non Combustible Liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

584223-25MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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