Basic information
- CAS
18771-50-1- Standard SMILES
O=C1NC(O)CCN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O- InChIKey
UCKYOOZPSJFJIZ-XVKVHKPRSA-N- Molecular formula
- C9H16N2O6
- Average molar mass
- 248.23 g/mol
- Monoisotopic mass
- 248.10083623
Overview
Tetrahydrouridine has been used in trials studying the treatment of Neoplasms, Lung Neoplasms, Breast Neoplasms, Sickle Cell Disease, and Head and Neck Cancer, among others.
Names & identifiers
- Preferred name
- Tetrahydrouridine
- IUPAC
- 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one
- English name
- Tetrahydrouridine
- Molecular formula
- C9H16N2O6
- Molecular weight
- 248.23
Names & synonyms
TETRAHYDROURIDINE18771-50-1NSC-1129070NIZ8H6OL8NSC-112907-DNSC 112907NSC112907U-232842(1H)-pyrimidinone, tetrahydro-4-hydroxy-1-beta-D-ribofuranosyl-RefChem:1887183,4,5,6-Tetrahydrouridine1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-hydroxytetrahydropyrimidin-2(1H)-one
Show more names
DFMA | RMI 71897Tetrahydrouridine dihydrate3,4,5,6-Tetrahydrouridine (>3,4,5,6-Tetrahydrouridine (>80%)Tetrahydrouridine (aqueous solution)
CHEMBL23111283,4,5,6-Tetrahydrouridine (>80%)U 232842(1H)-Pyrimidinone, tetrahydro-4-hydroxy-1-.beta.-D-ribofuranosyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-hydroxy-hexahydropyrimidin-2-oneUridine, 3,4,5,6-tetrahydro-MFCD00063468BRN 0752319
Database identifiers
- CAS
18771-50-1- PubChem CID
- 29243
Properties
Computed structural properties
- XLogP
- -2.4
- Topological polar surface area
- 122 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 301
Physicochemical properties
- Melting point
- 195 °C · >195°C (dec.)
- Boiling point
- 668.6 · 668.6±55.0 °C(Predicted)
- Density
- 1.622 · 1.622±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- Solid
- pka
- 12.5 · 12.50±0.40(Predicted)
- color
- White to Off-White
- Water Solubility
- 200 mg/mL · water: 200mg/mL
- Stability
- Light Sensitive
- 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
- InChIKey
- UCKYOOZPSJFJIZ-XVKVHKPRSA-N
- SMILES
- OC1CCN([C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2)C(N1)=O
- NCI Dictionary of Cancer Terms
- tetrahydrouridine
- FDA UNII
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 12 - Non Combustible Liquids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationDrugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)
Applications
DescriptionTetrahydrouridine is a competitive, reversible inhibitor of cytidine deaminase (Ki values = 54 and 240 nM for human and E. coli enzymes, respectively).Its use, alone or in combination with the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine, is being evaluated in animal models and clinical trials for diseases, including cancer and mitochondrial DNA depletion syndrome.
DescriptionTetrahydrouridine is a competitive, reversible inhibitor of cytidine deaminase (Ki values = 54 and 240 nM for human and E. coli enzymes, respectively). Its use, alone or in combination with the DNA methyltransferase inhibitor 5-fluoro-2’-deoxycytidine, is being evaluated in animal models and clinical trials for diseases, including cancer and mitochondrial DNA depletion syndrome.
Uses3,4,5,6-Tetrahydrouridine, is a derivative of Uridine (U829910). Tetrahydrouridine (THU), is a potent inhibitor of cytidine. It inhibits cell proliferation through cell cycle regulation regardless of cytidine deaminase expression levels deaminase (CDA), and thus can be used as a potential and promising treatment for tumors with highly expressed CDA.
Suppliers73 total
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
武汉敬康恩生物医药科技有限公司
Related reactions
3 records
Compound notes
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