azaribine
Azaribine (2′, 3′, 5′-triacetyl-6-azauridine) is the orally absorbable triacetylated derivative of the pyrimidine analog 6-azauridine. Ribonucleoside of 6-azauracil, which can be derived in the tissues by the deacetylation of azaribine, has been shown, after its intracellular conversion to 6-azauridine-5'-monophosphate, to serve as an inhibitor of the activity of a key enzyme, orotidine-5'-monophosphate (OMP) decarboxylase, critically concerned with the biosynthesis de novo of pyrimidines essential for the formation of nucleic acids. Azaribine exerts antineoplastic action. In 1975 azaribine was approved for the treatment of psoriasis. The drug was withdrawn because it may cause life-threatening or fatal blood clots in the veins and arteries. — NCATS
Clinical trial activity
0 trials · 0 clinical orgs · 0 marketing orgs
Mechanism of action
- Uridine 5'-monophosphate synthaseINHIBITOR
UMPS inhibitor
The primary action of this compound is related to the activity of the nucleoside 6-azauridine, which is a structural analog of uridine. In mammalian systems, 6-azauridine, after its metabolic conversion to 6-azauridine-5¿-phosphate, competitively inhibits intracellular pyrimidine nucleotide synthesis. The mechanism of inhibition is related to a competition beween orotidine-5'-phosphate and 6-azauridine-5'-phosphate for the enzyme orotidylate decarboxylase.
Chemistry & pharmacology
SMILES
CC(=O)OC[C@H]1O[C@H]([C@H](OC(C)=O)[C@@H]1OC(C)=O)N2N=CC(=O)NC2=O- Mol. weight
- 371.2995 g/mol
- Lipinski Ro5
- 1 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- NCATSK1U80DO9EB ↗
- ChEMBLCHEMBL564201 ↗
- ChEMBLCHEMBL515914 ↗
Also known as
- 2-beta-d-ribofuranosyl-as-triazine-3,5(2h,4h)-dione 2',3',5'-triacetate
- 6-azauridine triacetate
- 6-azauridine triacetate
- azaribin
- azaribine
- azaribine
- azaribine
- azaribine
- azaribine
- azaribine
- azaribine
- cb 304
- cb-304
- cb-304
- cb-304
- triacetyl-6-azauridine
- triacetyl-6-azauridine
- triacetyl azauridine
- triacetyl azauridine
- triazure
- triazure
- triazure
- triazure