5-METHYL-4-PHENYL-1,2,3-THIADIAZOLE Property

storage temp. 

Store at -20°C

solubility 

insoluble in H2O; ≥10.38 mg/mL in EtOH; ≥7.85 mg/mL in DMSO

form 

solid

color 

Red-brown

Safety

Hazard Codes 

Xn

Risk Statements 

22

Hazard Note 

Harmful

HS Code 

2934999090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

5-METHYL-4-PHENYL-1,2,3-THIADIAZOLE Chemical Properties,Usage,Production

Uses

4-phenyl-5-methyl-1,2,3-Thiadiazole is a selective, mechanism-based inhibitor of CYP2B4 and CYP2E1.

Biological Activity

4-phenyl-5-methyl-1,2,3-thiadiazole is a cyp2b4 and cyp2e1 inhibitor.cytochrome p450 (cyp450) enzymes, a superfamily of oxidative catalysts, are important in the biosynthesis and metabolism of a wide range of endogenous molecules and the metabolism of xenobiotics. cyp2b4 can metabolize substituted amines, while cyp2e1 metabolizes various alcohols and halogenated alkenes.

in vitro

4-phenyl-5-methyl-1,2,3-thiadiazole (pmt) was found to be slightly more inhibitory to p450s 2e1 and 1a2 than its close analog, 4,5-diphenyl-1,2,3-thiadiazole (dpt). by contrast, 4-phenyl-5-hydrogen-1,2,3-thiadiazole (pt), a weaker inhibitor than dpt and pmt with p450s 2e1 and 2b4, was comparable to pmt and more effective than dpt with p450 1a2. moreover, pmt, dpt, as well as pt showed no inactivation of either p450 2e1 or 2b4, though they were fairly effective inhibitors, and the thiadiazole ring could be oxidized by the p450 system. furthremore, the lack of inactivation of the p450 isoforms by pmt, dpt, and pt suggested that a transient reactive intermediate was not formed on oxidation of the thiadiazole ring. in additioin, the 1,2,3-thiadiazole ring could be oxidized by the p450 system [1].

References

[1] babu, b. r. and vaz, a.d.n. 1,2,3-thiadiazole: a novel heterocyclic heme ligand for the design of cytochrome p450 inhibitors. biochemistry 36, 7209-7216 (1997).