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ChemicalBook--->CAS DataBase List--->76530-44-4

76530-44-4

76530-44-4 Structure

76530-44-4 Structure
IdentificationBack Directory
[Name]

Azamulin
[CAS]

76530-44-4
[Synonyms]

Azamulin
SA 85530b
Antibiotic TDM 85-530
TMD 85-530, SA 85530b
14-O-(5-(2-Amino1,3,4-triazolyl)thioacetyl)dihydromutilin
[(5-Amino-1H-1,2,4-triazol-3-yl)thio]acetic acid (3aS,4R,5S,6R,8R,9R,9aR,10R)-6-ethyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester
[Molecular Formula]

C24H38N4O4S
[MDL Number]

MFCD00865055
[MOL File]

76530-44-4.mol
[Molecular Weight]

478.65
Chemical PropertiesBack Directory
[Melting point ]

128-130°C
[storage temp. ]

-20°C
[solubility ]

DMSO: soluble10mg/mL (clear solution)
[form ]

powder
[color ]

white to beige
[Stability:]

Store at -2℃.
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26
[WGK Germany ]

3
Hazard InformationBack Directory
[Description]

Azamulin is a selective, irreversible inhibitor of cytochrome P450 (CYP) 3A isoforms (IC50 values range from 26 to 240 nM for CYP3A4 and CYP3A4/5 from different sources). It is at least 50-fold less potent against CYP2J2 and 100-fold less effective against all other CYP isoforms. Azamulin potently blocks the hydroxylation of testosterone and midazolam by CYP3A4.
[Chemical Properties]

White Solid
[Uses]

Azamulin has been used as a selective CYP3A4 inhibitor to pretreat primary hepatocyte cells and in prostate cancer cell lines LNCaP and MDAPCa2b.
[Uses]

Azamulin is a semi-synthetic pleuromutilin prepared by sequential reaction of dihydropleuromutilin tosylate with 2-amino-1,2,4-triazole-5-thiol. While azamulin is a broad spectrum antibiotic in the pleuromutilin class, this aspect of its bioprofile has received little attention. In fact, the triazole substituent added to nominally improve the drugs bioavailability, imparted an unusual selectivity for the inhibition of specific cytochrome P450 mixed function oxidase sub-types, important for understanding the manner in which the body metabolises drugs or xenobiotics.
[Uses]

It is a highly selective human CYP3A4 inhibitor. A mutilin derivative
[General Description]

Azamulin isolated from fungus Pleurotus mutilis is a diterpene antibiotic. It is related to pleuromutilin being its synthetic azole derivative.
[Biochem/physiol Actions]

Azamulin is a derivative of the antibiotic pleuromutilin. The compound is a very specific inhibitor of the CYP3A family (IC50 = 0.03-0.24 μM). Azamulin is 15 and 13 fold more active against CYP3A4 compared to CYP3A5 or CYP3A7, respectively, and is at least 100 fold selective over other CYP isoforms, with the exception of CYP2J2 (approximately 50-fold).
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