Azamulin

Base Information

• Chemical Name: Azamulin
• CAS No.: 76530-44-4
• Molecular Formula: C24H38N4O4S
• Molecular Weight: 478.65
• European Community (EC) Number: 686-875-5
• UNII: 875AQ866X1
• ChEMBL ID: CHEMBL2103760
• DSSTox Substance ID: DTXSID301046434
• NCI Thesaurus Code: C83608
• Nikkaji Number: J33.129E
• Pharos Ligand ID: SS5K4QK84YFN
• Wikidata: Q27269792
• Wikipedia: Azamulin
• Mol file: 76530-44-4.mol

Synonyms:azamulin

Chemical Property of Azamulin

Chemical Property:

• Vapor Pressure: 2.76E-18mmHg at 25°C
• Melting Point: 128-130°C
• Refractive Index: 1.59
• Boiling Point: 659.4 °C at 760 mmHg
• Flash Point: 352.6 °C
• PSA: 156.49000
• Density: 1.27 g/cm³
• LogP: 4.19070
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: soluble10mg/mL (clear solution)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 478.26137688
• Heavy Atom Count: 33
• Complexity: 786

Purity/Quality:

98%,99%, ^*data from raw suppliers

Azamulin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(CC(C2(C(CCC3(C2C(=O)CC3)C(C1O)C)C)C)OC(=O)CSC4=NNC(=N4)N)C
• Isomeric SMILES: CC[C@@]1(C[C@H]([C@@]2([C@@H](CC[C@@]3([C@H]2C(=O)CC3)[C@H]([C@@H]1O)C)C)C)OC(=O)CSC4=NNC(=N4)N)C
• 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.
• 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. It is a highly selective human CYP3A4 inhibitor. A mutilin derivative Azamulin has been used as a selective CYP3A4 inhibitor to pretreat primary hepatocyte cells and in prostate cancer cell lines LNCaP and MDAPCa2b.