Azamulin

Azamulin
Clinical data
ATC code	None;
Identifiers
	IUPAC name (1S,2R,3S,4R,6R,7R,8R,14R)-4-Ethyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.01,8]tetradec-6-yl [(5-amino-1H-1,2,4-triazol-3-yl)sulfanyl]acetate;
CAS Number	76530-44-4;
PubChem CID	16072188;
ChemSpider	17231671;
UNII	875AQ866X1;
ChEMBL	ChEMBL2103760;
Chemical and physical data
Formula	C24H38N4O4S
Molar mass	478.65 g·mol−1
3D model (JSmol)	Interactive image;
	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)CSc4nc([nH]n4)N)C;
	InChI InChI=1S/C24H38N4O4S/c1-6-22(4)11-16(32-17(30)12-33-21-26-20(25)27-28-21)23(5)13(2)7-9-24(14(3)19(22)31)10-8-15(29)18(23)24/h13-14,16,18-19,31H,6-12H2,1-5H3,(H3,25,26,27,28)/t13-,14+,16-,18+,19+,22-,23+,24+/m1/s1; Key:FMHQJXGMLMSMLC-WBUYAQKGSA-N;

Azamulin is a pleuromutilin antibiotic.^[1] As of 2016^[update], it is not marketed in the US or Europe.

In pharmacological studies, the substance is used as an inhibitor of the liver enzymes CYP3A4 and CYP3A5.^[2]^[3]

References

^ Stresser, D. M.; Broudy, M. I.; Ho, T; Cargill, C. E.; Blanchard, A. P.; Sharma, R; Dandeneau, A. A.; Goodwin, J. J.; Turner, S. D.; Erve, J. C.; Patten, C. J.; Dehal, S. S.; Crespi, C. L. (2004). "Highly selective inhibition of human CYP3Aa in vitro by azamulin and evidence that inhibition is irreversible". Drug Metabolism and Disposition. 32 (1): 105–12. doi:10.1124/dmd.32.1.105. PMID 14709627.
^ Ghosal, A; Ramanathan, R; Yuan, Y; Hapangama, N; Chowdhury, S. K.; Kishnani, N. S.; Alton, K. B. (2007). "Identification of human liver cytochrome P450 enzymes involved in biotransformation of vicriviroc, a CCR5 receptor antagonist". Drug Metabolism and Disposition. 35 (12): 2186–95. doi:10.1124/dmd.107.017517. PMID 17827338.
^ Mitra, R; Goodman Jr, O. B. (2015). "CYP3A5 regulates prostate cancer cell growth by facilitating nuclear translocation of AR". The Prostate. 75 (5): 527–38. doi:10.1002/pros.22940. PMID 25586052.

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