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-oxotricyclotetradec-6-yl 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 CC1(C(2((CC3(2C(=O)CC3)(1O)C)C)C)OC(=O)CSc4nc(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 2021^[update], it is not marketed in the US or Europe.^{[citation needed]}

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

References

^ Stresser DM, Broudy MI, Ho T, Cargill CE, Blanchard AP, Sharma R, et al. (January 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. S2CID 9869322.
^ Ghosal A, Ramanathan R, Yuan Y, Hapangama N, Chowdhury SK, Kishnani NS, Alton KB (December 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. S2CID 1866233.
^ Mitra R, Goodman OB (April 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. S2CID 19910736.

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[Stresser-1] Stresser DM, Broudy MI, Ho T, Cargill CE, Blanchard AP, Sharma R, et al. (January 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. S2CID 9869322.

[Ghosal-2] Ghosal A, Ramanathan R, Yuan Y, Hapangama N, Chowdhury SK, Kishnani NS, Alton KB (December 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. S2CID 1866233.

[Mitra-3] Mitra R, Goodman OB (April 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. S2CID 19910736.

[1]

[2]

[3]

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-oxotricyclotetradec-6-yl 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 CC1(C(2((CC3(2C(=O)CC3)(1O)C)C)C)OC(=O)CSc4nc(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