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SML0485

Sigma-Aldrich

Azamulin

≥98% (HPLC), powder, pleuromutilin antibiotic

Synonym(s):

(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;, 14-O-(5-(2-Amino1,3,4-triazolyl)thioacetyl)dihydromutilin, Antibiotic TDM 85-530

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About This Item

Empirical Formula (Hill Notation):
C24H38N4O4S
CAS Number:
76530-44-4
Molecular Weight:
478.65
MDL number:
MFCD00865055
UNSPSC Code:
12161501
PubChem Substance ID:
329825436
NACRES:
NA.77

product name

Azamulin, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL (clear solution)

shipped in

wet ice

storage temp.

−20°C

SMILES string

CC[C@]1(C)C[C@@H](OC(=O)CSc2nnc(N)[nH]2)[C@]3(C)[C@H](C)CC[C@]4(CCC(=O)[C@@H]34)[C@@H](C)[C@@H]1O

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

InChI key

FMHQJXGMLMSMLC-WBUYAQKGSA-N

General description

Azamulin isolated from fungus Pleurotus mutilis is a diterpene antibiotic. It is related to pleuromutilin being its synthetic azole derivative.

Application

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

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).

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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ITag-RNA Allows in Vivo Cell-Type Specific Transcriptional Characterization and Tracking of Circulating Transcripts
Darr J, et al.
Cell, 32(1), 105-112 (2018)
David M Stresser et al.
Drug metabolism and disposition: the biological fate of chemicals, 32(1), 105-112 (2004-01-08)
Azamulin [14-O-(5-(2-amino-1,3,4-triazolyl)thioacetyl)-dihydromutilin] is an azole derivative of the pleuromutilin class of antiinfectives. We tested the inhibition potency of azamulin toward 18 cytochromes P450 using human liver microsomes or microsomes from insect cells expressing single isoforms. In a competitive inhibition model
Priyatham Gorjala et al.
Cancers, 12(4) (2020-04-23)
Androgen receptor signaling is crucial for prostate cancer growth and is positively regulated in part by intratumoral CYP3A5. As African American (AA) men often carry the wild type CYP3A5 and express high levels of CYP3A5 protein, we blocked the wild
Jonatan Darr et al.
Cell reports, 30(9), 3183-3194 (2020-03-05)
Biofluids contain various circulating cell-free RNAs (ccfRNAs). The composition of these ccfRNAs varies among biofluids. They constitute tantalizing biomarker candidates for several pathologies and have been demonstrated to be mediators of cellular communication. Little is known about their function in physiological
Ramakrishna Nirogi et al.
Xenobiotica; the fate of foreign compounds in biological systems, 45(2), 95-106 (2014-07-30)
1. Chemical inhibition is the widely used method in reaction phenotyping assays for estimation of specific enzyme contribution to a given metabolic pathway. The results from phenotyping assays depend on the selectivity of chemical inhibitor and the concentration of inhibitor used

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