Azamulin | CAS# 76530-44-4 | P450 (CYP) 3A isoform inhibitor

Azamulin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 574571

CAS#: 76530-44-4

Description: Azamulin is a selective, irreversible inhibitor of cytochrome P450 (CYP) 3A isoforms. Azamulin potently blocks the hydroxylation of testosterone and midazolam by CYP3A4.

Chemical Structure

Azamulin

CAS# 76530-44-4

Instruction

Theoretical Analysis

MedKoo Cat#: 574571
Name: Azamulin
CAS#: 76530-44-4
Chemical Formula: C24H38N4O4S
Exact Mass: 478.26
Molecular Weight: 478.650
Elemental Analysis: C, 60.22; H, 8.00; N, 11.71; O, 13.37; S, 6.70

Price and Availability

Size	Price	Availability
1mg	USD 255	2 Weeks
5mg	USD 575	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Antibiotic TDM 85-530; Azamulin; SA 85530b

IUPAC/Chemical Name: (3aR,4R,5R,7R,8S,9R,9aS,12R)-7-ethyl-8-hydroxy-4,7,9,12-tetramethyl-3-oxodecahydro-4,9a-propanocyclopenta[8]annulen-5-yl 2-((5-amino-4H-1,2,4-triazol-3-yl)thio)acetate

InChi Key: FMHQJXGMLMSMLC-WBUYAQKGSA-N

InChi Code: 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

SMILES Code: O=C1CC[C@@]23[C@@H](C)[C@H](O)[C@@](CC)(C)C[C@@H](OC(CSC4=NN=C(N)N4)=O)[C@](C)([C@H](C)CC3)[C@@]21[H]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 478.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Chanteux H, Rosa M, Delatour C, Nicolaï J, Gillent E, Dell'Aiera S, Ungell AL. Application of Azamulin to Determine the Contribution of CYP3A4/5 to Drug Metabolic Clearance Using Human Hepatocytes. Drug Metab Dispos. 2020 Sep;48(9):778-787. doi: 10.1124/dmd.120.000017. Epub 2020 Jun 12. PMID: 32532738.

2: Hsu MH, Johnson EF. Structural characterization of the homotropic cooperative binding of azamulin to human cytochrome P450 3A5. J Biol Chem. 2022 May;298(5):101909. doi: 10.1016/j.jbc.2022.101909. Epub 2022 Apr 6. PMID: 35398097; PMCID: PMC9079302.

3: Sevrioukova IF. Structural Insights into the Interaction of Cytochrome P450 3A4 with Suicide Substrates: Mibefradil, Azamulin and 6',7'-Dihydroxybergamottin. Int J Mol Sci. 2019 Aug 30;20(17):4245. doi: 10.3390/ijms20174245. PMID: 31480231; PMCID: PMC6747129.

4: Stresser DM, Broudy MI, Ho T, Cargill CE, Blanchard AP, Sharma R, Dandeneau AA, Goodwin JJ, Turner SD, Erve JC, Patten CJ, Dehal SS, Crespi CL. Highly selective inhibition of human CYP3Aa in vitro by azamulin and evidence that inhibition is irreversible. Drug Metab Dispos. 2004 Jan;32(1):105-12. doi: 10.1124/dmd.32.1.105. PMID: 14709627.

5: Uehara S, Shimizu M, Suemizu H, Yamazaki H. Roles of human cytochrome P450 3A4/5 in dexamethasone 6β-hydroxylation mediated by liver microsomes and humanized liver in chimeric mice metabolically suppressed with azamulin. Drug Metab Pharmacokinet. 2023 Jun;50:100504. doi: 10.1016/j.dmpk.2023.100504. Epub 2023 Mar 6. PMID: 37031476.

6: Mitra R, Goodman OB Jr. CYP3A5 regulates prostate cancer cell growth by facilitating nuclear translocation of AR. Prostate. 2015 Apr 1;75(5):527-38. doi: 10.1002/pros.22940. Epub 2015 Jan 13. PMID: 25586052.

7: Khojasteh SC, Prabhu S, Kenny JR, Halladay JS, Lu AY. Chemical inhibitors of cytochrome P450 isoforms in human liver microsomes: a re-evaluation of P450 isoform selectivity. Eur J Drug Metab Pharmacokinet. 2011 Mar;36(1):1-16. doi: 10.1007/s13318-011-0024-2. Epub 2011 Feb 19. PMID: 21336516.

8: Jin Y, Zollinger M, Borell H, Zimmerlin A, Patten CJ. CYP4F enzymes are responsible for the elimination of fingolimod (FTY720), a novel treatment of relapsing multiple sclerosis. Drug Metab Dispos. 2011 Feb;39(2):191-8. doi: 10.1124/dmd.110.035378. Epub 2010 Nov 2. PMID: 21045201.

9: Li YG, Wang JX, Zhang GN, Zhu M, You XF, Hu XX, Zhang F, Wang YC. Antibacterial Activity and Structure-Activity Relationship of a Series of Newly Synthesized Pleuromutilin Derivatives. Chem Biodivers. 2019 Feb;16(2):e1800560. doi: 10.1002/cbdv.201800560. Epub 2019 Jan 28. PMID: 30467968.

10: Cheng CY, Slominski AT, Tuckey RC. Hydroxylation of 20-hydroxyvitamin D3 by human CYP3A4. J Steroid Biochem Mol Biol. 2016 May;159:131-41. doi: 10.1016/j.jsbmb.2016.03.014. Epub 2016 Mar 9. PMID: 26970587; PMCID: PMC4821771.

11: Perloff ES, Mason AK, Dehal SS, Blanchard AP, Morgan L, Ho T, Dandeneau A, Crocker RM, Chandler CM, Boily N, Crespi CL, Stresser DM. Validation of cytochrome P450 time-dependent inhibition assays: a two-time point IC50 shift approach facilitates kinact assay design. Xenobiotica. 2009 Feb;39(2):99-112. doi: 10.1080/00498250802638155. PMID: 19255936.

12: Thuy Phuong NT, Kim JW, Kim JA, Jeon JS, Lee JY, Xu WJ, Yang JW, Kim SK, Kang KW. Role of the CYP3A4-mediated 11,12-epoxyeicosatrienoic acid pathway in the development of tamoxifen-resistant breast cancer. Oncotarget. 2017 Aug 18;8(41):71054-71069. doi: 10.18632/oncotarget.20329. PMID: 29050342; PMCID: PMC5642617.

13: Smith S, Lyman M, Ma B, Tweedie D, Menzel K. Reaction Phenotyping of Low- Turnover Compounds in Long-Term Hepatocyte Cultures Through Persistent Selective Inhibition of Cytochromes P450. Drug Metab Dispos. 2021 Nov;49(11):995-1002. doi: 10.1124/dmd.121.000601. Epub 2021 Aug 18. PMID: 34407991.

14: Seo KA, Lee SJ, Kim KB, Bae SK, Liu KH, Kim DH, Shin JG. Ilaprazole, a new proton pump inhibitor, is primarily metabolized to ilaprazole sulfone by CYP3A4 and 3A5. Xenobiotica. 2012 Mar;42(3):278-84. doi: 10.3109/00498254.2011.622416. Epub 2011 Oct 24. PMID: 22022918.

15: Parmentier Y, Pothier C, Delmas A, Caradec F, Trancart MM, Guillet F, Bouaita B, Chesne C, Brian Houston J, Walther B. Direct and quantitative evaluation of the human CYP3A4 contribution (fm) to drug clearance using the in vitro SILENSOMES model. Xenobiotica. 2017 Jul;47(7):562-575. doi: 10.1080/00498254.2016.1208854. Epub 2016 Aug 3. PMID: 27485383.

16: Ohhira S, Enomoto M, Matsui H. In vitro metabolism of tributyltin and triphenyltin by human cytochrome P-450 isoforms. Toxicology. 2006 Dec 7;228(2-3):171-7. doi: 10.1016/j.tox.2006.08.023. Epub 2006 Aug 24. PMID: 16978758.

17: Ghosal A, Ramanathan R, Yuan Y, Hapangama N, Chowdhury SK, Kishnani NS, Alton KB. Identification of human liver cytochrome P450 enzymes involved in biotransformation of vicriviroc, a CCR5 receptor antagonist. Drug Metab Dispos. 2007 Dec;35(12):2186-95. doi: 10.1124/dmd.107.017517. Epub 2007 Sep 7. PMID: 17827338.

18: Lim HK, Duczak N Jr, Brougham L, Elliot M, Patel K, Chan K. Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes. Drug Metab Dispos. 2005 Aug;33(8):1211-9. doi: 10.1124/dmd.104.003475. Epub 2005 Apr 28. PMID: 15860655.

19: Murayama N, Yajima K, Hikawa M, Shimura K, Ishii Y, Takada M, Uno Y, Utoh M, Iwasaki K, Yamazaki H. Assessment of multiple cytochrome P450 activities in metabolically inactivated human liver microsomes and roles of P450 2C isoforms in reaction phenotyping studies. Biopharm Drug Dispos. 2018 Feb;39(2):116-121. doi: 10.1002/bdd.2115. Epub 2017 Dec 21. PMID: 29136681.

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