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MedKoo Cat#: 573379 | Name: Azalanstat free base

Description:

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

Azalanstat is an inhibitor of hepatic cholesterol biosynthesis, inhibiting the cytochrome P450 enzyme lanosterol 14alpha-demethylase.

Chemical Structure

Azalanstat free base
Azalanstat free base
CAS#143393-27-5 (free base)

Theoretical Analysis

MedKoo Cat#: 573379

Name: Azalanstat free base

CAS#: 143393-27-5 (free base)

Chemical Formula: C22H24ClN3O2S

Exact Mass: 429.1278

Molecular Weight: 429.96

Elemental Analysis: C, 61.46; H, 5.63; Cl, 8.24; N, 9.77; O, 7.44; S, 7.46

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
143484-82-6 (HCl) 143393-27-5 (free base) 143484-77-9 (sulfate) 143484-80-4 (mesylate) 143484-81-5 (phosphate) 143484-78-0 (maleate) 143484-79-1 (2 maleate)
Synonym
Azalanstat free base; Azalanstat; RS-21607; RS21607; RS 21607;
IUPAC/Chemical Name
4-((((2S,4S)-2-((1H-imidazol-1-yl)methyl)-2-(4-chlorophenethyl)-1,3-dioxolan-4-yl)methyl)thio)aniline
InChi Key
VYNIUBZKEWJOJP-UNMCSNQZSA-N
InChi Code
InChI=1S/C22H24ClN3O2S/c23-18-3-1-17(2-4-18)9-10-22(15-26-12-11-25-16-26)27-13-20(28-22)14-29-21-7-5-19(24)6-8-21/h1-8,11-12,16,20H,9-10,13-15,24H2/t20-,22-/m0/s1
SMILES Code
NC1=CC=C(SC[C@H]2O[C@](CN3C=CN=C3)(CCC4=CC=C(Cl)C=C4)OC2)C=C1
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 429.96 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.

Recalculate based on batch purity %
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
1: Burton PM, Swinney DC, Heller R, Dunlap B, Chiou M, Malonzo E, Haller J, Walker KA, Salari A, Murakami S, et al. Azalanstat (RS-21607), a lanosterol 14 alpha-demethylase inhibitor with cholesterol-lowering activity. Biochem Pharmacol. 1995 Aug 8;50(4):529-44. doi: 10.1016/0006-2952(95)00152-p. PMID: 7646560. 2: Vlahakis JZ, Kinobe RT, Bowers RJ, Brien JF, Nakatsu K, Szarek WA. Synthesis and evaluation of azalanstat analogues as heme oxygenase inhibitors. Bioorg Med Chem Lett. 2005 Mar 1;15(5):1457-61. doi: 10.1016/j.bmcl.2004.12.075. PMID: 15713406. 3: Morisawa T, Wong RJ, Bhutani VK, Vreman HJ, Stevenson DK. Inhibition of heme oxygenase activity in newborn mice by azalanstat. Can J Physiol Pharmacol. 2008 Oct;86(10):651-9. doi: 10.1139/y08-069. PMID: 18841169. 4: Salerno L, Floresta G, Ciaffaglione V, Gentile D, Margani F, Turnaturi R, Rescifina A, Pittalà V. Progress in the development of selective heme oxygenase-1 inhibitors and their potential therapeutic application. Eur J Med Chem. 2019 Apr 1;167:439-453. doi: 10.1016/j.ejmech.2019.02.027. Epub 2019 Feb 12. PMID: 30784878. 5: Vlahakis JZ, Kinobe RT, Bowers RJ, Brien JF, Nakatsu K, Szarek WA. Imidazole- dioxolane compounds as isozyme-selective heme oxygenase inhibitors. J Med Chem. 2006 Jul 13;49(14):4437-41. doi: 10.1021/jm0511435. PMID: 16821802. 6: Rahman MN, Vukomanovic D, Vlahakis JZ, Szarek WA, Nakatsu K, Jia Z. Structural Insights into Azole-based Inhibitors of Heme Oxygenase-1: Development of Selective Compounds for Therapeutic Applications. Curr Med Chem. 2018;25(42):5803-5821. doi: 10.2174/0929867325666180606082512. PMID: 30674243. 7: Rahman MN, Vlahakis JZ, Roman G, Vukomanovic D, Szarek WA, Nakatsu K, Jia Z. Structural characterization of human heme oxygenase-1 in complex with azole- based inhibitors. J Inorg Biochem. 2010 Mar;104(3):324-30. doi: 10.1016/j.jinorgbio.2009.10.011. Epub 2009 Oct 24. PMID: 19917515. 8: Intagliata S, Salerno L, Ciaffaglione V, Leonardi C, Fallica AN, Carota G, Amata E, Marrazzo A, Pittalà V, Romeo G. Heme Oxygenase-2 (HO-2) as a therapeutic target: Activators and inhibitors. Eur J Med Chem. 2019 Dec 1;183:111703. doi: 10.1016/j.ejmech.2019.111703. Epub 2019 Sep 17. PMID: 31550661. 9: Pittalà V, Salerno L, Romeo G, Modica MN, Siracusa MA. A focus on heme oxygenase-1 (HO-1) inhibitors. Curr Med Chem. 2013;20(30):3711-32. doi: 10.2174/0929867311320300003. PMID: 23746277. 10: Vaknin KM, Lazar S, Popliker M, Tsafriri A. Role of meiosis-activating sterols in rat oocyte maturation: effects of specific inhibitors and changes in the expression of lanosterol 14alpha-demethylase during the preovulatory period. Biol Reprod. 2001 Jan;64(1):299-309. doi: 10.1095/biolreprod64.1.299. PMID: 11133687. 11: Rahman MN, Vukomanovic D, Vlahakis JZ, Szarek WA, Nakatsu K, Jia Z. Structural insights into human heme oxygenase-1 inhibition by potent and selective azole-based compounds. J R Soc Interface. 2013 Jan 6;10(78):20120697. doi: 10.1098/rsif.2012.0697. Epub 2012 Nov 8. PMID: 23097500; PMCID: PMC3565801. 12: Ahmed H, McLaughlin BE, Soong J, Marks GS, Brien JF, Nakatsu K. The source of endogenous carbon monoxide formation in human placental chorionic villi. Cell Mol Biol (Noisy-le-grand). 2005 Oct 3;51(5):447-51. PMID: 16309566. 13: Vlahakis JZ, Hum M, Rahman MN, Jia Z, Nakatsu K, Szarek WA. Synthesis and evaluation of imidazole-dioxolane compounds as selective heme oxygenase inhibitors: effect of substituents at the 4-position of the dioxolane ring. Bioorg Med Chem. 2009 Mar 15;17(6):2461-75. doi: 10.1016/j.bmc.2009.01.078. Epub 2009 Feb 12. PMID: 19268600. 14: Sloane DL, So OY, Leung R, Scarafia LE, Saldou N, Jarnagin K, Swinney DC. Cloning and functional expression of the cDNA encoding rat lanosterol 14-alpha demethylase. Gene. 1995 Aug 19;161(2):243-8. doi: 10.1016/0378-1119(95)00211-n. PMID: 7665087. 15: Floresta G, Fallica AN, Romeo G, Sorrenti V, Salerno L, Rescifina A, Pittalà V. Identification of a potent heme oxygenase-2 (HO-2) inhibitor by targeting the secondary hydrophobic pocket of the HO-2 western region. Bioorg Chem. 2020 Nov;104:104310. doi: 10.1016/j.bioorg.2020.104310. Epub 2020 Sep 24. PMID: 33010625. 16: Wang C, Xie H, Song X, Ning G, Yan J, Chen X, Xu B, Ouyang H, Xia G. Lanosterol 14alpha-demethylase expression in the mouse ovary and its participation in cumulus-enclosed oocyte spontaneous meiotic maturation in vitro. Theriogenology. 2006 Sep 15;66(5):1156-64. doi: 10.1016/j.theriogenology.2006.01.065. Epub 2006 May 2. PMID: 16650467. 17: Xie H, Xia G, Byskov AG, Andersen CY, Bo S, Tao Y. Roles of gonadotropins and meiosis-activating sterols in meiotic resumption of cultured follicle- enclosed mouse oocytes. Mol Cell Endocrinol. 2004 Apr 15;218(1-2):155-63. doi: 10.1016/j.mce.2003.11.030. PMID: 15130520. 18: Jin S, Zhang M, Lei L, Wang C, Fu M, Ning G, Xia G. Meiosis activating sterol (MAS) regulate FSH-induced meiotic resumption of cumulus cell-enclosed porcine oocytes via PKC pathway. Mol Cell Endocrinol. 2006 Apr 25;249(1-2):64-70. doi: 10.1016/j.mce.2006.01.008. Epub 2006 Feb 24. PMID: 16500744. 19: Swinney DC, So OY, Watson DM, Berry PW, Webb AS, Kertesz DJ, Shelton EJ, Burton PM, Walker KA. Selective inhibition of mammalian lanosterol 14 alpha- demethylase by RS-21607 in vitro and in vivo. Biochemistry. 1994 Apr 19;33(15):4702-13. doi: 10.1021/bi00181a030. PMID: 8161528. 20: Hrboticky N, Becker A, Kruse HJ, Weber PC. Increased cellular triglyceride levels in human monocytic and rat smooth muscle cells after lovastatin. Biochim Biophys Acta. 1997 Nov 30;1349(3):211-21. doi: 10.1016/s0005-2760(97)00136-7. PMID: 9434135.