Talarozole | R115866 | CAS#201410-53-9 | CAS#870093-23-5 | CYP26 Inhibitor

MedKoo Cat#: 319876 | Name: Talarozole

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Description:

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

Talarozole, also known as R115866, is a CYP26 inhibitor under development for the treatment of acne, psoriasis and other keratinization disorders. Talarozole inhibits the metabolism of retinoic acid by blocking the cytochrome P450 enzyme isoform CYP26, a retinoic acid hydroxylase. Because of this mechanism, it is called a retinoic acid metabolism blocking agent (RAMBA).

Chemical Structure

Talarozole

CAS#870093-23-5

Theoretical Analysis

MedKoo Cat#: 319876

Name: Talarozole

CAS#: 870093-23-5

Chemical Formula: C21H23N5S

Exact Mass: 377.1674

Molecular Weight: 377.51

Elemental Analysis: C, 66.81; H, 6.14; N, 18.55; S, 8.49

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 475.00	2 Weeks
25mg	USD 1,250.00	2 Weeks

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Related CAS #

201410-53-9 870093-23-5 (R-)

Synonym

R115866, R 115866, R-115866, Talarozole, Rambazole

IUPAC/Chemical Name

(R)-N-(4-(2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl)phenyl)benzo[d]thiazol-2-amine

InChi Key

SNFYYXUGUBUECJ-HXUWFJFHSA-N

InChi Code

InChI=1S/C21H23N5S/c1-3-15(4-2)20(26-14-22-13-23-26)16-9-11-17(12-10-16)24-21-25-18-7-5-6-8-19(18)27-21/h5-15,20H,3-4H2,1-2H3,(H,24,25)/t20-/m1/s1

SMILES Code

CCC(CC)[C@H](C1=CC=C(NC2=NC3=CC=CC=C3S2)C=C1)N4N=CN=C4

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, not in water

Shelf Life

>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 377.51 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

1: Kędzierski J, Jäger MC, Naeem S, Odermatt A, Smieško M. In silico and in vitro assessment of drugs potentially causing adverse effects by inhibiting CYP17A1. Toxicol Appl Pharmacol. 2024 May;486:116945. doi: 10.1016/j.taap.2024.116945. Epub 2024 Apr 28. PMID: 38688424. 2: Iqbal L, Zameer U, Iqbal Malick M. Exploring Talarozole as a Novel Therapeutic Approach for Osteoarthritis: Insights From Experimental Studies. Clin Med Insights Arthritis Musculoskelet Disord. 2024 Jan 27;17:11795441231222494. doi: 10.1177/11795441231222494. PMID: 38292917; PMCID: PMC10823836. 3: Cao DL, Ma LJ, Jiang BC, Gu Q, Gao YJ. Cytochrome P450 26A1 Contributes to the Maintenance of Neuropathic Pain. Neurosci Bull. 2024 Mar;40(3):293-309. doi: 10.1007/s12264-023-01101-1. Epub 2023 Aug 28. PMID: 37639183; PMCID: PMC10912416. 4: Zhu L, Kamalathevan P, Koneva LA, Zarebska JM, Chanalaris A, Ismail H, Wiberg A, Ng M, Muhammad H, Walsby-Tickle J, McCullagh JSO, Watt FE; Oxford Hand Surgical Team; Sansom SN, Furniss D, Gardiner MD, Vincent TL, Riley N, Spiteri M, McNab I, Little C, Cogswell L, Critchley P, Giele H, Shirley R. Variants in ALDH1A2 reveal an anti-inflammatory role for retinoic acid and a new class of disease-modifying drugs in osteoarthritis. Sci Transl Med. 2022 Dec 21;14(676):eabm4054. doi: 10.1126/scitranslmed.abm4054. Epub 2022 Dec 21. PMID: 36542696. 5: Shindo S, Shioya A, Watanabe M, Sasaki T, Suzuki H, Kumagai T, Hwang GW, Nagata K. Development of an adenovirus-mediated reporter assay system to detect a low concentration of retinoic acid in MCF-7 cells. J Toxicol Sci. 2022;47(6):249-255. doi: 10.2131/jts.47.249. PMID: 35650141. 6: Hanna C, Boily M, Jumarie C. Pesticides Inhibit Retinoic Acid Catabolism in PLHC-1 and ZFL Fish Hepatic Cell Lines. Chem Res Toxicol. 2022 Jun 20;35(6):1045-1058. doi: 10.1021/acs.chemrestox.2c00050. Epub 2022 May 24. PMID: 35608517; PMCID: PMC9214766. 7: Yang N, Parker LE, Yu J, Jones JW, Liu T, Papanicolaou KN, Talbot CC Jr, Margulies KB, O'Rourke B, Kane MA, Foster DB. Cardiac retinoic acid levels decline in heart failure. JCI Insight. 2021 Apr 22;6(8):e137593. doi: 10.1172/jci.insight.137593. PMID: 33724958; PMCID: PMC8119182. 8: Yamazoe Y, Yamada T, Nagata K. Prediction and Characterization of CYP3A4-mediated Metabolisms of Azole Fungicides: an Application of the Fused- grid Template* system. Food Saf (Tokyo). 2020 Jun 26;8(2):34-51. doi: 10.14252/foodsafetyfscj.D-20-00010. PMID: 32626635; PMCID: PMC7329915. 9: Veit JGS, De Glas V, Balau B, Liu H, Bourlond F, Paller AS, Poumay Y, Diaz P. Characterization of CYP26B1-Selective Inhibitor, DX314, as a Potential Therapeutic for Keratinization Disorders. J Invest Dermatol. 2021 Jan;141(1):72-83.e6. doi: 10.1016/j.jid.2020.05.090. Epub 2020 Jun 4. PMID: 32505549; PMCID: PMC8183296. 10: Stevison F, Hogarth C, Tripathy S, Kent T, Isoherranen N. Inhibition of the all-trans Retinoic Acid (atRA) Hydroxylases CYP26A1 and CYP26B1 Results in Dynamic, Tissue-Specific Changes in Endogenous atRA Signaling. Drug Metab Dispos. 2017 Jul;45(7):846-854. doi: 10.1124/dmd.117.075341. Epub 2017 Apr 26. PMID: 28446509; PMCID: PMC5469401. 11: Tripathy S, Chapman JD, Han CY, Hogarth CA, Arnold SL, Onken J, Kent T, Goodlett DR, Isoherranen N. All-Trans-Retinoic Acid Enhances Mitochondrial Function in Models of Human Liver. Mol Pharmacol. 2016 May;89(5):560-74. doi: 10.1124/mol.116.103697. Epub 2016 Feb 26. Retraction in: Mol Pharmacol. 2020 Feb;97(2):61. doi: 10.1124/mol.116.103697retraction. PMID: 26921399; PMCID: PMC4851298. 12: Jeradi S, Hammerschmidt M. Retinoic acid-induced premature osteoblast-to- preosteocyte transitioning has multiple effects on calvarial development. Development. 2016 Apr 1;143(7):1205-16. doi: 10.1242/dev.129189. Epub 2016 Feb 22. PMID: 26903503; PMCID: PMC4852491. 13: Kasimanickam VR, Kasimanickam RK, Dernell WS. Dysregulated microRNA clusters in response to retinoic acid and CYP26B1 inhibitor induced testicular function in dogs. PLoS One. 2014 Jun 9;9(6):e99433. doi: 10.1371/journal.pone.0099433. PMID: 24911586; PMCID: PMC4049822. 14: Kasimanickam V, Kasimanickam R. Exogenous retinoic acid and cytochrome P450 26B1 inhibitor modulate meiosis-associated genes expression in canine testis, an in vitro model. Reprod Domest Anim. 2014 Apr;49(2):315-23. doi: 10.1111/rda.12276. Epub 2014 Jan 27. PMID: 24467691. 15: Lind T, Sundqvist A, Hu L, Pejler G, Andersson G, Jacobson A, Melhus H. Vitamin a is a negative regulator of osteoblast mineralization. PLoS One. 2013 Dec 10;8(12):e82388. doi: 10.1371/journal.pone.0082388. PMID: 24340023; PMCID: PMC3858291. 16: Cuervo R, Chimal-Monroy J. Chemical activation of RARβ induces post- embryonically bilateral limb duplication during Xenopus limb regeneration. Sci Rep. 2013;3:1886. doi: 10.1038/srep01886. PMID: 23703360; PMCID: PMC3662968. 17: Saenz-Méndez P, Elmabsout AA, Sävenstrand H, Awadalla MK, Strid Å, Sirsjö A, Eriksson LA. Homology models of human all-trans retinoic acid metabolizing enzymes CYP26B1 and CYP26B1 spliced variant. J Chem Inf Model. 2012 Oct 22;52(10):2631-7. doi: 10.1021/ci300264u. Epub 2012 Sep 25. PMID: 22985482. 18: Eguizabal C, Montserrat N, Vassena R, Barragan M, Garreta E, Garcia-Quevedo L, Vidal F, Giorgetti A, Veiga A, Izpisua Belmonte JC. Complete meiosis from human induced pluripotent stem cells. Stem Cells. 2011 Aug;29(8):1186-95. doi: 10.1002/stem.672. PMID: 21681858. 19: Baert B, De Spiegeleer B. Local skin pharmacokinetics of talarozole, a new retinoic acid metabolism-blocking agent. Skin Pharmacol Physiol. 2011;24(3):151-9. doi: 10.1159/000323012. Epub 2011 Jan 12. PMID: 21228620. 20: Ocaya PA, Elmabsout AA, Olofsson PS, Törmä H, Gidlöf AC, Sirsjö A. CYP26B1 plays a major role in the regulation of all-trans-retinoic acid metabolism and signaling in human aortic smooth muscle cells. J Vasc Res. 2011;48(1):23-30. doi: 10.1159/000317397. Epub 2010 Jul 6. PMID: 20606468.