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

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

MedKoo CAT#: 319876

CAS#: 870093-23-5

Description: 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

Instruction

Theoretical Analysis

MedKoo Cat#: 319876
Name: Talarozole
CAS#: 870093-23-5
Chemical Formula: C21H23N5S
Exact Mass: 377.17
Molecular Weight: 377.510
Elemental Analysis: C, 66.81; H, 6.14; N, 18.55; S, 8.49

Price and Availability

Size	Price	Availability
2mg	USD 300	2 Weeks
5mg	USD 460	2 Weeks
10mg	USD 670	2 Weeks
50mg	USD 1130	2 Weeks
100mg	USD 1635	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.

Related CAS #: 201410-53-9 870093-23-5 (R-)

Synonym: R115866, R 115866, R-115866, Talarozole, Rambazole

IUPAC/Chemical Name: 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

Biological target:
In vitro activity:
In vivo activity:

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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. eCollection 2014. PubMed PMID: 24911586; PubMed Central PMCID: PMC4049822.

2: 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. PubMed PMID: 24467691.

3: 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. eCollection 2013. PubMed PMID: 24340023; PubMed Central PMCID: PMC3858291.

4: 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. PubMed PMID: 23703360; PubMed Central PMCID: PMC3662968.

5: 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. PubMed PMID: 22985482.

6: 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. PubMed PMID: 21681858.

7: 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. PubMed PMID: 21228620.

8: 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. PubMed PMID: 20606468.

9: Fritzsche B, Schuchardt JP, Schmidt A, Nau H, Schweigert FJ, Rühl R. CYP26A1-specific antagonist influence on embryonic implantation, gene expression and endogenous retinoid concentration in rats. Reprod Toxicol. 2010 Nov;30(3):446-51. doi: 10.1016/j.reprotox.2010.05.005. Epub 2010 May 16. PubMed PMID: 20580668.

10: Pavez Loriè E, Chamcheu JC, Vahlquist A, Törmä H. Both all-trans retinoic acid and cytochrome P450 (CYP26) inhibitors affect the expression of vitamin A metabolizing enzymes and retinoid biomarkers in organotypic epidermis. Arch Dermatol Res. 2009 Aug;301(7):475-85. doi: 10.1007/s00403-009-0937-7. Epub 2009 Mar 18. PubMed PMID: 19294396.

11: Pavez Loriè E, Li H, Vahlquist A, Törmä H. The involvement of cytochrome p450 (CYP) 26 in the retinoic acid metabolism of human epidermal keratinocytes. Biochim Biophys Acta. 2009 Mar;1791(3):220-8. doi: 10.1016/j.bbalip.2008.12.004. Epub 2008 Dec 24. PubMed PMID: 19171200.

12: Giltaire S, Herphelin F, Frankart A, Hérin M, Stoppie P, Poumay Y. The CYP26 inhibitor R115866 potentiates the effects of all-trans retinoic acid on cultured human epidermal keratinocytes. Br J Dermatol. 2009 Mar;160(3):505-13. doi: 10.1111/j.1365-2133.2008.08960.x. Epub 2008 Dec 11. PubMed PMID: 19120344.

13: Pavez Loriè E, Cools M, Borgers M, Wouters L, Shroot B, Hagforsen E, Törmä H, Vahlquist A. Topical treatment with CYP26 inhibitor talarozole (R115866) dose dependently alters the expression of retinoid-regulated genes in normal human epidermis. Br J Dermatol. 2009 Jan;160(1):26-36. doi: 10.1111/j.1365-2133.2008.08895.x. Epub 2008 Oct 21. PubMed PMID: 19016711.

14: Geria AN, Scheinfeld NS. Talarozole, a selective inhibitor of P450-mediated all-trans retinoic acid for the treatment of psoriasis and acne. Curr Opin Investig Drugs. 2008 Nov;9(11):1228-37. Review. PubMed PMID: 18951302.

15: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Jun;30(5):383-408. PubMed PMID: 18806898.

16: Verfaille CJ, Thissen CA, Bovenschen HJ, Mertens J, Steijlen PM, van de Kerkhof PC. Oral R115866 in the treatment of moderate to severe plaque-type psoriasis. J Eur Acad Dermatol Venereol. 2007 Sep;21(8):1038-46. PubMed PMID: 17714122.

17: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 May;29(4):303-11. PubMed PMID: 17609744.

18: Ocaya P, Gidlöf AC, Olofsson PS, Törmä H, Sirsjö A. CYP26 inhibitor R115866 increases retinoid signaling in intimal smooth muscle cells. Arterioscler Thromb Vasc Biol. 2007 Jul;27(7):1542-8. Epub 2007 May 17. PubMed PMID: 17510468.

19: Verfaille CJ, Coel M, Boersma IH, Mertens J, Borgers M, Roseeuw D. Oral R115866 in the treatment of moderate to severe facial acne vulgaris: an exploratory study. Br J Dermatol. 2007 Jul;157(1):122-6. Epub 2007 Apr 25. PubMed PMID: 17459036.

20: Bovenschen HJ, Otero ME, Langewouters AM, van Vlijmen-Willems IM, van Rens DW, Seyger MM, van de Kerkhof PC. Oral retinoic acid metabolism blocking agent Rambazole for plaque psoriasis: an immunohistochemical study. Br J Dermatol. 2007 Feb;156(2):263-70. PubMed PMID: 17223865.

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