CAS 870093-23-5|Talarozole (R enantiomer)

Introduction：Basic information about CAS 870093-23-5|Talarozole (R enantiomer), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Talarozole (R enantiomer) BiologicalActivity
3. Chemical & Physical Properties
4. Synonyms

Common Name	Talarozole (R enantiomer)
CAS Number	870093-23-5	Molecular Weight	377.50600
Density	1.26	Boiling Point	561.016ºC at 760 mmHg
Molecular Formula	C₂₁H₂₃N₅S	Melting Point	/
MSDS	/	Flash Point	293.092ºC

Names

Name	N-[4-[(1R)-2-ethyl-1-(1,2,4-triazol-1-yl)butyl]phenyl]-1,3-benzothiazol-2-amine
Synonym	More Synonyms

Talarozole (R enantiomer) BiologicalActivity

Description	Talarozole R enantiomer is a potent and selective inhibitor of cytochrome P450 26-mediated breakdown of endogenous all-trans retinoic acid for the treatment of psoriasis and acne.Target: CYP26in vitro: Talarozole R enantiomer treatment increased the mRNA expression of CRABP2, KRT4, CYP26A1 and CYP26B1 dose dependently, and decreased theexpression of KRT2 and IL-1alpha compared with vehicle-treated skin. No mRNA change in retinol-metabolizing enzymes was obtained. There was no induction of epidermal thickness or overt skin inflammation in talarozole-treated skin. Immunofluorescence analysis confirmed an upregulation of KRT4 protein, but no upregulation of CYP26A1 and CYP26B1 expression was detected [1] [2].in vivo: Talarozole R enantiomer slightly diffused into the skin only when dissolved in propylene glycol, isopropyl myristate or ethanol. Although only 0.1% of the dose applied was found in the skin itself after 12-24 h, this was sufficient to achieve local concentrations well above the half-maximal inhibitory concentration value for talarozole. The distribution of talarozole within the skin was investigated: 80% was located in the epidermis, while the remaining 20% was found in the dermis [3].
Related Catalog	Signaling Pathways >>Metabolic Enzyme/Protease >>Cytochrome P450Research Areas >>Cancer
References	[1]. Pavez Loriè E, Cools M, Borgers M, 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 [2]. 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. [3]. 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.

Description

Talarozole R enantiomer is a potent and selective inhibitor of cytochrome P450 26-mediated breakdown of endogenous all-trans retinoic acid for the treatment of psoriasis and acne.Target: CYP26in vitro: Talarozole R enantiomer treatment increased the mRNA expression of CRABP2, KRT4, CYP26A1 and CYP26B1 dose dependently, and decreased theexpression of KRT2 and IL-1alpha compared with vehicle-treated skin. No mRNA change in retinol-metabolizing enzymes was obtained. There was no induction of epidermal thickness or overt skin inflammation in talarozole-treated skin. Immunofluorescence analysis confirmed an upregulation of KRT4 protein, but no upregulation of CYP26A1 and CYP26B1 expression was detected [1] [2].in vivo: Talarozole R enantiomer slightly diffused into the skin only when dissolved in propylene glycol, isopropyl myristate or ethanol. Although only 0.1% of the dose applied was found in the skin itself after 12-24 h, this was sufficient to achieve local concentrations well above the half-maximal inhibitory concentration value for talarozole. The distribution of talarozole within the skin was investigated: 80% was located in the epidermis, while the remaining 20% was found in the dermis [3].

Related Catalog

Signaling Pathways >>Metabolic Enzyme/Protease >>Cytochrome P450Research Areas >>Cancer

References

[1]. Pavez Loriè E, Cools M, Borgers M, 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

[2]. 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.

[3]. 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.

Chemical & Physical Properties

Density	1.26
Boiling Point	561.016ºC at 760 mmHg
Molecular Formula	C₂₁H₂₃N₅S
Molecular Weight	377.50600
Flash Point	293.092ºC
Exact Mass	377.16700
PSA	83.87000
LogP	5.73000
InChIKey	SNFYYXUGUBUECJ-HXUWFJFHSA-N
SMILES	CCC(CC)C(c1ccc(Nc2nc3ccccc3s2)cc1)n1cncn1

Synonyms

Talarozole (R enantiomer)

Recommended......