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| | Talarozole Basic information |
| Product Name: | Talarozole | | Synonyms: | talarozole;N-[4-[(1R)-2-Ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl]-2-benzothiazolamine;(R)-Talarozole;Talarozole (R enantiomer);2-Benzothiazolamine, N-[4-[(1R)-2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl]- | | CAS: | 870093-23-5 | | MF: | C21H23N5S | | MW: | 377.51 | | EINECS: | | | Product Categories: | | | Mol File: | 870093-23-5.mol |  |
| | Talarozole Chemical Properties |
| Boiling point | 561.0±60.0 °C(Predicted) | | density | 1.26 | | storage temp. | Store at -20°C | | solubility | DMSO: ≥ 51 mg/mL (135.10 mM) | | pka | 2.70±0.10(Predicted) | | form | film | | color | colorless | | 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 | | InChIKey | SNFYYXUGUBUECJ-HXUWFJFHSA-N | | SMILES | [s]1c2c(nc1Nc3ccc(cc3)[C@H]([n]4ncnc4)C(CC)CC)cccc2 |
| WGK Germany | WGK 3 | | Storage Class | 11 - Combustible Solids |
| | Talarozole Usage And Synthesis |
| Uses | Talarozole is a retinoic acid metabolism blocking agent (RAMBA) that can be used for treating dermatalogical diseases such as psoriasis and acne. | | Definition | ChEBI: An N-{4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl}-1,3-benzothiazol-2-amine that is the (R)-enantiomer of talarozole. The racemate is used for the treatment of keratinization disorders, psoriasis
nd acne. | | Biological Activity | R115866 (Talarozole) is an orally active all-trans retinoic acid (RA) metabolism blocking agent (RAMBA; IC50 = 4 nM against RA metablism in yeast microsomes expressing human CYP26) with much reduced or little potency against CYP19 (aromatase), CYP17 (17,20-lyase), CYP2C11, CYP3A, and CYP2A1 (IC50 from 1.2 to >10 μM). Plasma and tissue RA upregulation via R115866 oral treatment exhibits in vivo efficacy in several retinoid-responsive rodent models, including vaginal keratinization suppression (ED50 = 1.0 mg/kg/day vs. 5.1 mg/kg/day with RA in rats), pinnal hyperplasia induction (ear epidermis thickness = 35.5 μm with 2.5 mg/kg/day R115866 vs. 16.5 μm in control mice), conversion of caudal para- to ortho-keratosis (90% with 1.25 mg/kg/day R115866 vs. 30.3% in control mice). Comparing to liarozole, R115866 is CYP26-selective and does not inhibit CYP-mediated biosynthesis of adrenal and gonadal steroid hormones. |
| | Talarozole Preparation Products And Raw materials |
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