Talarozole

Talarozole (formerly R115866, planned trade name Rambazole) was an investigational drug for the treatment of acne, psoriasis and other keratinization disorders. Development for that purpose has been discontinued.^[1] However, its effect in increasing retinoic acid is now being investigated in hand and knee osteoarthritis.^[2]

Routes of
administrationBy mouth, topical

ATC code

• none

CAS Number

• 201410-53-9 ^Y

PubChem CID

• 9799888

Quick facts Clinical data, Routes ofadministration ...

Talarozole

Clinical data
Routes of administration	By mouth, topical
ATC code	none
Identifiers
IUPAC name N-(2-Benzothioazolyl)-N-[4-[2-ethyl-1-(1,2,4-triazo-1-yl)butyl]phenyl]amine
CAS Number	201410-53-9 Y
PubChem CID	9799888
ChemSpider	7975653 N
UNII	XKD9N5CJ6W
ChEBI	CHEBI:101854 N
CompTox Dashboard (EPA)	DTXSID70942185
Chemical and physical data
Formula	C21H23N5S
Molar mass	377.51 g·mol−1
3D model (JSmol)	Interactive image
SMILES c2ncnn2C(C(CC)CC)c(cc3)ccc3Nc4nc1ccccc1s4
InChI 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) N Key:SNFYYXUGUBUECJ-UHFFFAOYSA-N N
NY (what is this?)  (verify)

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Talarozole inhibits the metabolism of retinoic acid by blocking cytochrome P450 enzyme CYP26 isoenzymes (CYP26A1 and possibly also CYP26B1), retinoic acid hydroxylases.^[3] Because of this mechanism, it is called a retinoic acid metabolism blocking agent (RAMBA).^[3][4]

It has 750-fold higher potency than the earlier drug liarozole as well as greater selectivity, with more than 300-fold selectivity for inhibition of CYP26A1 over other steroid-metabolizing enzymes like CYP17A1 (17α-hydroxylase/17,20-lyase) and aromatase (CYP19A1).^[3][5]