Talarozole

Talarozole
Clinical data

Routes of administration	oral, 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^Y
ChEBI	CHEBI:101854^N
Chemical and physical data
Formula	C₂₁H₂₃N₅S
Molar mass	377.505 g/mol
3D model (Jmol)	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)

Talarozole (formerly R115866, planned trade name Rambazole) is an investigational drug 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).^[1]

References

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

Androgen receptor modulators

Agonists	Testosterone derivatives: 4-Androstenediol 4-Androstenedione 4-Dehydroepiandrosterone (4-DHEA) 4-Hydroxytestosterone 5-Androstenediol 5-Androstenedione 11-Ketotestosterone 11β-Hydroxyandrostenedione Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione) Atamestane Boldenone Boldenone undecylenate Boldione (1,4-androstadienedione) Clostebol Clostebol acetate Clostebol caproate Clostebol propionate Cloxotestosterone Cloxotestosterone acetate DHEA (androstenolone, prasterone; 5-DHEA) DHEA enanthate (prasterone enanthate) DHEA sulfate Exemestane Formestane Plomestane Quinbolone Silandrone Testosterone^# Testosterone acetate Testosterone acetate butyrate Testosterone acetate propionate Testosterone benzoate Testosterone butyrate Testosterone buciclate Testosterone capropate Testosterone cyclohexylpropionate Testosterone cypionate Testosterone decanoate Testosterone diacetate Testosterone dipropionate Testosterone enanthate Testosterone formate Testosterone furoate Testosterone hexahydrobenzoate Testosterone hexahydrobenzylcarbonate Testosterone hexyloxyphenylpropionate Testosterone isobutyrate Testosterone isocaproate Testosterone isovalerate Testosterone ketolaurate Testosterone nicotinate Testosterone palmitate Testosterone phenylacetate Testosterone phenylbutyrate Testosterone phenylpropionate Testosterone phosphate Testosterone propionate Testosterone stearate Testosterone sulfate Testosterone undecanoate Testosterone valerate Dihydrotestosterone derivatives: 1-Androstenediol 1-Androstenedione 1-Androsterone (1-andro, 1-DHEA) 1-Testosterone 3α-Androstanediol 5α-Androst-2-en-17-one 7β-Hydroxyepiandrosterone 11-Ketodihydrotestosterone Androsterone Bolazine Bolazine capronate Dihydrotestosterone (androstanolone, stanolone) Dihydrotestosterone acetate Dihydrotestosterone benzoate Dihydrotestosterone butyrate Dihydrotestosterone enanthate Dihydrotestosterone formate Dihydrotestosterone propionate Dihydrotestosterone valerate Drostanolone Drostanolone propionate Epiandrosterone Epitiostanol Mepitiostane Mesabolone Mesterolone Nisterime Nisterime acetate Prostanozol Stenbolone Stenbolone acetate 19-Nortestosterone derivatives: 7α-Methyl-19-norandrostenedione (MENT dione, trestione) 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione Bolandiol Bolandiol dipropionate Bolandione (19-nor-4-androstenedione) Bolmantalate (nandrolone adamantoate) Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate LS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate) Methoxydienone (methoxygonadiene) Nandrolone Nandrolone acetate Nandrolone caproate Nandrolone cypionate Nandrolone cyclohexanecarboxylate Nandrolone cyclohexylpropionate Nandrolone cyclotate Nandrolone decanoate Nandrolone formate Nandrolone furylpropionate Nandrolone hexyloxyphenylpropionate Nandrolone hydrogen succinate Nandrolone laurate Nandrolone phenylpropionate Nandrolone propionate Nandrolone sulfate Nandrolone sulfate sodium Nandrolone undecanoate Norclostebol Norclostebol acetate Normethandrone (methylestrenolone, normethisterone) Oxabolone Oxabolone cipionate (oxabolone cypionate) Trenbolone Trenbolone acetate Trenbolone enanthate Trenbolone hexahydrobenzylcarbonate Trestolone (MENT) Trestolone acetate Dihydrotestosterone and 19-nortestosterone derivatives: 5α-Dihydronandrolone 19-Norandrosterone 17α-Alkylated testosterone derivatives: Bolasterone Calusterone Chlorodehydromethylandrostenediol (CDMA) Chlorodehydromethyltestosterone (CDMT) Chloromethylandrostenediol (CMA) Enestebol Ethyltestosterone Fluoxymesterone Formebolone Hydroxystenozole Metandienone (methandrostenolone) Methandriol (methylandrostenediol) Methandriol bisenanthoyl acetate Methandriol diacetate Methandriol dipropionate Methandriol propionate Methylclostebol (chloromethyltestosterone) Methyltestosterone Oxymesterone Penmesterol Tiomesterone 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole Desoxymethyltestosterone Furazabol Mebolazine (dimethazine) Mestanolone Metenolone Metenolone acetate Metenolone enanthate Methasterone Methyl-1-testosterone Methylepitiostanol Methylstenbolone Oxandrolone Oxymetholone Stanozolol 17α-Alkylated 19-nortestosterone derivatives: Bolenol Dimethyltrienolone (7α-methylmetribolone, 7α,17α-dimethyltrenbolone) Ethyldienolone Ethylestrenol Methyldienolone Methylhydroxynandrolone (MOHN, MHN) Metribolone Mibolerone Norboletone Norethandrolone Propetandrol Tetrahydrogestrinone 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone) Vinyltestosterone 17α-Ethynyltestosterone derivatives: Δ⁴-Tibolone Chloroethynyl norgestrel Danazol Desogestrel Ethisterone (ethynyltestosterone) Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel butanoate Lynestrenol Norethisterone Norethisterone acetate Norethisterone acetate oxime Norethisterone enanthate Norgestrel Norgestrienone Quingestanol Quingestanol acetate Tibolone Progesterone derivatives: Medroxyprogesterone acetate Others/unsorted: Cl-4AS-1

Mixed (SARMs)	Non-steroidal: 198RL26 ACP-105 AC-262,356 Acetothiolutamide Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4) BMS-564,929 Enobosarm (ostarine, MK-2866, GTx-024, S-22) FTBU-1 GSK-4336A GSK-8698 LG-121071 (LGD-121071) LGD-2226 LGD-2941 (LGD-122941) LGD-3303 LGD-4033 JNJ-26146900 JNJ-28330835 JNJ-37654032 ORM-11984 RAD140 R-1 R-2 R-3 S-1 S-23 S-40503 S-101479 Steroidal: MK-0773 TFM-4AS-1 YK-11

Antagonists	Steroidal: 3α-Hydroxytibolone 3β-Hydroxytibolone 9,11-Dehydrocortexolone 17α-butyrate (CB-03-04) 11α-Hydroxyprogesterone 15β-Hydroxycyproterone acetate Abiraterone acetate Allyltestosterone Benorterone BOMT Canrenoic acid Canrenone Chlormadinone acetate Clometerone Cortexolone 17α-propionate (CB-03-01) Cyproterone Cyproterone acetate Delanterone Dienogest Drospirenone Edogestrone Epitestosterone Galeterone Guggulsterone Medrogestone Megestrol acetate Mespirenone Metogest Mexrenone Mifepristone Nomegestrol acetate Nordinone Osaterone Osaterone acetate Oxendolone Potassium canrenoate Prorenone Rosterolone SC-5233 (spirolactone) Spironolactone Spirorenone Topterone Trimethyltrienolone (R-2956) Zanoterone Non-steroidal: AA560 Apalutamide Atraric acid AZD-3514 BAY-1024767 Bicalutamide Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S) BMS-641,988 Cimetidine Cioteronel Darolutamide DDT (via metabolite p,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 EPI-506 Fenarimol Flutamide Hydroxyflutamide Inocoterone Inocoterone acetate Ketoconazole Lavender oil LG-105 LG-120907 Linuron Methiocarb N-Butylbenzenesulfonamide N-Desmethylenzalutamide Nilutamide ONC1-13B ORM-15341 Pentomone PF-998425 Phenothrin Prochloraz Procymidone RU-22930 RU-58642 RU-58841 Seviteronel Thalidomide Topilutamide (fluridil) Valproic acid Vinclozolin

GPRC6A

Agonists	Cations (incl. aluminum, calcium, gadolinium, magnesium, strontium) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin Testosterone

See also: Estrogenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators • List of androgens/anabolic steroids

Estrogen receptor modulators

Agonists	Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3α-Androstanediol 3β-Androstanediol 3α-Hydroxytibolone 3β-Hydroxytibolone 4-Androstenediol 4-Androstenedione 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodo-E2 16α-LE2 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17β-Dihydroequilenin 17β-Dihydroequilin Abiraterone Abiraterone acetate 17α-Estradiol (alfatradiol) Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites) Androstene-3,5-dienes Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate DHEA DHEA-S Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Estetrol Estradiol Estradiol 3-propionate Estradiol acetate Estradiol benzoate Estradiol butyrate benzoate Estradiol butyrylacetate Estradiol cyclooctyl acetate Estradiol cypionate Estradiol decanoate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol glucuronide Estradiol hemihydrate Estradiol hemisuccinate (estradiol succinate) Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol mustard Estradiol palmitate Estradiol pivalate (trimethyl estradiol acetate) Estradiol propoxyphenylpropionate Estradiol stearate Estradiol sulfate Estradiol undecylate Estradiol valerate Lipoidal estradiol Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol acetate benzoate Estriol glucuronide Estriol sodium succinate Estriol succinate Estriol sulfate Estriol sulfate glucuronide Estriol triacetate Estriol tripropionate Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone glucuronide Estrone sulfate Estrone tetraacetylglucoside Estropipate Etamestrol (eptamestrol) Ethinylestradiol Ethinylestradiol sulfonate Ethinylestriol Etynodiol diacetate Hexolame Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Noretynodrel Orestrate Pentolame Polyestradiol phosphate Prodiame Prolame Promestriene Quinestradol Quinestrol Non-steroidal: (R,R)-THC (S,S)-THC 1-Keto-1,2,3,4-tetrahydrophenanthrene 2,8-DHHHC Allenestrol Allenoic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Carbestrol Diarylpropionitrile Dienestrol Dienestrol acetate Diethylstilbestrol Diethylstilbestrol diacetate Diethylstilbestrol dilaurate Diethylstilbestrol dipalmitate Diethylstilbestrol dipropionate Diethylstilbestrol disulfate Diethylstilbestrol monobenzyl ether Dimestrol (dianisylhexene) Doisynoestrol (fenocycline) Doisynolic acid Efavirenz ERB-196 (WAY-202196) Erteberel (SERBA-1, LY-500307) Estrobin (DBE) Fenestrel FERb 033 Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate ICI-85966 (Stilbostat) Mestilbol Methallenestril Methestrol Methestrol dipropionate Miroestrol Paroxypropione Pentafluranol Phenestrol Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene (triphenylpropene) WAY-166818 WAY-200070 WAY-214156 Xenoestrogens: Anethole Anol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Coumestans (e.g., coumestrol, psoralidin) Deoxymiroestrol Dianethole Dianol Digitoxin (digitalis) Diosgenin Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Guggulsterone Lavender oil Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol)) Metalloestrogens (e.g., cadmium) Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, methiocarb, methoxychlor) Photoanethole Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol)) Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Unknown/unsorted: ERB-26 ERA-45 ERB-79

Mixed (SERMs)	27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordrin Anordriol Arzoxifene Bazedoxifene Brilanestrant Broparestrol Elacestrant Chlorotrianisene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Epitiostanol Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW-7604 ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LY-117018 Menerba Mepitiostane Methylepitiostanol Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Phenytoin Pipendoxifene Raloxifene SS1010 Tamoxifen TAS-108 (SR-16234) Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene

Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Cytestrol acetate ERA-90 ERB-88 Fulvestrant (ICI-182780) Glyceollins (I, II, III, IV) ICI-164384 Methylpiperidinopyrazole MIBE PHTPP Prochloraz RU-58668 SS1020 TAS-108 (SR-16234) XCT-790 ZK-164015 ZK-191703

GPER

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol Tamoxifen Tectoridin Zearalanone Zearalenol Zearalenone Zeranol (zearalanol))

Antagonists	CCL18 Estriol G-15 G-36 MIBE

See also: Androgenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators

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