Lapisteride

Lapisteride
Clinical data

Routes of administration	Oral^[1]
ATC code	None
Legal status
Legal status	Non-regulated
Identifiers
IUPAC name N-[1-(4-methoxyphenyl)-1-methylethyl]-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
CAS Number	142139-60-4^Y
PubChem (CID)	9847295
ChemSpider	8023009^Y
UNII	T50SJ23G82^Y
Chemical and physical data
Formula	C₂₉H₄₀N₂O₃
Molar mass	464.6395 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(NC(c1ccc(OC)cc1)(C)C)[C@@H]3[C@]2(CC[C@H]4[C@H]([C@@H]2CC3)CC[C@H]5NC(=O)\C=C/[C@]45C)C
InChI InChI=1S/C29H40N2O3/c1-27(2,18-6-8-19(34-5)9-7-18)31-26(33)23-12-11-21-20-10-13-24-29(4,17-15-25(32)30-24)22(20)14-16-28(21,23)3/h6-9,15,17,20-24H,10-14,16H2,1-5H3,(H,30,32)(H,31,33)/t20-,21-,22-,23+,24+,28-,29+/m0/s1^Y Key:NAGKTIAFDQEFJI-DPMIIFTQSA-N^Y
(verify)

Lapisteride (INN; CS-891) is a dual inhibitor of both isoforms of the enzyme 5α-reductase.^[2] It was under investigation for the treatment of benign prostatic hyperplasia (BPH) and androgenic alopecia,^[2]^[3] but was never marketed.

References

↑ Yada S, Ohya M, Ohuchi Y, et al. (April 2003). "Solid phase transition of CS-891 enantiotropes during grinding". International Journal of Pharmaceutics. 255 (1-2): 69–79. doi:10.1016/S0378-5173(03)00084-X. PMID 12672603.
1 2 Niiyama S, Kojima K, Hamada T, Happle R, Hoffmann R (December 2000). "The novel drug CS-891 inhibits 5alpha-reductase activity in freshly isolated dermal papilla of human hair follicles". European Journal of Dermatology. 10 (8): 593–5. PMID 11125319.
↑ Bernan; British Pharmacopoeia Commission (February 2002). British Approved Names 2002. The Stationery Office. p. 157. ISBN 978-0-11-322558-3. Retrieved 17 November 2011.

Drugs used in benign prostatic hyperplasia (G04C)

5α-Reductase inhibitors	Dutasteride Epristeride Finasteride

Alpha blockers (α₁)	Alfuzosin Doxazosin Silodosin Tamsulosin Terazosin

Herbals	Pygeum africanum Saw palmetto extract

Other	Mepartricin Osaterone acetate Oxendolone

Other dermatological preparations (D11)

Anti-seborrheics	Antiandrogens Bicalutamide Cyproterone acetate Flutamide Spironolactone Antifungals Bifonazole Cetrimonium bromide (cetrimide) Ciclopirox olamine (ciclopirox) Climbazole Clotrimazole Ketoconazole Miconazole Piroctone olamine Selenium disulfide (selenium sulfide) Xenysalate Zinc pyrithione (pyrithione zinc) Antihistamines Calcineurin inhibitors Cyclosporin Pimecrolimus Tacrolimus Isotretinoin Keratolytics Coal tar Resorcinol Salicylic acid Sulfur Urea (urea-containing cream) Lithium salts Lithium gluconate Lithium succinate Topical corticosteroids (e.g., hydrocortisone)

Skin lightening	Hydroquinone Mequinol Monobenzone

Skin darkening	Afamelanotide Melanotan II

Anti-inflammatories	Oxaceprol Gamolenic acid Pimecrolimus Tacrolimus Alitretinoin

Baldness treatments	5α-Reductase inhibitors Alfatradiol Finasteride Dutasteride Saw palmetto extract Antiandrogens Bicalutamide Cyproterone acetate Flutamide Spironolactone Topilutamide (fluridil) Potassium channel openers Minoxidil

Hair growth inhibitors	5α-Reductase inhibitors Dutasteride Finasteride Antiandrogens Bicalutamide Cyproterone acetate Flutamide Spironolactone Eflornithine

Others	Brimonidine Calcium gluconate Magnesium sulfate Povidone-iodine Tiratricol

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

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