15β-Hydroxycyproterone acetate Other names 15β-Hydroxy-CPA; 15β-OH-CPA; 6-Chloro-15β,17α-dihydroxy-1α,2α-methylenepregna-4,6-diene-3,20-dione 17α-acetate; 6-Chloro-1,2α-methylene-15β,17α-dihydroxy-δ6 -progesterone 17α-acetate
(1R ,3aS ,3bR ,8bS ,8cS ,10aS )-1-acetyl-5-chloro-3-hydroxy-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,7,7a,8,8a,8b,8c,9,10,10a-tetradecahydrocyclopenta[a ]cyclopropa[g ]phenanthren-1-yl acetate
CAS Number 65423-26-9 Y 114884-50-3 (non-specific stereochemistry) PubChem CID ChemSpider UNII Formula C 24 H 29 Cl O 5 Molar mass 432.94 g·mol−1 3D model (JSmol )
CC(=O)[C@]1(CC([C@@H]2[C@@]1(CC[C@H]3[C@H]2C=C(C4=CC(=O)[C@@H]5C[C@@H]5[C@]34C)Cl)C)O)OC(=O)C
InChI=1S/C24H29ClO5/c1-11(26)24(30-12(2)27)10-20(29)21-14-8-18(25)17-9-19(28)13-7-16(13)23(17,4)15(14)5-6-22(21,24)3/h8-9,13-16,20-21,29H,5-7,10H2,1-4H3/t13-,14-,15+,16+,20?,21-,22+,23+,24+/m1/s1
Key:HRANPRDGABOKNQ-XHLVMSDXSA-N
15β-Hydroxycyproterone acetate (15β-OH-CPA ) is a steroidal antiandrogen and the major metabolite of cyproterone acetate (CPA).[1] [2] [3] It is formed from CPA in the liver by hydroxylation via the cytochrome P450 enzyme CYP3A4 .[1] [2] [3] During therapy with CPA, 15β-OH-CPA circulates at concentrations that are approximately twice those of CPA.[4] 15β-OH-CPA has similar or even greater antiandrogen activity compared to CPA.[5] However, it has only about one-tenth of the activity of CPA as a progestogen .[6] 15β-OH-CPA also shows some glucocorticoid activity, similarly to CPA and unesterified cyproterone .[7] [8]
See also [ ]
List of steroidal antiandrogens
References [ ]
^ a b Fabian M. Saleh (11 February 2009). Sex Offenders: Identification, Risk Assessment, Treatment, and Legal Issues . Oxford University Press, USA. pp. 197–. ISBN 978-0-19-517704-6 .
^ a b Bińkowska M, Woroń J (June 2015). "Progestogens in menopausal hormone therapy" . Przegla̜d Menopauzalny = Menopause Review . 14 (2): 134–43. doi :10.5114/pm.2015.52154 . PMC 4498031 . PMID 26327902 .
^ a b Michael Boarder; David Newby; Phyllis Navti (25 March 2010). Pharmacology for Pharmacy and the Health Sciences: A Patient-centred Approach . OUP Oxford. pp. 632–. ISBN 978-0-19-955982-4 .
^ Frith RG, Phillipou G (1985). "15-Hydroxycyproterone acetate and cyproterone acetate levels in plasma and urine". J. Chromatogr . 338 (1): 179–86. doi :10.1016/0378-4347(85)80082-7 . PMID 3160716 .
^ V. H. T. James; J. R. Pasqualini (22 October 2013). Hormonal Steroids: Proceedings of the Sixth International Congress on Hormonal Steroids . Elsevier. pp. 398–. ISBN 978-1-4831-9067-9 .
^ Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric . 8 Suppl 1: 3–63. doi :10.1080/13697130500148875 . PMID 16112947 . S2CID 24616324 .
^ Bhargava AS, Kapp JF, Poggel HA, Heinick J, Nieuweboer B, Günzel P (1981). "Effect of cyproterone acetate and its metabolites on the adrenal function in man, rhesus monkey and rat". Arzneimittelforschung . 31 (6): 1005–9. PMID 6266428 .
^ Excerpta medica. Section 30. Pharmacology and toxicology . 1982. In addition, cyprosterone acetate and its main metabolite, 15β-hydroxy acetate, as well as the newly isolated free alcohol of the main metabolite were characterized for their corticosteroid-like activity in rats. Cyproterone acetate treatment of male hypersexual subjects and female rhesus monkeys did not reveal any signs of adrenal suppression. Cyproterone acetate and its metabolites gave no indication of any appreciable antiinflammatory effect in the adjuvant edema test in rats. However, there was a general increase in the level of blood glucose and liver glycogen as well as a reduction in body weight and organ weight (spleen, thymus and adrenal) in rats, in which 15β-hydroxy cyproterone was slightly more active with the exception of adrenal weight reduction, which was almost equal in all three compounds tested. It can also be concluded that adult man and rhesus monkey are much less sensitive, if at all so, to some corticosteroid-like activities of cyproterone acetate and its main metabolites than the rat.
Cyproterone acetate
Topics
Side effects of cyproterone acetate
Pharmacology of cyproterone acetate
Metabolites Combinations Related drugs
Steroidal antiandrogens : Pure antiandrogens: Cyproterone ; Antigonadotropic: Chlormadinone acetate
Medroxyprogesterone acetate
Megestrol acetate
AR
Agonists
Testosterone derivatives: 4-Androstenediol
4-Dehydroepiandrosterone (4-DHEA)
4-Hydroxytestosterone
5-Androstenedione
11-Ketotestosterone
11β-Hydroxyandrostenedione
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
Androstenediol (5-androstenediol)
Androstenedione (4-androstenedione)
Atamestane
Boldenone
Boldione (1,4-androstadienedione)
Clostebol
Clostebol acetate
Clostebol caproate
Clostebol propionate
Cloxotestosterone
Cloxotestosterone acetate
Dehydroandrosterone
DHEA (androstenolone, prasterone; 5-DHEA)
DHEA enanthate (prasterone enanthate)
DHEA sulfate
Exemestane
Formestane
Plomestane
Quinbolone
Silandrone
Testosterone # (+dutasteride )
Testosterone esters
Polytestosterone phloretin phosphate
5α-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
Dihydrofluoxymesterone
Dihydrotestosterone (DHT) (androstanolone, stanolone )
Dihydrotestosterone esters
Drostanolone
Epiandrosterone
Epitiostanol
Mepitiostane
Mesabolone
Mesterolone
Methyldiazinol
Nisterime
Prostanozol
Stenbolone
Testifenon (testiphenon, testiphenone)
19-Nortestosterone derivatives: 7α-Methyl-19-norandrostenedione (MENT dione, trestione)
11β-Methyl-19-nortestosterone
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
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
Norclostebol
Normethandrone (methylestrenolone, normethisterone)
Oxabolone
Oxabolone cipionate (oxabolone cypionate)
Trenbolone
Trenbolone acetate
Trenbolone enanthate
Trenbolone hexahydrobenzylcarbonate
Trenbolone undecanoate
Trendione
Trestolone (MENT)
Trestolone acetate
Trestolone enanthate
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 (+esterified estrogens )
Oxymesterone
Penmesterol
Tiomesterone
17α-Alkylated 5α-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
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol
Methyldienolone
Methylhydroxynandrolone (MOHN, MHN)
Metribolone
Mibolerone
Norboletone
Norethandrolone
Propetandrol
RU-2309
Tetrahydrogestrinone
17α-Vinyl-19-nortestosterone derivatives: Vinyltestosterone
17α-Ethynyltestosterone derivatives: Danazol
Ethinylandrostenediol
Ethisterone (ethynyltestosterone)
17α-Ethynyl-19-nortestosterone derivatives: Δ4 -Tibolone
Desogestrel
Etonogestrel
Etynodiol
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Norethisterone
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Norgestrel
Norgestrienone
Quingestanol
Tibolone
Mixed (SARMs )
Steroidal:
MK-0773
TFM-4AS-1
YK-11
Antagonists
Nonsteroidal: 5N -Bicalutamide
AA560
Apalutamide
Atraric acid
Bakuchiol
Bicalutamide
Bisphenols (e.g., BADGE , , bisphenol A , bisphenol F , bisphenol S )
BMS-641988
Cimetidine
Cioteronel
Cyanonilutamide
Darolutamide
DDT (via metabolite p,p’-DDE )
Dieldrin
DIMP
Endosulfan
Enzalutamide
EPI-001
EPI-7386
Fenarimol
Flutamide
Hydroxyflutamide
Inocoterone
Inocoterone acetate
Ketoconazole
Ketodarolutamide
Lavender oil
LG-120907
Linuron
Methiocarb
N -Desmethylapalutamide
N -Desmethylenzalutamide
Nilutamide
Pentomone
Phenothrin
Prochloraz
Procymidone
Proxalutamide
Ralaniten (EPI-002)
Ralaniten acetate (EPI-506)
RD-162
Rezvilutamide
RU-22930
RU-56187
RU-57073
RU-58642
RU-58841
Seviteronel
Thalidomide
Topilutamide (fluridil)
Valproic acid
Vinclozolin
GPRC6A
Agonists
Cations (incl. aluminum , calcium , gadolinium , magnesium , strontium , zinc )
Dehydroandrosterone
Dihydrotestosterone
Estradiol
L -α-Amino acids (incl. L -arginine , L -lysine , L -ornithine )
Osteocalcin
SHBG
Testosterone
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens/anabolic steroids
GR
Agonists Mixed (SEGRMs )
Dagrocorat
Fosdagrocorat
Mapracorat
Antagonists Others
See also
Receptor/signaling modulators
Glucocorticoids and antiglucocorticoids
Mineralocorticoid receptor modulators
List of corticosteroids
PR
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g., nandrolone decanoate , nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g., trenbolone acetate , trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Spirolactone derivatives: Canrenoic acid
Canrenone
Drospirenone
Mespirenone
Potassium canrenoate
Prorenone
SC-5233 (spirolactone)
SC-8109
Spironolactone
Spirorenone
Mixed (SPRMs )
Nonsteroidal: Apigenin
Kaempferol
Naringenin
Syringic acid
Antagonists
Nonsteroidal: Darolutamide
Valproic acid
mPR (PAQR )
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens