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Zanoterone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Zanoterone
Clinical data
Other namesWIN-49596; (5α,17α)-1'-(methylsulfonyl)-1'-H-pregn-20-yno[3,2-c]pyrazol-17-ol
Routes of
administration		By mouth
Drug classSteroidal antiandrogen
Identifiers
  • (1R,3aS,3bR,5aS,10aS,10bS,12aS)-1-ethynyl-10a,12a-dimethyl-8-(methylsulfonyl)-1,2,3,3a,3b,4,5,5a,6,8,10,10a,10b,11,12,12a-hexadecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-ol
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC23H32N2O3S
Molar mass416.58 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CC[C@@H]4[C@@]3(CC5=CN(N=C5C4)S(=O)(=O)C)C
  • InChI=1S/C23H32N2O3S/c1-5-23(26)11-9-19-17-7-6-16-12-20-15(14-25(24-20)29(4,27)28)13-21(16,2)18(17)8-10-22(19,23)3/h1,14,16-19,26H,6-13H2,2-4H3/t16-,17+,18-,19-,21-,22-,23-/m0/s1
  • Key:MHDDZDPNIDVLNK-ZGIWMXSJSA-N

Zanoterone (INNTooltip International Nonproprietary Name,USANTooltip United States Adopted Name) (former developmental code nameWIN-49596), also known as(5α,17α)-1'-(methylsulfonyl)-1'-H-pregn-20-yno[3,2-c]pyrazol-17-ol,[1] is asteroidal antiandrogen which was never marketed.[2][3][4] It was investigated for the treatment ofbenign prostatic hyperplasia (BPH) but failed to demonstrate sufficient efficacy inphase IIclinical trials, and also showed an unacceptable incidence rate and severity ofside effects (e.g.,breast pain andgynecomastia).[4][5] As such, it was not further developed.[4][5]

Zanoterone was derived from5α-dihydroethisterone (5α-dihydro-17α-ethynyltestosterone).[6][7] It is anantagonist of theandrogen receptor (Ki = 2.2 μM;RBATooltip relative binding affinity compared tometribolone = 2.2%), and with the exception ofantiprogestogenic activity in rat and rabbit models, is devoid of other hormonal activities.[6][8] Zanoterone does not inhibit5α-reductase,aromatase, or3α- or3β-hydroxysteroid dehydrogenasein vitro.[6] The drug significantly increasestestosterone andestradiol levels in men.[9] Zanoterone has been found to not significantly inhibit mating performance or fertility in adult male rats at high dosages for an extended period of time.[6] It has been found to act as aninducer of theenzymeCYP3A4in vivo in rats.[10]

Relative potencies of selected antiandrogens
AntiandrogenRelativepotency
Bicalutamide4.3
Hydroxyflutamide3.5
Flutamide3.3
Cyproterone acetate1.0
Zanoterone0.4
Description: Relative potencies oforally administered antiandrogens in antagonizing 0.8 to 1.0 mg/kgs.c.Tooltip subcutaneous injectiontestosterone propionate-inducedventral prostate weight increase incastratedimmature male rats. Higher values mean greater potency.Sources: See template.

See also

[edit]

References

[edit]
  1. ^William Andrew Publishing (22 October 2013).Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 3517–3518.ISBN 978-0-8155-1856-3.
  2. ^Morton IK, Hall JM (31 October 1999).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 294–.ISBN 978-0-7514-0499-9.
  3. ^Ganellin CR, Triggle DJ (1997).Dictionary of Pharmacological Agents. Taylor & Francis. pp. 540–.ISBN 978-0-412-46630-4.
  4. ^abcSchröder FH, Radlmaier A (2009). "Steroidal Antiandrogens". In Jordan VC, Furr BJ (eds.).Hormone Therapy in Breast and Prostate Cancer. Cancer Drug Discovery and Development. Humana Press. pp. 325–346.doi:10.1007/978-1-59259-152-7_15.ISBN 978-1-60761-471-5.
  5. ^abWein AJ, Kavoussi LR, Novick AC,Partin AW, Peters CA (28 September 2011).Campbell-Walsh Urology. Elsevier Health Sciences. pp. 2637–.ISBN 978-1-4557-2298-3.
  6. ^abcdMallamo JP, Juniewicz PE (8 September 1989)."New horizons in the treatment of proliferative prostatic disease.".Annual Reports in Medicinal Chemistry. Academic Press. pp. 197-206 (200).ISBN 978-0-08-058368-6.
  7. ^Lednicer D, Mitscher LA (5 November 1998).The Organic Chemistry of Drug Synthesis. John Wiley & Sons. p. 65.ISBN 978-0-471-24510-0.
  8. ^Winneker RC, Wagner MM, Batzold FH (December 1989). "Studies on the mechanism of action of Win 49596: a steroidal androgen receptor antagonist".Journal of Steroid Biochemistry.33 (6):1133–1138.doi:10.1016/0022-4731(89)90420-2.PMID 2615358.
  9. ^Berger BM, Naadimuthu A, Boddy A, Fisher HA, McConnell JD, Milam D, et al. (September 1995). "The effect of zanoterone, a steroidal androgen receptor antagonist, in men with benign prostatic hyperplasia. The Zanoterone Study Group".The Journal of Urology.154 (3):1060–1064.doi:10.1016/S0022-5347(01)66976-3.PMID 7543598.
  10. ^Roberts AE, Ritz MA, Hoekstra S, Descotes G, Hincks JR (1996). "Induction of liver cytochrome P-450 (CYP) 3A in male and female rats by a steroidal androgen receptor antagonist, zanoterone".Journal of Biochemical Toxicology.11 (3):101–110.doi:10.1002/(SICI)1522-7146(1996)11:3<101::AID-JBT1>3.0.CO;2-O.PMID 9029268.
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
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