Substance

ID:449650

Names and Identifiers
IUPAC name
(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
Synonyms
TestosteroneAtmosAndropatch
IUPAC Traditional name
(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
Registration numbers
CAS Number
58-22-0
Properties
Product Information
Biological Source
Constit. of human urine
Application(s)
Used in the treatment of male hypogonadism (transdermal administration)
Pharmacology Properties
Mechanism of Action
High dose: spermatogenesis inhibitor
FSH antagonist.
Activity in many tissues appears to depend on reduction to dihydrotestosterone which binds to cytosolic receptor proteins
The steroid receptor complex is transported to the nucleus where it initiates transcription events and cellular changes related to androgen action
Exogenous administration inhibits endogenous release via feedback inhibition of pituitary ICSH
Androgen
ICSH antagonist
Gonadotropin antagonist
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
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• Kuroyagi, M. et al., Yakugaku Zasshi, 1970, 90, 1467; CA, 74, 61612a, (isol)
• Dyrssen, D.W. et al., Anal. Chim. Acta, 1972, 60, 139, (detn, B)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 52C, (ir)
• Kashina, C. et al., Heterocycles, 1977, 7, 241, (synth)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 800B, (nmr)
• Sastry, B.S., Res. Ind., 1970, 15, 258; CA, 75, 75063e, (isol)
• Holder, G.M. et al., Xenobiotica, 1978, 8, 761, (metab)
• Encyclopedia of Food and Color Additives, (ed. Burdock, G.A.), CRC Press, 1997, 2856-2858
• Lampe, V., Ber., 1918, 51, 1347, (synth)
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• Tonnesen, H.H. et al., Acta Chem. Scand., Ser. B, 1982, 36, 475, (cryst struct, bibl)
• Khar, A. et al., FEBS Lett., 1999, 445, 165-168, (antitumour props)
• Ammon, H.P.T. et al., Planta Med., 1991, 57, 1-7, (rev, pharmacol)
• Roughley, P.J. et al., J.C.S. Perkin 1, 1973, 2379-2388, (biosynth)
• Karig, F., Dtsch. Apoth. -Ztg., 1975, 115, 325; CA, 83, 65372f, (derivs)
• Wahlstrom, B. et al., Acta Pharmacol. Toxicol., 1978, 43, 86, (metab)
• Cheng, K.L. et al., Handbook of Organic Analytical Reagents, CRC Press, Boca Raton, 1982, 511, (use)
• Jitoe, A. et al., J. Agric. Food Chem., 1992, 40, 1337-1340, (occur)
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