11β-Hydroxytestosterone
Appearance
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Names | |
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IUPAC name
11β,17β-Dihydroxyandrost-4-en-3-one
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Systematic IUPAC name
(1S,3aS,3bS,9aR,9bS,11aS)-1,10-Dihydroxy-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.162.057 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C19H28O3 | |
Molar mass | 304.430 g·mol−1 |
Hazards | |
GHS labelling: | |
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Danger | |
H351, H360 | |
P201, P202, P281, P308+P313, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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11β-Hydroxytestosterone is an endogenous steroid, a metabolite of testosterone.[1][2][3][4] Although it may not have significant androgenic activity, it may still be an important precursor to androgenic molecules.[4]
See also
[edit]- Testosterone
- Steroid 11β-hydroxylase
- 4-Hydroxytestosterone
- 11-Ketotestosterone
- 11β-Hydroxydihydrotestosterone
References
[edit]- ^ Storbeck KH, Mostaghel EA (2019). "Canonical and Noncanonical Androgen Metabolism and Activity". Prostate Cancer. Advances in Experimental Medicine and Biology. Vol. 1210. Springer. pp. 239–277. doi:10.1007/978-3-030-32656-2_11. ISBN 978-3-030-32655-5. PMID 31900912. S2CID 209748543.
CYP11B1 and 2 have also been shown to 11β-hydroxylate T, yielding 11β-hydroxytestosterone (11OHT), though the levels produced by the adrenal are low due to the limited availability of adrenal derived T
- ^ Stárka L, Dušková M, Vítků J (September 2020). "11-Keto-testosterone and other androgens of adrenal origin". Physiological Research. 69 (Suppl 2): S187–S192. doi:10.33549/physiolres.934516. PMC 8603739. PMID 33094617.
- ^ van Rooyen D, Gent R, Barnard L, Swart AC (2018). "The in vitro metabolism of 11β-hydroxyprogesterone and 11-ketoprogesterone to 11-ketodihydrotestosterone in the backdoor pathway". The Journal of Steroid Biochemistry and Molecular Biology. 178: 203–212. doi:10.1016/j.jsbmb.2017.12.014. PMID 29277707. S2CID 3700135.
- ^ a b Masiutin M, Yadav M (2023). "Alternative androgen pathways". WikiJournal of Medicine. 10: X. doi:10.15347/WJM/2023.003. S2CID 257943362.