5α-Pregnan-17α-ol-3,20-dione

5α-Pregnan-17α-ol-3,20-dione, also known as 17α-hydroxy-dihydroprogesterone (17‐OH-DHP) is an endogenous steroid.

5α-Pregnan-17α-ol-3,20-dione
Names
IUPAC name
(5α)-17-Hydroxypregnane-3,20-dione
Other names
5α-17-Hydroxypregnane-3,20-dione,[1] 17‐OH-DHP,[2] 5α-Pregnane-17α-ol-3,20-dione,[2] 17α-Hydroxy-5α-pregnane-3,20-dione,[3][4] 17-Hydroxydihydroprogesterone,[5] 17α-hydroxy-dihydroprogesterone[6]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
Properties
C21H32O3
Molar mass 332.484 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Function

5α-Pregnan-17α-ol-3,20-dione is the first intermediate product within the androgen backdoor pathway in which 17α-hydroxyprogesterone (17‐OHP) is 5α-reduced and finally converted to 5α-dihydrotestosterone (DHT) without testosterone intermediate. The subsequent intermediate products in the pathway are 5α-pregnane-3α,17α-diol-20-one, androsterone and 5α-androstane-3α,17β-diol.[7][8]

Biosynthesis

5α-Pregnan-17α-ol-3,20-dione is produced by 5α-reduction of 17-OHP. The reaction is catalyzed by SRD5A1/SRD5A2 enzymes.[2][9][10]

See also

References
  1. "(5alpha)-17-Hydroxypregnane-3,20-dione - PubChem Compound Summary".
  2. Fukami M, Homma K, Hasegawa T, Ogata T (April 2013). "Backdoor pathway for dihydrotestosterone biosynthesis: implications for normal and abnormal human sex development". Developmental Dynamics. 242 (4): 320–9. doi:10.1002/dvdy.23892. PMID 23073980. S2CID 44702659.
  3. Asahina K, Suzuki K, Aida K, Hibiya T, Tamaoki B (February 1985). "Relationship between the structures and steroidogenic functions of the testes of the urohaze-goby (Glossogobius olivaceus)". General and Comparative Endocrinology. 57 (2): 281–92. doi:10.1016/0016-6480(85)90273-4. PMID 3156787.
  4. Gal M, Orly J (2014). "Selective inhibition of steroidogenic enzymes by ketoconazole in rat ovary cells". Clinical Medicine Insights. Reproductive Health. 8: 15–22. doi:10.4137/CMRH.S14036. PMC 4007567. PMID 24812532.
  5. Miller WL (January 2012). "The syndrome of 17,20 lyase deficiency". The Journal of Clinical Endocrinology and Metabolism. 97 (1): 59–67. doi:10.1210/jc.2011-2161. PMC 3251937. PMID 22072737.
  6. Hastings C, Hansson V (August 1981). "Kinetic properties of the soluble 3 alpha-hydroxysteroid dehydrogenase from rat testis and epididymis". Journal of Steroid Biochemistry. 14 (8): 705–11. doi:10.1016/0022-4731(81)90005-4. PMID 6946263.
  7. Miller WL, Auchus RJ (April 2019). "The "backdoor pathway" of androgen synthesis in human male sexual development". PLOS Biology. 17 (4): e3000198. doi:10.1371/journal.pbio.3000198. PMC 6464227. PMID 30943210.
  8. Wilson JD, Auchus RJ, Leihy MW, Guryev OL, Estabrook RW, Osborn SM, Shaw G, Renfree MB (February 2003). "5alpha-androstane-3alpha,17beta-diol is formed in tammar wallaby pouch young testes by a pathway involving 5alpha-pregnane-3alpha,17alpha-diol-20-one as a key intermediate". Endocrinology. 144 (2): 575–80. doi:10.1210/en.2002-220721. PMID 12538619.
  9. Reisch N, Taylor AE, Nogueira EF, Asby DJ, Dhir V, Berry A, Krone N, Auchus RJ, Shackleton CH, Hanley NA, Arlt W (October 2019). "Alternative pathway androgen biosynthesis and human fetal female virilization". Proceedings of the National Academy of Sciences of the United States of America. 116 (44): 22294–22299. doi:10.1073/pnas.1906623116. PMC 6825302. PMID 31611378.
  10. Kamrath C, Hochberg Z, Hartmann MF, Remer T, Wudy SA (March 2012). "Increased activation of the alternative "backdoor" pathway in patients with 21-hydroxylase deficiency: evidence from urinary steroid hormone analysis". The Journal of Clinical Endocrinology and Metabolism. 97 (3): E367–75. doi:10.1210/jc.2011-1997. PMID 22170725.
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