fbpx
Wikipedia

11β-Hydroxyprogesterone

January 07, 2024

11β-Hydroxyprogesterone (11β-OHP), also known as 21-deoxycorticosterone, as well as 11β-hydroxypregn-4-ene-3,20-dione, is a naturally occurring, endogenous steroid and derivative of progesterone.[1] It is a potent mineralocorticoid.[1] Syntheses of 11β-OHP from progesterone is catalyzed by the steroid 11β-hydroxylase (CYP11B1) enzyme,[2][3] and, to a lesser extent, by the aldosterone synthase enzyme (CYP11B2).[2]

11β-Hydroxyprogesterone
Names
IUPAC name
11β-Hydroxypregn-4-ene-3,20-dione
Systematic IUPAC name
(1S,3aS,3bS,9aR,9bS,10S,11aS)-1-Acetyl-10-hydroxy-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one
Other names
11β-OHP; 21-Deoxycorticosterone; 21-Desoxycorticosterone
Identifiers
  • 600-57-7
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28247
ChEMBL
  • ChEMBL2440888
ChemSpider
  • 91968
ECHA InfoCard 100.009.088
KEGG
  • C05498
  • 101788
  • InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18-,19+,20-,21+/m0/s1
    Key: BFZHCUBIASXHPK-ATWVFEABSA-N
  • CC(=O)[C@H]1CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)O)C
Properties
C21H30O3
Molar mass 330.468 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Function edit

Along with its epimer 11α-hydroxyprogesterone (11α-OHP), 11β-OHP has been identified as a very potent competitive inhibitor of both isoforms (1 and 2) of 11β-hydroxysteroid dehydrogenase (11β-HSD).[4][5]

Outcome of 21-hydroxylase deficiency edit

It has been known since 1987 that increased levels of 11β-OHP occur in 21-hydroxylase deficiency.[6][7] A study in 2017 has shown that in subjects with 21-hydroxylase deficiency, serum 11β-OHP concentrations range from 0.012 to 3.37 ng/mL, while in control group it was below detection limit of 0.012 ng/mL.[8] 21-hydroxylase is an enzyme that is also involved in progesterone metabolism, producing 11-deoxycorticosterone. In normal conditions, 21-hydroxylase has higher activity on progesterone than steroid 11β-hydroxylase (CYP11B1) and aldosterone synthase (CYP11B2) that convert progesterone to 11β-OHP.[verification needed] That's why in 21-hydroxylase deficiency, given the normal function of the CYP11B enzymes, the progesterone is directed towards 11β-OHP pathway rather than towards 11-deoxycorticosterone pathway, that is also usually accompanied by an increase in progesterone levels.[9] In the normal route to aldosterone and cortisol, progesterone and 17α-hydroxyprogesterone are first hydroxylated at position 21 and then hydroxylated at other positions. In 21-hydroxylase deficiency, progesterone and 17α-hydroxyprogesterone accumulate and are the substrates of steroid 11β-hydroxylase, leading to 1β-OHP and 21-deoxycortisol, respectively.[10] In the 2017 study mentioned above, serum progesterone concentrations in boys (10 days to 18 years old) with 21-hydroxylase deficiency reached levels similar to female luteal values (up to 10.14 ng/mL, depending on severity and treatment), while in the control group of boys progesterone was 0.07 ng/mL (0.22 nmol/L) on average, ranged from 0.05 to 0.40 ng/mL.[8]

In a 2016 study, classical CAH patients receiving glucocorticoid therapy had C19 11-oxygenated steroid serum levels that were elevated 3-4 fold compared to healthy controls.[11] In that same study, the levels of C19 11-oxygenated androgens correlated positively with conventional androgens in women but negatively in men. The levels of 11KT were four times higher than that of T in women with the condition. In adult women with CAH, the ratio of DHT produced in a backdoor pathway to that produced in a conventional pathway increases as control of androgen excess by glucocorticoid therapy deteriorates.[12] In CAH patients with poor disease control, 11-oxygenated androgens remain elevated for longer than 17OHP, thus serving as a better biomarker for the effectiveness of the disease control.[13][14] In males with CAH, 11-oxygenated androgen levels may indicate the presence testicular adrenal rest tumors.[14][15][16]

While studies suggest that 11β-OHP, also known as 21-deoxycorticosterone, can be used as marker for adrenal 21-hydroxylase deficiency,[6] another 21-carbon steroid — 21-deoxycortisol (produced from 17α-hydroxyprogesterone) gained acceptance for this purpose.[17][18][19]

See also edit

References edit

  1. ^ a b "Human Metabolome Database: Showing metabocard for 11b-Hydroxyprogesterone (HMDB04031)". hmdb.ca. Retrieved 16 December 2016.
  2. ^ a b Strushkevich N, Gilep AA, Shen L, Arrowsmith CH, Edwards AM, Usanov SA, Park HW (February 2013). "Structural insights into aldosterone synthase substrate specificity and targeted inhibition". Molecular Endocrinology. 27 (2): 315–24. doi:10.1210/me.2012-1287. PMC 5417327. PMID 23322723.
  3. ^ van Rooyen D, Gent R, Barnard L, Swart AC (April 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.
  4. ^ Souness GW, Latif SA, Laurenzo JL, Morris DJ (April 1995). "11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase (isoforms 1 and 2), confer marked mineralocorticoid activity on corticosterone in the ADX rat". Endocrinology. 136 (4): 1809–12. doi:10.1210/endo.136.4.7895695. PMID 7895695.
  5. ^ Souness GW, Morris DJ (March 1996). "11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase, possess hypertensinogenic activity in the rat". Hypertension. 27 (3 Pt 1): 421–5. doi:10.1161/01.hyp.27.3.421. PMID 8698448.
  6. ^ a b Gueux B, Fiet J, Galons H, Boneté R, Villette JM, Vexiau P, et al. (January 1987). "The measurement of 11 beta-hydroxy-4-pregnene-3,20-dione (21-deoxycorticosterone) by radioimmunoassay in human plasma". primary. Journal of Steroid Biochemistry. 26 (1): 145–50. doi:10.1016/0022-4731(87)90043-4. PMID 3546944.
  7. ^ Fiet J, Gueux B, Raux-DeMay MC, Kuttenn F, Vexiau P, Brerault JL, et al. (March 1989). "Increased plasma 21-deoxycorticosterone (21-DB) levels in late-onset adrenal 21-hydroxylase deficiency suggest a mild defect of the mineralocorticoid pathway". primary. The Journal of Clinical Endocrinology and Metabolism. 68 (3): 542–7. doi:10.1210/jcem-68-3-542. PMID 2537337.
  8. ^ a b Fiet J, Le Bouc Y, Guéchot J, Hélin N, Maubert MA, Farabos D, Lamazière A (March 2017). "A Liquid Chromatography/Tandem Mass Spectometry [sic] Profile of 16 Serum Steroids, Including 21-Deoxycortisol and 21-Deoxycorticosterone, for Management of Congenital Adrenal Hyperplasia". primary. Journal of the Endocrine Society. 1 (3): 186–201. doi:10.1210/js.2016-1048. PMC 5686660. PMID 29264476.
  9. ^ Nie M, Cui MX, Mao JF, Tong AL, Chen S, Wang X, et al. (December 2016). "[Possibility of progesterone as the diagnostic biomarker of 21-hydroxylase deficiency]". Zhonghua Yi Xue Za Zhi. 96 (48): 3866–3869. doi:10.3760/cma.j.issn.0376-2491.2016.48.003. PMID 28057154.
  10. ^ Turcu AF, Auchus RJ (June 2015). "Adrenal steroidogenesis and congenital adrenal hyperplasia". Endocrinology and Metabolism Clinics of North America. 44 (2): 275–96. doi:10.1016/j.ecl.2015.02.002. PMC 4506691. PMID 26038201.
  11. ^ Turcu AF, Nanba AT, Chomic R, Upadhyay SK, Giordano TJ, Shields JJ, Merke DP, Rainey WE, Auchus RJ (2016). "Adrenal-derived 11-oxygenated 19-carbon steroids are the dominant androgens in classic 21-hydroxylase deficiency". Eur J Endocrinol. 174 (5): 601–9. doi:10.1530/EJE-15-1181. PMC 4874183. PMID 26865584.
  12. ^ Auchus RJ, Buschur EO, Chang AY, Hammer GD, Ramm C, Madrigal D, Wang G, Gonzalez M, Xu XS, Smit JW, Jiao J, Yu MK (2014). "Abiraterone acetate to lower androgens in women with classic 21-hydroxylase deficiency". J Clin Endocrinol Metab. 99 (8): 2763–70. doi:10.1210/jc.2014-1258. PMC 4121028. PMID 24780050.
  13. ^ Turcu AF, Mallappa A, Nella AA, Chen X, Zhao L, Nanba AT, Byrd JB, Auchus RJ, Merke DP (2021). "24-Hour Profiles of 11-Oxygenated C19 Steroids and Δ5-Steroid Sulfates during Oral and Continuous Subcutaneous Glucocorticoids in 21-Hydroxylase Deficiency". Front Endocrinol (Lausanne). 12: 751191. doi:10.3389/fendo.2021.751191. PMC 8636728. PMID 34867794.
  14. ^ a b Turcu AF, Mallappa A, Elman MS, Avila NA, Marko J, Rao H, Tsodikov A, Auchus RJ, Merke DP (2017). "11-Oxygenated Androgens Are Biomarkers of Adrenal Volume and Testicular Adrenal Rest Tumors in 21-Hydroxylase Deficiency". The Journal of Clinical Endocrinology and Metabolism. 102 (8): 2701–2710. doi:10.1210/jc.2016-3989. PMC 5546849. PMID 28472487.
  15. ^ Schröder MAM, Turcu AF, O'Day P, van Herwaarden AE, Span PN, Auchus RJ, Sweep FCGJ, Claahsen-van der Grinten HL (2022). "Production of 11-Oxygenated Androgens by Testicular Adrenal Rest Tumors". J Clin Endocrinol Metab. 107 (1): e272–e280. doi:10.1210/clinem/dgab598. PMC 8684463. PMID 34390337.
  16. ^ Masiutin M, Yadav M (2023). "Alternative androgen pathways". WikiJournal of Medicine. 10: X. doi:10.15347/WJM/2023.003. S2CID 257943362.
  17. ^ Greaves RF, Kumar M, Mawad N, Francescon A, Le C, O'Connell M, Chi J, Pitt J (October 2023). "Best Practice for Identification of Classical 21-Hydroxylase Deficiency Should Include 21 Deoxycortisol Analysis with Appropriate Isomeric Steroid Separation". Int J Neonatal Screen. 9 (4): 58. doi:10.3390/ijns9040058. PMC 10594498. PMID 37873849.
  18. ^ Cristoni S, Cuccato D, Sciannamblo M, Bernardi LR, Biunno I, Gerthoux P, et al. (2004). "Analysis of 21-deoxycortisol, a marker of congenital adrenal hyperplasia, in blood by atmospheric pressure chemical ionization and electrospray ionization using multiple reaction monitoring". primary. Rapid Communications in Mass Spectrometry. 18 (1): 77–82. Bibcode:2004RCMS...18...77C. doi:10.1002/rcm.1284. PMID 14689562.
  19. ^ Sarathi V, Atluri S, Pradeep TV, Rallapalli SS, Rakesh CV, Sunanda T, Kumar KD (2019). "Utility of a Commercially Available Blood Steroid Profile in Endocrine Practice". primary. Indian Journal of Endocrinology and Metabolism. 23 (1): 97–101. doi:10.4103/ijem.IJEM_531_18. PMC 6446682. PMID 31016162.

External links edit

  • Metabocard for 11β-Hydroxyprogesterone (HMDB04031) - Human Metabolome Database

January 07, 2024
11β, hydroxyprogesterone, 11β, also, known, deoxycorticosterone, well, 11β, hydroxypregn, dione, naturally, occurring, endogenous, steroid, derivative, progesterone, potent, mineralocorticoid, syntheses, 11β, from, progesterone, catalyzed, steroid, 11β, hydrox. 11b Hydroxyprogesterone 11b OHP also known as 21 deoxycorticosterone as well as 11b hydroxypregn 4 ene 3 20 dione is a naturally occurring endogenous steroid and derivative of progesterone 1 It is a potent mineralocorticoid 1 Syntheses of 11b OHP from progesterone is catalyzed by the steroid 11b hydroxylase CYP11B1 enzyme 2 3 and to a lesser extent by the aldosterone synthase enzyme CYP11B2 2 11b Hydroxyprogesterone NamesIUPAC name 11b Hydroxypregn 4 ene 3 20 dioneSystematic IUPAC name 1S 3aS 3bS 9aR 9bS 10S 11aS 1 Acetyl 10 hydroxy 9a 11a dimethyl 1 2 3 3a 3b 4 5 8 9 9a 9b 10 11 11a tetradecahydro 7H cyclopenta a phenanthren 7 oneOther names 11b OHP 21 Deoxycorticosterone 21 DesoxycorticosteroneIdentifiersCAS Number 600 57 73D model JSmol Interactive imageChEBI CHEBI 28247ChEMBL ChEMBL2440888ChemSpider 91968ECHA InfoCard 100 009 088KEGG C05498PubChem CID 101788InChI InChI 1S C21H30O3 c1 12 22 16 6 7 17 15 5 4 13 10 14 23 8 9 20 13 2 19 15 18 24 11 21 16 17 3 h10 15 19 24H 4 9 11H2 1 3H3 t15 16 17 18 19 20 21 m0 s1Key BFZHCUBIASXHPK ATWVFEABSA NSMILES CC O C H 1CC C H 2 C 1 C C H C H 3 C H 2CCC4 CC O CC C 34C O CPropertiesChemical formula C 21H 30O 3Molar mass 330 468 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Function 2 Outcome of 21 hydroxylase deficiency 3 See also 4 References 5 External linksFunction editAlong with its epimer 11a hydroxyprogesterone 11a OHP 11b OHP has been identified as a very potent competitive inhibitor of both isoforms 1 and 2 of 11b hydroxysteroid dehydrogenase 11b HSD 4 5 Outcome of 21 hydroxylase deficiency editIt has been known since 1987 that increased levels of 11b OHP occur in 21 hydroxylase deficiency 6 7 A study in 2017 has shown that in subjects with 21 hydroxylase deficiency serum 11b OHP concentrations range from 0 012 to 3 37 ng mL while in control group it was below detection limit of 0 012 ng mL 8 21 hydroxylase is an enzyme that is also involved in progesterone metabolism producing 11 deoxycorticosterone In normal conditions 21 hydroxylase has higher activity on progesterone than steroid 11b hydroxylase CYP11B1 and aldosterone synthase CYP11B2 that convert progesterone to 11b OHP verification needed That s why in 21 hydroxylase deficiency given the normal function of the CYP11B enzymes the progesterone is directed towards 11b OHP pathway rather than towards 11 deoxycorticosterone pathway that is also usually accompanied by an increase in progesterone levels 9 In the normal route to aldosterone and cortisol progesterone and 17a hydroxyprogesterone are first hydroxylated at position 21 and then hydroxylated at other positions In 21 hydroxylase deficiency progesterone and 17a hydroxyprogesterone accumulate and are the substrates of steroid 11b hydroxylase leading to 1b OHP and 21 deoxycortisol respectively 10 In the 2017 study mentioned above serum progesterone concentrations in boys 10 days to 18 years old with 21 hydroxylase deficiency reached levels similar to female luteal values up to 10 14 ng mL depending on severity and treatment while in the control group of boys progesterone was 0 07 ng mL 0 22 nmol L on average ranged from 0 05 to 0 40 ng mL 8 In a 2016 study classical CAH patients receiving glucocorticoid therapy had C19 11 oxygenated steroid serum levels that were elevated 3 4 fold compared to healthy controls 11 In that same study the levels of C19 11 oxygenated androgens correlated positively with conventional androgens in women but negatively in men The levels of 11KT were four times higher than that of T in women with the condition In adult women with CAH the ratio of DHT produced in a backdoor pathway to that produced in a conventional pathway increases as control of androgen excess by glucocorticoid therapy deteriorates 12 In CAH patients with poor disease control 11 oxygenated androgens remain elevated for longer than 17OHP thus serving as a better biomarker for the effectiveness of the disease control 13 14 In males with CAH 11 oxygenated androgen levels may indicate the presence testicular adrenal rest tumors 14 15 16 While studies suggest that 11b OHP also known as 21 deoxycorticosterone can be used as marker for adrenal 21 hydroxylase deficiency 6 another 21 carbon steroid 21 deoxycortisol produced from 17a hydroxyprogesterone gained acceptance for this purpose 17 18 19 See also edit21 Deoxycortisol 11b 17a dihydroxyprogesterone 11 Deoxycorticosterone 21 hydroxyprogesterone Corticosterone 11b 21 dihydroxyprogesterone Cortisol 11b 17a 21 trihydroxyprogesterone 11 Deoxycortisol 17a 21 dihydroxyprogesterone 9a Bromo 11 ketoprogesteroneReferences edit nbsp This article incorporates text available under the CC BY SA 3 0 license a b Human Metabolome Database Showing metabocard for 11b Hydroxyprogesterone HMDB04031 hmdb ca Retrieved 16 December 2016 a b Strushkevich N Gilep AA Shen L Arrowsmith CH Edwards AM Usanov SA Park HW February 2013 Structural insights into aldosterone synthase substrate specificity and targeted inhibition Molecular Endocrinology 27 2 315 24 doi 10 1210 me 2012 1287 PMC 5417327 PMID 23322723 van Rooyen D Gent R Barnard L Swart AC April 2018 The in vitro metabolism of 11b 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 Souness GW Latif SA Laurenzo JL Morris DJ April 1995 11 alpha and 11 beta hydroxyprogesterone potent inhibitors of 11 beta hydroxysteroid dehydrogenase isoforms 1 and 2 confer marked mineralocorticoid activity on corticosterone in the ADX rat Endocrinology 136 4 1809 12 doi 10 1210 endo 136 4 7895695 PMID 7895695 Souness GW Morris DJ March 1996 11 alpha and 11 beta hydroxyprogesterone potent inhibitors of 11 beta hydroxysteroid dehydrogenase possess hypertensinogenic activity in the rat Hypertension 27 3 Pt 1 421 5 doi 10 1161 01 hyp 27 3 421 PMID 8698448 a b Gueux B Fiet J Galons H Bonete R Villette JM Vexiau P et al January 1987 The measurement of 11 beta hydroxy 4 pregnene 3 20 dione 21 deoxycorticosterone by radioimmunoassay in human plasma primary Journal of Steroid Biochemistry 26 1 145 50 doi 10 1016 0022 4731 87 90043 4 PMID 3546944 Fiet J Gueux B Raux DeMay MC Kuttenn F Vexiau P Brerault JL et al March 1989 Increased plasma 21 deoxycorticosterone 21 DB levels in late onset adrenal 21 hydroxylase deficiency suggest a mild defect of the mineralocorticoid pathway primary The Journal of Clinical Endocrinology and Metabolism 68 3 542 7 doi 10 1210 jcem 68 3 542 PMID 2537337 a b Fiet J Le Bouc Y Guechot J Helin N Maubert MA Farabos D Lamaziere A March 2017 A Liquid Chromatography Tandem Mass Spectometry sic Profile of 16 Serum Steroids Including 21 Deoxycortisol and 21 Deoxycorticosterone for Management of Congenital Adrenal Hyperplasia primary Journal of the Endocrine Society 1 3 186 201 doi 10 1210 js 2016 1048 PMC 5686660 PMID 29264476 Nie M Cui MX Mao JF Tong AL Chen S Wang X et al December 2016 Possibility of progesterone as the diagnostic biomarker of 21 hydroxylase deficiency Zhonghua Yi Xue Za Zhi 96 48 3866 3869 doi 10 3760 cma j issn 0376 2491 2016 48 003 PMID 28057154 Turcu AF Auchus RJ June 2015 Adrenal steroidogenesis and congenital adrenal hyperplasia Endocrinology and Metabolism Clinics of North America 44 2 275 96 doi 10 1016 j ecl 2015 02 002 PMC 4506691 PMID 26038201 Turcu AF Nanba AT Chomic R Upadhyay SK Giordano TJ Shields JJ Merke DP Rainey WE Auchus RJ 2016 Adrenal derived 11 oxygenated 19 carbon steroids are the dominant androgens in classic 21 hydroxylase deficiency Eur J Endocrinol 174 5 601 9 doi 10 1530 EJE 15 1181 PMC 4874183 PMID 26865584 Auchus RJ Buschur EO Chang AY Hammer GD Ramm C Madrigal D Wang G Gonzalez M Xu XS Smit JW Jiao J Yu MK 2014 Abiraterone acetate to lower androgens in women with classic 21 hydroxylase deficiency J Clin Endocrinol Metab 99 8 2763 70 doi 10 1210 jc 2014 1258 PMC 4121028 PMID 24780050 Turcu AF Mallappa A Nella AA Chen X Zhao L Nanba AT Byrd JB Auchus RJ Merke DP 2021 24 Hour Profiles of 11 Oxygenated C19 Steroids and D5 Steroid Sulfates during Oral and Continuous Subcutaneous Glucocorticoids in 21 Hydroxylase Deficiency Front Endocrinol Lausanne 12 751191 doi 10 3389 fendo 2021 751191 PMC 8636728 PMID 34867794 a b Turcu AF Mallappa A Elman MS Avila NA Marko J Rao H Tsodikov A Auchus RJ Merke DP 2017 11 Oxygenated Androgens Are Biomarkers of Adrenal Volume and Testicular Adrenal Rest Tumors in 21 Hydroxylase Deficiency The Journal of Clinical Endocrinology and Metabolism 102 8 2701 2710 doi 10 1210 jc 2016 3989 PMC 5546849 PMID 28472487 Schroder MAM Turcu AF O Day P van Herwaarden AE Span PN Auchus RJ Sweep FCGJ Claahsen van der Grinten HL 2022 Production of 11 Oxygenated Androgens by Testicular Adrenal Rest Tumors J Clin Endocrinol Metab 107 1 e272 e280 doi 10 1210 clinem dgab598 PMC 8684463 PMID 34390337 Masiutin M Yadav M 2023 Alternative androgen pathways WikiJournal of Medicine 10 X doi 10 15347 WJM 2023 003 S2CID 257943362 Greaves RF Kumar M Mawad N Francescon A Le C O Connell M Chi J Pitt J October 2023 Best Practice for Identification of Classical 21 Hydroxylase Deficiency Should Include 21 Deoxycortisol Analysis with Appropriate Isomeric Steroid Separation Int J Neonatal Screen 9 4 58 doi 10 3390 ijns9040058 PMC 10594498 PMID 37873849 Cristoni S Cuccato D Sciannamblo M Bernardi LR Biunno I Gerthoux P et al 2004 Analysis of 21 deoxycortisol a marker of congenital adrenal hyperplasia in blood by atmospheric pressure chemical ionization and electrospray ionization using multiple reaction monitoring primary Rapid Communications in Mass Spectrometry 18 1 77 82 Bibcode 2004RCMS 18 77C doi 10 1002 rcm 1284 PMID 14689562 Sarathi V Atluri S Pradeep TV Rallapalli SS Rakesh CV Sunanda T Kumar KD 2019 Utility of a Commercially Available Blood Steroid Profile in Endocrine Practice primary Indian Journal of Endocrinology and Metabolism 23 1 97 101 doi 10 4103 ijem IJEM 531 18 PMC 6446682 PMID 31016162 External links editMetabocard for 11b Hydroxyprogesterone HMDB04031 Human Metabolome Database Retrieved from https en wikipedia org w index php title 11b Hydroxyprogesterone amp oldid 1190338986, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.