11β-Hydroxytestosterone

Last updated

11β-Hydroxytestosterone
11-beta-hydroxytestosterone.svg
Names
IUPAC name
11β,17β-Dihydroxyandrost-4-en-3-one
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.162.057 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 634-040-0
KEGG
PubChem CID
UNII
  • InChI=1S/C19H28O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14-,15-,16-,17+,18-,19-/m0/s1
  • C1C2=CC(CC[C@@]2([C@]3([C@H](C[C@]4([C@]([C@@]3(C1)[H])(CC[C@@H]4O)[H])C)O)[H])C)=O
Properties
C19H28O3
Molar mass 304.430 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-silhouette.svg
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).

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

Related Research Articles

<span class="mw-page-title-main">Dehydroepiandrosterone</span> Chemical compound

Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids in humans. DHEA is produced in the adrenal glands, the gonads, and the brain. It functions as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids both in the gonads and in various other tissues. However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors, and acting as a neurosteroid and modulator of neurotrophic factor receptors.

<span class="mw-page-title-main">Androgen</span> Any steroid hormone that promotes male characteristics

An androgen is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes the embryological development of the primary male sex organs, and the development of male secondary sex characteristics at puberty. Androgens are synthesized in the testes, the ovaries, and the adrenal glands.

<span class="mw-page-title-main">Androsterone</span> Endogenous steroid hormone

Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone, neurosteroid, and putative pheromone. It is a weak androgen with a potency that is approximately 1/7 that of testosterone. Androsterone is a metabolite of testosterone and dihydrotestosterone (DHT). In addition, it can be converted back into DHT via 3α-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase, bypassing conventional intermediates such as androstanedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right.

<span class="mw-page-title-main">Dihydrotestosterone</span> Human hormone

Dihydrotestosterone is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis. Also the production of sebum and body hair composition.

<span class="mw-page-title-main">Aldosterone synthase</span> Protein-coding gene in the species Homo sapiens

Aldosterone synthase, also called steroid 18-hydroxylase, corticosterone 18-monooxygenase or P450C18, is a steroid hydroxylase cytochrome P450 enzyme involved in the biosynthesis of the mineralocorticoid aldosterone and other steroids. The enzyme catalyzes sequential hydroxylations of the steroid angular methyl group at C18 after initial 11β-hydroxylation. It is encoded by the CYP11B2 gene in humans.

<span class="mw-page-title-main">Fluoxymesterone</span> Chemical compound

Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia. It is taken by mouth.

<span class="mw-page-title-main">Steroid 11β-hydroxylase</span> Protein found in mammals

Steroid 11β-hydroxylase, also known as steroid 11β-monooxygenase, is a steroid hydroxylase found in the zona glomerulosa and zona fasciculata of the adrenal cortex. Named officially the cytochrome P450 11B1, mitochondrial, it is a protein that in humans is encoded by the CYP11B1 gene. The enzyme is involved in the biosynthesis of adrenal corticosteroids by catalyzing the addition of hydroxyl groups during oxidation reactions.

17β-Hydroxysteroid dehydrogenases, also 17-ketosteroid reductases (17-KSR), are a group of alcohol oxidoreductases which catalyze the reduction of 17-ketosteroids and the dehydrogenation of 17β-hydroxysteroids in steroidogenesis and steroid metabolism. This includes interconversion of DHEA and androstenediol, androstenedione and testosterone, and estrone and estradiol.

<span class="mw-page-title-main">Anabolic steroid</span> Steroidal androgen that is structurally related and has similar effects to testosterone

Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor. Anabolic steroids have a number of medical uses, but are also used by athletes to increase muscle size, strength, and performance.

<span class="mw-page-title-main">11-Ketotestosterone</span> Chemical compound

11-Ketotestosterone (11-KT) is an oxidized form of testosterone that contains a keto group at the C11 position. It is related to adrenosterone, an androgen found in trace quantities in humans. In fish, 11-ketotestosterone functions as the endogenous androgenic sex hormone. In midshipman fish, 11-ketotestosterone is not present in females or Type II Males — Type II Males reach sexual maturation later, are less territorial, and have higher testosterone than Type I Males.

<span class="mw-page-title-main">Androstanediol glucuronide</span> Chemical compound

3α-Androstanediol glucuronide (3α-ADG) is a metabolite formed from human androgens; compounds involved in the development and maintenance of sexual characteristics. It is formed by the glucuronidation of both dihydrotestosterone and testosterone, and has been proposed as means of measuring androgenic activity.

<span class="mw-page-title-main">Dimethandrolone</span> Chemical compound

Dimethandrolone (DMA), also known by its developmental code name CDB-1321, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under investigation for potential clinical use.

<span class="mw-page-title-main">11β-Methyl-19-nortestosterone dodecylcarbonate</span> Chemical compound

11β-Methyl-19-nortestosterone 17β-dodecylcarbonate (11β-MNTDC) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed for medical use at this time. It is an androgen ester – specifically, the C17β dodecylcarbonate ester of 11β-methyl-19-nortestosterone (11β-MNT) – and acts as a prodrug of 11β-MNT in the body.

<span class="mw-page-title-main">21-Deoxycortisol</span> Chemical compound

21-Deoxycortisol, also known as 11β,17α-dihydroxyprogesterone or as 11β,17α-dihydroxypregn-4-ene-3,20-dione, is a naturally occurring, endogenous steroid related to cortisol (11β,17α,21-trihydroxyprogesterone) which is formed as a metabolite from 17α-hydroxyprogesterone via 11β-hydroxylase.

<span class="mw-page-title-main">11β-Hydroxyprogesterone</span> Chemical compound

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. It is a potent mineralocorticoid. Syntheses of 11β-OHP from progesterone is catalyzed by the steroid 11β-hydroxylase (CYP11B1) enzyme, and, to a lesser extent, by the aldosterone synthase enzyme (CYP11B2).

<span class="mw-page-title-main">Steroidogenic enzyme</span>

Steroidogenic enzymes are enzymes that are involved in steroidogenesis and steroid biosynthesis. They are responsible for the biosynthesis of the steroid hormones, including sex steroids and corticosteroids, as well as neurosteroids, from cholesterol. Steroidogenic enzymes are most highly expressed in classical steroidogenic tissues, such as the testis, ovary, and adrenal cortex, but are also present in other tissues in the body.

The androgen backdoor pathway sometimes also referred to as the marsupial pathway is a collective name for all metabolic pathways where clinically significant androgens are synthesized from 21-carbon steroids (pregnanes) by their 5α-reduction, bypassing testosterone and/or androstenedione.

<span class="mw-page-title-main">11-Ketoandrosterone</span> Chemical compound

11-Ketoandrosterone is an endogenous steroid.

<span class="mw-page-title-main">11β-Hydroxydihydrotestosterone</span> Chemical compound

11β-Hydroxydihydrotestosterone is an endogenous steroid. Although it may not have significant androgenic activity, it may still be an important precursor to androgenic molecules.

References

  1. 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
  2. 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.
  3. 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.
  4. 1 2 Masiutin M, Yadav M (2023). "Alternative androgen pathways". WikiJournal of Medicine. 10: X. doi: 10.15347/WJM/2023.003 . S2CID   257943362.