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| - | '''Androstenedione''' Pubchem(6128) (also known as '''4-androstenedione''') is a 19-[[carbon]] [[steroid]] [[hormone]] produced in the [[adrenal gland]]s and the [[gonad]]s as an intermediate step in the [[biochemistry|biochemical]] pathway that produces the [[androgen]] [[testosterone]] and the [[estrogen]]s [[estrone]] and [[estradiol]]. A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL.
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| - | '''KEGG Pathway'''(C00280,D00051)
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| - | *Androgen and estrogen metabolism
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| - | *Prostate cancer
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| - | '''Drug Type''': Small Molecule; Illicit; Experimental | + | <table align='right' border=1> |
| - | {| border="1;width:100%; height:200px;style=text-align:center"
| + | <tr><td> |
| - | |+'''List of PDB files having Androstenedione as a Ligand:'''
| + | <jmol><jmolApplet> |
| - | |-
| + | <size>200</size> |
| - | ! style="background:brown; color:white" |MMDB ID
| + | <script>spin on;color atoms amino;</script> |
| - | ! style="background:brown; color:white" |PDB ID
| + | <uploadedFileContents>NPH117.SDF</uploadedFileContents> |
| - | ! style="background:brown; color:white" |Reference
| + | <color>black</color> |
| - | |-
| + | </jmolApplet> |
| - | |28531
| + | </jmol> |
| - | |1QYX
| + | </td></tr></table> |
| - | |Shi R, Lin SXCofactor hydrogen bonding onto the protein main chain is conserved in the short chain dehydrogenase/reductase family and contributes to nicotinamide orientationJ. Biol. Chem. v279, p.16778-16785
| + | ==Description== |
| - | |-
| + | A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL. |
| - | |}
| + | ==General Properties== |
| - | {| border="1;width:100%; height:200px;style=text-align:center"
| + | |
| - | |+'''Physiochemical properties of Androstenedione:'''
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| - | |-
| + | |
| - | ! style="background:brown; color:white" |Physical Property
| + | |
| - | ! style="background:brown; color:white" |Value
| + | |
| - | ! style="background:brown; color:white" |Units
| + | |
| - | ! style="background:brown; color:white" |Temp (deg C)
| + | |
| - | ! style="background:brown; color:white" |Source
| + | |
| - | |-
| + | |
| - | |Melting Point
| + | |
| - | |158
| + | |
| - | |deg C
| + | |
| - | |
| + | |
| - | |EXP
| + | |
| - | |-
| + | |
| - | |log P (octanol-water)
| + | |
| - | |2.75
| + | |
| - | |(none)
| + | |
| - | |
| + | |
| - | |EXP
| + | |
| - | |-
| + | |
| - | |Water Solubility
| + | |
| - | |57.8
| + | |
| - | |mg/L
| + | |
| - | |25
| + | |
| - | |EXP
| + | |
| - | |-
| + | |
| - | |Vapor Pressure
| + | |
| - | |2.46E-06
| + | |
| - | |mm Hg
| + | |
| - | |25
| + | |
| - | |EST
| + | |
| - | |-
| + | |
| - | |Henry's Law Constant
| + | |
| - | |3.68E-08
| + | |
| - | |atm-m3/mole
| + | |
| - | |25
| + | |
| - | |EST
| + | |
| - | |-
| + | |
| - | |Atmospheric OH Rate Constant
| + | |
| - | |1.11E-10
| + | |
| - | |cm3/molecule-sec
| + | |
| - | |25
| + | |
| - | |EST
| + | |
| - | |-
| + | |
| - | |}
| + | |
| - | ==Synthesis== | + | |
| - | Androstenedione is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma, and may be converted in peripheral tissues to testosterone and estrogens.
| + | |
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| - | Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. Conversion of dehydroepiandrosterone to androstenedione requires 17,20 lyase. 17-hydroxyprogesterone, on the other hand, requires 17,20 lyase for its synthesis. Thus, both reactions that produce androstenedione directly or indirectly depend on 17,20 lyase.
| + | <b>*Molecular Weight</b> |
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| - | Androstenedione is further converted to either testosterone or estrogen. Conversion of androstenedione to testosterone requires the enzyme 17β-hydroxysteroid dehydrogenase, while conversion of androstenedione to estrogen (e.g. [[estrone]] and [[estradiol]] requires the enzyme [[aromatase]].
| + | 286.41 |
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| - | The production of adrenal androstenedione is governed by [[ACTH]], whereas production of gonadal androstenedione is under control by [[gonadotropin]]s. In premenopausal women, the adrenal glands and ovaries each produce about half of the total androstendione (about 3 mg/day). After [[menopause]],
| + | <b>*Molecular Formula</b> |
| - | androstenedione production is about halved, primarily due to the reduction of the steroid secreted by the ovary. Nevertheless, androstenedione is the principal steroid produced by the postmenopausal ovary.
| + | |
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| - | ==Endocrine function==
| + | C<sub>1</sub><sub>9</sub>H<sub>2</sub><sub>6</sub>O<sub>2</sub> |
| - | In females, androstenedione is released into the blood by [[theca cells]]. The function of this is to provide androstenedione substrate for [[estrogen]] production in [[granulosa cells]], since these cells lack 17,20 lyase required for androstenedione. Similarly, theca cells lack the enzyme aromatase required to make estrogens themselves. Thus, theca cells and granulosa cells work together to form estrogen.<ref> Medical Physiology, Boron & Boulpaep, ISBN 1-4160-2328-3, Elsevier Saunders 2005. Updated edition. Page 1155 </ref>
| + | |
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| - | ==Androstenedione as a supplement==
| + | <b>*IUPAC NAME</b> |
| - | ===History===
| + | |
| - | Androstenedione was manufactured as a [[dietary supplement]], often called '''''andro''''' (or ''andros'') for short. Andro was in common use in [[Major League Baseball]] throughout the 1990s by record-breaking sluggers like [[Mark McGwire]]. The supplement is banned by the [[World Anti-Doping Agency]], and hence from the [[Olympic Games]].
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| - | On [[March 12]], [[2004]], the Anabolic Steroid Control Act of 2004 was introduced into the United States Senate. It amended the [[Controlled Substance Act]] to place both [[anabolic steroid]]s and [[prohormone]]s on a list of [[controlled substance]]s, making possession of the banned substances a federal crime. The law took effect on [[January 20]], [[2005]]. Surprisingly, andro was legally defined as an anabolic steroid, even though there is scant evidence that androstenedione itself is anabolic in nature.
| + | (8R,9S,10R,13S,14S)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione |
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| - | On [[April 11]], [[2004]], the United States [[Food and Drug Administration]] banned the sale of Andro, citing that the drug poses significant health risks commonly associated with steroids.
| + | <b>*Canonical Smiles</b> |
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| - | Androstenedione is currently banned by the [[Military of the United States|US military]].<ref>[http://airforcemedicine.afms.mil/sg_newswire/jan_05/Andro.htm USAF Medical Service Home Page<!-- Bot generated title -->]</ref>
| + | CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4=O)C |
| | | | |
| - | ===Biological Effects===
| + | <b>*Isomeric Smiles</b> |
| - | Androstenedione has been shown to increase serum testosterone levels over an eight-hour period in men when taken as a single oral dose of 300mg per day, but a 100mg dose had no significant effect on serum testosterone. However, serum levels of estradiol increased following both the 100mg and 300mg doses. The study also reported that the serum level of estrogens and testosterone produced varied widely between individuals.<ref>Leder, B., Longcope, C., Catlin, D., Ahrens, B. Shoenfeld, D., and Finkelstein, J.: "Oral Androstenedione Administration and Serum Testosterone Concentrations in Young Men", ''JAMA'', 283(6):779-782</ref> A 2006 review paper summarized several studies which examined the effect of androstenedione on strength training. At dosages of 50mg or 100mg per day, andro had no effect on muscle strength or size, or on body fat levels. One study utilized a daily dosage of 300mg of androstenedione combined with several other supplements, and also found no increase in strength when compared to a control group that did not take the supplements. The review authors speculate that sufficiently high doses may indeed lead to increased muscle size and strength. However, due to the federal ban on androstenedione supplements, it is difficult to carry out new research on its positive and negative effects. The review authors conclude that individuals should not use androstenedione supplements due to the lack of evidence of beneficial effects, the wide variation in individual responses to the supplement, and the risk of unknown side effects.<ref> Brown, G., Vukovich, M., and King, D.:"Testosterone Prohormone Supplements", ''Medicine and Science in Sports and Exercise'', 38(8):1451-1461.</ref>
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| - | Because androstenedione is converted in part to estrogens, persons taking this supplement may have estrogenic side-effects, although none of the studies cited above used a sufficiently high dosage to draw any conclusions.
| + | C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C |
| | | | |
| - | ==References==
| |
| - | <references/>
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| | | | |
| - | {{Steroids}}
| + | ==PhysioChemical Properties== |
| | | | |
| - | [[Category:Androgens]] | + | <b>*Melting Point</b> |
| - | [[Category:Withdrawn drugs]] | + | |
| - | [[Category:Steroids]] | + | 158(EXP) |
| - | [[Category:Anabolic steroids]] | + | |
| | + | <b>*LogP</b> |
| | + | |
| | + | 2.75(EXP) |
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| | + | <b>*Water Solubility</b> |
| | + | |
| | + | 57.8(EXP) at 25C |
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| | + | ==External Links== |
| | + | *[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6128]Pubchem |
| | + | *[http://www.rcsb.org/pdb/cgi/explore.cgi?pdbId=1QYX]]1QYX, |
| | + | *[http://www.genome.jp/dbget-bin/www_bget?compound+C00280]]KEGG Compound |
| | + | *[http://www.genome.jp/dbget-bin/www_bget?drug+D00051]]KEGG Drug |
| | + | *[http://www.hmdb.ca/metabolites/HMDB00053]Human Metabolome DataBase |
| | + | *[http://www.drugbank.ca/drugs/DB01536]Drugbank |
| | + | |
| | + | [[Categories:Hormones]] |
A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL.
(8R,9S,10R,13S,14S)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
