Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H30O2 |
Molecular Weight | 290.4403 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])C[C@H](O)CC[C@]34C
InChI
InChIKey=QGXBDMJGAMFCBF-HLUDHZFRSA-N
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1
Molecular Formula | C19H30O2 |
Molecular Weight | 290.4403 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Androsterone, a neurosteroid, acts as a positive allosteric modulator of GABA(A) receptors, that can cross into the brain and could have effects on brain function. It was discovered, that the association of beta subunits with alpha subunits GABA(A) receptor affects the sensitivity of glycine receptors to androsterone. In spite of that, androsteron is considered as an inactive metabolite of testosterone. In addition, was studied that androsterone possessed anticonvulsant properties. Although of low potency, the androsterone was present in high abundance and was able to represent endogenous modulator of seizure susceptibility.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19705103 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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MOLECULAR GEOMETRY OF ANDROSTERONE. | 1964 Aug 15 |
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Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b). | 2001 Jun |
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Characterization of the oxidative 3alpha-hydroxysteroid dehydrogenase activity of human recombinant 11-cis-retinol dehydrogenase. | 2001 Jun 11 |
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Subunit-specific modulation of glycine receptors by neurosteroids. | 2001 Sep |
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Human 17beta-hydroxysteroid dehydrogenase type 5 is inhibited by dietary flavonoids. | 2002 |
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Detection of epitestosterone doping by isotope ratio mass spectrometry. | 2002 |
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Artifact formation due to ethyl thio-incorporation into silylated steroid structures as determined in doping analysis. | 2002 Apr 19 |
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Reproducibility studies and interlaboratory concordance for androgen assays of male plasma hormone levels. | 2002 Aug |
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A genome-wide linkage scan for steroids and SHBG levels in black and white families: the HERITAGE Family Study. | 2002 Aug |
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Syntheses and advanced NMR structure determination of androsteno-[17,16-d]-pyrimidine derivatives. | 2002 Aug |
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Testosterone rapidly reduces anxiety in male house mice (Mus musculus). | 2002 Dec |
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Characterization of urinary and fecal metabolites of testosterone and their measurement for assessing gonadal endocrine function in male nonhuman primates. | 2002 Dec |
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Use of bioconversion for the preparation of [4-14C]-labeled 7 alpha- and 7 beta-hydroxylated derivatives of dehydroepiandrosterone and epiandrosterone. | 2002 Dec |
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Conversion of dehydroepiandrosterone sulfate at physiological plasma concentration into estrogens in MCF-7 cells. | 2002 Dec |
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An assessment of in vitro androgenic activity and the identification of environmental androgens in United Kingdom estuaries. | 2002 Jul |
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Does place of birth influence endogenous hormone levels in Asian-American women? | 2002 Jul 1 |
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Isolation and characterization of the monkey UGT2B30 gene that encodes a uridine diphosphate-glucuronosyltransferase enzyme active on mineralocorticoid, glucocorticoid, androgen and oestrogen hormones. | 2002 Jul 1 |
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Androsterone derivatives substituted at position 16: chemical synthesis, inhibition of type 3 17beta-hydroxysteroid dehydrogenase, binding affinity for steroid receptors and proliferative/antiproliferative activity on Shionogi (AR+) cells. | 2002 Jun |
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Epiandrosterone, a metabolite of testosterone precursor, blocks L-type calcium channels of ventricular myocytes and inhibits myocardial contractility. | 2002 Jun |
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Ergosteroids V: preparation and biological activity of various D-ring derivatives in the 7-oxo-dehydroepiandrosterone series. | 2002 Mar |
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Identification of human urine stains by HPLC analysis of 17-ketosteroid conjugates. | 2002 May |
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The association of serum androsterone glucuronide with inflammatory lesions in women with adult acne. | 2002 Oct |
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Urinary steroids in men with male-pattern alopecia. | 2002 Oct-Nov |
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Relationship between urinary profile of the endogenous steroids and postmenopausal women with stress urinary incontinence. | 2003 |
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Isolation and characterization of FSH and LH from pituitary glands of Atlantic halibut (Hippoglossus hippoglossus L.). | 2003 Apr |
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16alpha-Bromo-epiandrosterone therapy modulates experimental feline immunodeficiency virus viremia: initial enhancement leading to long-term suppression. | 2003 Aug 15 |
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Pentose phosphate pathway coordinates multiple redox-controlled relaxing mechanisms in bovine coronary arteries. | 2003 Dec |
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Headspace solid-phase microextraction (SPME) and gas chromatography-mass spectrometry (GC-MS) for the determination of 5alpha-androst-2-en-17-one and -17beta-ol in the female Asian elephant: application for reproductive monitoring and prediction of parturition. | 2003 Feb |
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Detection of quantitative trait loci for fat androstenone levels in pigs. | 2003 Feb |
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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. | 2003 Feb |
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Characterization of truncated mutants of human microsomal short-chain dehydrogenase/reductase RoDH-4. | 2003 Feb 1 |
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A facile and high yielding synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide--an internal standard in dope. | 2003 Jan |
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Discriminative stimulus effects of positive GABAA modulators and other anxiolytics, sedatives, and anticonvulsants in untreated and diazepam-treated monkeys. | 2003 Jan |
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Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines. | 2003 Jan |
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Immunization against 5alpha-androstane-3alpha,17beta-diol affects ovarian folliculogenesis in Merino ewes. | 2003 Jul |
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Beyond adrenal and ovarian androgen generation: Increased peripheral 5 alpha-reductase activity in women with polycystic ovary syndrome. | 2003 Jun |
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Glucuronidation of arachidonic and linoleic acid metabolites by human UDP-glucuronosyltransferases. | 2003 Jun |
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Chronic effects of dehydroepiandrosterone on rat adipose tissue metabolism. | 2003 Mar |
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13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? | 2003 Mar 28 |
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17 beta-hydroxysteroid dehydrogenase type XI localizes to human steroidogenic cells. | 2003 May |
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Steroidogenic acute regulatory protein in ovarian follicles of gonadotropin-stimulated rats is regulated by a gonadotropin-releasing hormone agonist. | 2003 May |
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In vivo modification of the UDP-glucuronosyltransferase functional state in rat liver following hypophysectomy and partial or complete hormonal restoration. | 2003 Nov |
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Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
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Endogenous urinary steroids in premenopausal women with uterine leiomyomas. | 2004 Jan |
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Evidence for peripheral plasticity in human odour response. | 2004 Jan 1 |
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The scents of androstenone in humans. | 2004 Jan 1 |
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Discriminative stimulus effects of ethanol in mice lacking the gamma-aminobutyric acid type A receptor delta subunit. | 2004 Jun |
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The pig CYP2E1 promoter is activated by COUP-TF1 and HNF-1 and is inhibited by androstenone. | 2004 Nov 15 |
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Mechanistic roles of Ser-114, Tyr-155, and Lys-159 in 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni. | 2005 Feb 4 |
|
The sexually active states of free-ranging male African elephants (Loxodonta africana): defining musth and non-musth using endocrinology, physical signals, and behavior. | 2005 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24705905
Anticonvulsant potency in mice:
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15946323
Solutions of androsterone (5α,3α-A), its 5β-epimer etiocholanolone (5β,3α-A) and unnatural enantiomers: ent-5α,3α-A and ent-5β,3α-A were made fresh daily in 40% hydroxypropyl-β-cyclodextrin in sterile 0.9% saline. The convulsant agent pentylenetetrazol (PTZ) was dissolved in saline immediately before use. All drug solutions were administered in a volume equaling 0.01 ml/g body weight. In the convulsant pentylenetetrazol (PTZ), 6-Hz and maximal electroshock (MES) seizure tests, the steroids or vehicle were administered intraperitoneally 15 min before PTZ or electrical stimulation. It was found that in addition to greater potency, the eutomers have more prolonged durations of action likely as a result of greater metabolic stability.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:14:37 GMT 2023
by
admin
on
Fri Dec 15 15:14:37 GMT 2023
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Record UNII |
C24W7J5D5R
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Record Status |
Validated (UNII)
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Record Version |
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82881-4
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34242-8
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CFR |
21 CFR 862.1430
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EPA PESTICIDE CODE |
126501
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34243-6
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21 CFR 862.1080
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C243
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m1903
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ANDROSTERONE
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PARENT -> METABOLITE |
MAJOR
URINE
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METABOLITE -> PARENT |
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ACTIVE MOIETY |