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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
Structure of ANDROSTERONE

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
MOLECULAR GEOMETRY OF ANDROSTERONE.
1964 Aug 15
Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b).
2001 Jun
Characterization of the oxidative 3alpha-hydroxysteroid dehydrogenase activity of human recombinant 11-cis-retinol dehydrogenase.
2001 Jun 11
Subunit-specific modulation of glycine receptors by neurosteroids.
2001 Sep
Human 17beta-hydroxysteroid dehydrogenase type 5 is inhibited by dietary flavonoids.
2002
Detection of epitestosterone doping by isotope ratio mass spectrometry.
2002
Artifact formation due to ethyl thio-incorporation into silylated steroid structures as determined in doping analysis.
2002 Apr 19
Reproducibility studies and interlaboratory concordance for androgen assays of male plasma hormone levels.
2002 Aug
A genome-wide linkage scan for steroids and SHBG levels in black and white families: the HERITAGE Family Study.
2002 Aug
Syntheses and advanced NMR structure determination of androsteno-[17,16-d]-pyrimidine derivatives.
2002 Aug
Testosterone rapidly reduces anxiety in male house mice (Mus musculus).
2002 Dec
Characterization of urinary and fecal metabolites of testosterone and their measurement for assessing gonadal endocrine function in male nonhuman primates.
2002 Dec
Use of bioconversion for the preparation of [4-14C]-labeled 7 alpha- and 7 beta-hydroxylated derivatives of dehydroepiandrosterone and epiandrosterone.
2002 Dec
Conversion of dehydroepiandrosterone sulfate at physiological plasma concentration into estrogens in MCF-7 cells.
2002 Dec
An assessment of in vitro androgenic activity and the identification of environmental androgens in United Kingdom estuaries.
2002 Jul
Does place of birth influence endogenous hormone levels in Asian-American women?
2002 Jul 1
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
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
Epiandrosterone, a metabolite of testosterone precursor, blocks L-type calcium channels of ventricular myocytes and inhibits myocardial contractility.
2002 Jun
Ergosteroids V: preparation and biological activity of various D-ring derivatives in the 7-oxo-dehydroepiandrosterone series.
2002 Mar
Identification of human urine stains by HPLC analysis of 17-ketosteroid conjugates.
2002 May
The association of serum androsterone glucuronide with inflammatory lesions in women with adult acne.
2002 Oct
Urinary steroids in men with male-pattern alopecia.
2002 Oct-Nov
Relationship between urinary profile of the endogenous steroids and postmenopausal women with stress urinary incontinence.
2003
Isolation and characterization of FSH and LH from pituitary glands of Atlantic halibut (Hippoglossus hippoglossus L.).
2003 Apr
16alpha-Bromo-epiandrosterone therapy modulates experimental feline immunodeficiency virus viremia: initial enhancement leading to long-term suppression.
2003 Aug 15
Pentose phosphate pathway coordinates multiple redox-controlled relaxing mechanisms in bovine coronary arteries.
2003 Dec
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
Detection of quantitative trait loci for fat androstenone levels in pigs.
2003 Feb
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
Characterization of truncated mutants of human microsomal short-chain dehydrogenase/reductase RoDH-4.
2003 Feb 1
A facile and high yielding synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide--an internal standard in dope.
2003 Jan
Discriminative stimulus effects of positive GABAA modulators and other anxiolytics, sedatives, and anticonvulsants in untreated and diazepam-treated monkeys.
2003 Jan
Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines.
2003 Jan
Immunization against 5alpha-androstane-3alpha,17beta-diol affects ovarian folliculogenesis in Merino ewes.
2003 Jul
Beyond adrenal and ovarian androgen generation: Increased peripheral 5 alpha-reductase activity in women with polycystic ovary syndrome.
2003 Jun
Glucuronidation of arachidonic and linoleic acid metabolites by human UDP-glucuronosyltransferases.
2003 Jun
Chronic effects of dehydroepiandrosterone on rat adipose tissue metabolism.
2003 Mar
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
17 beta-hydroxysteroid dehydrogenase type XI localizes to human steroidogenic cells.
2003 May
Steroidogenic acute regulatory protein in ovarian follicles of gonadotropin-stimulated rats is regulated by a gonadotropin-releasing hormone agonist.
2003 May
In vivo modification of the UDP-glucuronosyltransferase functional state in rat liver following hypophysectomy and partial or complete hormonal restoration.
2003 Nov
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
2003 Oct
Endogenous urinary steroids in premenopausal women with uterine leiomyomas.
2004 Jan
Evidence for peripheral plasticity in human odour response.
2004 Jan 1
The scents of androstenone in humans.
2004 Jan 1
Discriminative stimulus effects of ethanol in mice lacking the gamma-aminobutyric acid type A receptor delta subunit.
2004 Jun
The pig CYP2E1 promoter is activated by COUP-TF1 and HNF-1 and is inhibited by androstenone.
2004 Nov 15
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

Anticonvulsant potency in mice:
Route of Administration: Intraperitoneal
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 Fri Dec 15 15:14:37 GMT 2023
Edited
by admin
on Fri Dec 15 15:14:37 GMT 2023
Record UNII
C24W7J5D5R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANDROSTERONE
MI  
Common Name English
3.ALPHA.-HYDROXY-17-ANDROSTANONE
Systematic Name English
NSC-9898
Code English
3.ALPHA.-HYDROXY-5.ALPHA.-ANDROSTAN-17-ONE
Systematic Name English
ANDROSTERONE [MI]
Common Name English
(3.ALPHA.,5.ALPHA.)-3-HYDROXYANDROSTAN-17-ONE
Systematic Name English
Classification Tree Code System Code
LOINC 82881-4
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LOINC 27110-6
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LOINC 82851-7
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LOINC 82853-3
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LOINC 82882-2
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LOINC 30509-4
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LOINC 34242-8
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CFR 21 CFR 862.1430
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EPA PESTICIDE CODE 126501
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LOINC 15029-2
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LOINC 34243-6
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CFR 21 CFR 862.1080
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LOINC 6705-8
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LOINC 82852-5
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LOINC 15030-0
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NCI_THESAURUS C243
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LOINC 82850-9
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LOINC 82846-7
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LOINC 1856-4
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LOINC 44297-0
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LOINC 34241-0
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LOINC 56487-2
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LOINC 12479-2
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LOINC 82847-5
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Code System Code Type Description
MERCK INDEX
m1903
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY Merck Index
CAS
53-41-8
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY
MESH
D000738
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-173-4
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY
DAILYMED
C24W7J5D5R
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY
CHEBI
16032
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY
PUBCHEM
5879
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY
NCI_THESAURUS
C29783
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID3036525
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY
WIKIPEDIA
ANDROSTERONE
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY
FDA UNII
C24W7J5D5R
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY
NSC
9898
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY
RXCUI
1312359
Created by admin on Fri Dec 15 15:14:37 GMT 2023 , Edited by admin on Fri Dec 15 15:14:37 GMT 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> METABOLITE
MAJOR
URINE
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY