ANDROSTERONE

Investigational

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15946323 | https://www.ncbi.nlm.nih.gov/pubmed/19705103

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; alpha-1/beta-2/gamma-2 27 Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19705103	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
MOLECULAR GEOMETRY OF ANDROSTERONE.	1964 Aug 15	14207275
Relationship between urinary profile of the endogenous steroids and postmenopausal women with stress urinary incontinence.	2003	12707870
Isolation and characterization of FSH and LH from pituitary glands of Atlantic halibut (Hippoglossus hippoglossus L.).	2003 Apr	12679086
16alpha-Bromo-epiandrosterone therapy modulates experimental feline immunodeficiency virus viremia: initial enhancement leading to long-term suppression.	2003 Aug 15	12909410
Assessment of olfactory function and androstenone odor thresholds in humans with or without functional occlusion of the vomeronasal duct.	2003 Dec	14674834
Altered cortisol metabolism in polycystic ovary syndrome: insulin enhances 5alpha-reduction but not the elevated adrenal steroid production rates.	2003 Dec	14671189
Inactivation of androgens by UDP-glucuronosyltransferase enzymes in humans.	2003 Dec	14643063
Pentose phosphate pathway coordinates multiple redox-controlled relaxing mechanisms in bovine coronary arteries.	2003 Dec	12933338
Unsolved problems in male physiology: studies in a marsupial.	2003 Dec 15	14656473
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	12711027
Detection of quantitative trait loci for fat androstenone levels in pigs.	2003 Feb	12643481
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	12538619
Characterization of truncated mutants of human microsomal short-chain dehydrogenase/reductase RoDH-4.	2003 Feb 1	12604214
A facile and high yielding synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide--an internal standard in dope.	2003 Jan	12575693
Human type 3 3alpha-hydroxysteroid dehydrogenase (aldo-keto reductase 1C2) and androgen metabolism in prostate cells.	2003 Jul	12810547
Immunization against 5alpha-androstane-3alpha,17beta-diol affects ovarian folliculogenesis in Merino ewes.	2003 Jul	12749944
The prevalence of androstenone anosmia.	2003 Jun	12826538
Beyond adrenal and ovarian androgen generation: Increased peripheral 5 alpha-reductase activity in women with polycystic ovary syndrome.	2003 Jun	12788885
Glucuronidation of arachidonic and linoleic acid metabolites by human UDP-glucuronosyltransferases.	2003 Jun	12639971
Chronic effects of dehydroepiandrosterone on rat adipose tissue metabolism.	2003 Mar	12647261
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	12646198
17 beta-hydroxysteroid dehydrogenase type XI localizes to human steroidogenic cells.	2003 May	12697717
Steroidogenic acute regulatory protein in ovarian follicles of gonadotropin-stimulated rats is regulated by a gonadotropin-releasing hormone agonist.	2003 May	12606484
In vivo modification of the UDP-glucuronosyltransferase functional state in rat liver following hypophysectomy and partial or complete hormonal restoration.	2003 Nov	14688229
Oxidative 3alpha-hydroxysteroid dehydrogenase activity of human type 10 17beta-hydroxysteroid dehydrogenase.	2003 Nov	14672739
Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia.	2003 Nov 17	14612892
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003 Oct	14565775
Assessment of xenoestrogenic exposure by a biomarker approach: application of the E-Screen bioassay to determine estrogenic response of serum extracts.	2003 Oct 15	14613489
5alpha-reduced C21 steroids are substrates for human cytochrome P450c17.	2003 Oct 15	14522586
UDP-glucuronosyltransferase and sulfotransferase polymorphisms, sex hormone concentrations, and tumor receptor status in breast cancer patients.	2004	15318931
Prenatal diagnosis of P450 oxidoreductase deficiency (ORD): a disorder causing low pregnancy estriol, maternal and fetal virilization, and the Antley-Bixler syndrome phenotype.	2004 Aug 30	15316970
Urinary excretion of steroid metabolites after chronic androstenedione ingestion.	2004 Dec	15579782
Endogenous urinary steroids in premenopausal women with uterine leiomyomas.	2004 Jan	14698830
Evidence for peripheral plasticity in human odour response.	2004 Jan 1	14678505
The scents of androstenone in humans.	2004 Jan 1	14678483
Identifying androsterone (ADT) as a cognate substrate for human dehydroepiandrosterone sulfotransferase (DHEA-ST) important for steroid homeostasis: structure of the enzyme-ADT complex.	2004 Jan 23	14573603
Steroid 5alpha-reductase 1 promotes 5alpha-androstane-3alpha,17beta-diol synthesis in immature mouse testes by two pathways.	2004 Jul 30	15249131
Discriminative stimulus effects of ethanol in mice lacking the gamma-aminobutyric acid type A receptor delta subunit.	2004 Jun	15201633
A look at nutritional supplement use in adolescents.	2004 Jun	15145408
Identification of UGT2B9*2 and UGT2B33 isolated from female rhesus monkey liver.	2004 Jun 1	15130782
Responsivity to two odorants, androstenone and amyl acetate, and the affective impact of odors on interpersonal relationships.	2004 Mar	15008668
Characterisation of androstenone metabolism in pig liver microsomes.	2004 Mar 15	15013816
Alanine scanning mutagenesis of the testosterone binding site of rat 3 alpha-hydroxysteroid dehydrogenase demonstrates contact residues influence the rate-determining step.	2004 May 18	15134457
The pig CYP2E1 promoter is activated by COUP-TF1 and HNF-1 and is inhibited by androstenone.	2004 Nov 15	15488474
Simultaneous expression of guinea pig UDP-glucuronosyltransferase 2B21 (UGT2B21) and 2B22 in COS-7 cells enhances UGT2B21-catalyzed chloramphenicol glucuronidation.	2004 Oct	15377639
Urinary analysis of 16(5alpha)-androsten-3alpha-ol by gas chromatography/combustion/isotope ratio mass spectrometry: implications in anti-doping analysis.	2004 Oct 15	15358320
Urinary analysis of four testosterone metabolites and pregnanediol by gas chromatography-combustion-isotope ratio mass spectrometry after oral administrations of testosterone.	2004 Sep	15516291
Production rates of cortisol in obesity.	2004 Sep	15483206
Mechanistic roles of Ser-114, Tyr-155, and Lys-159 in 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni.	2005 Feb 4	15572373
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	15579269

Patents

Sample Use Guides

In Vivo Use Guide

Anticonvulsant potency in mice:

Route of Administration: Intraperitoneal

In Vitro Use Guide

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

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Name

Type

Language

ANDROSTERONE

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