Etiocholanolone

Names

[ CAS No. ]:
53-42-9

[ Name ]:
Etiocholanolone

[Synonym ]:
3a-Hydroxy-5b-androstane-17-one
Androsterone, (5β)-
3alpha-hydroxy-5beta-androstan-17-one
5β-Androsterone
(5b)-Androsterone
5-Isoandrosterone
3α-hydroxy-5β-androstane-17-one
5β-Androstan-17-one, 3α-hydroxy-
5BETA-ANDROSTERONE
MFCD00064133
(3α,5β)-3-Hydroxyandrostan-17-one
ETIOCHOLANOLON
3α-Etiocholanolone
Androstan-17-one, 3-hydroxy-, (3α,5β)-
19-noretiocholanolone
ETIOCHOLANONE
3a-Etiocholanolone
3α-hydroxy-5β-androstan-17-one
5b-Androsterone
Etiocholan-3a-ol-17-one
Etiocholan-3α-ol-17-one
Etiocholan-3.α.-ol-17-one
EINECS 200-835-2
Etiocholanolone

Biological Activity

[Description]:

Etiocholanolone (5β-Androsterone) is the excreted metabolite of testosterone and has anticonvulsant activity[1]. Etiocholanolone is a less potent neurosteroid positive allosteric modulator (PAM) of the GABAA receptor than its enantiomer form[2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[In Vitro]

Etiocholanolone (10 μM) coapplication with GABA leads to an increase in the relative frequency of long openings (fraction of OT3, site A2 effect), but it is ineffective at increasing the duration of long openings (site B effect) or at decreasing the relative frequency of the activation-related closed time component (site A1 effect)[2].

[In Vivo]

Etiocholanolone (intraperitoneal injection; 0-109.1 mg/kg; single dose) exhibits ED50 values of 57.6 and 109.1 mg/kg in the 6-Hz and PTZ tests, respectively. Protective activity in the 6-Hz test of 5β,3α-A persists for 2 h and is shorter than ent-5β,3α-A treatment (3 hours) in mice[1].

[References]

[1]. Ping Li,et al. Natural and Enantiomeric Etiocholanolone Interact With Distinct Sites on the Rat alpha1beta2gamma2L GABAA Receptor. Mol Pharmacol. 2007 Jun;71(6):1582-90.

[2]. Dorota Zolkowska, et al. Anticonvulsant Potencies of the Enantiomers of the Neurosteroids Androsterone and Etiocholanolone Exceed Those of the Natural Forms. Psychopharmacology (Berl). 2014 Sep;231(17):3325-32.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
413.1±45.0 °C at 760 mmHg

[ Melting Point ]:
148～150°C (lit.)

[ Molecular Formula ]:
C₁₉H₃₀O₂

[ Molecular Weight ]:
290.440

[ Flash Point ]:
176.4±21.3 °C

[ Exact Mass ]:
290.224579

[ PSA ]:
37.30000

[ LogP ]:
3.75

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.536

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
F,Xn

[ Risk Phrases ]:
11-20/21/22-36

[ Safety Phrases ]:
16-36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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A benchmark data set of steroids with known affinity for sex hormone-binding globulin (SHBG) has been widely used to validate popular molecular field-based QSAR techniques. We have expanded the data s...

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Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.

Eur. J. Med. Chem. 43 , 107-13, (2008)

Allopregnanolone (1) and pregnanolone (2), steroids containing a 17beta-acetyl group, are potent enhancers of GABA (gamma-aminobutyric acid) action at GABAA receptors. Their effects are enantioselecti...