An androgenically inactive metabolite of testosterone and androstenedione
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Isomer(s)
15872Androsterone
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Etiocholanolone

Item No. 34501

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5β)-3α-hydroxy-androstan-17-one
CAS Number
53-42-9
Synonyms
  • 5β-Androsterone
  • 3α-Etiocholanolone
  • NSC 50908
Molecular Formula
C19H30O2
Formula Weight
290.4
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: 10 mg/ml
SMILES
C[C@@]12[C@]3([H])[C@](CC[C@]1([H])C[C@@H](CC2)O)([H])[C@@]4([H])[C@](CC3)(C(CC4)=O)C
InChi Code
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+/m1/s1
InChi Key
QGXBDMJGAMFCBF-BNSUEQOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $36

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    10 mg

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    25 mg

    $120

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    50 mg

    $169

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    Product Description

    Etiocholanolone is an androgenically inactive metabolite of testosterone and androstenedione and the 5β epimer of androsterone (Item No. 15872).1,2 It increases the frequency of long channel openings and potentiates GABA-induced chloride currents in HEK293 cells expressing rat α1β2γ2L subunit-containing GABAA receptors when used at a concentration of 10 µM.3 Etiocholanolone is protective against seizures induced by 6 Hz electroshock or pentylenetetrazol (PTZ; ED50s = 76.9 and 139 mg/kg, respectively).4 It is also pyretic in an IL-1-dependent manner, inducing increases in body temperature in rhesus macaques but not squirrel monkeys that lack testosterone and androstenedione metabolizing enzymes.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chouinard, S., Yueh, M.-F., Tukey, R.H., et al. Inactivation by UDP-glucuronosyltransferase enzymes: The end of androgen signaling. J. Steroid. Biochem. Mol. Biol. 109(3-5), 247-253 (2008).

    2. Baulieu, E.-E., and Mauvais-Jarvis, P. Studies on testosterone metabolism. The Journal of Biological Chemisty 239(5), 1569-1577 (1964).

    3. Li, P., Bracamontes, J., Katona, B.W., et al. Natural and enantiomeric etiocholanolone interact with distinct sites on the rat α1β2γ2L GABAA receptor. Mol. Pharmacol. 71(6), 1582-1590 (2007).

    4. Kaminski, R.M., Marini, H., Kim, W.-J., et al. Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia 46(6), 819-827 (2005).

    5. Steinetz, B.G., Randolph, C., Werner, R., et al. Pyrogenicity of etiocholanolone and interleukin-1 in new and old world monkeys. Proc. Soc. Exp. Biol. Med. 217(4), 435-438 (1998).