Pregnanolone

Not to be confused with Pregnenolone.
This article is about the 3α,5β-reduced metabolite of progesterone. For other pregnanolone isomers of progesterone, see Pregnanolone (disambiguation).
Pregnanolone
Names
IUPAC name
3α-Hydroxy-5β-pregnan-20-one
Systematic IUPAC name
1-[(1S,3aS,3bR,5aR,7R,9aS,9bS,11aS)-7-Hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one
Other names
Eltanolone; 5β-Pregnan-3α-ol-20-one; 3α,5β-Tetrahydroprogesterone; 3α,5β-THP; 3α-Hydroxy-5β-tetrahydroprogesterone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.162.192 Edit this at Wikidata
UNII
  • InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15-,16+,17-,18+,19+,20+,21-/m1/s1
    Key: AURFZBICLPNKBZ-YZRLXODZSA-N
  • InChI=1/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15-,16+,17-,18+,19+,20+,21-/m1/s1
    Key: AURFZBICLPNKBZ-YZRLXODZBF
  • CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C
Properties
C21H34O2
Molar mass 318.501 g·mol−1
Pharmacology
Intravenous injection[1]
Pharmacokinetics:
0.9–3.5 hours[1][2][3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pregnanolone, also known as eltanolone, is an endogenous inhibitory neurosteroid which is produced in the body from progesterone.[4] It is closely related to allopregnanolone, which has similar properties.[4]

  1. ^ a b Cite error: The named reference pmid7839787 was invoked but never defined (see the help page).
  2. ^ Gray HS, Holt BL, Whitaker DK, Eadsforth P (March 1992). "Preliminary study of a pregnanolone emulsion (Kabi 2213) for i.v. induction of general anaesthesia". Br J Anaesth. 68 (3): 272–6. doi:10.1093/bja/68.3.272. PMID 1547051. S2CID 19193898.
  3. ^ Carl P, Høgskilde S, Nielsen JW, Sørensen MB, Lindholm M, Karlen B, Bäckstrøm T (March 1990). "Pregnanolone emulsion. A preliminary pharmacokinetic and pharmacodynamic study of a new intravenous anaesthetic agent". Anaesthesia. 45 (3): 189–97. doi:10.1111/j.1365-2044.1990.tb14683.x. PMID 2334030. S2CID 28358731.
  4. ^ a b Reddy DS (2003). "Pharmacology of endogenous neuroactive steroids". Crit Rev Neurobiol. 15 (3–4): 197–234. doi:10.1615/critrevneurobiol.v15.i34.20. PMID 15248811.