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Substance Name: 3,20-Allopregnanedione
RN: 566-65-4
UNII: 98G4S1OH0Z
InChIKey: XMRPGKVKISIQBV-BJMCWZGWSA-N

Note

  • A biologically active 5-alpha-reduced metabolite of plasma PROGESTERONE. It is the immediate precursor of 5-alpha-pregnan-3-alpha-ol-20-one (ALLOPREGNANOLONE), a neuroactive steroid that binds with GABA(A) RECEPTOR.

Molecular Formula

  • C21-H32-O2

Molecular Weight

  • 316.482
 

Classification Codes

  • Drug / Therapeutic Agent
  • Hormone
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Names and Synonyms

Name of Substance

  • 3,20-Allopregnanedione
  • 5-alpha-Dihydroprogesterone

MeSH Heading

  • 5-alpha-Dihydroprogesterone

Synonyms

  • 3,20-Allopregnanedione
  • 3,20-Dioxo-5alpha-pregnane
  • 4-07-00-02199 (Beilstein Handbook Reference)
  • 5-alpha-Dihydroprogesterone
  • 5alpha-Dihydroprogesterone
  • 5beta-Pregnane-3,20-dione
  • BRN 2058506
  • EINECS 209-297-3
  • NSC 18319
  • UNII-98G4S1OH0Z

Systematic Names

  • 5alpha-Pregnane-3,20-dione (8CI)
  • Pregnane-3,20-dione, (5alpha)- (9CI)

Registry Numbers

CAS Registry Number

  • 566-65-4

FDA UNII

  • 98G4S1OH0Z

System Generated Number

  • 0000566654

Structure Descriptors

InChI

1S/C21H32O2/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/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1

InChIKey

XMRPGKVKISIQBV-BJMCWZGWSA-N

Smiles

C1[C@@]2([C@H](CC[C@H]2[C@@H]2CC[C@@H]3[C@@](CCC(C3)=O)(C)[C@@H]2C1)C(=O)C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intraperitoneal 80mg/kg (80mg/kg)   Journal of Medicinal Chemistry. Vol. 11, Pg. 117, 1968.
mouse LDLo intravenous 10mg/kg (10mg/kg)   Journal of Medicinal Chemistry. Vol. 11, Pg. 117, 1968.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 200 deg C   EXP
log P (octanol-water) 3.460 (none)   EST
Atmospheric OH Rate Constant 3.85E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.