Chemicals and Drugs

5-alpha-Dihydroprogesterone

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.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

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.

Chemical Identity

Chemical Information

Molecular Formula
C21H32O2
Molecular Weight
316.5 g/mol
CAS Registry No.
566-65-4
IUPAC Name
(5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
InChIKey
XMRPGKVKISIQBV-BJMCWZGWSA-N
SMILES
CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CCC(=O)C4)C)C
MeSH Unique ID
D043582
Source
PubChem CID 92810

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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MeSH Record

Synonyms

21 entry terms
  • 3,20-Allopregnanedione
  • 3,20-Allopregnanedione, (5alpha)-Isomer
  • 5 alpha-Dihydroprogesterone
  • 5 alpha-Pregnane-3,20-dione
  • 5-alpha-Pregnane-3,20-dione
  • 5-alpha-Pregnanedione
  • 5alpha-DHP
  • 5alpha-Pregnane-3,20-dione
  • 3,20 Allopregnanedione
  • 5 alpha Dihydroprogesterone
  • 5 alpha Pregnane 3,20 dione
  • 5 alpha Pregnanedione
  • 5alpha DHP
  • 5alpha Pregnane 3,20 dione
  • 3,20-Allopregnanedione, (5beta,13alpha,17alpha)-Isomer
  • 5 beta-Pregnane-3,20-dione
  • 5-beta-Dihydroprogesterone
  • 5beta-DHP
  • 5 beta Dihydroprogesterone
  • 5 beta Pregnane 3,20 dione
  • 5beta DHP

MeSH Record

Aspects Covered

29 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, deficiency, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, physiology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

2004; for 3,20-ALLOPREGNANEDIONE use PREGNANEDIONES (NM) 1971-2003

MeSH Record

Previous Indexing

  • Dihydroprogesterone (1976-2003)
  • Progesterone (1974-2003)

MeSH Hierarchy

Tree Numbers

  1. D04w.210.500w.745.558w.075w
  2. D06.472w.334.851w.687w.750w.070w

AMA Style

References

  1. National Library of Medicine. 5-alpha-Dihydroprogesterone. Medical Subject Headings (MeSH). 2026. Unique ID D043582. http://id.nlm.nih.gov/mesh/2026/D043582
  2. 5-alpha-Dihydroprogesterone. In: Wikipedia. https://en.wikipedia.org/wiki/5%CE%B1-Dihydroprogesterone
  3. 5-alpha-Dihydroprogesterone. In: Wikidata. https://www.wikidata.org/wiki/Q4641508
  4. 5-alpha-Dihydroprogesterone. In: PubChem Compound. CID 92810. https://pubchem.ncbi.nlm.nih.gov/compound/92810