Pregnenolone acetate

Pregnenolone acetate (brand names Antofin, Previsone, Pregno-Pan), also known as pregn-5-en-3β-ol-20-one 3β-acetate, is a synthetic pregnane steroid and an ester of pregnenolone which is described as a glucocorticoid and as a skin-conditioning and skin anti-aging agent.[2][3] It has been reported to reduce wrinkles in elderly women when applied in the form of a 0.5% topical cream, effects which were suggested to be due to improved hydration of the skin.[3] Pregnenolone acetate has been marketed in France in a topical cream containing 1% pregnenolone acetate and 10% "sex hormone" for the treatment of premature skin aging but was withdrawn from the market in 1992.[3] Although the medication has been described by some sources as a glucocorticoid, other authors have stated that systemic pregnenolone acetate has no undesirable metabolic or toxic effects even at high doses.[4]

Pregnenolone acetate
Clinical data
Trade namesAntofin, Previsone, Pregno-Pan
Other namesPregn-5-en-3β-ol-20-one 3β-acetate, Antofin, Artivis, Enescorb, Previsone, Sharmone, Pregnenolone-3-acetate, 1778-02-5, 3α-Acetoxy-5-pregnen-20-one, ZINC6304690, NSC 64827, Acetic acid 20-oxopregn-5-en-3alpha-yl ester[1]
Routes of
administration		Topical
Identifiers
IUPAC name
  • [(3S,8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.015.648
Chemical and physical data
FormulaC23H34O3
Molar mass358.522 g·mol−1
3D model (JSmol)
SMILES
  • CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OC(=O)C)C)C
InChI
  • InChI=1S/C23H34O3/c1-14(24)19-7-8-20-18-6-5-16-13-17(26-15(2)25)9-11-22(16,3)21(18)10-12-23(19,20)4/h5,17-21H,6-13H2,1-4H3/t17-,18-,19+,20-,21-,22-,23+/m0/s1
  • Key:CRRKVZVYZQXICQ-RJJCNJEVSA-N

See also

References
  1. National Center for Biotechnology Information. PubChem Compound Database; CID=11013784, https://pubchem.ncbi.nlm.nih.gov/compound/11013784 (accessed Mar. 10, 2019).
  2. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 665–. ISBN 978-1-4757-2085-3.
  3. Council of Europe. Committee of Experts on Cosmetic Products (2008). Active Ingredients Used in Cosmetics: Safety Survey. Council of Europe. pp. 325–. ISBN 978-92-871-6298-4.
  4. Lamb JH, Kelly FC, Shackelford PO, Rebell G, Koons RC (1953). "Pregnenolone acetate in treatment of mycetoma (nocardiosis)". AMA Arch Derm Syphilol. 67 (2): 141–5. doi:10.1001/archderm.1953.01540020019004. PMID 13029897.



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