Pregnenolone succinate

Pregnenolone succinate (USAN; brand names Panzalone, Formula 405; also known as pregnenolone hemisuccinate or pregn-5-en-3β-ol-20-one 3β-(hydrogen succinate)) is a synthetic pregnane steroid and an ester of pregnenolone which is described as a glucocorticoid and anti-inflammatory drug and has been patented and marketed as a topical medication in the form of a cream for the treatment of allergic, pruritic, and inflammatory dermatitis.[1][2][3] It has also been described as a non-hormonal sterol, having neurosteroid activity, and forming a progesterone analogue via dehydrogenation.[4]

Pregnenolone succinate
Clinical data
Trade namesPanzalone, Formula 405
Other namesPregnenolone hemisuccinate; Pregn-5-en-3β-ol-20-one 3β-(hydrogen succinate)
Routes of
administration		Topical
Identifiers
IUPAC name
  • 4-[[(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]oxy]-4-oxobutanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.022.728
Chemical and physical data
FormulaC25H36O5
Molar mass416.558 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)CCC(=O)O)C)C
InChI
  • InChI=1S/C25H36O5/c1-15(26)19-6-7-20-18-5-4-16-14-17(30-23(29)9-8-22(27)28)10-12-24(16,2)21(18)11-13-25(19,20)3/h4,17-21H,5-14H2,1-3H3,(H,27,28)/t17-,18-,19+,20-,21-,24-,25+/m0/s1
  • Key:OZZAYJQNMKMUSD-DMISRAGPSA-N

In addition to its glucocorticoid effects, pregnenolone succinate has been found to act as a negative allosteric modulator of the GABAA receptor and a positive allosteric modulator of the NMDA receptor similarly to pregnenolone sulfate.[5][6][7][8]

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 666–. ISBN 978-1-4757-2085-3.
  2. Martin Negwer; Hans-Georg Scharnow (4 October 2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 2649. ISBN 978-3-527-30247-5. 3β-Hydroxypregn-5-en-20-one hydrogen succinate = (3β)-3-(3-Carboxy-1-oxo-propoxy)pregn-5-en-20-one. S: Formula 405. Panzalone. Pregnenolone succinate. U: Glucocorticoid (anti-inflammatory, anti-allergic).
  3. Maison G. De Navarre (1988). The chemistry and manufacture of cosmetics. Van Nostrand. p. 631. ISBN 9780931710162. Pregnenolone hemisuccinate has been patented for topical use in alleviating allergic, pruritic and inflammatory dermatitis (29).
  4. George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1408–. ISBN 978-1-351-78989-9.
  5. Sheryl S. Smith (27 October 2003). Neurosteroid Effects in the Central Nervous System: The Role of the GABA-A Receptor. CRC Press. pp. 344, 356. ISBN 978-0-203-50816-9.
  6. Irwin RP, Lin SZ, Rogawski MA, Purdy RH, Paul SM (1994). "Steroid potentiation and inhibition of N-methyl-D-aspartate receptor-mediated intracellular Ca++ responses: structure-activity studies". J. Pharmacol. Exp. Ther. 271 (2): 677–82. PMID 7965782.
  7. Yaghoubi N, Malayev A, Russek SJ, Gibbs TT, Farb DH (1998). "Neurosteroid modulation of recombinant ionotropic glutamate receptors". Brain Res. 803 (1–2): 153–60. doi:10.1016/s0006-8993(98)00644-1. PMID 9729352. S2CID 41180982.
  8. Shirakawa H, Katsuki H, Kume T, Kaneko S, Ito J, Akaike A (2002). "Regulation of N-methyl-D-aspartate cytotoxicity by neuroactive steroids in rat cortical neurons". Eur. J. Pharmacol. 454 (2–3): 165–75. doi:10.1016/s0014-2999(02)02493-7. PMID 12421643.



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