Pregnenolone succinate

Pregnenolone succinate
Clinical data
Trade names	Panzalone, Formula 405
Other names	Pregnenolone 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	4598-67-8;
PubChem CID	10070529;
ChemSpider	8246069;
UNII	6LN4W6JJK6;
KEGG	D05604;
ChEMBL	ChEMBL2105373;
CompTox Dashboard (EPA)	DTXSID40196673 ;
ECHA InfoCard	100.022.728
Chemical and physical data
Formula	C25H36O5
Molar mass	416.558 g·mol−1
3D model (JSmol)	Interactive image;
	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;

Pregnenolone succinate (USANTooltip United States Adopted Name; 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]

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

References

^ 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.
^ 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).
^ Maison G. De Navarre (1988). The chemistry and manufacture of cosmetics. Van Nostrand. p. 631. Pregnenolone hemisuccinate has been patented for topical use in alleviating allergic, pruritic and inflammatory dermatitis (29).
^ George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1408–. ISBN 978-1-351-78989-9.
^ 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.
^ 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.
^ 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.
^ 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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[Elks2014-1] 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.

[NegwerScharnow2001-2] 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).

[Navarre1988-3] Maison G. De Navarre (1988). The chemistry and manufacture of cosmetics. Van Nostrand. p. 631. Pregnenolone hemisuccinate has been patented for topical use in alleviating allergic, pruritic and inflammatory dermatitis (29).

[Milne2018-4] George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1408–. ISBN 978-1-351-78989-9.

[Smith2003-5] 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.

[pmid7965782-6] 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.

[pmid9729352-7] 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.

[pmid12421643-8] 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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See also

References