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;
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;

Short description: Chemical compound

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]

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

↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 666–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA666.
↑ Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. 4 October 2001. p. 2649. ISBN 978-3-527-30247-5. https://books.google.com/books?id=1XBqAAAAMAAJ. "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)."
↑ The chemistry and manufacture of cosmetics. Van Nostrand. 1988. p. 631. ISBN 9780931710162. https://books.google.com/books?id=1BVtAAAAMAAJ. "Pregnenolone hemisuccinate has been patented for topical use in alleviating allergic, pruritic and inflammatory dermatitis (29)."
↑ Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. 8 May 2018. pp. 1408–. ISBN 978-1-351-78989-9. https://books.google.com/books?id=xUlaDwAAQBAJ&pg=PT1408.
↑ "Direct Modulation of Amino Acid Receptors by Neuroactive Steroids: Physiological and Pharmacological Implications". Neurosteroid Effects in the Central Nervous System: The Role of the GABA-A Receptor. CRC Press. 27 October 2003. pp. 344,356. ISBN 978-0-203-50816-9. https://books.google.com/books?id=00JbUu4lLsgC&pg=PA344.
↑ "Steroid potentiation and inhibition of N-methyl-D-aspartate receptor-mediated intracellular Ca++ responses: structure-activity studies". The Journal of Pharmacology and Experimental Therapeutics 271 (2): 677–682. November 1994. PMID 7965782.
↑ "Neurosteroid modulation of recombinant ionotropic glutamate receptors". Brain Research 803 (1–2): 153–160. August 1998. doi:10.1016/s0006-8993(98)00644-1. PMID 9729352.
↑ "Regulation of N-methyl-D-aspartate cytotoxicity by neuroactive steroids in rat cortical neurons". European Journal of Pharmacology 454 (2–3): 165–175. November 2002. doi:10.1016/s0014-2999(02)02493-7. PMID 12421643.

{{Navbox | name = GABA receptor modulators | title = GABA receptor modulators | state = collapsed | bodyclass = hlist | groupstyle = text-align:center;

 | group1 = Ionotropic
 |  list1 = {{Navbox|subgroup
 | groupstyle = text-align:center
 | groupwidth = 5em

   | group1 = GABA_A
   | list1  =

Agonists: (+)-Catechin
Bamaluzole
Barbiturates (e.g., phenobarbital)
BL-1020
DAVA
Dihydromuscimol
GABA
Gabamide
GABOB
Gaboxadol (THIP)
Homotaurine (tramiprosate, 3-APS)
Ibotenic acid
iso-THAZ
iso-THIP
Isoguvacine
Isomuscimol
Isonipecotic acid
Kojic amine
Lignans (e.g., honokiol)
Methylglyoxal
Monastrol
Muscimol
Nefiracetam
Neuroactive steroids (e.g., allopregnanolone)
Org 20599
PF-6372865
Phenibut
Picamilon
P4S
Progabide
Propofol
Quisqualamine
SL-75102
TACA
TAMP
Terpenoids (e.g., borneol)
Thiomuscimol
Tolgabide
ZAPA

Positive modulators (abridged; see here for a full list): α-EMTBL
Alcohols (e.g., ethanol)
Anabolic steroids
Avermectins (e.g., ivermectin)
Barbiturates (e.g., phenobarbital)
Benzodiazepines (e.g., diazepam)
Bromide compounds (e.g., potassium bromide)
Carbamates (e.g., meprobamate)
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g., ergoloid (dihydroergotoxine))
Etazepine
Etifoxine
Fenamates (e.g., mefenamic acid)
Flavonoids (e.g., apigenin, hispidulin)
Fluoxetine
Flupirtine
Imidazoles (e.g., etomidate)
Kava constituents (e.g., kavain)
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g., allopregnanolone, [[Chemistry:Cholecholesterol]], THDOC)
Niacin
Nicotinamide (niacinamide)
Nonbenzodiazepines (e.g., β-carbolines (e.g., [[abecarnil), cyclopyrrolones (e.g., zopiclone), imidazopyridines (e.g., zolpidem), pyrazolopyrimidines (e.g., zaleplon))
Norfluoxetine
Petrichloral
Phenols (e.g., propofol)
Phenytoin
Piperidinediones (e.g., glutethimide)
Propanidid
Pyrazolopyridines (e.g., etazolate)
Quinazolinones (e.g., methaqualone)
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g., baicalin)
Stiripentol
Sulfonylalkanes (e.g., sulfonmethane (sulfonal))
Topiramate
Valerian constituents (e.g., valerenic acid)
Volatiles/gases (e.g., chloral hydrate, chloroform, [[Chemistry:Diethyl diethyl ether, Par paraldehyde]], sevoflurane)

Negative modulators: 1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
α5IA (LS-193,268)
β-CCB
β-CCE
β-CCM
β-CCP
β-EMGBL
Anabolic steroids
Amiloride
Anisatin
β-Lactams (e.g., penicillins, cephalosporins, carbapenems)
Basmisanil
Bemegride
Bicyclic phosphates (TBPS, TBPO, IPTBO)
BIDN
Bilobalide
Bupropion
CHEB
Chlorophenylsilatrane
Cicutoxin
Cloflubicyne
Cyclothiazide
DHEA
DHEA-S
Dieldrin
(+)-DMBB
DMCM
DMPC
EBOB
Etbicyphat
FG-7142 (ZK-31906)
Fiproles (e.g., fipronil)
Flavonoids (e.g., amentoflavone, oroxylin A)
Flumazenil
Fluoroquinolones (e.g., ciprofloxacin)
Flurothyl
Furosemide
Golexanolone
Iomazenil (¹²³I)
IPTBO
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Leptazol
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g., [[apalutamide, [[Chemistry:Bicalutbicalutamide, Enzalut enzalutamide, Chemistry:Flutamide|flut]]amide]], nilutamide)
Oenanthotoxin
Pentylenetetrazol (pentetrazol)
Phenylsilatrane
Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin)
Pregnenolone sulfate
Propybicyphat
PWZ-029
Radequinil
Ro 15-4513
Ro 19-4603
RO4882224
RO4938581
Sarmazenil
SCS
Suritozole
TB-21007
TBOB
TBPS
TCS-1105
Terbequinil
TETS
Thujone
U-93631
Zinc
ZK-93426

   | group2 = GABA_A-ρ
   | list2  =

Negative modulators: 5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin, picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

}}

 | group2 = Metabotropic

| list2 =

 | below =

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

}}

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Original source: https://en.wikipedia.org/wiki/Pregnenolone succinate. Read more

[Elks2014-1] The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 666–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA666.

[NegwerScharnow2001-2] Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. 4 October 2001. p. 2649. ISBN 978-3-527-30247-5. https://books.google.com/books?id=1XBqAAAAMAAJ. "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] The chemistry and manufacture of cosmetics. Van Nostrand. 1988. p. 631. ISBN 9780931710162. https://books.google.com/books?id=1BVtAAAAMAAJ. "Pregnenolone hemisuccinate has been patented for topical use in alleviating allergic, pruritic and inflammatory dermatitis (29)."

[Milne2018-4] Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. 8 May 2018. pp. 1408–. ISBN 978-1-351-78989-9. https://books.google.com/books?id=xUlaDwAAQBAJ&pg=PT1408.

[Smith2003-5] "Direct Modulation of Amino Acid Receptors by Neuroactive Steroids: Physiological and Pharmacological Implications". Neurosteroid Effects in the Central Nervous System: The Role of the GABA-A Receptor. CRC Press. 27 October 2003. pp. 344,356. ISBN 978-0-203-50816-9. https://books.google.com/books?id=00JbUu4lLsgC&pg=PA344.

[pmid7965782-6] "Steroid potentiation and inhibition of N-methyl-D-aspartate receptor-mediated intracellular Ca++ responses: structure-activity studies". The Journal of Pharmacology and Experimental Therapeutics 271 (2): 677–682. November 1994. PMID 7965782.

[pmid9729352-7] "Neurosteroid modulation of recombinant ionotropic glutamate receptors". Brain Research 803 (1–2): 153–160. August 1998. doi:10.1016/s0006-8993(98)00644-1. PMID 9729352.

[pmid12421643-8] "Regulation of N-methyl-D-aspartate cytotoxicity by neuroactive steroids in rat cortical neurons". European Journal of Pharmacology 454 (2–3): 165–175. November 2002. doi:10.1016/s0014-2999(02)02493-7. PMID 12421643.

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Pregnenolone Succinate

See also

References