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Chemical compound
Pregnenolone succinate
Trade names Panzalone, Formula 405 Other names Pregnenolone hemisuccinate; Pregn-5-en-3β-ol-20-one 3β-(hydrogen succinate)
Routes of administration
Topical
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 InfoCard
100.022.728
Formula C 25 H 36 O 5
Molar mass 416.558 g·mol−1 3D model (
JSmol )
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=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 (
USAN Tooltip 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
GABAA receptor and a
positive allosteric modulator of the
NMDA receptor similarly to
pregnenolone sulfate .
[5]
[6]
[7]
[8]
See also
References
^ Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 666–.
ISBN
978-1-4757-2085-3 .
^ Negwer M, Scharnow HG (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).
^ De Navarre MG (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).
^ Milne GW (8 May 2018).
Drugs: Synonyms and Properties: Synonyms and Properties . Taylor & Francis. pp. 1408–.
ISBN
978-1-351-78989-9 .
^ Gibbs TT, Farb DH (27 October 2003).
"Direct Modulation of Amino Acid Receptors by Neuroactive Steroids: Physiological and Pharmacological Implications" . In Smith SS (ed.). 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 (November 1994). "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.
PMID
7965782 .
^ Yaghoubi N, Malayev A, Russek SJ, Gibbs TT, Farb DH (August 1998).
"Neurosteroid modulation of recombinant ionotropic glutamate receptors" . Brain Research . 803 (1–2): 153–160.
doi :
10.1016/s0006-8993(98)00644-1 .
PMID
9729352 .
S2CID
41180982 .
^ Shirakawa H, Katsuki H, Kume T, Kaneko S, Ito J, Akaike A (November 2002). "Regulation of N-methyl-D-aspartate cytotoxicity by neuroactive steroids in rat cortical neurons". European Journal of Pharmacology . 454 (2–3): 165–175.
doi :
10.1016/s0014-2999(02)02493-7 .
PMID
12421643 .
GR Tooltip Glucocorticoid receptor
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Positive modulators (abridged; see
here for a full list):
α-EMTBL
Alcohols (e.g.,
drinking alcohol ,
2M2B )
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 ,
cholesterol ,
THDOC )
Niacin
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 ,
diethyl ether ,
paraldehyde ,
sevoflurane )
Negative modulators:
1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
α3IA
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 (123 I)
IPTBO
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g.,
apalutamide ,
bicalutamide ,
enzalutamide ,
flutamide ,
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
GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor
AMPAR Tooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KAR Tooltip Kainate receptor
NMDAR Tooltip N-Methyl-D-aspartate receptor
Group I
mGluR1 Tooltip Metabotropic glutamate receptor 1
mGluR5 Tooltip Metabotropic glutamate receptor 5
Group II
mGluR2 Tooltip Metabotropic glutamate receptor 2
mGluR3 Tooltip Metabotropic glutamate receptor 3
Group III
mGluR4 Tooltip Metabotropic glutamate receptor 4
mGluR6 Tooltip Metabotropic glutamate receptor 6
mGluR7 Tooltip Metabotropic glutamate receptor 7
mGluR8 Tooltip Metabotropic glutamate receptor 8