From Wikipedia, the free encyclopedia
Selective GABAA receptor antagonist
Famiraprinium
Names
IUPAC name
4-(6-Imino-5-methyl-3-phenylpyridazin-1-yl)butanoic acid
Other names
SR-95103
Identifiers
ChEMBL
ChemSpider
UNII
InChI=1S/C15H17N3O2/c1-11-10-13(12-6-3-2-4-7-12)17-18(15(11)16)9-5-8-14(19)20/h2-4,6-7,10,16H,5,8-9H2,1H3,(H,19,20)
Key: LLZVAIDABZBAGE-UHFFFAOYSA-N
HCl: InChI=1S/C15H17N3O2.ClH/c1-11-10-13(12-6-3-2-4-7-12)17-18(15(11)16)9-5-8-14(19)20;/h2-4,6-7,10,16H,5,8-9H2,1H3,(H,19,20);1H
Key: MDCYBLVSLOPFAZ-UHFFFAOYSA-N
CC1=CC(=NN(C1=N)CCCC(=O)O)C2=CC=CC=C2
HCl: CC1=CC(=NN(C1=N)CCCC(=O)O)C2=CC=CC=C2.Cl
Properties
C 15 H 17 N 3 O 2
Molar mass
271.320 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Famiraprinium (also known as SR-95103 ) is a GABAA receptor antagonist used in scientific research.[ 1]
It antagonizes certain GABAA receptors with an inhibition constant of 2.2 μM.[ 2]
Like other GABA antagonists, it triggers epilepsy-like symptoms. These effects can be antagonized by GABAA agonists like muscimol, proving it is an antagonist.[ 3]
^ Schmitt, P.; Di Scala, G.; Brandao, M. L.; Karli, P. (1985-11-05). "Behavioral effects of microinjections of SR 95103, a new GABA-A antagonist, into the medial hypothalamus or the mesencephalic central gray" . European Journal of Pharmacology . 117 (2): 149–158. doi :10.1016/0014-2999(85)90599-0 . ISSN 0014-2999 . PMID 3000802 .
^ Chambon, J. P.; Feltz, P.; Heaulme, M.; Restle, S.; Schlichter, R.; Biziere, K.; Wermuth, C. G. (March 1985). "An arylaminopyridazine derivative of gamma-aminobutyric acid (GABA) is a selective and competitive antagonist at the GABAA receptor site" . Proceedings of the National Academy of Sciences of the United States of America . 82 (6): 1832–1836. doi :10.1073/pnas.82.6.1832 . ISSN 0027-8424 . PMC 397367 . PMID 2984669 .
^ Santucci, V.; Fournier, M.; Chambon, J. P.; Biziere, K. (1985-08-15). "Electroencephalographic study of SR 95103, a GABAA antagonist: interaction with inhibitory amino acids and muscimol" . European Journal of Pharmacology . 114 (2): 219–222. doi :10.1016/0014-2999(85)90630-2 . ISSN 0014-2999 . PMID 2995080 .
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