Chemistry:Gabazine

Gabazine
	Gabazine bromide
Clinical data
ATC code	none;
Identifiers
	IUPAC name 2-(3-carboxypropyl)-6-(4-methoxyphenyl)-2,3-dihydropyridazin-3-iminium bromide;
CAS Number	104104-50-9 ;
PubChem CID	107895;
ChemSpider	4925141 ;
UNII	99460MG420;
ChEMBL	ChEMBL303580 ;
Chemical and physical data
Formula	C15H18BrN3O3
Molar mass	368.226 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [Br-].C(=O)(O)CCCN1N=C(C=CC1=[NH2+])C1=CC=C(C=C1)OC;
	InChI InChI=1S/C15H17N3O3.BrH/c1-21-12-6-4-11(5-7-12)13-8-9-14(16)18(17-13)10-2-3-15(19)20;/h4-9,16H,2-3,10H2,1H3,(H,19,20);1H ; Key:GFZHNFOGCMEYTA-UHFFFAOYSA-N ;
	(verify)

Short description: Chemical compound

Gabazine (SR-95531) is a drug that acts as an antagonist at GABA_A receptors. It is used in scientific research and has no role in medicine, as it would be expected to produce convulsions if used in humans.^[1]

Gabazine binds to the GABA recognition site of the receptor-channel complex and acts as an allosteric inhibitor of channel opening.^[2] The net effect is to reduce GABA-mediated synaptic inhibition by inhibiting chloride flux across the cell membrane, and thus inhibiting neuronal hyperpolarization. While phasic (synaptic) inhibition is gabazine-sensitive, tonic (extrasynaptic) inhibition is relatively gabazine-insensitive.^[3]

Gabazine has been found to bind to and antagonize α₄βδ subunit-containing GABA_A receptors, which may represent the GHB receptor.^[4]

References

↑ "Effects of the GABA(A) receptor antagonists bicuculline and gabazine on stimulus-induced sharp wave-ripple complexes in adult rat hippocampus in vitro". The European Journal of Neuroscience 25 (7): 2170–2181. April 2007. doi:10.1111/j.1460-9568.2007.05462.x. PMID 17419756.
↑ "Bicuculline and gabazine are allosteric inhibitors of channel opening of the GABAA receptor". The Journal of Neuroscience 17 (2): 625–634. January 1997. doi:10.1523/jneurosci.17-02-00625.1997. PMID 8987785.
↑ "Tonically activated GABAA receptors in hippocampal neurons are high-affinity, low-conductance sensors for extracellular GABA". Molecular Pharmacology 63 (1): 2–8. January 2003. doi:10.1124/mol.63.1.2. PMID 12488530.
↑ "α4βδ GABA(A) receptors are high-affinity targets for γ-hydroxybutyric acid (GHB)". Proceedings of the National Academy of Sciences of the United States of America 109 (33): 13404–13409. August 2012. doi:10.1073/pnas.1204376109. PMID 22753476. Bibcode: 2012PNAS..10913404A.

{{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/Gabazine. Read more

[1] "Effects of the GABA(A) receptor antagonists bicuculline and gabazine on stimulus-induced sharp wave-ripple complexes in adult rat hippocampus in vitro". The European Journal of Neuroscience 25 (7): 2170–2181. April 2007. doi:10.1111/j.1460-9568.2007.05462.x. PMID 17419756.

[2] "Bicuculline and gabazine are allosteric inhibitors of channel opening of the GABAA receptor". The Journal of Neuroscience 17 (2): 625–634. January 1997. doi:10.1523/jneurosci.17-02-00625.1997. PMID 8987785.

[3] "Tonically activated GABAA receptors in hippocampal neurons are high-affinity, low-conductance sensors for extracellular GABA". Molecular Pharmacology 63 (1): 2–8. January 2003. doi:10.1124/mol.63.1.2. PMID 12488530.

[pmid22753476-4] "α4βδ GABA(A) receptors are high-affinity targets for γ-hydroxybutyric acid (GHB)". Proceedings of the National Academy of Sciences of the United States of America 109 (33): 13404–13409. August 2012. doi:10.1073/pnas.1204376109. PMID 22753476. Bibcode: 2012PNAS..10913404A.

[1]

[2]

[3]

[4]

v t e Convulsants
GABA receptor antagonists	Picrotoxin Gabazine Tetramethylenedisulfotetramine Cicutoxin Phenylsilatrane Tutin Pentylenetetrazol Thujone Endosulfan Bicuculline Oenanthotoxin Fipronil EBOB BIDN Dihydropicrotoxinin DMCM FG-7142 Chlorophenylsilatrane Bicyclic phosphates (TBPS, TBPO, IPTBO)
GABA synthesis inhibitors	Allylglycine Crimidine Ginkgotoxin Toxopyrimidine Isoniazid 3-Mercaptopropionic acid 4-Deoxypyridoxine
Glycine receptor antagonists	Strychnine Tutin Picrotoxin Dendrobine
Glutamate receptor agonists	AMPA NMDA Kainic acid Domoic acid Quisqualic acid Tetrazolylglycine
Other	Methyl fluoroacetate Fluoroethyl fluoroacetate Nitrocyclohexane Methionine sulfoximine

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Clinical data
Gabazine bromide
ATC code	none
Identifiers
IUPAC name 2-(3-carboxypropyl)-6-(4-methoxyphenyl)-2,3-dihydropyridazin-3-iminium bromide
CAS Number	104104-50-9^Y
PubChem CID	107895
ChemSpider	4925141^Y
UNII	99460MG420
ChEMBL	ChEMBL303580^Y
Chemical and physical data
Formula	C₁₅H₁₈BrN₃O₃
Molar mass	368.226 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES [Br-].C(=O)(O)CCCN1N=C(C=CC1=[NH2+])C1=CC=C(C=C1)OC
InChI InChI=1S/C15H17N3O3.BrH/c1-21-12-6-4-11(5-7-12)13-8-9-14(16)18(17-13)10-2-3-15(19)20;/h4-9,16H,2-3,10H2,1H3,(H,19,20);1H^Y Key:GFZHNFOGCMEYTA-UHFFFAOYSA-N^Y
(verify)

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