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Details

Stereochemistry ACHIRAL
Molecular Formula C32H32N4O3
Molecular Weight 520.6215
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SB 224289

SMILES

CN1CCC2(COC3=CC4=C(C=C23)N(CC4)C(=O)C5=CC=C(C=C5)C6=C(C)C=C(C=C6)C7=NOC(C)=N7)CC1

InChI

InChIKey=ATQMRMGXINTJHV-UHFFFAOYSA-N
InChI=1S/C32H32N4O3/c1-20-16-25(30-33-21(2)39-34-30)8-9-26(20)22-4-6-23(7-5-22)31(37)36-13-10-24-17-29-27(18-28(24)36)32(19-38-29)11-14-35(3)15-12-32/h4-9,16-18H,10-15,19H2,1-3H3

HIDE SMILES / InChI
Molecular Formula C32H32N4O3
Molecular Weight 520.6215
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

SB-224289 was originally developed by SmithKline, now known as GlaxoSmithKline. It was identified as an antagonist of the 5-hydroxytryptamine receptor 1B (5-HT1B) and subsequently investigated for potential antidepressant activity, although no human trials have been reported. Interestingly, SB-224289 was also found to exhibit antagonistic activity for the antifungal mechanism of Marine Depsipeptide Papuamide A in Candida albicans; although the specific mechanism of action remains unknown.

CNS Activity

CNS Active
3913
Curator's Comment: referenced study was conducted in guinea pig

Originator

SmithKline
6
Curator's Comment: SmithKline Beecham has merged with Glaxo Wellcome to form GlaxoSmithKline

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
5-hydroxytryptamine receptor 1B
21
Target ID: P28222
Gene ID: 3351.0
Gene Symbol: HTR1B
Target Organism: Homo sapiens (Human)
Inverse Agonist
80
 8.0 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Agonist properties of pindolol at h5-HT1A receptors coupled to mitogen-activated protein kinase.
2001 Jul 13
Effects of 5-HT drugs in prefrontal cortex during memory formation and the ketamine amnesia-model.
2008
Effects of 5-HT in globus pallidus on haloperidol-induced catalepsy in rats.
2009 Apr 17
Patents

Patents

05972951
2
20090076019
7
6515027
2

Sample Use Guides

In Vivo Use Guide
The regulation of extracellular 5-HT1B receptors by SB-224289 was investigated in Guinea pigs which were dosed via intraperitoneal injection at a concentration of 4 mg/kg. SB-224289 had no effect on 5-HT levels in frontal cortex or striatum. In the dentate gyrus SB-224289 significantly increased extracellular 5-HT, reaching maxima of 151+/-19% of basal levels.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Human 5-HT1B and 5-HT1D receptors were stably transfected into the Chinese Hamster Ovary (ACC098) cell line. Competition studies were performed to determine the affinity of SB-224289 at both h5-HT1B and h5-HT1D receptor subtypes. SB-224289 was also equal to or greater than 75 fold selective for the h5-HT1B receptor over the other human 5-HT receptor subtypes exhibiting a pKi of 8 for human 5HT1B.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:14:44 GMT 2023
Edited
by admin
on Sat Dec 16 05:14:44 GMT 2023
Record UNII
F95C648W4N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SB 224289
Common Name English
J854.001B
Code English
SPIRO(2H-FURO(2,3-F)INDOLE-3(5H),4'-PIPERIDINE), 6,7-DIHYDRO-1'-METHYL-5-((2'-METHYL-4'-(5-METHYL-1,2,4-OXADIAZOL-3-YL)(1,1'-BIPHENYL)-4-YL)CARBONYL)-
Systematic Name English
SB-224289
Code English
(4-(2-METHYL-4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)PHENYL)PHENYL)-(1'-METHYLSPIRO(6,7-DIHYDRO-2H-FURO(2,3-F)INDOLE-3,4'-PIPERIDINE)-5-YL)METHANONE
Systematic Name English
(1'-METHYL-6,7-DIHYDRO-5H-SPIRO(FURO(2,3-F)INDOLE-3,4'-PIPERIDIN)-5-YL)(2'-METHYL-4'-(5-METHYL-1,2,4-OXADIAZOL-3-YL)BIPHENYL-4-YL)METHANONE
Systematic Name English
METHANONE, (2'-METHYL-4'-(5-METHYL-1,2,4-OXADIAZOL-3-YL)(1,1'-BIPHENYL)-4-YL)(2,5,6,7-TETRAHYDRO-1'-METHYLSPIRO(3H-FURO(2,3-F)INDOLE-3,4'-PIPERIDIN)-5-YL)-
Systematic Name English
(2'-METHYL-4'-(5-METHYL-1,2,4-OXADIAZOL-3-YL)-(1,1'-BIPHENYL)-4-YL)(1'-METHYL-6,7-DIHYDROSPIRO(FURO(2,3-F)INDOLE-3,4'-PIPERIDIN)-5(2H)-YL)METHANONE
Systematic Name English
6,7-DIHYDRO-1'-METHYL-5-((2'-METHYL-4'-(5-METHYL-1,2,4-OXADIAZOL-3-YL)-1,1'-BIPHENYL-4-YL)CARBONYL)SPIRO(2H-FURO(2,3-F)INDOLE-3(5H),4'-PIPERIDINE)
Systematic Name English
Code System Code Type Description
FDA UNII
F95C648W4N
Created by admin on Sat Dec 16 05:14:44 GMT 2023 , Edited by admin on Sat Dec 16 05:14:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID4043987
Created by admin on Sat Dec 16 05:14:44 GMT 2023 , Edited by admin on Sat Dec 16 05:14:44 GMT 2023
PRIMARY
CAS
180083-23-2
Created by admin on Sat Dec 16 05:14:44 GMT 2023 , Edited by admin on Sat Dec 16 05:14:44 GMT 2023
PRIMARY
PUBCHEM
3378093
Created by admin on Sat Dec 16 05:14:44 GMT 2023 , Edited by admin on Sat Dec 16 05:14:44 GMT 2023
PRIMARY
Related Record Type Details
Structure of SB 224289 HYDROCHLORIDE
SALT/SOLVATE -> PARENT
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