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Details

Stereochemistry ACHIRAL
Molecular Formula C22H17F4N3O2
Molecular Weight 431.3829
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SB-228357

SMILES

COC1=C(C=C2N(CCC2=C1)C(=O)NC3=CC(=CC(F)=C3)C4=CC=CN=C4)C(F)(F)F

InChI

InChIKey=RRJLJKRFFRZRAF-UHFFFAOYSA-N
InChI=1S/C22H17F4N3O2/c1-31-20-9-13-4-6-29(19(13)11-18(20)22(24,25)26)21(30)28-17-8-15(7-16(23)10-17)14-3-2-5-27-12-14/h2-3,5,7-12H,4,6H2,1H3,(H,28,30)

HIDE SMILES / InChI

Molecular Formula C22H17F4N3O2
Molecular Weight 431.3829
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

SB-228357 was originally developed by scientists at Smith Kline Beecham (now merged with Glaxo Welcome to form GlaxoSmithKline). SB-228357 was identified as an antagonist of the serotonin receptors 5-HT2a/b/c with the highest affinity exhibited towards the 5-HT2C receptor. SB-228357 was identified for preclinical development as a treatment for depression, anxiety, and cataplexy but has not progressed beyond animal trials.

CNS Activity

Curator's Comment: Referenced study was conducted in rats

Originator

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.0 null [pKi]
6.9 null [pKi]
8.0 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Attenuation of haloperidol-induced catalepsy by a 5-HT2C receptor antagonist.
1999 Feb
Biarylcarbamoylindolines are novel and selective 5-HT(2C) receptor inverse agonists: identification of 5-methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]- 5-pyridyl]carbamoyl]-6-trifluoromethylindoline (SB-243213) as a potential antidepressant/anxiolytic agent.
2000 Mar 23
5-HT(2B) antagonism arrests non-canonical TGF-β1-induced valvular myofibroblast differentiation.
2012 Nov
Patents

Sample Use Guides

Catalepsy was induced in Male Sprague-Dawley rats by intraperitoneal injection of 1 ml kg−1 Haloperidol dissolved with an equal weight of tartaric acid. Rats were tested for catalepsy by positioning them such that their hindquarters rested on the bench while their forelimbs rested on a 1 cm diameter horizontal bar, 10 cm above the bench. The time that the rats maintained this position was recorded up to 120 seconds maximum. Rats were labeled cataplexic if they maintained the position for more than 30 seconds. The test was repeated 30, 60 and 90 min after drug administration. SB-228357 significantly attenuated haloperidol-induced catalepsy when dosed orally at 0.32–10 mg/kg by dissolving in one drop of BRIJ-35 and diluting in 1% methylcellulose (final delivery volume of 2 ml/kg).
Route of Administration: Oral
Radioligand binding assays were carried out with homogenates of human recombinant 5-HT2A, 5-HT2B, and 5-HT2C receptors expressed in Human Embryo Kidney (HEK293) cells. Cells were incubated with 0.01 nM – 0.01 mM SB-22837 for 30–45 min along with 0.5 nm [3H]-ketanserin (5-HT2A), 8 nm [3H]-5-HT (5-HT2B) or 0.6 nm [3H]-mesulergine (5-HT2C). SB-22837 exhibited the following pKi binding profiles: 5-HT2A pKi = 6.97; 5-HT2B pKi = 8.14; and 5-HT2C pKi = 9.14.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:09:17 GMT 2023
Edited
by admin
on Sat Dec 16 08:09:17 GMT 2023
Record UNII
5RDN2E8E97
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SB-228357
Common Name English
1H-INDOLE-1-CARBOXAMIDE, N-(3-FLUORO-5-(3-PYRIDINYL)PHENYL)-2,3-DIHYDRO-5-METHOXY-6-(TRIFLUOROMETHYL)-
Systematic Name English
J1.060.588A
Code English
N-(3-(3-PYRIDINYL)-5-FLUOROPHENYL)-5-METHOXY-6-(TRIFLUOROMETHYL)INDOLINE-1-CARBOXAMIDE
Systematic Name English
Code System Code Type Description
WIKIPEDIA
SB-228357
Created by admin on Sat Dec 16 08:09:17 GMT 2023 , Edited by admin on Sat Dec 16 08:09:17 GMT 2023
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CAS
181629-93-6
Created by admin on Sat Dec 16 08:09:17 GMT 2023 , Edited by admin on Sat Dec 16 08:09:17 GMT 2023
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EPA CompTox
DTXSID9042621
Created by admin on Sat Dec 16 08:09:17 GMT 2023 , Edited by admin on Sat Dec 16 08:09:17 GMT 2023
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PUBCHEM
443390
Created by admin on Sat Dec 16 08:09:17 GMT 2023 , Edited by admin on Sat Dec 16 08:09:17 GMT 2023
PRIMARY
FDA UNII
5RDN2E8E97
Created by admin on Sat Dec 16 08:09:17 GMT 2023 , Edited by admin on Sat Dec 16 08:09:17 GMT 2023
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