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
SMILES
COC1=CC2=C(C=C1C(F)(F)F)N(CC2)C(=O)NC3=CC(=CC(F)=C3)C4=CC=CN=C4
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)
| 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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10188965
Curator's Comment: Referenced study was conducted in rats
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10188965
Curator's Comment: SmithKline Beecham has merged with Glaxo Wellcome to form GlaxoSmithKline
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10737744 |
9.0 null [pKi] | ||
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10737744 |
6.9 null [pKi] | ||
Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10737744 |
8.0 null [pKi] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 5-HT(2B) antagonism arrests non-canonical TGF-β1-induced valvular myofibroblast differentiation. | 2012-11 |
|
| 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. | 2000-03-23 |
|
| Attenuation of haloperidol-induced catalepsy by a 5-HT2C receptor antagonist. | 1999-02 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10188965
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10188965
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
Edited
Mon Mar 31 21:54:43 GMT 2025
by
admin
on
Mon Mar 31 21:54:43 GMT 2025
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| Record UNII |
5RDN2E8E97
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| Record Status |
Validated (UNII)
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| Record Version |
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SB-228357
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181629-93-6
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DTXSID9042621
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443390
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5RDN2E8E97
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