Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H17N3O2S |
Molecular Weight | 303.379 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C(N[C@H]1CN2CCC1CC2)C3=CNC4=C(SC=C4)C3=O
InChI
InChIKey=AFUWQWYPPZFWCO-LBPRGKRZSA-N
InChI=1S/C15H17N3O2S/c19-13-10(7-16-11-3-6-21-14(11)13)15(20)17-12-8-18-4-1-9(12)2-5-18/h3,6-7,9,12H,1-2,4-5,8H2,(H,16,19)(H,17,20)/t12-/m0/s1
Pumosetrag is a novel, orally active and selective 5-HT 3 agonist. It is a partial agonist in rats and guinea-pig and a full agonist in the mouse, suggesting important species differences in 5-HT3 receptor structure. Pumosetrag had been in phase II clinical trials for the treatment of gastroesophageal reflux disease and irritable bowel syndrome. No serious adverse events were reported. Diarrhea was not more common on the drug and only one subject experienced pruritus. All researches on this drug candidate are discontinued.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14616171 |
0.8 nM [Ki] | ||
Target ID: 483776.0 Gene Symbol: CHRM1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14616171 |
7.7 µM [Ki] | ||
Target ID: 403858.0 Gene Symbol: CHRM2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14616171 |
3.3 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [IC50 >10 uM] | ||||
inconclusive [IC50 >10 uM] | ||||
inconclusive [IC50 >10 uM] | ||||
inconclusive [IC50 >10 uM] | ||||
inconclusive [IC50 >10 uM] | ||||
yes [IC50 9.3 uM] |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of a novel 5-HT3 receptor agonist MKC-733 on upper gastrointestinal motility in humans. | 2003 Nov 15 |
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Effect of MKC-733, a 5-HT receptor partial agonist, on bowel motility and symptoms in subjects with constipation: an exploratory study. | 2005 Dec |
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Drug evaluation: Pumosetrag for the treatment of irritable bowel syndrome and gastroesophageal reflux disease. | 2007 May |
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Effects of the novel 5-HT3 agonist MKC-733 on the rat, mouse and guinea pig digestive tract. | 2008 |
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Inotropic effects of prokinetic agents with 5-HT(4) receptor agonist actions on human isolated myocardial trabeculae. | 2012 Apr 9 |
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Novel partial 5HT3 agonist pumosetrag reduces acid reflux events in uninvestigated GERD patients after a standard refluxogenic meal: a randomized, double-blind, placebo-controlled pharmacodynamic study. | 2014 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24001105
0.2, 0.5, or 0.8 mg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17952012
In the presence of methysergide (1 mol/l) and GR125487 (0.1 mol/l), MKC-733 appeared to have little to no contractile effect in the jejunum (E max = 11.85 %), ileum (E max = 9.65 %) and distal colon of the rat (E max = 14.30 %).
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C47794
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C84126
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DTXSID70165211
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153062-94-3
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1G26B32139
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CHEMBL1643880
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154104
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C482040
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DB12402
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)