General Information of Drug (ID: DMSPJX9)

Drug Name
BEMESETRON
Synonyms
3-Tropanyl-3,5-dichlorobenzoate; MDL 72222; MDL-72222; C15H17Cl2NO2; CHEMBL376379; 40796-97-2; Tropyl 3,5-dichlorobenzoate; 8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3,5-dichlorobenzoate; Bemesetron [USAN:INN]; Bemesetronum [INN-Latin]; 3,5-Dichloro-benzoic acid 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester; SR-01000075587; Tropanyl 3,5-dichlorobenzoate; 1alphaH,5alphaH-Tropan-3alpha-yl 3,5-dichlorobenzoate; endo-8-Methyl-8-azabicyclo(3.2.1)oct-3-yl 3,5-dichlorobenzoate; (8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 3,5-dichlorobenzo
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 314.2
Topological Polar Surface Area (xlogp) 4.2
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C15H17Cl2NO2
IUPAC Name
[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3,5-dichlorobenzoate
Canonical SMILES
CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C3=CC(=CC(=C3)Cl)Cl
InChI
InChI=1S/C15H17Cl2NO2/c1-18-12-2-3-13(18)8-14(7-12)20-15(19)9-4-10(16)6-11(17)5-9/h4-6,12-14H,2-3,7-8H2,1H3/t12-,13+,14?
InChIKey
MNJNPLVXBISNSX-PBWFPOADSA-N
Cross-matching ID
PubChem CID
671690
CAS Number
40796-97-2
TTD ID
D0V3GT

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
5-HT 3A receptor (HTR3A) TTPC4TU 5HT3A_HUMAN Inhibitor [1]
5-HT 3B receptor (HTR3B) TTR6K75 5HT3B_HUMAN Inhibitor [1]
Adenosine A3 receptor (ADORA3) TTJFY5U AA3R_HUMAN Inhibitor [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
5-HT 3B receptor (HTR3B) DTT HTR3B 3.82E-01 0.04 0.1
5-HT 3A receptor (HTR3A) DTT HTR3A 6.60E-01 1.08E-02 0.04
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Zatosetron, a potent, selective, and long-acting 5HT3 receptor antagonist: synthesis and structure-activity relationships. J Med Chem. 1992 Jan 24;35(2):310-9.
2 2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and analogues as A2A adenosine receptor antagonists. Design, synthesis, and pharmacolog... J Med Chem. 2005 Nov 3;48(22):6887-96.
3 A role for central A3-adenosine receptors. Mediation of behavioral depressant effects. FEBS Lett. 1993 Dec 20;336(1):57-60.
4 2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists. Bioorg Med Chem. 2010 Mar 15;18(6):2195-2203.
5 Spiroindolones, a potent compound class for the treatment of malaria. Science. 2010 Sep 3;329(5996):1175-80.
6 2011 Pipeline of Can-Fite BioPharm.
7 Synthesis and evaluation of 1,2,4-triazolo[1,5-c]pyrimidine derivatives as A2A receptor-selective antagonists. Bioorg Med Chem Lett. 2010 Oct 1;20(19):5690-4.
8 Protein kinase C protects preconditioned rabbit hearts by increasing sensitivity of adenosine A2b-dependent signaling during early reperfusion. J Mol Cell Cardiol. 2007 Sep;43(3):262-71.
9 Novel amino acid derived natural products from the ascidian Atriolum robustum: identification and pharmacological characterization of a unique aden... J Med Chem. 2004 Apr 22;47(9):2243-55.
10 Novel potent and selective central 5-HT3 receptor ligands provided with different intrinsic efficacy. 2. Molecular basis of the intrinsic efficacy ... J Med Chem. 1999 May 6;42(9):1556-75.
11 The 5-HT3B subunit is a major determinant of serotonin-receptor function. Nature. 1999 Jan 28;397(6717):359-63.
12 Novel and highly potent 5-HT3 receptor agonists based on a pyrroloquinoxaline structure. J Med Chem. 1997 Oct 24;40(22):3670-8.
13 Ginkgolide B and bilobalide block the pore of the 5-HT eceptor at a location that overlaps the picrotoxin binding site. Neuropharmacology. 2011 Feb-Mar;60(2-3):488-95.
14 Synthesis and structure-affinity relationships of novel N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)pyridine-3-carboxamides with potent serotoni... J Med Chem. 2003 Feb 27;46(5):702-15.
15 Co-expression of the 5-HT(3B) subunit with the 5-HT(3A) receptor reduces alcohol sensitivity. Brain Res Mol Brain Res. 2005 Dec 14;142(2):146-50.
16 Pharmacological comparison of human homomeric 5-HT3A receptors versus heteromeric 5-HT3A/3B receptors. Neuropharmacology. 2001 Aug;41(2):282-4.
17 Palonosetron plus dexamethasone versus granisetron plus dexamethasone for prevention of nausea and vomiting during chemotherapy: a double-blind, do... Lancet Oncol. 2009 Feb;10(2):115-24.
18 Efficacy of 5-HT3 antagonists and 5-HT4 agonists in irritable bowel syndrome: systematic review and meta-analysis. Am J Gastroenterol. 2009 Jul;104(7):1831-43; quiz 1844.
19 Emerging therapies for fibromyalgia. Expert Opin Emerg Drugs. 2008 Mar;13(1):53-62.
20 Management of postoperative nausea and vomiting: focus on palonosetron. Ther Clin Risk Manag. 2009 Feb;5(1):21-34.
21 2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
22 Local anesthetics have different mechanisms and sites of action at recombinant 5-HT3 receptors. Reg Anesth Pain Med. 2007 Nov-Dec;32(6):462-70.
23 Cilansetron: a new serotonergic agent for the irritable bowel syndrome with diarrhoea.Expert Opin Investig Drugs.2005 Feb;14(2):185-93.
24 mu-Opioid/5-HT4 dual pharmacologically active agents-efforts towards an effective opioid analgesic with less GI and respiratory side effects (Part I). Bioorg Med Chem Lett. 2009 Oct 1;19(19):5679-83.
25 Effect of serotonin (5-HT)3-receptor antagonists YM060, YM114 (KAE-393), ondansetron and granisetron on 5-HT4 receptors and gastric emptying in rodents. Jpn J Pharmacol. 1995 Nov;69(3):205-14.