SR 140333

Identification

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Name
SR 140333
Accession Number
DB05790
Type
Small Molecule
Groups
Investigational
Description

SR 140333 is tachykinin antagonist which has potential to treat diarrhoea due to food allergy or inflammatory bowel disease.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 656.124
Monoisotopic: 654.254661815
Chemical Formula
C37H45Cl3N2O2
InChI Key
NQHFSECYQAQZBN-SJYHNBSJSA-M
InChI
InChI=1S/C37H45Cl2N2O2.ClH/c1-28(2)43-32-11-6-8-29(24-32)25-35(42)40-19-7-14-37(27-40,31-12-13-33(38)34(39)26-31)18-23-41-20-15-36(16-21-41,17-22-41)30-9-4-3-5-10-30;/h3-6,8-13,24,26,28H,7,14-23,25,27H2,1-2H3;1H/q+1;/p-1/t36?,37-,41?;/m0./s1
IUPAC Name
1-{2-[(3R)-3-(3,4-dichlorophenyl)-1-{2-[3-(propan-2-yloxy)phenyl]acetyl}piperidin-3-yl]ethyl}-4-phenyl-1-azabicyclo[2.2.2]octan-1-ium chloride
SMILES
[Cl-].CC(C)OC1=CC=CC(CC(=O)N2CCC[C@](CC[N+]34CCC(CC3)(CC4)C3=CC=CC=C3)(C2)C2=CC(Cl)=C(Cl)C=C2)=C1

Pharmacology

Indication

Investigated for use/treatment in asthma and inflammatory bowel disease.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USubstance-P receptorNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Biyah K, Molimard M, Emonds-Alt X, Advenier C: SR 140333 prevents potentiation by citric acid of plasma exudation induced by histamine in airways. Eur J Pharmacol. 1996 Jul 25;308(3):325-8. [PubMed:8858307]
  2. Girard V, Naline E, Vilain P, Emonds-Alt X, Advenier C: Effect of the two tachykinin antagonists, SR 48968 and SR 140333, on cough induced by citric acid in the unanaesthetized guinea pig. Eur Respir J. 1995 Jul;8(7):1110-4. [PubMed:7589394]
External Links
PubChem Compound
5311449
PubChem Substance
175427031
ChemSpider
4470935

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.87e-07 mg/mLALOGPS
logP4.44ALOGPS
logP3.45ChemAxon
logS-9.1ALOGPS
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity189.03 m3·mol-1ChemAxon
Polarizability70.41 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5326
Blood Brain Barrier+0.9843
Caco-2 permeable+0.549
P-glycoprotein substrateSubstrate0.7519
P-glycoprotein inhibitor IInhibitor0.7379
P-glycoprotein inhibitor IIInhibitor0.8435
Renal organic cation transporterInhibitor0.5611
CYP450 2C9 substrateNon-substrate0.8304
CYP450 2D6 substrateNon-substrate0.5824
CYP450 3A4 substrateSubstrate0.8339
CYP450 1A2 substrateNon-inhibitor0.7494
CYP450 2C9 inhibitorNon-inhibitor0.7366
CYP450 2D6 inhibitorNon-inhibitor0.527
CYP450 2C19 inhibitorNon-inhibitor0.5732
CYP450 3A4 inhibitorNon-inhibitor0.8502
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6063
Ames testNon AMES toxic0.7741
CarcinogenicityNon-carcinogens0.8017
BiodegradationNot ready biodegradable0.9571
Rat acute toxicity2.8055 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8739
hERG inhibition (predictor II)Inhibitor0.8234
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Phenylacetamides / N-acylpiperidines / Quinuclidines / Phenoxy compounds / Phenol ethers / Dichlorobenzenes / Alkyl aryl ethers / Aralkylamines / Aryl chlorides / Tetraalkylammonium salts
show 8 more
Substituents
Phenylpiperidine / Phenylacetamide / N-acyl-piperidine / 1,2-dichlorobenzene / Phenoxy compound / Phenol ether / Quinuclidine / Alkyl aryl ether / Chlorobenzene / Halobenzene
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tachykinin receptor activity
Specific Function
This is a receptor for the tachykinin neuropeptide substance P. It is probably associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of aff...
Gene Name
TACR1
Uniprot ID
P25103
Uniprot Name
Substance-P receptor
Molecular Weight
46250.5 Da

Drug created on November 18, 2007 11:27 / Updated on June 04, 2019 06:19