Arylacenamide

Identification

Name
Arylacenamide
Accession Number
DB05792
Type
Small Molecule
Groups
Investigational
Description

Arylacenamide (SR31747) is a peripheral [sigma] ligand that binds four proteins in human cells, i.e. SRBP-1, [sigma]-2, HSI and its relative SRBP-2. It is a dual agent with both immunomodulatory and antiproliferative activities.

Structure
Thumb
Synonyms
Not Available
External IDs
SR 31747 / SR-31747
Categories
UNII
9K6U3I1UR0
CAS number
132173-07-0
Weight
Average: 396.437
Monoisotopic: 395.214655539
Chemical Formula
C23H35Cl2N
InChI Key
HKHPCMBPASXYGP-KVVVOXFISA-N
InChI
InChI=1S/C23H34ClN.ClH/c1-2-25(21-13-7-4-8-14-21)17-9-10-19-15-16-22(23(24)18-19)20-11-5-3-6-12-20;/h9-10,15-16,18,20-21H,2-8,11-14,17H2,1H3;1H/b10-9-;
IUPAC Name
N-[(2Z)-3-(3-chloro-4-cyclohexylphenyl)prop-2-en-1-yl]-N-ethylcyclohexanamine hydrochloride
SMILES
Cl.CCN(C\C=C/C1=CC(Cl)=C(C=C1)C1CCCCC1)C1CCCCC1

Pharmacology

Indication

Investigated for use/treatment in cancer/tumors (unspecified), immunosuppressive, and prostate cancer.

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action

SR31747 blocks proliferation of human lymphocytes, modulates the expression of pro- and anti-inflammatory cytokines, and was shown to protect animals in vivo against acute and chronic inflammatory conditions such as acute graft-versus-host reaction, lethality induced by staphylococcal enterotoxin B and lipopolysaccharide or rheumatoid arthritis. Besides these immunomodulatory activities, the molecule also inhibits the proliferation of various tumor cell lines in vitro in a time- and concentration-dependent manner.

TargetActionsOrganism
UHCG20471, isoform CRA_cNot AvailableHuman
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. Paul R, Silve S, De Nys N, Dupuy PH, Bouteiller CL, Rosenfeld J, Ferrara P, Le Fur G, Casellas P, Loison G: Both the immunosuppressant SR31747 and the antiestrogen tamoxifen bind to an emopamil-insensitive site of mammalian Delta8-Delta7 sterol isomerase. J Pharmacol Exp Ther. 1998 Jun;285(3):1296-302. [PubMed:9618436]
  2. Casellas P, Galiegue S, Bourrie B, Ferrini JB, Jbilo O, Vidal H: SR31747A: a peripheral sigma ligand with potent antitumor activities. Anticancer Drugs. 2004 Feb;15(2):113-8. [PubMed:15075666]
External Links
PubChem Compound
6439330
PubChem Substance
175427033
ChemSpider
4943746

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
logP7.4ChemAxon
pKa (Strongest Basic)9.95ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity111.68 m3·mol-1ChemAxon
Polarizability44.23 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9704
Caco-2 permeable+0.6889
P-glycoprotein substrateSubstrate0.6038
P-glycoprotein inhibitor IInhibitor0.8012
P-glycoprotein inhibitor IIInhibitor0.6996
Renal organic cation transporterInhibitor0.6689
CYP450 2C9 substrateNon-substrate0.7062
CYP450 2D6 substrateNon-substrate0.5748
CYP450 3A4 substrateSubstrate0.5727
CYP450 1A2 substrateInhibitor0.8699
CYP450 2C9 inhibitorNon-inhibitor0.8809
CYP450 2D6 inhibitorInhibitor0.7277
CYP450 2C19 inhibitorInhibitor0.7907
CYP450 3A4 inhibitorNon-inhibitor0.8447
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9049
Ames testNon AMES toxic0.7998
CarcinogenicityNon-carcinogens0.6462
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7869 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5173
hERG inhibition (predictor II)Inhibitor0.8518
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Styrenes
Direct Parent
Styrenes
Alternative Parents
Cyclohexylamines / Chlorobenzenes / Aryl chlorides / Trialkylamines / Organopnictogen compounds / Organochlorides / Hydrochlorides / Hydrocarbon derivatives
Substituents
Styrene / Chlorobenzene / Cyclohexylamine / Halobenzene / Aryl chloride / Aryl halide / Tertiary aliphatic amine / Tertiary amine / Organochloride / Organohalogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
SIGMAR1
Uniprot ID
Q5T1J1
Uniprot Name
HCG20471, isoform CRA_c
Molecular Weight
14852.655 Da

Drug created on November 18, 2007 11:27 / Updated on December 01, 2017 15:37