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Identification
NameSR 31747
Accession NumberDB05792
TypeSmall Molecule
GroupsInvestigational
DescriptionSR31747 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
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII9K6U3I1UR0
CAS numberNot Available
WeightAverage: 396.437
Monoisotopic: 395.214655539
Chemical FormulaC23H35Cl2N
InChI KeyHKHPCMBPASXYGP-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
IndicationInvestigated for use/treatment in cancer/tumors (unspecified), immunosuppressive, and prostate cancer.
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionSR31747 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
HCG20471, isoform CRA_cProteinunknownNot AvailableHumanQ5T1J1 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropenes. These are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropenes
Direct ParentPhenylpropenes
Alternative Parents
Substituents
  • Phenylpropene
  • Styrene
  • Halobenzene
  • Cyclohexylamine
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hydrocarbon derivative
  • Hydrochloride
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
SIGMAR1
Uniprot ID:
Q5T1J1
Molecular Weight:
14852.655 Da
Comments
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Drug created on November 18, 2007 11:27 / Updated on August 17, 2016 12:24