Arylacenamide
Identification
- Generic Name
- Arylacenamide
- DrugBank Accession Number
- DB05792
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 396.437
Monoisotopic: 395.214655539 - Chemical Formula
- C23H35Cl2N
- Synonyms
- Not Available
- External IDs
- SR 31747
- SR-31747
Pharmacology
- Indication
Investigated for use/treatment in cancer/tumors (unspecified), immunosuppressive, and prostate cancer.
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- 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.
Target Actions Organism UHCG20471, isoform CRA_c Not Available Humans - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Amine / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Cyclohexylamine / Halobenzene / Hydrocarbon derivative / Hydrochloride / Organic nitrogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 9K6U3I1UR0
- CAS number
- 132173-07-0
- 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
References
- General References
- 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. [Article]
- 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. [Article]
- External Links
Clinical Trials
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
Property Value Source Water Solubility 1.93e-05 mg/mL ALOGPS logP 7.48 ALOGPS logP 7.4 Chemaxon logS -7.3 ALOGPS pKa (Strongest Basic) 9.95 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 3.24 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 111.68 m3·mol-1 Chemaxon Polarizability 44.21 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9704 Caco-2 permeable + 0.6889 P-glycoprotein substrate Substrate 0.6038 P-glycoprotein inhibitor I Inhibitor 0.8012 P-glycoprotein inhibitor II Inhibitor 0.6996 Renal organic cation transporter Inhibitor 0.6689 CYP450 2C9 substrate Non-substrate 0.7062 CYP450 2D6 substrate Non-substrate 0.5748 CYP450 3A4 substrate Substrate 0.5727 CYP450 1A2 substrate Inhibitor 0.8699 CYP450 2C9 inhibitor Non-inhibitor 0.8809 CYP450 2D6 inhibitor Inhibitor 0.7277 CYP450 2C19 inhibitor Inhibitor 0.7907 CYP450 3A4 inhibitor Non-inhibitor 0.8447 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9049 Ames test Non AMES toxic 0.7998 Carcinogenicity Non-carcinogens 0.6462 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7869 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5173 hERG inhibition (predictor II) Inhibitor 0.8518
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 186.56691 predictedDeepCCS 1.0 (2019) [M+H]+ 188.92491 predictedDeepCCS 1.0 (2019) [M+Na]+ 195.82036 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- 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 at November 18, 2007 18:27 / Updated at June 12, 2020 16:52