Compound: proadifen
SMILES: O=C(OCCN(CC)CC)C(c1ccccc1)(c2ccccc2)CCC
InChIKey: SNTQPLDRUZOSDP-UHFFFAOYSA-N
Synonyms: proadifen, 302-33-0, Proadifene, Proadifeno, Proadifenum, Propyladiphenin, A510CA4CBT, DTXSID2048452, Benzeneacetic acid, alpha-phenyl-alpha-propyl-, 2-(diethylamino)ethyl ester, RefChem:176093, DTXCID8028426, Acetate, Diethylaminoethyldiphenylpropyl, Diethylaminoethyldiphenylpropyl Acetate, Ethyl aprofen, Proadifen [INN], 2-(Diethylamino)ethyl 2,2-diphenylpentanoate, HL 8727, 2-Diethylaminoethyl propyldiphenylacetate, 2-Diethylaminoethyl-2,2-diphenylvalerate, ACETIC ACID, PROPYLDIPHENYL-, 2-(DIETHYLAMINO)ETHYL ESTER, AV 54315, Benzeneacetic acid, .alpha.-phenyl-.alpha.-propyl-, 2-(diethylamino)ethyl ester, CHEMBL282567, Valeric acid, 2,2-diphenyl-, 2-(diethylamino)ethyl ester, Proadifene [INN-French], Proadifenum [INN-Latin], Proadifeno [INN-Spanish], NSC39690, CCRIS 7248, NSC170997, CAS-62-68-0, UNII-A510CA4CBT, BRN 2478573, AI3-22951, 2-(Diethylamino)ethyl 2,2-diphenylvalerate hydrochloride, 2,2-Diphenylpentansaeure-2-diethylaminoethylester, 2-Diethylaminoethyl .alpha.,.alpha.-diphenyl valerate hydrochloride, Spectrum_001487, 2-diethylaminoethyl 2,2-diphenylpentanoate, Prestwick0_000778, Prestwick1_000778, Prestwick2_000778, Prestwick3_000778, Spectrum2_000924, Spectrum3_001172, Spectrum4_000328, Spectrum5_001164, Lopac-P-1061, Lopac0_000906, BSPBio_000856, BSPBio_002783, KBioGR_000675, KBioSS_001967, 4-09-00-02566 (Beilstein Handbook Reference), 5171 RP (Salt/Mix), RP 5171 (Salt/Mix), DivK1c_000737, SCHEMBL122630, SPBio_000828, SPBio_002795, SKF-525-A (Salt/Mix), BPBio1_000942, orb1707016, NSC-39690 (Salt/Mix), CHEBI:92811, KBio1_000737, KBio2_001967, KBio2_004535, KBio2_007103, KBio3_002283, NINDS_000737, SNTQPLDRUZOSDP-UHFFFAOYSA-N, Proadifen hydrochloride (Salt/Mix), BDBM50017716, HSCI1_000231, STK049476, AKOS003658590, CCG-204988, SDCCGSBI-0050881.P004, IDI1_000737, NCGC00015799-01, NCGC00015799-02, NCGC00015799-03, NCGC00015799-04, NCGC00015799-11, NCGC00162290-01, SBI-0050881.P003, AB00053629, CS-0083304, NS00015025, 2-(Diethylamino)ethyl 2,2-diphenylpentanoate #, AB00053629_10, AB00053629_11, 2-(DIETHYLAMINO)ETHYL-2,2-DIPHENYLVALERATE, Q7246819, 2,2-Diphenylvaleric acid 2-(diethylamino)ethyl ester, 2-Benzhydryl-pentanoic acid 2-diethylamino-ethyl ester, BRD-K46317332-003-05-3, BRD-K46317332-003-06-1, BRD-K46317332-003-10-3, BRD-K46317332-003-16-0, BRD-K46317332-003-17-8, BRD-K46317332-003-18-6, 2,2-Diphenyl-pentanoic acid 2-diethylamino-ethyl ester
Theoretical properties:
molecular_formula: C23H31NO2
molecular_weight: 353.5 g/mol
exact_mass: 353.235479232 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 11
heavy_atom_count: 26
topological_polar_surface_area: 29.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 2,2-diphenylpentanoic acid 2-(diethylamino)ethyl ester is a diarylmethane.
chembl: PROADIFEN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Proadifen (SKF-525A) is a non-selective inhibitor of cytochrome P450 enzymes, preventing some types of drug metabolism. It is also an inhibitor of neuronal nitric oxide synthase (NOS), CYP-dependent (cytochrome P450-dependent) arachidonate metabolism, transmembrane calcium influx, and platelet thromboxane synthesis. Further documented effects include the blockade of ATP-sensitive inward rectifier potassium channel 8 (KIR6.1), and stimulation of endothelial cell prostacyclin production.
Proadifen exerts apoptotic/anti-proliferate (tumour suppressing) effects in certain forms of cancer (HT-29 colon adenocarcinoma), believed to be caused by mediation of glycogen synthase kinase 3 β (GSK-3β). In the same study administration of proadifen was demonstrated to produce time- and dose-dependent phosphatidylserine externalization, caspase-3 activation and PARP cleavage. Intense upregulation of NAG-1 and ATF3 and downregulation of Mcl-1 and Egr-1 were also observed.
Proadifen has been demonstrated to normally inhibit the nicotinic acetylcholine receptor (NAChR) and muscarinic acetylcholine receptor (MAChR) in rats.