Proadifen

Proadifen
Names
	IUPAC name 2-Diethylaminoethyl 2,2-diphenylpentanoate
	Other names SKF 525-A
Identifiers
CAS Number	302-33-0;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL282567;
ChemSpider	4741;
PubChem CID	4910;
UNII	A510CA4CBT ;
CompTox Dashboard (EPA)	DTXSID2048452 ;
	InChI InChI=1S/C23H31NO2/c1-4-17-23(20-13-9-7-10-14-20,21-15-11-8-12-16-21)22(25)26-19-18-24(5-2)6-3/h7-16H,4-6,17-19H2,1-3H3;
	SMILES O=C(OCCN(CC)CC)C(c1ccccc1)(c2ccccc2)CCC;
Properties
Chemical formula	C23H31NO2
Molar mass	353.506 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Proadifen (SKF-525A) is a non-selective inhibitor of cytochrome P450 enzymes, preventing some types of drug metabolism.[1] 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.[2]

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.[3]

Proadifen has been demonstrated to inhibit the nicotinic acetylcholine receptor (NAChR) and muscarinic acetylcholine receptor (MAChR) in rats.[2]

References

Marshall, FN; Williamson, HE (1964). "Natruretic Response During Infusion of Beta-Diethylaminoethyl-Diphenylpropyl Acetate Hydrocloride (Skf 525-A)". The Journal of Pharmacology and Experimental Therapeutics. 143: 395–400. PMID 14161153.
"Proadifen hydrochloride (CAS 62-68-0)". Santa Cruz Biotech.
Jendželovský R, Koval J, Mikeš J, Papčová Z, Plšíková J, Fedoročko P (September 2012). "Inhibition of GSK-3β reverses the pro-apoptotic effect of proadifen (SKF-525A) in HT-29 colon adenocarcinoma cells". Toxicol In Vitro. 26 (6): 775–82. doi:10.1016/j.tiv.2012.05.014. PMID 22683934.

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[1] Marshall, FN; Williamson, HE (1964). "Natruretic Response During Infusion of Beta-Diethylaminoethyl-Diphenylpropyl Acetate Hydrocloride (Skf 525-A)". The Journal of Pharmacology and Experimental Therapeutics. 143: 395–400. PMID 14161153.

[datasheet-2] "Proadifen hydrochloride (CAS 62-68-0)". Santa Cruz Biotech.

[pmid22683934-3] Jendželovský R, Koval J, Mikeš J, Papčová Z, Plšíková J, Fedoročko P (September 2012). "Inhibition of GSK-3β reverses the pro-apoptotic effect of proadifen (SKF-525A) in HT-29 colon adenocarcinoma cells". Toxicol In Vitro. 26 (6): 775–82. doi:10.1016/j.tiv.2012.05.014. PMID 22683934.