OPC-28326

Status : investigational

Description

At low doses, OPC 28326 selectively vasodilates the femoral arterial bed due to its inhibitory action at alpha-2-adrenoceptors while having minimal action on systemic blood pressure, heart rate and coronary, carotid, vertebral, renal, and mesenteric blood flows. It is the only clinical compound with this profile. It is currently being investigated in the treatment of peripheral vascular diseases and Raynaud’s syndrome.

Used

Investigated for use/treatment in peripheral vascular disease and raynaud’s disease.

Mechanism Of Action

At low doses, OPC 28326 selectively vasodilates the femoral arterial bed due to its inhibitory action at alpha-2C-adrenoceptors. Other studies have also reported selectivity for a-2B-adrenoceptors.

Pharmacodynamics

At low doses, OPC 28326 selectively vasodilates the femoral arterial bed due to its inhibitory action at alpha-2-adrenoceptors while having minimal action on systemic blood pressure, heart rate and coronary, carotid, vertebral, renal, and mesenteric blood flows.

Toxic Effect

10 mg and 40 mg was well tolerated during clinical trials with Raynaud’s patients

Chemical Classification

This compound belongs to the class of organic compounds known as 1-benzoylpiperidines. These are compounds containing a piperidine ring substituted at the 1-position with a benzoyl group.

1-benzoylpiperidines

Organic compounds

Benzenoids

Benzene and substituted derivatives

Benzoyl derivatives

Calculated Property

kind Value Source
logP 4.28 ChemAxon
IUPAC Name N-(2,6-dimethyl-4-{4-[methyl(2-phenylethyl)amino]piperidine-1-carbonyl}phenyl)propanamide hydrate hydrochloride ChemAxon
Traditional IUPAC Name N-(2,6-dimethyl-4-{4-[methyl(2-phenylethyl)amino]piperidine-1-carbonyl}phenyl)propanamide hydrate hydrochloride ChemAxon
Molecular Weight 476.051 ChemAxon
Monoisotopic Weight 475.260169804 ChemAxon
SMILES O.Cl.CCC(=O)NC1=C(C)C=C(C=C1C)C(=O)N1CCC(CC1)N(C)CCC1=CC=CC=C1 ChemAxon
Molecular Formula C26H38ClN3O3 ChemAxon
InChI InChI=1S/C26H35N3O2.ClH.H2O/c1-5-24(30)27-25-19(2)17-22(18-20(25)3)26(31)29-15-12-23(13-16-29)28(4)14-11-21-9-7-6-8-10-21;;/h6-10,17-18,23H,5,11-16H2,1-4H3,(H,27,30);1H;1H2 ChemAxon
InChIKey InChIKey=QRNMKZJPTYRAIL-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 52.65 ChemAxon
Refractivity 129.32 ChemAxon
Polarizability 49.91 ChemAxon
Rotatable Bond Count 7 ChemAxon
H Bond Acceptor Count 3 ChemAxon
H Bond Donor Count 1 ChemAxon
pKa (strongest acidic) 13.85 ChemAxon
pKa (strongest basic) 9.71 ChemAxon
Physiological Charge 1 ChemAxon
Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 1 ChemAxon

Target within organism

  • 5-hydroxytryptamine receptor 2B : in Human
  • Alpha-2C adrenergic receptor : in Human
  • Alpha-2B adrenergic receptor : in Human