Adimolol

Chemical compound

none

Identifiers

IUPAC name

3-[3-[[2-hydroxy-3-(1-naphthyloxy)propyl]amino]-3-methyl-butyl]-1H-benzimidazol-2-one

CAS Number

78459-19-5^N

PubChem CID

71227

ChemSpider

64362^Y

UNII

B6CJY5K2ST

ChEMBL

ChEMBL1742448^N

Chemical and physical dataFormulaC₂₅H₂₉N₃O₃Molar mass419.525 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=C2Nc1ccccc1N2CCC(NCC(O)COc4c3ccccc3ccc4)(C)C

InChI

InChI=1S/C25H29N3O3/c1-25(2,14-15-28-22-12-6-5-11-21(22)27-24(28)30)26-16-19(29)17-31-23-13-7-9-18-8-3-4-10-20(18)23/h3-13,19,26,29H,14-17H2,1-2H3,(H,27,30)^Y
Key:YWRIUGFSIQMHJK-UHFFFAOYSA-N^Y

^NY (what is this?) (verify)

Adimolol (developmental code name MEN-935) is antihypertensive agent which acts as a non-selective α₁-, α₂-, and β-adrenergic receptor antagonist.^[1]

Synthesis

The reaction between 1-Naphthyl glycidyl ether [2461-42-9] (1) and 3-(3-amino-3-methylbutyl)-1H-benzimidazol-2-one [64928-58-1] (2) gives adimolol (3).

References

^ Palluk R, Hoefke W, Gaida W, Mierau J, Bechtel WD (July 1986). "Interactions of MEN 935 (adimolol), a long acting beta- and alpha-adrenolytic antihypertensive agent, with postsynaptic alpha-adrenoceptors in different isolated blood vessels--influence of angiotensin II". Naunyn-Schmiedeberg's Archives of Pharmacology. 333 (3): 277–83. doi:10.1007/bf00512941. PMID 3020439. S2CID 24300936.
^ Hoefke W, Gaida W, Palluk R, Mentrup A (1986). "Adimolol Hydrochloride Hydrate". Drugs of the Future. 11: 9. doi:10.1358/dof.1986.011.01.62036.
^ US 4255430, Koppe H, Mentrup A, Renth EO, Schromm K, Hoefke W, Muacevic G, issued 1981, assigned to Boehringer Ingelheim Gmbh.

Sympatholytic (and closely related) antihypertensives (C02)

Sympatholytics
(antagonize α-adrenergic
vasoconstriction)

Central

α₂-Adrenergic receptor agonists	Clonidine Guanabenz Guanfacine Guanoxabenz Methyldopa^# Tiamenidine^‡
Adrenergic release inhibitors	Bethanidine Bretylium Debrisoquine Guanadrel Guanazodine Guancydine Guanethidine Guanoclor Guanoxan
Imidazoline receptor agonists	Moxonidine Rilmenidine Tolonidine
Ganglion-blocking/nicotinic antagonists	Hexamethonium^‡ Mecamylamine Pentolinium Trimethaphan

Peripheral

Indirect

Monoamine oxidase inhibitors	Pargyline^‡
VMAT inhibitors	Bietaserpine Deserpidine Methoserpidine Reserpine Syrosingopine
Tyrosine hydroxylase inhibitors	Metirosine

Direct

α₁-Adrenergic receptor blockers	Doxazosin Ketanserin Indoramin Prazosin Trimazosin Urapidil
Non-selective α-adrenergic receptor blockers	Phentolamine

Other antagonists

Serotonin receptor antagonists	Ketanserin Lidanserin
Endothelin receptor antagonists (for PHTooltip Pulmonary hypertension)	dual (Aprocitentan, Bosentan, Macitentan (+tadalafil)) selective (Ambrisentan, Sitaxentan)