Adimolol

{{Short description|Chemical compound}}

{{Distinguish|alimadol}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 477242598

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

| image = Adimolol.png

| width =

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 78459-19-5

| ATC_prefix = none

| ATC_suffix =

| PubChem = 71227

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1742448

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 64362

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = B6CJY5K2ST

| C=25 | H=29 | N=3 | O=3

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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = YWRIUGFSIQMHJK-UHFFFAOYSA-N

}}

Adimolol (developmental code name MEN-935) is antihypertensive agent which acts as a non-selective α1-, α2-, and β-adrenergic receptor antagonist.{{cite journal | vauthors = Palluk R, Hoefke W, Gaida W, Mierau J, Bechtel WD | title = 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 | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 333 | issue = 3 | pages = 277–83 |date=July 1986| pmid = 3020439 | doi = 10.1007/bf00512941| s2cid = 24300936 }}

Synthesis

The reaction between 1-naphthyl glycidyl ether (1) and 3-(3-amino-3-methylbutyl)-1H-benzimidazol-2-one (2) gives adimolol (3).{{cite journal | vauthors = Hoefke W, Gaida W, Palluk R, Mentrup A | title = Adimolol Hydrochloride Hydrate | journal = Drugs of the Future | date = 1986 | volume = 11 | page = 9 | doi = 10.1358/dof.1986.011.01.62036 }}{{cite patent | inventor = Koppe H, Mentrup A, Renth EO, Schromm K, Hoefke W, Muacevic G | country = US | number = 4255430 | gdate = 1981 | assign1 = Boehringer Ingelheim Gmbh }}

:File:Adimolol synthesis.svg{{clear-left}}

References