Structure via PubChem · Public domain (PubChem)
Amosulalol
Sign in to saveAmosulalol (INN) is an antihypertensive drug. It has much higher affinity for α1-adrenergic receptors than for β-adrenergic receptors. It is not approved for use in the United States. ==Synthesis== upright=2|class=skin-invert-image
Chemical data
- Formula
- C18H24N2O5S
- Molecular weight
- 380.5 g/mol
- IUPAC name
- 5-[1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide
- SMILES
- CC1=C(C=C(C=C1)C(CNCCOC2=CC=CC=C2OC)O)S(=O)(=O)N
- InChIKey
- LVEXHFZHOIWIIP-UHFFFAOYSA-N
- XLogP
- 1.2
- Polar surface area
- 119 Ų
- H-bond donors
- 3
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
45 papers- Effects of (+)- and (-)-amosulalol on the rat isolated right ventricle.Journal of cardiovascular pharmacology · 1987
- Adrenoceptor blocking properties of the stereoisomers of amosulalol (YM-09538) and the corresponding desoxy derivative (YM-11133).The Journal of pharmacology and experimental therapeutics · 1986
- The effects of amosulalol, a novel combined alpha- and beta-adrenoreceptor antagonist, on the rat isolated right ventricle and aorta.Journal of autonomic pharmacology · 1985
- Amosulalol, a combined alpha and beta adrenoceptor antagonist: kinetics after intravenous and oral doses.Clinical pharmacology and therapeutics · 1984
- Effect of topical amosulalol on tissue circulation in the optic nerve head.Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics · 1999
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 380.141
Show 4 more facts
- chemical formula
- C₁₈H₂₄N₂O₅S
- canonical SMILES
- CC1=C(C=C(C=C1)C(CNCCOC2=CC=CC=C2OC)O)S(=O)(=O)N
- subject has role
- beta blocker
- Commons category
- Amosulalol
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
Amosulalol (INN) is an antihypertensive drug. It has much higher affinity for α1-adrenergic receptors than for β-adrenergic receptors. It is not approved for use in the United States. ==Synthesis== upright=2|class=skin-invert-image
Guaiacol (1) reacts with ethylene oxide to give 2-(2-methoxyphenoxy)ethanol (2). Halogenation with thionyl chloride converts the alcohol group to a chloride, (3), which is used to alkylate benzylamine (4) to give the secondary amine (5). This forms a tertiary amine (7) when combined with 5-bromoacetyl-2-methylbenzenesulfonamide (6). The reduction of the carbonyl group with sodium borohydride produces (8) and catalytic hydrogenation removes the benzyl group, yielding amosulalol.
Excerpted from Wikipedia’s “Amosulalol” article, available under the CC BY-SA 4.0 licence.