Amosulalol

Amosulalol
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (RS)-5-[1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide;
CAS Number	85320-68-9 ;
PubChem CID	2169;
ChemSpider	2084 ;
UNII	C69JI1BAU8;
KEGG	D07451 ;
ChEMBL	ChEMBL152231 ;
CompTox Dashboard (EPA)	DTXSID90868893 ;
Chemical and physical data
Formula	C18H24N2O5S
Molar mass	380.46 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C=C(C=C1)C(CNCCOC2=CC=CC=C2OC)O)S(=O)(=O)N;
	InChI InChI=1S/C18H24N2O5S/c1-13-7-8-14(11-18(13)26(19,22)23)15(21)12-20-9-10-25-17-6-4-3-5-16(17)24-2/h3-8,11,15,20-21H,9-10,12H2,1-2H3,(H2,19,22,23) ; Key:LVEXHFZHOIWIIP-UHFFFAOYSA-N ;

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Amosulalol (INN) is an antihypertensive drug. It has much higher affinity for α₁-adrenergic receptors than for β-adrenergic receptors.^[1] It is not approved for use in the United States.

Synthesis

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.^[2]^[3]^[4]

References

^ Sponer G, Bartsch W, Hooper RG (1990). "Drugs acting on multiple receptors: β-blockers with additional properties.". Pharmacology of antihypertensive therapeutics. Handbook of Experimental Pharmacology. Vol. 93. Berlin, Heidelberg: Springer. pp. 131–226 (183). doi:10.1007/978-3-642-74209-5_5. ISBN 978-3-642-74209-5.
^ US patent 4217305, Kazuo Imai, et al., "Phenylethanolamine derivatives", issued 1980-08-12, assigned to Yamanouchi Pharmaceutical Co. Ltd.
^ Arima, H.; Tamazawa, K.; Synthesis of 14C-labeled 5-[1-hydroxy-2-[2-(o-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide hydochloride (YM-09538). J Label Compd Radiopharm 1983, 20, 7, 803-811.
^ "Amosulalol". Pharmaceutical Substances. Thieme. Retrieved 2024-07-12.

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[1] Sponer G, Bartsch W, Hooper RG (1990). "Drugs acting on multiple receptors: β-blockers with additional properties.". Pharmacology of antihypertensive therapeutics. Handbook of Experimental Pharmacology. Vol. 93. Berlin, Heidelberg: Springer. pp. 131–226 (183). doi:10.1007/978-3-642-74209-5_5. ISBN 978-3-642-74209-5.

[2] US patent 4217305, Kazuo Imai, et al., "Phenylethanolamine derivatives", issued 1980-08-12, assigned to Yamanouchi Pharmaceutical Co. Ltd.

[3] Arima, H.; Tamazawa, K.; Synthesis of 14C-labeled 5-[1-hydroxy-2-[2-(o-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide hydochloride (YM-09538). J Label Compd Radiopharm 1983, 20, 7, 803-811.

[4] "Amosulalol". Pharmaceutical Substances. Thieme. Retrieved 2024-07-12.

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