Urapidil

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Urapidil
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	C02CA06 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 6-({3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}amino)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione;
CAS Number	34661-75-1 ; 64887-14-5 (HCl);
PubChem CID	5639;
ChemSpider	5437;
UNII	A78GF17HJS;
ChEMBL	ChEMBL279229;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C20H29N5O3
Molar mass	387.48 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C1\C=C(/N(C(=O)N1C)C)NCCCN3CCN(c2ccccc2OC)CC3;

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Urapidil is a sympatholytic antihypertensive drug. It acts as an α₁-adrenoceptor antagonist and as an 5-HT_1A receptor agonist^[1] Although an initial report suggested that urapidil was also an α₂-adrenoceptor agonist,^[2] this was not substantiated in later studies that demonstrated it was devoid of agonist actions in the dog saphenous vein and the guinea-pig ileum.^[3] Unlike some other α₁-adrenoceptor antagonists, urapidil does not elicit reflex tachycardia, and this may be related to its weak β₁-adrenoceptor antagonist activity,^[4]^[5] as well as its effect on cardiac vagal drive.^[6] Urapidil is currently not approved by the U.S. Food and Drug Administration, but it is available in Europe.

↑ Ramage AG (April 1991). "The mechanism of the sympathoinhibitory action of urapidil: role of 5-HT1A receptors". Br. J. Pharmacol. 102 (4): 998–1002. PMC 1917978. PMID 1855130.
↑ Eltze M (1979). "Investigations on the mode of action of a new antihypertensive drug, urapidil, in the isolated vas deferens". Eur. J. Pharmacol. 59 (1–2): 1–9. doi:10.1016/0014-2999(79)90018-9. PMID 228944.
↑ Verberne AJM, Rand MJ (1984). "Pharmacological activities of the antihypertensive drug urapidil in the rat". Clin. Exp. Pharmacol. Physiol. 11 (4): 407–412. doi:10.1111/j.1440-1681.1984.tb00289.x. PMID 6097380.
↑ Schoetensack W, Bruckschen EG, Zech K (1983). Urapidil. New Drugs Annual: Cardiovascular Drugs. p. 19.
↑ Verberne AJM, Rand MJ (1985). "Effect of urapidil on β-adrenoceptors of rat atria". Eur. J. Pharmacol. 108 (2): 193–196. doi:10.1016/0014-2999(85)90725-3. PMID 2984023.
↑ Ramage AG (1990). "Influence of 5-HT1A receptor agonists on sympathetic and parasympathetic nerve activity". J. Cardiovasc. Pharmacol. 15: S75–S85. PMID 1702490.

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	C02CA06 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 6-({3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}amino)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
CAS Number	34661-75-1 64887-14-5 (HCl)
PubChem CID	5639
ChemSpider	5437
UNII	A78GF17HJS
ChEMBL	ChEMBL279229
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₀H₂₉N₅O₃
Molar mass	387.48 g/mol
3D model (JSmol)	Interactive image
SMILES O=C1\C=C(/N(C(=O)N1C)C)NCCCN3CCN(c2ccccc2OC)CC3