Urapidil

Urapidil is a sympatholytic antihypertensive drug. It acts as an α1-adrenoceptor antagonist and as an 5-HT1A 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.

Urapidil
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
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
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.047.377
Chemical and physical data
FormulaC20H29N5O3
Molar mass387.484 g·mol−1
3D model (JSmol)
SMILES
  • O=C1\C=C(/N(C(=O)N1C)C)NCCCN3CCN(c2ccccc2OC)CC3

See also

References

  1. Ramage AG (April 1991). "The mechanism of the sympathoinhibitory action of urapidil: role of 5-HT1A receptors". Br. J. Pharmacol. 102 (4): 998–1002. doi:10.1111/j.1476-5381.1991.tb12290.x. PMC 1917978. PMID 1855130.
  2. 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.
  3. 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. S2CID 22522953.
  4. Schoetensack W, Bruckschen EG, Zech K (1983). Urapidil. New Drugs Annual: Cardiovascular Drugs. p. 19.
  5. 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.
  6. Ramage AG (1990). "Influence of 5-HT1A receptor agonists on sympathetic and parasympathetic nerve activity". J. Cardiovasc. Pharmacol. 15: S75–S85. doi:10.1097/00005344-199001001-00010. PMID 1702490.
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