URAPIDIL HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H29N5O3.ClH
Molecular Weight	423.937
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.COC1=C(C=CC=C1)N2CCN(CCCNC3=CC(=O)N(C)C(=O)N3C)CC2

InChI

InChIKey=KTMLZVUAXJERAT-UHFFFAOYSA-N

InChI=1S/C20H29N5O3.ClH/c1-22-18(15-19(26)23(2)20(22)27)21-9-6-10-24-11-13-25(14-12-24)16-7-4-5-8-17(16)28-3;/h4-5,7-8,15,21H,6,9-14H2,1-3H3;1H

HIDE SMILES / InChI

Description
Sources: http://agence-prd.ansm.sante.fr/php/ecodex/frames.php?specid=62329077&typedoc=N&ref=N0300791.htm | http://www.selleckchem.com/products/urapidil-hydrochloride.htmlhttp://agence-prd.ansm.sante.fr/html/par_eu/20081209_fr342_urapidil-spc.pdf
Curator's Comment: description was created based on several sources, including, http://www.staff.science.uu.nl/~koste101/products/urapidil.pdf

Urapidil is an anti-hypertensive agent approved in Europe for the treatment of the corresponding disease. The drug acts by activating 5HT1a receptor and inhibiting alpha1-adrenergic receptors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Adrenergic receptor alpha-1 169 Target ID: CHEMBL2094251 Sources: http://agence-prd.ansm.sante.fr/php/ecodex/frames.php?specid=62329077&typedoc=N&ref=N0300791.htm	Antagonist 2778	0.2 µM [IC50]
5-hydroxytryptamine receptor 1A 54 Target ID: P08908 Gene ID: 3350.0 Gene Symbol: HTR1A Target Organism: Homo sapiens (Human) Sources: http://agence-prd.ansm.sante.fr/php/ecodex/frames.php?specid=62329077&typedoc=N&ref=N0300791.htm	Agonist 2678	390.0 nM [EC50]
Adrenergic receptor alpha-1 169 Target ID: CHEMBL2094251 Sources: http://www.abcam.com/urapidil-hydrochloride-ab142960.html	Antagonist 2778	0.7 µM [IC50]
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: http://www.selleckchem.com/products/urapidil-hydrochloride.html	Agonist 2678	6.4 null [pIC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Severe hypertension 3 Sources: http://agence-prd.ansm.sante.fr/php/ecodex/frames.php?specid=62329077&typedoc=N&ref=N0300791.htm	Primary		Approved 8429	URAPIDIL Approved Use Severe hypertension: Associated with short term life threatening or internal end organ damage (hypertensive emergency); During and/or after surgery.
Hypertension 567 Sources: http://www.doctissimo.fr/medicament-URAPIDIL-MYLAN.htm	Primary		Approved 8429	Urapidil Approved Use Severe hypertension: • Associated with short term life threatening or internal end organ damage (hypertensive emergency) • During and/or after surgery

PubMed

Title	Date	PubMed
[Effect of Urapidil in antihypertensive therapy of preeclampsia on newborns].	2001 Sep	11709746
Management of patients with hypertensive urgencies and emergencies: a systematic review of the literature.	2002 Dec	12472930
Urapidil reduces elevated pulmonary vascular resistance in patients before heart transplantation.	2002 Mar	11897523
[Observation on the effects of urapidil on hemodynamics in heart dysfunction dogs by thoracic electrical bioimpedance].	2003 Aug	12919650
The effect of exogenous epinephrine on the incidence of hypotensive/bradycardic events during shoulder surgery in the sitting position during interscalene block.	2003 Aug	12873958
[When hypertension becomes an emergency case: lower the blood pressure, but slowly!].	2003 May 29	12866264
Sympathetic regulation of glucose uptake by the alpha1-adrenoceptor in human obesity.	2004 Apr	15090628
Effects of perioperative alpha1 block on haemodynamic control during laparoscopic surgery for phaeochromocytoma.	2004 Apr	14766711
Multivessel variant angina unresponsive to urapidil.	2004 Aug	15368808
Effects of tamsulosin on hypogastric nerve stimulation-induced intraurethral pressure elevation in male and female dogs under anesthesia.	2004 Aug 30	15336951
The alpha1-adrenergic blocker urapidil improves contractile function in patients 3 months after coronary stenting: a randomized, double-blinded study.	2004 Feb	14760340
[Drug Safety. Preventing medication errors].	2004 Jul-Aug	15369443
[Effects of modified anaesthesia for patients undergoing brain artery aneurysm repair operation].	2004 Sep	15628051
Determinants of outcome in patients eligible for thrombolysis for ischemic stroke.	2007	18078026
Voltammetric behavior of urapidil and its determination at multi-wall carbon nanotube paste electrode.	2007 Oct 31	19073125
Year in review 2007: Critical Care--shock.	2008	18983707
Treatment of fragile X-associated tremor ataxia syndrome (FXTAS) and related neurological problems.	2008	18686748
[Effect of urapidil on heart function and ventricular systolic synchrony in acute myocardial infarction patients with no-reflow phenomenon after percutaneous coronary intervention].	2008 Apr	18419949
[Nitrospray in hypertensive crisis with acute nosebleed. Suddenly the patient collapsed].	2008 Apr 17	18557212
Effects of alpha-adrenoreceptor antagonists on apoptosis and proliferation of pancreatic cancer cells in vitro.	2008 Apr 21	18416462
Increased diastolic time fraction as beneficial adjunct of alpha1-adrenergic receptor blockade after percutaneous coronary intervention.	2008 Nov	18790830
Decrease in blood pressure after intravenous administration of urapidil during recombinant tissue plasminogen activator thrombolysis for acute ischemic stroke.	2008 Sep	18840373
A comparative study on in vitro and in vivo effects of topical vasodilators in human internal mammary, radial artery and great saphenous vein.	2008 Sep	18632282
Neonatal transient respiratory depression after maternal urapidil infusion for hypertension.	2009 Feb	18461359
Therapeutic effect of urapidil on myocardial perfusion in patients with ST-elevation acute coronary syndrome.	2009 Mar	19327603
Acute neurotoxicity after yohimbine ingestion by a body builder.	2009 Sep	19640235
Preparation for surgery of phaeochromocytoma by blockade of alpha-adrenergic receptors with urapidil: what dose?	2009 Sep	19225531
Expression of alpha1-adrenoceptors on thymic cells and their role in fine tuning of thymopoiesis.	2009 Sep 29	19646768
One life ends, another begins: Management of a brain-dead pregnant mother-A systematic review-.	2010 Nov 18	21087498
Capillary electrophoresis with end-column electrochemiluminescence for ultrasensitive determination of urapidil hydrochloride in rat plasma and its application to pharmacokinetics study.	2015 Dec 1	26551206

Patents

Sample Use Guides

In Vivo Use Guide

Initiation of treatment: One ampoule of urapidil 25 mg is to be injected over 20 seconds via injection or as 6 mg/min infusion. Maintenance treatment: infusion or syringe pump at rate from 60 to 180 mg/h.

Route of Administration: Intravenous

In Vitro Use Guide

Urapidil hydrochloride (25-200 umol/L) increased DNA synthesis in the PC-2 cell line, expressing a1 and a2-adrenoceptors, in a concentration-dependent manner

Name

Type

Language

URAPIDIL HYDROCHLORIDE

Common Name

English

Urapidil hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

CAS

64887-14-5