URAPIDIL FUMARATE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H29N5O3.C4H4O4
Molecular Weight	503.5481
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.COC1=CC=CC=C1N2CCN(CCCNC3=CC(=O)N(C)C(=O)N3C)CC2

InChI

InChIKey=SBBHYXXLIJEXFU-WLHGVMLRSA-N

InChI=1S/C20H29N5O3.C4H4O4/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;5-3(6)1-2-4(7)8/h4-5,7-8,15,21H,6,9-14H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula	C20H29N5O3
Molecular Weight	387.476
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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-1 171 Target ID: CHEMBL2094251 Sources: http://agence-prd.ansm.sante.fr/php/ecodex/frames.php?specid=62329077&typedoc=N&ref=N0300791.htm	Antagonist 2849	0.2 µM [IC50]
5-hydroxytryptamine receptor 1A 58 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 2752	390.0 nM [EC50]
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: http://www.abcam.com/urapidil-hydrochloride-ab142960.html	Antagonist 2849	0.7 µM [IC50]
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL214 Sources: http://www.selleckchem.com/products/urapidil-hydrochloride.html	Agonist 2752	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 8583	URAPIDIL Approved Use Severe hypertension: Associated with short term life threatening or internal end organ damage (hypertensive emergency); During and/or after surgery.
Hypertension 575 Sources: http://www.doctissimo.fr/medicament-URAPIDIL-MYLAN.htm	Primary		Approved 8583	Urapidil Approved Use Severe hypertension: • Associated with short term life threatening or internal end organ damage (hypertensive emergency) • During and/or after surgery

C_max

Value	Dose	Analyte	Population
460 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23463771/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
976.0297 ng/mL EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1005.6091 ng/mL EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
143.6 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=32 \| https://www.jstage.jst.go.jp/article/jscpt1970/18/2/18_2_407/_article/-char/en	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
271.4 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=32 \| https://www.jstage.jst.go.jp/article/jscpt1970/18/2/18_2_407/_article/-char/en	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
243.3 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/18/2/18_2_407/_article/-char/en	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
487.4 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/18/2/18_2_407/_article/-char/en	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
200.9 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=32 \| https://www.jstage.jst.go.jp/article/jscpt1970/18/3/18_3_579/_article/-char/en	30 mg 2 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
268.1 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=32 \| https://www.jstage.jst.go.jp/article/jscpt1970/18/3/18_3_579/_article/-char/en	30 mg 2 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
976.0297 ng/mL EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1005.6091 ng/mL EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
164.1 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/17/4/17_4_637/_article/-char/en	15 mg 2 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered:	URAPIDIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
205.5 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/17/4/17_4_637/_article/-char/en	15 mg 2 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered:	URAPIDIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
2838 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23463771/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
6084.7484 ng × h/mL EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6374.4837 ng × h/mL EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
849 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=32 \| https://www.jstage.jst.go.jp/article/jscpt1970/18/2/18_2_407/_article/-char/en	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2386 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/18/2/18_2_407/_article/-char/en	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
4523 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/18/2/18_2_407/_article/-char/en	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1624 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=32 \| https://www.jstage.jst.go.jp/article/jscpt1970/18/3/18_3_579/_article/-char/en	30 mg 2 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1709 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=32 \| https://www.jstage.jst.go.jp/article/jscpt1970/18/3/18_3_579/_article/-char/en	30 mg 2 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
6084.7484 ng × h/mL EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6374.4837 ng × h/mL EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1593 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/17/4/17_4_637/_article/-char/en	15 mg 2 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered:	URAPIDIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
1.83 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23463771/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.1779 h EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.6332 h EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.66 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=32 \| https://www.jstage.jst.go.jp/article/jscpt1970/18/2/18_2_407/_article/-char/en	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.8 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=32 \| https://www.jstage.jst.go.jp/article/jscpt1970/18/2/18_2_407/_article/-char/en	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5.92 h EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/18/2/18_2_407/_article/-char/en	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
4.37 h EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/18/2/18_2_407/_article/-char/en	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.7 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=32 \| https://www.jstage.jst.go.jp/article/jscpt1970/18/3/18_3_579/_article/-char/en	30 mg 2 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.8 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=32 \| https://www.jstage.jst.go.jp/article/jscpt1970/18/3/18_3_579/_article/-char/en	30 mg 2 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
4.1779 h EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.6332 h EXPERIMENT https://innovareacademics.in/journals/index.php/ijpps/article/view/2902	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	URAPIDIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
7.2 h EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/17/4/17_4_637/_article/-char/en	15 mg 2 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered:	URAPIDIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
8.4 h EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/17/4/17_4_637/_article/-char/en	15 mg 2 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered:	URAPIDIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

F_unbound

Value	Analyte	Population
24.7% EXPERIMENT https://link.springer.com/article/10.2165/00003495-198938060-00005	URAPIDIL plasma	Homo sapiens
12.6% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/200022_2149020N1031_1_120_1F.pdf#page=33	URAPIDIL serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
20% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25838996/	URAPIDIL plasma	Homo sapiens

Doses

Dose	Population	Adverse events
180 mg 1 times / day multiple, oral Highest studied dose Dose: 180 mg, 1 times / day Route: oral Route: multiple Dose: 180 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2969799/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2969799/	Disc. AE: Postural hypotension, Palpitations... AEs leading to discontinuation/dose reduction: Postural hypotension (grade 3, 11.1%) Palpitations (grade 3, 11.1%) Dizziness (22.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/2969799/
120 mg single, oral Studied dose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/	Other AEs: Postural hypotension... Other AEs: Postural hypotension (grade 3, 12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/
90 mg single, oral Studied dose Dose: 90 mg Route: oral Route: single Dose: 90 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/	Disc. AE: Postural hypotension... AEs leading to discontinuation/dose reduction: Postural hypotension (grade 3) Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/
120 mg single, oral Highest studied dose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/	Other AEs: Postural hypotension... Other AEs: Postural hypotension (grade 3, 9%) Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/
100 mg single, intravenous Recommended Dose: 100 mg Route: intravenous Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/11239257/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11239257/	Sources: https://pubmed.ncbi.nlm.nih.gov/11239257/
30 mg 2 times / day multiple, oral Recommended Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3886400/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3886400/	Sources: https://pubmed.ncbi.nlm.nih.gov/3886400/
60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/	Disc. AE: Palpitation, Flushing... Other AEs: Blurred vision... AEs leading to discontinuation/dose reduction: Palpitation (0.93%) Flushing (0.93%) Headache (0.93%) Eyelid ptosis (0.93%) Nausea (0.93%) Giddiness (0.93%) Discomfort epigastric (0.93%) General malaise (0.93%) Other AEs: Blurred vision (0.93%) Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/

AEs

PubMed

Title	Date	PubMed
Capillary electrophoresis with end-column electrochemiluminescence for ultrasensitive determination of urapidil hydrochloride in rat plasma and its application to pharmacokinetics study.	2015-12-01	26551206
Age-associated plasticity of α1-adrenoceptor-mediated tuning of T-cell development.	2010-12	20800673
Facilitation of expulsion of ureteral stones by addition of α1-blockers to conservative therapy.	2010-12	20604720
One life ends, another begins: Management of a brain-dead pregnant mother-A systematic review-.	2010-11-18	21087498
Bringing the hospital to the patient: first treatment of stroke patients at the emergency site.	2010-10-29	21060800
Prevention of hypertensive crises in rats induced by acute and chronic norepinephrine excess.	2010-10	20665428
Full recovery of Takotsubo cardiomyopathy (apical ballooning) in two days.	2010-09-03	19157601
Urapidil, a dual-acting antihypertensive agent: Current usage considerations.	2010-07	20652659
Alpha1A-adrenergic receptor-directed autoimmunity induces left ventricular damage and diastolic dysfunction in rats.	2010-02-24	20195525
Late Onset Postpartum Eclampsia: It is Really Never Too Late-A Case of Eclampsia 8 Weeks after Delivery.	2010	20798839
Glioblastoma cells express functional cell membrane receptors activated by daily used medical drugs.	2009-12	19543745
Expression of alpha1-adrenoceptors on thymic cells and their role in fine tuning of thymopoiesis.	2009-09-29	19646768
Acute neurotoxicity after yohimbine ingestion by a body builder.	2009-09	19640235
Preparation for surgery of phaeochromocytoma by blockade of alpha-adrenergic receptors with urapidil: what dose?	2009-09	19225531
Dexmedetomidine sedation for carotid endarterectomy.	2009-08-25	19697824
Marked hydronephrosis and hydroureter after distigmine therapy in an adult male patient with paraplegia due to spinal cord injury: a case report.	2009-08-06	19918519
[Treatment of peri- and postoperative hypertensive emergencies].	2009-04	19319772
Therapeutic effect of urapidil on myocardial perfusion in patients with ST-elevation acute coronary syndrome.	2009-03	19327603
Neonatal transient respiratory depression after maternal urapidil infusion for hypertension.	2009-02	18461359
[Hypertensive crisis--the present view].	2009	19899722
[Hypertensive emergency].	2008-12-11	19149310
Increased diastolic time fraction as beneficial adjunct of alpha1-adrenergic receptor blockade after percutaneous coronary intervention.	2008-11	18790830
Decrease in blood pressure after intravenous administration of urapidil during recombinant tissue plasminogen activator thrombolysis for acute ischemic stroke.	2008-09	18840373
A comparative study on in vitro and in vivo effects of topical vasodilators in human internal mammary, radial artery and great saphenous vein.	2008-09	18632282
Effects of alpha-adrenoreceptor antagonists on apoptosis and proliferation of pancreatic cancer cells in vitro.	2008-04-21	18416462
[Nitrospray in hypertensive crisis with acute nosebleed. Suddenly the patient collapsed].	2008-04-17	18557212
[Effect of urapidil on heart function and ventricular systolic synchrony in acute myocardial infarction patients with no-reflow phenomenon after percutaneous coronary intervention].	2008-04	18419949
Clinical review: Critical care management of spontaneous intracerebral hemorrhage.	2008	19108704
Year in review 2007: Critical Care--shock.	2008	18983707
Treatment of fragile X-associated tremor ataxia syndrome (FXTAS) and related neurological problems.	2008	18686748
Voltammetric behavior of urapidil and its determination at multi-wall carbon nanotube paste electrode.	2007-10-31	19073125
A probable case of nitroprusside intoxication.	2007-09	17660740
[Does alpha1-blocker provide additional improvement of quality-of-life in patients with overactive bladder?--a multi-center prospective randomized trial between anti-cholinergic (propiverine chloride) with and without alpha1-blocker (urapidil)].	2007-05	17564103
IL-1beta induces murine airway 5-HT2A receptor hyperresponsiveness via a non-transcriptional MAPK-dependent mechanism.	2007-04-02	17407556
Can a patient be successfully prepared for pheochromocytoma surgery in three days? A case report.	2007-04	17468737
Psoriasiform eruption induced by alpha1-adrenergic blocker, urapidil.	2007-04	17374017
Hypericin activates L-type Ca2+ channels in cardiac myocytes.	2007-04	17291039
Differential effects of urapidil and doxazosin on heart rate.	2007-03	17225141
Urinary retention and sympathetic sphincter obstruction in axonal Guillain-Barré syndrome.	2007-01	16969830
Determinants of outcome in patients eligible for thrombolysis for ischemic stroke.	2007	18078026
Meperidine and skin surface warming additively reduce the shivering threshold: a volunteer study.	2007	17316456
Improvement of donor myocardial function after treatment of autonomic storm during brain death.	2006-10-27	17060850
Effect of tamsulosin on spontaneous bladder contraction in conscious rats with bladder outlet obstruction: comparison with effect on intraurethral pressure.	2006-09-18	16887117
Comparison of intravenous urapidil and oral captopril in patients with hypertensive urgencies.	2006-09	16826189
Effect of isoflurane on echocardiographic left-ventricular relaxation indices in patients with diastolic dysfunction due to concentric hypertrophy and ischemic heart disease.	2006-08	16884980
Antihypertensive therapy in patients with pre-eclampsia: A prospective randomised multicentre study comparing dihydralazine with urapidil.	2006-08	16253414
Effects of tamsulosin on resting urethral pressure and arterial blood pressure in anaesthetized female dogs.	2006-03	16536901
Dihydralazine treatment limits liver injury after hemorrhagic shock in rats.	2006-03	16521277
Centrally acting imidazolines stimulate vascular alpha 1A-adrenergic receptors in Rat-Tail Artery.	2006-01-06	16897362
[Usefulness of urapidil during intraoperative rise of arterial blood pressure in patients operated under general anesthesia].	2005	16171143

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:50:46 GMT 2025` Edited by `admin` on `Mon Mar 31 20:50:46 GMT 2025`
Record UNII	7565ZXN22A
Record Status	`Validated (UNII)`
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Name

Type

Language

URAPIDIL FUMARATE

Common Name

English

2,4(1H,3H)-PYRIMIDINEDIONE, 6-((3-(4-(2-METHOXYPHENYL)-1-PIPERAZINYL)PROPYL)AMINO)-1,3-DIMETHYL-, (2E)-2-BUTENEDIOATE (1:1)

Preferred Name

English

Urapidil fumarate [WHO-DD]

Common Name

English

6-((3-(4-(2-METHOXYPHENYL)PIPERAZIN-1-YL)PROPYL)AMINO)-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE (2E)-BUT-2-ENEDIOATE (1:1)

Systematic Name

English

Code System Code Type Description

PUBCHEM

9870716

Created by admin on Mon Mar 31 20:50:46 GMT 2025 , Edited by admin on Mon Mar 31 20:50:46 GMT 2025

PRIMARY

FDA UNII

7565ZXN22A

Created by admin on Mon Mar 31 20:50:46 GMT 2025 , Edited by admin on Mon Mar 31 20:50:46 GMT 2025

PRIMARY

CAS

102411-11-0

Created by admin on Mon Mar 31 20:50:46 GMT 2025 , Edited by admin on Mon Mar 31 20:50:46 GMT 2025

PRIMARY

Related Record Type Details


					A78GF17HJS

URAPIDIL

ACTIVE MOIETY

AE	Significance	Dose	Population
Dizziness	22.2% Disc. AE	180 mg 1 times / day multiple, oral Highest studied dose Dose: 180 mg, 1 times / day Route: oral Route: multiple Dose: 180 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2969799/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2969799/
Palpitations	grade 3, 11.1% Disc. AE	180 mg 1 times / day multiple, oral Highest studied dose Dose: 180 mg, 1 times / day Route: oral Route: multiple Dose: 180 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2969799/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2969799/
Postural hypotension	grade 3, 11.1% Disc. AE	180 mg 1 times / day multiple, oral Highest studied dose Dose: 180 mg, 1 times / day Route: oral Route: multiple Dose: 180 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2969799/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2969799/
Postural hypotension	grade 3, 12.5%	120 mg single, oral Studied dose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/
Postural hypotension	grade 3 Disc. AE	90 mg single, oral Studied dose Dose: 90 mg Route: oral Route: single Dose: 90 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/
Postural hypotension	grade 3, 9%	120 mg single, oral Highest studied dose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3519043/
Blurred vision	0.93%	60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/
Discomfort epigastric	0.93% Disc. AE	60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/
Eyelid ptosis	0.93% Disc. AE	60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/
Flushing	0.93% Disc. AE	60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/
General malaise	0.93% Disc. AE	60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/
Giddiness	0.93% Disc. AE	60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/
Headache	0.93% Disc. AE	60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/
Nausea	0.93% Disc. AE	60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/
Palpitation	0.93% Disc. AE	60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3042355/

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