URAPIDIL

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H29N5O3
Molecular Weight	387.476
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=ICMGLRUYEQNHPF-UHFFFAOYSA-N

InChI=1S/C20H29N5O3/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

HIDE SMILES / InChI

Molecular Formula	C20H29N5O3
Molecular Weight	387.476
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Antagonist	0.2 µM [IC50]
5-hydroxytryptamine receptor 1A	Agonist	390.0 nM [EC50]
Adrenergic receptor alpha-1	Antagonist	0.7 µM [IC50]
Serotonin 1a (5-HT1a) receptor	Agonist	6.4 null [pIC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Severe hypertension	Primary		Approved	URAPIDIL
Hypertension	Primary		Approved	Urapidil

C_max

Value	Dose	Analyte	Population
460 ng/mL	25 mg single, oral	URAPIDIL plasma	Homo sapiens
976.0297 ng/mL	60 mg single, oral	URAPIDIL plasma	Homo sapiens
1005.6091 ng/mL	60 mg single, oral	URAPIDIL plasma	Homo sapiens
143.6 ng/mL	15 mg single, oral	URAPIDIL plasma	Homo sapiens
271.4 ng/mL	30 mg single, oral	URAPIDIL plasma	Homo sapiens
243.3 ng/mL	30 mg single, oral	URAPIDIL plasma	Homo sapiens
487.4 ng/mL	60 mg single, oral	URAPIDIL plasma	Homo sapiens
200.9 ng/mL	30 mg 2 times / day multiple, oral	URAPIDIL plasma	Homo sapiens
268.1 ng/mL	30 mg 2 times / day multiple, oral	URAPIDIL plasma	Homo sapiens
976.0297 ng/mL	60 mg single, oral	URAPIDIL plasma	Homo sapiens
1005.6091 ng/mL	60 mg single, oral	URAPIDIL plasma	Homo sapiens
164.1 ng/mL	15 mg 2 times / day multiple, oral	URAPIDIL plasma	Homo sapiens
205.5 ng/mL	15 mg 2 times / day multiple, oral	URAPIDIL plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
2838 ng × h/mL	25 mg single, oral	URAPIDIL plasma	Homo sapiens
6084.7484 ng × h/mL	60 mg single, oral	URAPIDIL plasma	Homo sapiens
6374.4837 ng × h/mL	60 mg single, oral	URAPIDIL plasma	Homo sapiens
849 ng × h/mL	15 mg single, oral	URAPIDIL plasma	Homo sapiens
2386 ng × h/mL	30 mg single, oral	URAPIDIL plasma	Homo sapiens
4523 ng × h/mL	60 mg single, oral	URAPIDIL plasma	Homo sapiens
1624 ng × h/mL	30 mg 2 times / day multiple, oral	URAPIDIL plasma	Homo sapiens
1709 ng × h/mL	30 mg 2 times / day multiple, oral	URAPIDIL plasma	Homo sapiens
6084.7484 ng × h/mL	60 mg single, oral	URAPIDIL plasma	Homo sapiens
6374.4837 ng × h/mL	60 mg single, oral	URAPIDIL plasma	Homo sapiens
1593 ng × h/mL	15 mg 2 times / day multiple, oral	URAPIDIL plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.83 h	25 mg single, oral	URAPIDIL plasma	Homo sapiens
4.1779 h	60 mg single, oral	URAPIDIL plasma	Homo sapiens
4.6332 h	60 mg single, oral	URAPIDIL plasma	Homo sapiens
2.66 h	15 mg single, oral	URAPIDIL plasma	Homo sapiens
3.8 h	30 mg single, oral	URAPIDIL plasma	Homo sapiens
5.92 h	30 mg single, oral	URAPIDIL plasma	Homo sapiens
4.37 h	60 mg single, oral	URAPIDIL plasma	Homo sapiens
3.7 h	30 mg 2 times / day multiple, oral	URAPIDIL plasma	Homo sapiens
3.8 h	30 mg 2 times / day multiple, oral	URAPIDIL plasma	Homo sapiens
4.1779 h	60 mg single, oral	URAPIDIL plasma	Homo sapiens
4.6332 h	60 mg single, oral	URAPIDIL plasma	Homo sapiens
7.2 h	15 mg 2 times / day multiple, oral	URAPIDIL plasma	Homo sapiens
8.4 h	15 mg 2 times / day multiple, oral	URAPIDIL plasma	Homo sapiens

F_unbound

Value	Analyte	Population
24.7%	URAPIDIL plasma	Homo sapiens
12.6%	URAPIDIL serum	Homo sapiens
20%	URAPIDIL plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
180 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT	Disc. AE: Postural hypotension, Palpitations...
120 mg single, oral Studied dose	unhealthy, ADULT	Other AEs: Postural hypotension...
90 mg single, oral Studied dose	unhealthy, ADULT	Disc. AE: Postural hypotension...
120 mg single, oral Highest studied dose	unhealthy, ADULT	Other AEs: Postural hypotension...
100 mg single, intravenous Recommended	unhealthy, ADULT

Showing 1 to 5 of 7 entries

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AEs

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AE	Significance	Dose	Population
Dizziness	22.2% Disc. AE	180 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Palpitations	grade 3, 11.1% Disc. AE	180 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Postural hypotension	grade 3, 11.1% Disc. AE	180 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Postural hypotension	grade 3, 12.5%	120 mg single, oral Studied dose	unhealthy, ADULT
Postural hypotension	grade 3 Disc. AE	90 mg single, oral Studied dose	unhealthy, ADULT

Showing 1 to 5 of 15 entries

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PubMed

Show entries

Title	Date	PubMed
[Accelerated arterial hypertension in a young male].	2004	15219076
Multivessel variant angina unresponsive to urapidil.	2004 Aug	15368808
[Hemorheological changes in hot and humid environment].	2004 Dec	15604067
[Drug Safety. Preventing medication errors].	2004 Jul-Aug	15369443
[Treatment of severe preeclampsia and HELLP syndrome].	2004 Oct	15478045

Showing 1 to 5 of 50 entries

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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
Record UNII	A78GF17HJS
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

URAPIDIL

Official Name

English

6-(3-(4-(O-METHOXYPHENYL)-1-PIPERAZINYL)PROPYLAMINO)-1,3-DIMETHYLURACIL

Common Name

English

NSC-310405

Code

English

urapidil [INN]

Common Name

English

URAPIDIL [MART.]

Common Name

English

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Classification Tree

Code System

Code

Alpha-adrenoreceptor antagonists

WHO-VATC

QC02CA06

Alpha-adrenoreceptor antagonists

WHO-ATC

C02CA06

Adrenergic Antagonist

NCI_THESAURUS

C29713

Agent Affecting Cardiovascular System

NCI_THESAURUS

C270

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Code System

Code

Type

Description

MERCK INDEX

m11320

PRIMARY

Merck Index

MESH

C015568

PRIMARY

CAS

34661-75-1

PRIMARY

DRUG CENTRAL

2796

PRIMARY

PUBCHEM

5639

PRIMARY

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Related Record

Type

Details


					PVU92PZO12

URAPIDIL HYDROCHLORIDE

SALT/SOLVATE -> PARENT

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Related Record

Type

Details


					A78GF17HJS

URAPIDIL

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound