5-METHYLURAPIDIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H31N5O3
Molecular Weight	401.5025
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=HIHZDNKKIUQQSC-UHFFFAOYSA-N

InChI=1S/C21H31N5O3/c1-16-19(23(2)21(28)24(3)20(16)27)22-10-7-11-25-12-14-26(15-13-25)17-8-5-6-9-18(17)29-4/h5-6,8-9,22H,7,10-15H2,1-4H3

HIDE SMILES / InChI

Molecular Formula	C21H31N5O3
Molecular Weight	401.5025
Charge	0
Count

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Alpha-1a adrenergic receptor 66 Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9490024	Antagonist 2778	9.2 null [pKi]
Alpha-1b adrenergic receptor 44 Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9249248	Antagonist 2778	7.7 null [pKi]
Alpha-1d adrenergic receptor 36 Target ID: CHEMBL223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9249248	Antagonist 2778	8.0 null [pKi]

PubMed

Title	Date	PubMed
Differential cardiovascular effects of 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT), flesinoxan, 5-methyl-urapidil and MDL 75,608A in conscious spontaneously hypertensive rats.	1993	7906241
The alpha 1-adrenergic receptor that mediates smooth muscle contraction in human prostate has the pharmacological properties of the cloned human alpha 1c subtype.	1994 Apr	8183249
Effect of alpha 1 adrenoceptor antagonists on prostatic pressure and blood pressure in the anesthetized dog.	1994 Jul	7913781
KMD-3213, a novel, potent, alpha 1a-adrenoceptor-selective antagonist: characterization using recombinant human alpha 1-adrenoceptors and native tissues.	1995 Aug	7651358
Structure activity relationships of a series of buspirone analogs at alpha-1 adrenoceptors: further evidence that rat aorta alpha-1 adrenoceptors are of the alpha-1D-subtype.	1996 Jul	8764344
Hypotensive and hypertensive effects of catecholamines intrathecally injected in anesthetized rats.	1996 Jun 10	8816361
Pharmacological pleiotropism of the human recombinant alpha1A-adrenoceptor: implications for alpha1-adrenoceptor classification.	1997 Jul	9249248
Pharmacology of tamsulosin: saturation-binding isotherms and competition analysis using cloned alpha 1-adrenergic receptor subtypes.	1997 Sep 15	9294627
Molecular cloning, genomic characterization and expression of novel human alpha1A-adrenoceptor isoforms.	1998 Jan 30	9490024
Characterization of alpha1-adrenoceptor subtypes mediating noradrenaline-induced contraction of rat epididymal vas deferens in calcium-free medium.	1999	10416824
Phe-308 and Phe-312 in transmembrane domain 7 are major sites of alpha 1-adrenergic receptor antagonist binding. Imidazoline agonists bind like antagonists.	2001 Jul 6	11331292
Affinity of serotonin receptor antagonists and agonists to recombinant and native alpha1-adrenoceptor subtypes.	2001 Jun	11459121
Use of antisense oligonucleotides to verify the role of the alpha(1A)-adrenergic receptor in the contractility of the rat uterus post partum.	2001 May	11306708
Chromatography studies on bio-affinity of nine ligands of alpha1-adrenoceptor to alpha1D subtypes overexpressed in cell membrane.	2004 Aug	15493479
Cloned human 5-HT1A receptor pharmacology determined using agonist binding and measurement of cAMP accumulation.	2004 Oct	15482641
Differential distribution of functional alph}1-adrenergic receptor subtypes along the rat tail artery.	2005 Aug	15872040
Correlation between mRNA levels and functional role of alpha1-adrenoceptor subtypes in arteries: evidence of alpha1L as a functional isoform of the alpha1A-adrenoceptor.	2005 Nov	15951348
Functional alpha(1)-adrenoceptor subtypes in human submandibular glands.	2006 Mar	16498073
Smooth muscle alpha1D-adrenoceptors mediate phenylephrine-induced vasoconstriction and increases in endothelial cell Ca2+ in hamster cremaster arterioles.	2008 Oct	18604236
Adventitia removal does not modify the alphaID-adrenoceptors response in aorta during hypertension and ageing.	2009 Jul	19566752
Cell membrane chromatography competitive binding analysis for characterization of α1A adrenoreceptor binding interactions.	2011 Jul	21544540

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:00:29 GMT 2023` Edited by `admin` on `Fri Dec 15 18:00:29 GMT 2023`
Record UNII	1HLS600135
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5-METHYLURAPIDIL

Common Name

English

5-METHYL-6((3-(4-(2-METHOXYPHENYL)-1-PIPERAZINYL)PROPYL)-AMINO)-1,3-DIMETHYLURACIL

Systematic Name

English

Code System Code Type Description

CAS

34661-85-3