6-({3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}amino)-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride

• ChemBase ID: 73241
• Molecular Formular: C20H30ClN5O3
• Molecular Mass: 423.9369
• Monoisotopic Mass: 423.20371753
• SMILES: n1(c(=O)n(c(cc1=O)NCCCN1CCN(CC1)c1ccccc1OC)C)C.Cl
• Canonical SMILES: COc1ccccc1N1CCN(CC1)CCCNc1cc(=O)n(c(=O)n1C)C.Cl
• InChI: 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
• InChIKey: KTMLZVUAXJERAT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-({3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}amino)-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride
• IUPAC Traditional name: urapidil hydrochloride
• Synonyms: Urapidil hydrochloride; 6-[[3-[4-(o-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil hydrochloride; Urapidil hydrochloride; 6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione Hydrochloride

Database IDs

• CAS Number: 64887-14-5
• MDL Number: MFCD00078601
• PubChem SID: 24277811; 162038161
• PubChem CID: 167980

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.3816706
• LogD (pH = 7.4): 0.39269504
• Log P: 1.1826149
• Molar Refractivity: 119.3696 cm^3
• Polarizability: 41.324097 Å^3
• Polar Surface Area: 68.36 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble; Methanol
• Apperance: white solid; White to Off-White Solid
• Melting Point: 236-241°C

Safety Information

• Storage Condition: -20°C; Refrigerator
• RTECS: YQ9862000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: adrenergic receptor
• Gene Information: human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), HTR1A(3350)

Product Information

• Salt Data: hydrochloride

DETAILS

Selleck Chemicals - S2025

Research Area: Cancer
Biological Activity:
Urapidil hydrochloride is a hydrochloride salt form of urapidil which is α1-adrenoceptor antagonist and 5-HT1A receptor agonist with pIC50 of 6.13 and 6.4 respectively. Urapidil has an alpha-blocking effect but, unlike other alpha-blockers, also has a central sympatholytic effect mediated via stimulation of serotonin 5HT1A receptors in the central nervous system. [1] Oral urapidil is effective and well tolerated when used as second-line therapy in patients with blood pressure inadequately controlled with other agents. Urapidil has also been demonstrated to ameliorate glucose and lipid metabolism in hypertensive patients with concomitant diabetes and/or hyperlipidemia. Intravenous urapidil is effective in the treatment of hypertensive crises, perioperative hypertension, and pre-eclampsia and may have a potential role in the management of acute stroke. [2]References on Urapidil HCl[1] Am J Cardiol., 1989, 64(7):1D-6D[2] Adv Ther., 2010, 27(7):426-43

Sigma Aldrich - U100

Biochem/physiol Actions
α1-adrenoceptor antagonist; 5-HT1A serotonin receptor partial agonist; anti-hypertensive.

Toronto Research Chemicals - U815400

α1-Adrenergic antagonist; derivative of Uracil (U801000). Antihypertensive.

REFERENCES

• Buch J.Adv Ther. 2010; 27(7):426-43.
• Eltze, M., et al.: Eur. J. Pharmacol., 59, 1 (1979)
• Barankay, A., et al.: Arzneim.-Forsch., 31, 849 (1979)
• Belz, G.G., et al.: Clin. Pharmacol. Ther., 37, 48 (1979)