6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]quinazolin-4-amine

• ChemBase ID: 1033
• Molecular Formular: C19H25N5O4
• Molecular Mass: 387.4329
• Monoisotopic Mass: 387.19065431
• SMILES: O1C(CCC1)C(=O)N1CCN(CC1)c1nc2c(c(n1)N)cc(OC)c(OC)c2
• Canonical SMILES: COc1cc2nc(nc(c2cc1OC)N)N1CCN(CC1)C(=O)C1CCCO1
• InChI: InChI=1S/C19H25N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h10-11,14H,3-9H2,1-2H3,(H2,20,21,22)
• InChIKey: VCKUSRYTPJJLNI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]quinazolin-4-amine
• IUPAC Traditional name: 6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]quinazolin-4-amine; terazosin
• Brand Name: Blavin; Flumarc; Fosfomic; Heitrin; Hytracin; Hytrin; Hytrinex; Itrin; Urodie; Vasomet; Vicard
• Synonyms: Terazosin HCl; Terazosin hydrochloride; Terazosina [INN-Spanish]; Terazosine; Terazosine [INN-French]; Terazosinum [INN-Latin]; Trazosin HCl; Abbott 45975; Terazosin; 6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]quinazolin-4-amine

Database IDs

• CAS Number: 63590-64-7
• MDL Number: MFCD00072144
• PubChem SID: 46509129; 160964496
• PubChem CID: 5401

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.929197
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -0.32373834
• LogD (pH = 7.4): 0.95433736
• Log P: 1.1797276
• Molar Refractivity: 105.1764 cm^3
• Polarizability: 40.394585 Å^3
• Polar Surface Area: 103.04 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.12
• LOG S: -2.41
• Solubility (Water): 1.50e+00 g/l

PROPERTIES

Physical Property

• Solubility: 29.7mg/mL
• Hydrophobicity(logP): 1; 2.182

Product Information

• Purity: 95%

DETAILS

DrugBank - DB01162

• Drug Groups: approved
• Description: Terazosin is a selective alpha1-antagonist used for treatment of symptoms of benign prostatic hyperplasia (BPH). It also acts to lower blood pressure, so it is a drug of choice for men with hypertension and prostate enlargement. It works by blocking the action of adrenaline on smooth muscle of the bladder and the blood vessel walls.
• Indication: For the treatment of symptomatic BPH and mild to moderate hypertension.
• Pharmacology: Terazosin, classified as a quinazoline, is similar to doxazosin and prazosin. As an α-adrenergic blocking agent, terazosin is used to treat hypertension and BPH. Terazosin produces vasodilation and reduces peripheral resistance but in general has only a slight effect on cardiac output. The antihypertensive effect with chronic dosing is not usually accompanied by reflex tachycardia.
• Toxicity: LD₅₀=259.3mg/kg (IV in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. One of the four metabolites identified (piperazine derivative of terazosin) has antihypertensive activity.
• Absorption: Essentially completely absorbed in man (90% bioavailability).
• Half Life: 12 hours
• Protein Binding: 90-94%
• Elimination: Approximately 10% of an orally administered dose is excreted as parent drug in the urine and approximately 20% is excreted in the feces.
• References: Cushman WC, Ford CE, Cutler JA, Margolis KL, Davis BR, Grimm RH, Black HR, Hamilton BP, Holland J, Nwachuku C, Papademetriou V, Probstfield J, Wright JT Jr, Alderman MH, Weiss RJ, Piller L, Bettencourt J, Walsh SM: Success and predictors of blood pressure control in diverse North American settings: the antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT). J Clin Hypertens (Greenwich). 2002 Nov-Dec;4(6):393-404. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Cushman WC, Ford CE, Cutler JA, Margolis KL, Davis BR, Grimm RH, Black HR, Hamilton BP, Holland J, Nwachuku C, Papademetriou V, Probstfield J, Wright JT Jr, Alderman MH, Weiss RJ, Piller L, Bettencourt J, Walsh SM: Success and predictors of blood pressure control in diverse North American settings: the antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT). J Clin Hypertens (Greenwich). 2002 Nov-Dec;4(6):393-404. Pubmed