CAS 63590-64-7|Trazosin HCl|Urodie|Hytrin|Itrin|Terazosina [INN-Spanish]|Abbott 45975|Terazosin hydrochloride|Blavin|Hytrinex|Vicard|Vasomet|Heitrin|Flumarc|Fosfomic|Hytracin|Terazosin|Terazosin HCl...

General Information

Structure

Molecular Formula

C₁₉H₂₅N₅O₄

Molecular Mass

387.4329

Exact Mass

387.19065431

Charge

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

Canonic Smiles

COc1cc2nc(nc(c2cc1OC)N)N1CCN(CC1)C(=O)C1CCCO1

Isomeric Smiles

O1C(CCC1)C(=O)N1CCN(CC1)c1nc2c(c(n1)N)cc(OC)c(OC)c2

Calculated Properties

JChem

LogD (pH = 7.4)

0.65

LogD (pH = 5.5)

-0.61

Log P

1.18

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

7.80

Polar Surface Area

103.04

Polarizability

41.73

Molar Refractivity

105.18

LOG S

-4.22

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

FosfomicHytracinHytrinVasometBlavinHytrinexFlumarcItrinHeitrinUrodieVicard

Synonyms

Terazosina [INN-Spanish]Abbott 45975Trazosin HClTerazosin hydrochlorideTerazosinTerazosineTerazosine [INN-French]Terazosin HClTerazosinum [INN-Latin]6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]quinazolin-4-amineterazosinTerazosine1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)piperazineTerazosin

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

API Name

Terazosin

International Nonproprietary Name (INN)

terazosinaterazosinumterazosineterazosin

Names and Identifiers

Registration numbers

CAS Number

63590-64-7

PubChem SID

4650912916096449656464178

PubChem CID

MDL Number

DrugBank ID

SureChEMBL Database

Reactom Database

R-HSA-390641R-HSA-9617370

CHEBI ID

CHEBI:9445

MetaboLights Database

MTBLS379MTBLS2145MTBLS1642MTBLS2871MTBLS2406MTBLS2878

LINCS Database

LSM-4997

Wikipedia Title

Terazosin

CompTox Database

DTXSID3023639

Drug Central Database

KEGG ID

Beilstein Number

KEGG DRUG Database

ACToR Database

CHEMBL

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

2.182

Solubility

29.7mg/mL

Product Information

Purity

95%

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

References

Bioactivity

PubChem BioAssay

Bioactivity