ContaminantDB: Terazosin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2009-07-30 17:59:10 UTC

Update Date

2026-05-14 16:58:21 UTC

Accession Number

CHEM002533

Identification

Common Name

Terazosin

Class

Small Molecule

Description

Terazosin is a selective alpha 1 antagonist used for treatment of symptoms of prostate enlargement (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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Adrenergic alpha-1 Receptor Antagonist
Adrenergic alpha-Antagonist
Amide
Amine
Antineoplastic Agent
Drug
Ether
Human Neurotoxin
Organic Compound
Platelet Aggregation Inhibitor
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)piperazine	ChEBI
Terazosina	ChEBI
Terazosine	ChEBI
Terazosinum	ChEBI
Terazosabb	Kegg
Abbott 45975	HMDB
Magnurol	HMDB
Nu-terazosin	HMDB
Ratio-terazosin	HMDB
Apo-terazosin	HMDB
Heitrin	HMDB
Hytrin	HMDB
Terazosin azu	HMDB
Terazosin hexal	HMDB
Terazosin hydrochloride	HMDB
Terazosina alter	HMDB
Terazosina kern	HMDB
Zayasel	HMDB
Adecur	HMDB
Deflox	HMDB
Dysalfa	HMDB
Flotrin	HMDB
Hytrine	HMDB
Novo-terazosin	HMDB
Sutif	HMDB
Tazusin	HMDB
Terazoflo	HMDB
Terazosin, monohydrochloride, dihydrate	HMDB
Hexal brand OF terazosin hydrochloride	HMDB
Hytrin BPH	HMDB
PMS-Terazosin	HMDB
Terazosina qualix	HMDB
Terazosin hydrochloride anhydrous	HMDB

Chemical Formula

C₁₉H₂₅N₅O₄

Average Molecular Mass

387.433 g/mol

Monoisotopic Mass

387.191 g/mol

CAS Registry Number

70024-40-7

IUPAC Name

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

Traditional Name

terazosin

SMILES

COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1CCCO1

InChI Identifier

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)

InChI Key

VCKUSRYTPJJLNI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

N-arylpiperazines

Alternative Parents

Substituents

N-arylpiperazine
Quinazolinamine
Diazanaphthalene
Quinazoline
Anisole
Dialkylarylamine
Alkyl aryl ether
Aminopyrimidine
Pyrimidine
Imidolactam
Benzenoid
Heteroaromatic compound
Tetrahydrofuran
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Azacycle
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

primary amino compound (CHEBI:9445 )
furans (CHEBI:9445 )
quinazolines (CHEBI:9445 )
piperazines (CHEBI:9445 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Terazosin is a white, crystalline substance,

Experimental Properties

Property	Value
Melting Point	273°C
Boiling Point	Not Available
Solubility	29.7mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	1.5 g/L	ALOGPS
logP	1.12	ALOGPS
logP	1.18	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	19.93	ChemAxon
pKa (Strongest Basic)	7.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.04 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.18 m³·mol⁻¹	ChemAxon
Polarizability	41.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9375000000-51e0b50a02ca9182132a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-0049000000-86650e3e374df663aa35	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0049000000-86650e3e374df663aa35	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0059000000-ca9adf5daab9e5e9b6e7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000e-1292000000-9081c5bb64e8d096db78	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0079-0019000000-d7e59834a3bdfe524c51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000l-0097000000-c8329e54acf1c8a72d7c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0029000000-b9509509936fd20822e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-007c-3069000000-196d536a1f876cf3fe0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-2090000000-f24db01089337864b16f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1019000000-f4c3728d09b25d55b2f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-6098000000-81e55b539bff87910453	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00em-3091000000-b40b6a5be295255d01ea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-6fee4cbd3c043ea0f36a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0009000000-0967bc8cd13ea8732283	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006y-3149000000-56db17d16ac03814def3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-8d31d2aa0ab8d99cf8d7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-0019000000-55003a7c1cdca21b9dfd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001v-0197000000-499a38ef1791a534e75c	Spectrum

Toxicity Profile

Route of Exposure

Oral. Essentially completely absorbed in man (90% bioavailability).

Mechanism of Toxicity

Terazosin selectively and competitively inhibits vascular postsynaptic alpha(1)-adrenergic receptors, resulting in peripheral vasodilation and a reduction of vascular resistance and blood pressure. Unlike the nonselective alph-adrenergic blockers phenoxybenzamine and phentolamine, terazosin does not block presynaptic alpha(2)-receptors and, hence, does not cause reflex activation of norepinephrine release to produce reflex tachycardia.

Metabolism

Hepatic. One of the four metabolites identified (piperazine derivative of terazosin) has antihypertensive activity. Route of Elimination: Approximately 10% of an orally administered dose is excreted as parent drug in the urine and approximately 20% is excreted in the feces. Half Life: 12 hours

Toxicity Values

LD50: 259.3mg/kg (parental-intravenous, Mouse) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Terazosin is indicated for the treatment of symptomatic benign prostatic hyperplasia (BPH). There is a rapid response, with approximately 70% of patients experiencing an increase in urinary flow and improvement in symptoms of BPH when treated with terazosin. The long-term effects of terazosin on the incidence of surgery, acute urinary obstruction or other complications of BPH are yet to be determined. Terazosin tablets are also indicated for the treatment of hypertension. Terazosin tablets can be used alone or in combination with other antihypertensive agents such as diuretics or beta-adrenergic blocking agents.

Minimum Risk Level

Not Available

Health Effects

Hypotension, palpitations, postural hypotension, syncope, peripheral edema, weight gain, dyspnea, nasal congestion/rhinitis, impotence.

Symptoms

Asthenia, postural hypotension, dizziness, somnolence, nasal congestion/rhinitis.

Treatment

Should overdosage of Terazosin lead to hypotension, support of the cardiovascular system is of first importance. Restoration of blood pressure and normalization of heart rate may be accomplished by keeping the patient in the supine position. If this measure is inadequate, shock should first be treated with volume expanders. If necessary, vasopressors should then be used and renal function should be monitored and supported as needed. Laboratory data indicate that Terazosin is highly protein bound; therefore, dialysis may not be of benefit. (4)

Concentrations

Not Available

External Links

DrugBank ID

DB01162

HMDB ID

HMDB0015293

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

K. S. Keshava Murthy, Gamini Weeratunga, Tianhao Zhou, Bhaskar Reddy Guntoori, “Process for the manufacture of intermediates suitable to make doxazosin, terazosin, prazosin, tiodazosin and related antihypertensive medicines.” U.S. Patent US5919931, issued September, 1986.

MSDS

Not Available

General References

1. 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.

Terazosin (CHEM002533)

Structure for CHEM002533: Terazosin