Terazosin Hydrochloride

HCID 63016CAS 70024-40-7

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Basic information

Standard SMILES: COc1cc2nc(N3CCN(C(=O)C4CCCO4)CC3)nc(N)c2cc1OC.Cl.O.O
InChIKey: NZMOFYDMGFQZLS-UHFFFAOYSA-N
Molecular formula: C19H30ClN5O6
Average molar mass: 459.9 g/mol
Monoisotopic mass: 459.18846136

Overview

Terazosin Hydrochloride is the hydrochloride salt form of terazosin, a quinazoline derivative with adrenergic antagonistic property. Terazosin hydrochloride selectively inhibits alpha-1 adrenergic receptors, resulting in vasodilation leading to decreased peripheral vascular resistance and a reduced venous return to the heart as well as decreased urethral resistance, which potentially improving urine flow and symptoms related to benign prostatic hyperplasia. In addition, terazosin decreases low-density lipoproteins (LDL) and triglycerides while increasing the concentration of high-density lipoproteins (HDL).

Names & identifiers

Preferred name: Terazosin Hydrochloride
IUPAC: [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(oxolan-2-yl)methanone;dihydrate;hydrochloride

Names & synonyms

Terazosin hydrochloride dihydrateUrodieItrinHytracinAbbott-45975TEZRULYTerazosin hcl 2h20Terazosin (as hydrochloride)1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(tetrahydro-2-furoyl)piperazine monohydrochloride dihydrateD32S14F082NSC-759168Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)-, monohydrochloride, dihydrate

Show more names

CHEBI:9446DTXCID5025493BenphRefChem:571796,7-dimethoxy-2-(4-(tetrahydrofuran-2-ylcarbonyl)piperazin-1-yl)quinazolin-4-amine hydrochloride dihydrateDTXSID7045493Terazosin Hydrochloride70024-40-7

Database identifiers

CAS: 70024-40-7
PubChem CID: 63016
DTXSID: DTXSID801366621
ChEMBL: CHEMBL1201091、CHEMBL3989562
UNII: D32S14F082

Properties

Computed structural properties

Topological polar surface area: 105 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 10
Rotatable bonds: 4
Heavy atoms: 31
Formal charge: 0
Complexity: 544

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

Safety & regulation

Toxicology

Treatment · 1 item

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. (L1712)

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

Exposure RoutesOral. Essentially completely absorbed in man (90% bioavailability).

Toxicity Summary · 1 item

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.

Signs and SymptomsAsthenia, postural hypotension, dizziness, somnolence, nasal congestion/rhinitis.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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

FDA Pharmacological Classification · 2 items

TERAZOSIN HYDROCHLORIDE

Adrenergic alpha-Antagonists [MoA]; alpha-Adrenergic Blocker [EPC]

MeSH Pharmacological Classification · 2 items

Drugs that bind to and block the activation of ADRENERGIC ALPHA-1 RECEPTORS.

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS.

Uses & manufacturing

Uses · 1 item

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.