TERAZOSIN HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H25N5O4.ClH.2H2O
Molecular Weight	459.924
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.Cl.COC1=CC2=C(C=C1OC)C(N)=NC(=N2)N3CCN(CC3)C(=O)C4CCCO4

InChI

InChIKey=NZMOFYDMGFQZLS-UHFFFAOYSA-N

InChI=1S/C19H25N5O4.ClH.2H2O/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);1H;2*1H2

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C19H25N5O4
Molecular Weight	387.4329
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/98/75140_Terazosin%20Hydrochloride_prntlbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10503165

Terazosin (marketed as Hytrin or Zayasel) 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. All three receptor subtypes appear to be involved in maintaining vascular tone. The α1A-receptor maintains basal vascular tone while the α1B-receptor mediates the vasocontrictory effects of exogenous α1-agonists. Activation of α1-receptors activates Gq-proteins, which results in intracellular stimulation of phospholipases C, A2, and D. This results in mobilization of Ca2+ from intracellular stores, activation of mitogen-activated kinase and PI3 kinase pathways and subsequent vasoconstriction.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2462301	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/98/75140_Terazosin%20Hydrochloride_prntlbl.pdf	Curative		Approved 8583	TERAZOSIN HYDROCHLORIDE Approved Use are used to treat high blood preassure (hypertension); are also used to treat benign prostatic hyperplasia (BPH) in men Launch Date 2000
Benign prostatic hyperplasia 28 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/98/75140_Terazosin%20Hydrochloride_prntlbl.pdf	Primary		Approved 8583	TERAZOSIN HYDROCHLORIDE Approved Use are used to treat high blood preassure (hypertension); are also used to treat benign prostatic hyperplasia (BPH) in men Launch Date 2000

C_max

Value	Dose	Co-administered	Analyte	Population
48 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1685091	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		TERAZOSIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
37 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1685091	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		TERAZOSIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
408 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1685091	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		TERAZOSIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
418 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1685091	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		TERAZOSIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1685091	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		TERAZOSIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
9.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1685091	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		TERAZOSIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
8% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2872802			TERAZOSIN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11028256	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/11028256	Disc. AE: Dizziness... AEs leading to discontinuation/dose reduction: Dizziness Sources: https://pubmed.ncbi.nlm.nih.gov/11028256
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1678920	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/1678920	Disc. AE: Syncope... AEs leading to discontinuation/dose reduction: Syncope (2.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/1678920
20 mg 1 times / day multiple, oral MTD Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf	Other AEs: Syncope, Postural hypotension... Other AEs: Syncope Postural hypotension Priapism Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf
20 mg 1 times / day multiple, oral Studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7533452	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/7533452	Disc. AE: Dizziness, Asthenia... AEs leading to discontinuation/dose reduction: Dizziness (6.7%) Asthenia (3.8%) Somnolence (2%) Chest pain (1.6%) Headache (1.2%) Dyspnea (1.2%) Prostate carcinoma (1%) Sources: https://pubmed.ncbi.nlm.nih.gov/7533452
20 mg 1 times / day multiple, oral Studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf	unhealthy Health Status: unhealthy Sex: M Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf	Disc. AE: Fever, Headache... AEs leading to discontinuation/dose reduction: Fever (0.5%) Headache (1.1%) Postural hypotension (0.5%) Syncope (0.5%) Nausea (0.5%) Dizziness (2%) Vertigo (0.5%) Dyspnea (0.5%) Blurred vision (0.6%) Amblyopia (0.6%) Urinary tract infection (0.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf
40 mg 1 times / day multiple, oral Studied dose Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf	Disc. AE: Asthenia, Headache... AEs leading to discontinuation/dose reduction: Asthenia (1.6%) Headache (1.3%) Palpitations (1.4%) Postural hypotension (0.5%) Syncope (0.5%) Tachycardia (0.6%) Nausea (0.8%) Peripheral edema (0.6%) Dizziness (3.1%) Paresthesia (0.8%) Somnolence (0.6%) Dyspnea (0.9%) Nasal congestion (0.6%) Blurred vision (0.6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP2 499	CYP 303

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22077101/	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0099542808605444	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/15098086/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9445	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9445
ChemicalBook	CB22630517	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB22630517
ChemicalBook	CB2285511	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2285511
ChemicalBook	CB73360180	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB73360180
ChemicalBook	CB9285510	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9285510
eMolecules	902550	https://www.emolecules.com/cgi-bin/more?vid=902550
MolPort	MolPort-001-684-489	https://www.molport.com/shop/molecule-link/MolPort-001-684-489

PubMed

Title	Date	PubMed
Alpha1-adrenergic receptors and their inhibitors in lower urinary tract symptoms and benign prostatic hyperplasia.	2004-03	14767264
Measurement of low-dose active pharmaceutical ingredient in a pharmaceutical blend using frequency-domain photon migration.	2004-03	14762902
Regulatory considerations of pharmaceutical solid polymorphism in Abbreviated New Drug Applications (ANDAs).	2004-02-23	14962589
Validated specific HPLC methods for determination of prazosin, terazosin and doxazosin in the presence of degradation products formed under ICH-recommended stress conditions.	2004-01-27	14738915
Immobility from administration of the alpha1-adrenergic antagonist, terazosin, in the IVth ventricle in rats.	2003-12-26	14665423
Use of alpha-blockers and the risk of hip/femur fractures.	2003-12	14641795
Growth inhibiting effects of terazosin on androgen-independent prostate cancer cell lines.	2003-11	14642133
Influence of hypertension on lower urinary tract symptoms in benign prostatic hyperplasia.	2003-11	14633079
Hormonal and morphologic evaluation of the effects of antiandrogens on the blood supply of the rat prostate.	2003-11	14624931
[Pharmacologic treatment of benign prostatic hyperplasia].	2003-09-14	14596018
Pharmacological characterization of isolated human prostate.	2003-09	12913765
Comparison of finasteride and alpha-blockers as independent risk factors for erectile dysfunction.	2003-08-16	12918887
[Serum nitric oxide and D-dimer before and after administering antihypertensive drugs in essential hypertension].	2003-08	14653123
The role of combination therapy for lower urinary tract symptoms secondary to benign prostatic hyperplasia.	2003-08	12882718
The alpha1-adrenoceptor antagonist terazosin induces prostate cancer cell death through a p53 and Rb independent pathway.	2003-07-29	12883741
Plasma atrial natriuretic peptide in essential hypertension after treatment with terazocin.	2003-07-25	12877573
Pharmacological characterization of unique prazosin-binding sites in human kidney.	2003-07	12827214
Effects of intravenous and infravesical administration of suramin, terazosin and BMY 7378 on bladder instability in conscious rats with bladder outlet obstruction.	2003-07	12823397
Changes in nocturia from medical treatment of benign prostatic hyperplasia: secondary analysis of the Department of Veterans Affairs Cooperative Study Trial.	2003-07	12796667
Role of epinephrine stimulation of CNS alpha1-adrenoceptors in motor activity in mice.	2003-07	12710017
Is terazosin helpful in chronic prostatitis?	2003-06	12791224
Quinazoline-based alpha 1-adrenoceptor antagonists induce prostate cancer cell apoptosis via TGF-beta signalling and I kappa B alpha induction.	2003-05-19	12771931
Review: terazosin improves urologic symptoms in benign prostatic hyperplasia.	2003-05-03	12725629
Drug treatment of benign prostatic hyperplasia and hospital admission for BPH-related surgery.	2003-05	12705998
Doxazosin and terazosin suppress prostate growth by inducing apoptosis: clinical significance.	2003-04	12629407
The ICH guidance in practice: stress decomposition studies on three piperazinyl quinazoline adrenergic receptor-blocking agents and comparison of their degradation behaviour.	2003-03-26	12644204
[Results of treatment of irritative symptoms and urinary retention in patients 1 year after radical retropubic prostatectomy].	2003-03-08	12621960
Effect of terazosin on clinical benign prostatic hyperplasia in older adults.	2003-03	12588590
Anoikis induction by quinazoline based alpha 1-adrenoceptor antagonists in prostate cancer cells: antagonistic effect of bcl-2.	2003-03	12576871
[Hepatotoxicity induced by terazosin].	2003-02-01	12605736
Sympathetic modulation of acute cutaneous flare induced by intradermal injection of capsaicin in anesthetized rats.	2003-02	12574463
Nitric oxide opposes glucose-induced hypertension by suppressing sympathetic activity.	2003-02	12574094
Identification of apoptotic and antiangiogenic activities of terazosin in human prostate cancer and endothelial cells.	2003-02	12544352
Terazosin therapy for chronic prostatitis/chronic pelvic pain syndrome: a randomized, placebo controlled trial.	2003-02	12544314
[Use of alpha1-adrenergic blockaders in voiding disorders in women].	2003-01-10	12518672
[Results of monotherapy with terazosin (kornam) in chronic infectious prostatitis patients].	2003-01-10	12518671
[Urodynamic criteria of predicting efficacy of therapy with alpha1-adrenergic blockaders in patients with benign prostatic hyperplasia].	2003-01-10	12518669
[Comparative evaluation of the efficacy of using terazosin and tamsulosin in patients with benign prostatic hyperplasia].	2003-01-10	12518668
Doxazosin induces apoptosis in cardiomyocytes cultured in vitro by a mechanism that is independent of alpha1-adrenergic blockade.	2003-01-07	12515754
Alpha 1-adrenoceptor effects mediated by protein kinase C alpha in human cultured prostatic stromal cells.	2003-01	12522093
Finasteride in the treatment of clinical benign prostatic hyperplasia: a systematic review of randomised trials.	2002-12-12	12477383
Influence of new evidence on prescription patterns.	2002-12-05	12463291
Success and predictors of blood pressure control in diverse North American settings: the antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT).	2002-12-04	12461301
[Effects of terazosine and atenolol on serum lipids in essential hypertension].	2002-09	12448067
[Chiral separation and preparation of three new antagonists of alpha 1-adrenoceptors by chiral mobile phase HPLC].	2002-06	12579804
Terazosin for benign prostatic hyperplasia.	2002	12519611
Induction of prostate apoptosis by alpha1-adrenoceptor antagonists: mechanistic significance of the quinazoline component.	2002	12496995
[Treatment of external RF hyperthermia combining with alpha 1-adrenergic receptor blocker for patients with prostatodynia and chronic non-bacterial prostatitis].	2002	12479049
Apoptotic and proliferative index after Alpha-1-adrenoceptor antagonist and/or finasteride treatment in benign prostatic hyperplasia.	2002	12444285
High-performance liquid chromatographic analysis and pharmacokinetics of terazosin in healthy volunteers.	2001	12889528

Patents

Sample Use Guides

In Vivo Use Guide

for Hypertension: Initial dose: 1 mg orally once a day at bedtime; Maintenance dose: 1-5 mg orally once a day. Maximum dose: 20 mg per day. Usual Adult Dose for Benign Prostatic Hyperplasia: Initial dose: 1 mg orally once a day at bedtime. Maintenance dose: Increased in a stepwise fashion to 2 mg, 5 mg, or 10 mg once a day to achieve desired improvement of symptoms.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:36:35 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:35 GMT 2025`
Record UNII	D32S14F082
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TERAZOSIN HYDROCHLORIDE

Official Name

English

TERAZOSIN HYDROCHLORIDE DIHYDRATE

Preferred Name

English

TERAZOSIN HYDROCHLORIDE DIHYDRATE [EP MONOGRAPH]

Common Name

English

TERAZOSIN HCL 2H20

Common Name

English

URODIE

Brand Name

English

ITRIN

Brand Name

English

TERAZOSIN HYDROCHLORIDE HYDRATE

Common Name

English

TERAZOSIN HYDROCHLORIDE [USP-RS]

Common Name

English

HYTRACIN

Brand Name

English

TERAZOSIN HYDROCHLORIDE HYDRATE [JAN]

Common Name

English

1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(tetrahydro-2-furoyl)piperazine monohydrochloride dihydrate

Systematic Name

English

TEZRULY

Brand Name

English

Terazosin hydrochloride [WHO-DD]

Common Name

English

HEITRIN

Brand Name

English

PIPERAZINE, 1-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)-4-((TETRAHYDRO-2-FURANYL)CARBONYL)-, MONOHYDROCHLORIDE, DIHYDRATE

Common Name

English

TERAZOSIN (AS HYDROCHLORIDE)

Common Name

English

TERAZOSIN MONOHYDROCHLORIDE DIHYDRATE

Common Name

English

TERAZOSIN HYDROCHLORIDE [USAN]

Common Name

English

TERAZOSIN HYDROCHLORIDE [VANDF]

Common Name

English

METHANONE, (4-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)-1-PIPERAZINYL)(TETRAHYDRO-2-FURANYL)-, HYDROCHLORIDE, HYDRATE (1:1:2)

Systematic Name

English

HYTRIN

Brand Name

English

ABBOTT-45975

Code

English

TERAZOSIN HYDROCHLORIDE DIHYDRATE [MI]

Common Name

English

TERAZOSIN HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

TERAZOSIN HYDROCHLORIDE DIHYDRATE [EP IMPURITY]

Common Name

English

TERAZOSIN HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

NSC-759168

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29713