TERAZOSIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H25N5O4
Molecular Weight	387.4329
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=NC(=NC(N)=C2C=C1OC)N3CCN(CC3)C(=O)C4CCCO4

InChI

InChIKey=VCKUSRYTPJJLNI-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

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-1 169 Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2462301	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/98/75140_Terazosin%20Hydrochloride_prntlbl.pdf	Curative		Approved 8429	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 8429	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 Page: p.1169	unhealthy n = 14 Health Status: unhealthy Condition: Hypertension Population Size: 14 Sources: https://pubmed.ncbi.nlm.nih.gov/11028256 Page: p.1169	Disc. AE: Dizziness... AEs leading to discontinuation/dose reduction: Dizziness Sources: https://pubmed.ncbi.nlm.nih.gov/11028256 Page: p.1169
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 Page: p.903	unhealthy n = 37 Health Status: unhealthy Condition: Hypertension Population Size: 37 Sources: https://pubmed.ncbi.nlm.nih.gov/1678920 Page: p.903	Disc. AE: Syncope... AEs leading to discontinuation/dose reduction: Syncope (2.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/1678920 Page: p.903
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 Page: p.9	unhealthy Health Status: unhealthy Condition: Benign Prostatic Hyperplasia\|Hypertension Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf Page: p.9	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf Page: p.9
10 mg 1 times / day multiple, oral (max) 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 Page: p.6	unhealthy Health Status: unhealthy Condition: Benign Prostatic Hyperplasia\|Hypertension Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf Page: p.6	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 Page: p.6
20 mg 1 times / day multiple, oral (max) 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 Page: p.409	unhealthy n = 494 Health Status: unhealthy Condition: Benign Prostatic Hyperplasia Sex: M Population Size: 494 Sources: https://pubmed.ncbi.nlm.nih.gov/7533452 Page: p.409	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 Page: p.409
20 mg 1 times / day multiple, oral (max) 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 Page: p.12	unhealthy n = 636 Health Status: unhealthy Condition: Benign Prostatic Hyperplasia Sex: M Population Size: 636 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf Page: p.12	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 Page: p.12
40 mg 1 times / day multiple, oral (max) 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 Page: p.16	unhealthy n = 859 Health Status: unhealthy Condition: Hypertension Population Size: 859 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19057Orig1s021,%2020347Orig1s009%20lbl.pdf Page: p.16	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 Page: p.16

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP2 383	CYP 270

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22077101/	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 270	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S0099542808605444	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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
MolPort	MolPort-001-684-489	https://www.molport.com/shop/molecule-link/MolPort-001-684-489
eMolecules	902550	https://www.emolecules.com/cgi-bin/more?vid=902550

PubMed

Title	Date	PubMed
High-performance liquid chromatographic analysis and pharmacokinetics of terazosin in healthy volunteers.	2001	12889528
Terazosin for benign prostatic hyperplasia.	2002	12519611
Apoptotic and proliferative index after Alpha-1-adrenoceptor antagonist and/or finasteride treatment in benign prostatic hyperplasia.	2002	12444285
Role of supraspinal alpha1-adrenoceptors for voiding in conscious rats with and without bladder outlet obstruction.	2002 Apr	11912454
Long-term risk of re-treatment of patients using alpha-blockers for lower urinary tract symptoms.	2002 Apr	11912399
Hypertension in L-NAME-treated diabetic rats depends on an intact sympathetic nervous system.	2002 Apr	11893611
Chronic cardiovascular and renal actions of leptin: role of adrenergic activity.	2002 Feb	11882597
Terazosin for treating symptomatic benign prostatic obstruction: a systematic review of efficacy and adverse effects.	2002 Feb	11856101
The use of alpha-adrenoceptor antagonists in lower urinary tract disease.	2002 Feb	11829730
Prior iontophoresis of saline enhances vasoconstriction to phenylephrine and clonidine in the skin of the human forearm.	2002 Jul	12100224
alpha-Adrenoceptor antagonists in the treatment of benign prostate hyperplasia.	2002 Jul	12037374
[Chiral separation and preparation of three new antagonists of alpha 1-adrenoceptors by chiral mobile phase HPLC].	2002 Jun	12579804
Urodynamic effects of terazosin treatment for Japanese patients with symptomatic benign prostatic hyperplasia.	2002 Jun	11992065
Characterization of some novel alpha 1-adrenoceptor antagonists in human hyperplastic prostate.	2002 Jun 7	12065203
The efficacy of terazosin for treating benign prostatic hyperplasia: a multicentre clinical trial.	2002 May	11966644
Alpha1-adrenoceptor antagonists radiosensitize prostate cancer cells via apoptosis induction.	2002 May-Jun	12168853
Mice expressing the alpha(1B)-adrenergic receptor induces a synucleinopathy with excessive tyrosine nitration but decreased phosphorylation.	2002 Nov	12390524
Prophylactic versus therapeutic alpha-blockers after permanent prostate brachytherapy.	2002 Oct	12385927
Terazosin for treating symptomatic benign prostatic obstruction: a systematic review of efficacy and adverse effects.	2002 Oct	12356082
[Effects of terazosine and atenolol on serum lipids in essential hypertension].	2002 Sep	12448067
[alpha 1-receptor blockade in therapy of benign prostatic hyperplasia syndrome. Correct dosing for optimal effectiveness].	2002 Sep	12426862
[Drug therapy of benign prostatic hyperplasia syndrome with alpha 1-receptor blockers. Basic principles and clinical results].	2002 Sep	12426859
[Comparison of prazosin, terazosin and tramsulosin: functional and binding studies in isolated prostatic and vascular human tissues].	2002 Sep	12384622
[Use of alpha1-adrenergic blockaders in voiding disorders in women].	2002 Sep-Oct	12518672
[Urodynamic criteria of predicting efficacy of therapy with alpha1-adrenergic blockaders in patients with benign prostatic hyperplasia].	2002 Sep-Oct	12518669
[Comparative evaluation of the efficacy of using terazosin and tamsulosin in patients with benign prostatic hyperplasia].	2002 Sep-Oct	12518668
Impact of alpha1-blockers in men with spinal cord injury and upper tract stasis.	2002 Summer	12137216
[Serum nitric oxide and D-dimer before and after administering antihypertensive drugs in essential hypertension].	2003 Aug	14653123
Immobility from administration of the alpha1-adrenergic antagonist, terazosin, in the IVth ventricle in rats.	2003 Dec 26	14665423
Nitric oxide opposes glucose-induced hypertension by suppressing sympathetic activity.	2003 Feb	12574094
[Hepatotoxicity induced by terazosin].	2003 Feb 1	12605736
Doxazosin induces apoptosis in cardiomyocytes cultured in vitro by a mechanism that is independent of alpha1-adrenergic blockade.	2003 Jan 7	12515754
[Results of treatment of irritative symptoms and urinary retention in patients 1 year after radical retropubic prostatectomy].	2003 Jan-Feb	12621960
Pharmacological characterization of unique prazosin-binding sites in human kidney.	2003 Jul	12827214
Effects of intravenous and infravesical administration of suramin, terazosin and BMY 7378 on bladder instability in conscious rats with bladder outlet obstruction.	2003 Jul	12823397
Changes in nocturia from medical treatment of benign prostatic hyperplasia: secondary analysis of the Department of Veterans Affairs Cooperative Study Trial.	2003 Jul	12796667
Role of epinephrine stimulation of CNS alpha1-adrenoceptors in motor activity in mice.	2003 Jul	12710017
Comparison of finasteride and alpha-blockers as independent risk factors for erectile dysfunction.	2003 Jul-Aug	12918887
Is terazosin helpful in chronic prostatitis?	2003 Jun	12791224
Effect of terazosin on clinical benign prostatic hyperplasia in older adults.	2003 Mar	12588590
Anoikis induction by quinazoline based alpha 1-adrenoceptor antagonists in prostate cancer cells: antagonistic effect of bcl-2.	2003 Mar	12576871
Quinazoline-based alpha 1-adrenoceptor antagonists induce prostate cancer cell apoptosis via TGF-beta signalling and I kappa B alpha induction.	2003 May 19	12771931
Review: terazosin improves urologic symptoms in benign prostatic hyperplasia.	2003 May-Jun	12725629
Growth inhibiting effects of terazosin on androgen-independent prostate cancer cell lines.	2003 Nov	14642133
Pharmacological characterization of isolated human prostate.	2003 Sep	12913765
The alpha1-adrenoceptor antagonist terazosin induces prostate cancer cell death through a p53 and Rb independent pathway.	2003 Sep-Oct	12883741
Regulatory considerations of pharmaceutical solid polymorphism in Abbreviated New Drug Applications (ANDAs).	2004 Feb 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 Jan 27	14738915
Alpha1-adrenergic receptors and their inhibitors in lower urinary tract symptoms and benign prostatic hyperplasia.	2004 Mar	14767264
Measurement of low-dose active pharmaceutical ingredient in a pharmaceutical blend using frequency-domain photon migration.	2004 Mar	14762902

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 `Fri Dec 15 16:10:24 GMT 2023` Edited by `admin` on `Fri Dec 15 16:10:24 GMT 2023`
Record UNII	8L5014XET7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TERAZOSIN

Official Name

English

Terazosin [WHO-DD]

Common Name

English

TERAZOSIN [MI]

Common Name

English

terazosin [INN]

Common Name

English

TERAZOCIN

Systematic Name

English

TERAZOSABB

Brand Name

English

TERAZOSIN [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QG04CA03