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 2760

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 549 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/98/75140_Terazosin%20Hydrochloride_prntlbl.pdf	Curative		Approved 8360	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 9.5022717E11
Benign prostatic hyperplasia 28 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/98/75140_Terazosin%20Hydrochloride_prntlbl.pdf	Primary		Approved 8360	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 9.501408E11

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 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP2 367	CYP 266

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MRP2 459	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/22077101/	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 266	substrate 3326 Sources: https://www.sciencedirect.com/science/article/pii/S0099542808605444	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1632	inhibitor 1613 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
Clinical comparison of selective and non-selective alpha 1A-adrenoceptor antagonists for bladder outlet obstruction associated with benign prostatic hyperplasia: studies on tamsulosin and terazosin in Chinese patients. The Chinese Tamsulosin Study Group.	1998	10503165
Suppression of human prostate cancer cell growth by alpha1-adrenoceptor antagonists doxazosin and terazosin via induction of apoptosis.	2000 Aug 15	10969806
High-performance liquid chromatographic analysis and pharmacokinetics of terazosin in healthy volunteers.	2001	12889528
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia.	2001	11583366
Effect of terazosin on the lipid profile in patients with symptomatic benign prostatic hyperplasia.	2001	11490211
Lower urinary tract symptoms suggestive of benign prostatic obstruction--Triumph: the role of general practice databases.	2001	11275742
5alpha-reductase inhibitors: what role should they play?	2001 Dec	11750255
Terazosin, doxazosin, and prazosin: current clinical experience.	2001 Dec	11750252
Magnetic resonance imaging and morphometric histologic analysis of prostate tissue composition in predicting the clinical outcome of terazosin therapy in benign prostatic hyperplasia.	2001 Feb	11240824
Overstimulation of the alpha1B-adrenergic receptor causes a "seizure plus" syndrome.	2001 Feb	11175818
Targeted transurethral microwave thermotherapy versus alpha-blockade in benign prostatic hyperplasia: outcomes at 18 months.	2001 Jan	11164146
alpha-Blockade improves symptoms suggestive of bladder outlet obstruction but fails to relieve it.	2001 Jan	11125359
Combined effect of terazosin and finasteride on apoptosis, cell proliferation, and transforming growth factor-beta expression in benign prostatic hyperplasia.	2001 Jan 1	11170131
Loss of nocturnal dipping of blood pressure and heart rate in obesity-induced hypertension in rabbits.	2001 Jul 20	11485285
Comparison of prazosin, terazosin and tamsulosin: functional and binding studies in isolated prostatic and vascular human tissues.	2001 Jun 1	11398170
Evaluating adverse cardiovascular effects of drug treatment for benign prostatic hyperplasia (BPH): methodological considerations.	2001 May	11337216
Pharmacological blockade of brain alpha1-adrenoceptors as measured by ex vivo [3H]prazosin binding is correlated with behavioral immobility.	2001 May 25	11408030
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
The use of alpha-adrenoceptor antagonists in lower urinary tract disease.	2002 Feb	11829730
Modeling of relationships between pharmacokinetics and blockade of agonist-induced elevation of intraurethral pressure and mean arterial pressure in conscious dogs treated with alpha(1)-adrenoceptor antagonists.	2002 Feb	11805209
Effect of fiduxosin, an antagonist selective for alpha(1A)- and alpha(1D)-adrenoceptors, on intraurethral and arterial pressure responses in conscious dogs.	2002 Feb	11805208
Prior iontophoresis of saline enhances vasoconstriction to phenylephrine and clonidine in the skin of the human forearm.	2002 Jul	12100224
Urodynamic effects of terazosin treatment for Japanese patients with symptomatic benign prostatic hyperplasia.	2002 Jun	11992065
The efficacy of terazosin for treating benign prostatic hyperplasia: a multicentre clinical trial.	2002 May	11966644
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 Nov-Dec	12461301
[alpha 1-receptor blockade in therapy of benign prostatic hyperplasia syndrome. Correct dosing for optimal effectiveness].	2002 Sep	12426862
[Results of monotherapy with terazosin (kornam) in chronic infectious prostatitis patients].	2002 Sep-Oct	12518671
[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
[Serum nitric oxide and D-dimer before and after administering antihypertensive drugs in essential hypertension].	2003 Aug	14653123
The role of combination therapy for lower urinary tract symptoms secondary to benign prostatic hyperplasia.	2003 Aug	12882718
Identification of apoptotic and antiangiogenic activities of terazosin in human prostate cancer and endothelial cells.	2003 Feb	12544352
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
Is terazosin helpful in chronic prostatitis?	2003 Jun	12791224
Drug treatment of benign prostatic hyperplasia and hospital admission for BPH-related surgery.	2003 May	12705998
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
Influence of hypertension on lower urinary tract symptoms in benign prostatic hyperplasia.	2003 Nov	14633079
[Pharmacologic treatment of benign prostatic hyperplasia].	2003 Sep 14	14596018
Regulatory considerations of pharmaceutical solid polymorphism in Abbreviated New Drug Applications (ANDAs).	2004 Feb 23	14962589

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 `Wed Jul 05 23:38:01 UTC 2023` Edited by `admin` on `Wed Jul 05 23:38:01 UTC 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