TERAZOSIN HYDROCHLORIDE ANHYDROUS

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H25N5O4.ClH
Molecular Weight	423.894
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TERAZOSIN HYDROCHLORIDE ANHYDROUS

Structure Search

SMILES

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

InChI

InChIKey=IWSWDOUXSCRCKW-UHFFFAOYSA-N

InChI=1S/C19H25N5O4.ClH/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

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	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
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
A meta-analysis on the efficacy and tolerability of alpha1-adrenoceptor antagonists in patients with lower urinary tract symptoms suggestive of benign prostatic obstruction.	1999	10364649
Alpha 1-adrenoceptor antagonists terazosin and doxazosin induce prostate apoptosis without affecting cell proliferation in patients with benign prostatic hyperplasia.	1999 Jun	10332490
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
Tamsulosin: an update of its role in the management of lower urinary tract symptoms.	2002	11790159
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
[Chiral separation and preparation of three new antagonists of alpha 1-adrenoceptors by chiral mobile phase HPLC].	2002 Jun	12579804
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
[Use of alpha1-adrenergic blockaders in voiding disorders in women].	2002 Sep-Oct	12518672
[Hepatotoxicity induced by terazosin].	2003 Feb 1	12605736
[Results of treatment of irritative symptoms and urinary retention in patients 1 year after radical retropubic prostatectomy].	2003 Jan-Feb	12621960
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
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 `Sat Dec 16 05:00:55 GMT 2023` Edited by `admin` on `Sat Dec 16 05:00:55 GMT 2023`
Record UNII	8QOP8Z9955
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TERAZOSIN HYDROCHLORIDE ANHYDROUS

Common Name

English

ABBOTT-45975 ANHYDROUS

Code

English

Terazosin hydrochloride anhydrous [WHO-DD]

Common Name

English

TERAZOSIN HYDROCHLORIDE, ANHYDROUS

Common Name

English

TERAZOSIN HCL

Common Name

English

TERAZOSIN HYDROCHLORIDE [MI]

Common Name

English

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

Systematic Name

English

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

Common Name

English

6,7-DIMETHOXY-2-(4-(TETRAHYDROFURAN-2-YLCARBONYL)PIPERAZIN-1-YL)QUINAZOLIN-4-AMINE HYDROCHLORIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29713