Terazosin

HCID 5401CAS 63590-64-7

기본 정보

표준 SMILES
COc1cc2nc(N3CCN(C(=O)C4CCCO4)CC3)nc(N)c2cc1OC
InChIKey
VCKUSRYTPJJLNI-UHFFFAOYSA-N
분자식
C19H25N5O4
평균 분자량
387.4 g/mol
단동위원소 질량
387.19065428

개요

Terazosin is a member of furans, a member of piperazines, a member of quinazolines and a primary amino compound. It has a role as an antineoplastic agent, an antihypertensive agent and an alpha-adrenergic antagonist.

이름 및 식별자

우선 이름
Terazosin
IUPAC
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(oxolan-2-yl)methanone
영어명
Terazosin
분자식
C19H25N5O4
분자량
387.43

이름 및 동의어

terazosin63590-64-7TerazosineFosfomicTerazosinaBlavinFlumarcTerazosinumTerazosabb1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)piperazineHytrinexVicard
이름 더 보기
TERAZOSIN HCLUrodieHYTRINerazosinarbonyl)-CID 663211Vasomet:VicardHytrin:Hytrinex
8L5014XET7CHEBI:9445DTXSID3023639Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)-6,7-dimethoxy-2-(4-((oxolan-2-yl)carbonyl)piperazin-1-yl)quinazolin-4-amine6,7-dimethoxy-2-(4-(oxolane-2-carbonyl)piperazin-1-yl)-3,4-dihydroquinazolin-4-imine6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]-3,4-dihydroquinazolin-4-imine6,7-dimethoxy-2-{4-[(oxolan-2-yl)carbonyl]piperazin-1-yl}quinazolin-4-amine

데이터베이스 식별자

CAS
63590-64-7
PubChem CID
5401
DTXSID
DTXSID3023639
ChEMBL
CHEMBL611
ChEBI
CHEBI:9445
UNII
8L5014XET7
EC Number
613-265-8
Nikkaji
J19.669J

물성

구조 계산 물성

XLogP
1.4
극성 표면적
103 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
8
회전 가능 결합 수
4
무거운 원자 수
28

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Antihypertensives

Pharmaceuticals

LogP · 2건

1

1.14

Solubility1.50e+00 g/L
Human Drugs · 2건

Breast Feeding; Lactation; Milk, Human; Adrenergic alpha-Antagonists; Antihypertensive Agents

Pharmaceuticals

Melting Point · 2건

271-274

273 °C

Physical DescriptionSolid

물리화학적 성질

녹는점
281 · 281-283°C
끓는 점
664.5 · 664.5±65.0 °C(Predicted)
밀도
1.332 · 1.332±0.06 g/cm3(Predicted)
저장 조건
-20 °C · -20°C Freezer
용해도
2 O: · H2O: 25 mg/mL
물리적 상태
가루

화학적 성질

White to Off-White Crystalline Powder

안전 및 규제

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 2.3% (1 of 44) of reports.

Warning

H302 (97.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 3 notifications to the ECHA C&L Inventory.

유해성 정보

Regulatory InformationStatus: Active Update: 25-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25502
Hazard Classes and CategoriesAcute Tox. 4 (97.7%)

독성 정보

Treatment · 1건

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.
Hepatotoxicity · 1건

Terazosin has been associated with a low rate of serum aminotransferase elevations that in controlled trials was no higher than with placebo therapy. These elevations were transient and did not require dose modification. Instances of serum enzyme elevations, but no instances of clinically apparent acute liver injury with jaundice due to terazosin, have been published. Furthermore, product labels do not include discussion of hepatic toxicity. Cholestatic hepatitis and jaundice have been reported with other alpha-adrenergic blockers. Thus, acute symptomatic liver injury due to terazosin must be exceedingly rare if it occurs at all.

Adverse EffectsTerazosin is generally well-tolerated. Many adverse effects of terazosin are explainable due to its blockade of alpha-1 adrenergic receptors.
Exposure RoutesOral. Essentially completely absorbed in man (90% bioavailability).
Toxicity Summary · 2건

Overdose of terazosin may lead to hypotension, and standard life-support protocols should be in place for instances of hemodynamic instability. There are no specific antidotes for terazosin toxicity. Vasopressors may be used to support physiologic blood pressure parameters in the event of terazosin overdose. Terazosin is long-acting, with an elimination half-life of approximately 12 hours, and is highly protein-bound. Elimination is via renal excretion (40%) and excretion of feces (60%).

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.

안전 데이터

wgk
3
rtecs
TK8044925
risk_code
22-36/37/38
hazard_code
Xn,Xi
safety_code
26-36

화학 및 산업

약리 정보

ATC Code · 2건

G04CA03

G - Genito urinary system and sex hormones

Protein Binding90-94%.
PharmacodynamicsTerazosin is a quinazoline derivative alpha-1-selective adrenergic blocker.
Mechanism of Action · 1건

Terazosin is selective for alpha-1-adrenoceptors but not their individual subtypes. Inhibition of these alpha-1-adrenoceptors results in relaxation of smooth muscle in blood vessels and the prostate, lowering blood pressure and improving urinary flow. Smooth muscle cells accounts for roughly 40% of the volume of the prostate and so their relaxation reduces pressure on the urethra. It has also been shown that catecholamines induce factors responsible for mitogenesis and alpha-1-adrenergic receptor blockers inhibit this effect. A final long term mechanism of terazosin and other alpha-1-adrenergic receptor blockers is the induction of apoptosis of prostate cells. Treatment with terazosin enhances the expression of transforming growth factor beta-1 (TGF-beta1), which upregulates p27kip1, and the caspase cascade.

Biological Half-LifeTerazosin has a mean half life 12 hours though this can be as high as 14 hours in patients over 70 years and as low as 11.4 hours in patients 20 to 39 years old.
Metabolism/Metabolites · 2건

The majority of terazosin is hepatically metabolized. The metabolites recovered include 6-O-demethyl terazosin, 7-O-methyl terazosin, a piperozine derivative, and a diamine derivative.

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

용도 및 제조

Uses · 2건

Use (kg; approx.) in Germany (2009): >75

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.

Use ClassificationPharmaceuticals

응용 분야

용도Terazosin is used for the same indications as is prazosin; however, it has the advantage of being able to be used once a day.

공급사50 곳

北京华美互利生物化工010-56205725 · [email protected]
陕西缔都新材料有限公司81124267 17392282731 · [email protected]
湖北威德利化学试剂有限公司181-6332-1995 18062128043 · [email protected]
Shaanxi LonierHerb Bio Technology Co Ltd+86-86-+86-86-029-87551862 15002946897 · [email protected]
山东海舟生物工程有限公司130-0567-0367 13006570367 · [email protected]

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