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テラゾシン

Terazosin

HCID 5401
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
63590-64-7
標準SMILES
COc1cc2nc(N3CCN(C(=O)C4CCCO4)CC3)nc(N)c2cc1OC
InChIKey
VCKUSRYTPJJLNI-UHFFFAOYSA-N
分子式
C19H25N5O4
平均分子量
387.4 g/mol
単同位体質量
387.1906543

概要

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.

名称と識別子

優先名称
Terazosin
IUPAC
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(oxolan-2-yl)methanone
現地名
テラゾシン
英語名
Terazosin
分子式
C19H25N5O4
分子量
387.43

名称と別名

terazosin63590-64-7TerazosineFosfomicTerazosinaBlavinFlumarcTerazosinumTerazosabbHytrinexVicard1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)piperazine
名称をさらに表示
4-(4-アミノ-6,7-ジメトキシキナゾリン-2-イル)ピペラジノ[(テトラヒドロフラン)-2-イル]ケトンテラゾシン1-(4-アミノ-6,7-ジメトキシキナゾリン-2-イル)-4-[[(テトラヒドロフラン)-2-イル]カルボニル]ピペラジンテラゾシン 塩酸塩6,7-ジメトキシ-2-[4-(オキソラン-2-カルボニル)ピペラジン-1-イル]キナゾリン-4-アミン[4-(4-アミノ-6,7-ジメトキシキナゾリン-2-イル)ピペラジン-1-イル](オキソラン-2-イル)メタノン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

データベース識別子

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

物性

構造計算による物性補完中

XLogP
1.4
極性表面積
103 Ų
水素結合供与体数
1
水素結合受容体数
8
回転可能結合数
4
重原子数
28
形式電荷
0
複雑度
544

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals

Pharmaceuticals -> Antihypertensives

LogP · 2 件

1

1.14

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

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

Pharmaceuticals

Melting Point · 2 件

271-274

273 °C

Physical DescriptionSolid
Collision Cross Section194.24 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
281 · 281-283°C
沸点
664.5 · 664.5±65.0 °C(Predicted)
比重(密度)
1.332 · 1.332±0.06 g/cm3(Predicted)
貯蔵温度
-20 °C · -20°C Freezer

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory InformationREACH registered substance: 6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]quinazolin-4-amine (EC: 613-265-8)
Hazard Classes and CategoriesAcute Tox. 4 (97.7%)

毒性情報

Treatment · 1 件

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 · 1 件

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.

化学と産業

薬理情報

ATC Code · 2 件

G04CA03

G - Genito urinary system and sex hormones

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

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 · 2 件

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

FDA Pharmacological Classification · 6 件

8L5014XET7

TERAZOSIN

Mechanisms of Action [MoA] - Adrenergic alpha-Antagonists

Established Pharmacologic Class [EPC] - alpha-Adrenergic Blocker

関連反応

24 件
反応記録を作成
HRID 35998 の反応式
HRID 35998反応物としてuspto-grants-1995_05
HRID 103285 の反応式
HRID 103285生成物として反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 113451 の反応式
HRID 113451生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 117851 の反応式
HRID 117851生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 202205 の反応式
HRID 202205生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 428379 の反応式
HRID 428379生成物としてuspto-grants-2001_11
HRID 619669 の反応式
HRID 619669生成物としてuspto-grants-1999_09
HRID 957030 の反応式
HRID 957030生成物としてValidation data from https://doi.org/10.1039/C8SC04228D
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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
溶解性
2 O: · H2O: 25 mg/mL
外見
粉
酸解離定数(Pka)
pKa (0.1N NaOH): 7.1(at 25℃)
色
ホワイトからオフホワイト
水溶解度
30.6 mg/L · 30.6mg/L(22.5℃)
BCS Class
1 · 1/3
InChIKey
VCKUSRYTPJJLNI-UHFFFAOYSA-N
CAS データベース
63590 · 63590-64-7(CAS DataBase Reference)

化学的性質

化学的特性White to Off-White Crystalline Powder

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 · 2 件

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.

Signs and SymptomsAsthenia, postural hypotension, dizziness, somnolence, nasal congestion/rhinitis.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

terazosin

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataLD50: 259.3mg/kg (parental-intravenous, Mouse) (A308)
EPA Human Health Benchmarks for Pharmaceuticals · 6 件

Terazosin

0.02

0.1

For hypertension, the dose may be slowly increased to achieve the desired blood pressure response. The usual recommended dose range is 1 mg to 5 mg terazosin administered once a day; however, some patients may benefit from doses as high as 20 mg per day.

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 1 mg/day, Lowest Therapeutic Dose (LTD): 0.01 mg/kg-day, and Screening Dose: 0.000004 mg/kg-day.

18-Aug-21

安全データ

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

Terazosin is an alpha-Adrenergic Blocker. The mechanism of action of terazosin is as an Adrenergic alpha-Antagonist.

TERAZOSIN

MeSH Pharmacological Classification · 2 件

Drugs that bind to and block the activation of ADRENERGIC ALPHA-1 RECEPTORS.

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS.

Absorption, Distribution and Excretion · 4 件

Approximately 90%.

Approximately 10% of the oral dose is excreted unchanged in the urine and approximately 20% is excreted in the feces. 40% of the total dose is eliminated in urine and 60% of the total dose is eliminated in the feces.

25L to 30L.

Plasma clearance is 80mL/min and renal clearance is 10mL/min.

Cellular LocationsMembrane

用途と製造

Uses · 2 件

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

応用分野

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

上流・下流製品情報

上流原料

2-フランカルボン酸ピペラジンキナゾリン2-フロイルクロリドテラゾシン塩酸塩