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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 544
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Antihypertensives
Pharmaceuticals
LogP
1
1.14
Human Drugs
Breast Feeding; Lactation; Milk, Human; Adrenergic alpha-Antagonists; Antihypertensive Agents
Pharmaceuticals
Melting Point
271-274
273 °C
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
- 산도 계수 (pKa)
- pKa (0.1N NaOH): 7.1(at 25℃)
- 색상
- 흰색에서 황백색까지
- 수용성
- 30.6 mg/L · 30.6mg/L(22.5℃)
- BCS Class
- 1 · 1/3
- InChIKey
- VCKUSRYTPJJLNI-UHFFFAOYSA-N
화학적 성질
White to Off-White Crystalline Powder
안전 및 규제
GHS 분류
GHS Classification
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
독성 정보
Treatment
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)
Hepatotoxicity
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.
Toxicity Summary
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.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
terazosin
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
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
G04CA03
G - Genito urinary system and sex hormones
Mechanism of Action
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.
Metabolism/Metabolites
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
8L5014XET7
TERAZOSIN
Mechanisms of Action [MoA] - Adrenergic alpha-Antagonists
Established Pharmacologic Class [EPC] - alpha-Adrenergic Blocker
Terazosin is an alpha-Adrenergic Blocker. The mechanism of action of terazosin is as an Adrenergic alpha-Antagonist.
TERAZOSIN
MeSH Pharmacological Classification
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
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.
용도 및 제조
Uses
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.
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.
상·하류 제품 정보
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