기본 정보
- CAS
22664-55-7- 표준 SMILES
CC(=O)Oc1c(C)cc(OCC(O)CNC(C)C)c(C)c1C- InChIKey
BQIPXWYNLPYNHW-UHFFFAOYSA-N- 분자식
- C17H27NO4
- 평균 분자량
- 309.4 g/mol
- 단동위원소 질량
- 309.19400834
개요
Metipranolol is 3-(Propan-2-ylamino)propane-1,2-diol in which the hydrogen of the primary hydroxy group is substituted by a 4-acetoxy-2,3,5-trimethylphenoxy group. A non-cardioselective beta-blocker, it is used to lower intra-ocular pressure in the management of open-angle glaucoma. It has a role as a beta-adrenergic antagonist, an antihypertensive agent, an anti-arrhythmia drug and an antiglaucoma drug. It is a propanolamine, an aromatic ether, an acetate ester and a secondary amino compound.
이름 및 식별자
- 우선 이름
- Metipranolol
- IUPAC
- [4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-2,3,6-trimethylphenyl] acetate
- 현지명
- 메티프라놀롤
- 영어명
- metipranolol
- 분자식
- C17H27NO4
- 분자량
- 309.4
이름 및 동의어
Metipranolol22664-55-7TrimepranolMetipranololumDTXSID4046078VUAB-6453VUAB6453X39AL81KEB(+-)-metipranololBM-01004BM01.004Phenol, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-2,3,6-trimethyl-, 1-acetate
이름 더 보기
메티프라놀롤DisoratGlausynGlaulineVUFB-64534-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)-2,3,6-TRIMETHYLPHENYL ACETATE4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-2,3,6-trimethylphenol 1-acetate
Methypranol4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-2,3,6-trimethylphenyl acetateBM-01.004CHEBI:6897DTXCID2026078Acetic acid 4-(2-hydroxy-3-isopropylamino-propoxy)-2,3,6-trimethyl-phenyl esterPhenol, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-2,3,6-trimethyl-, 1-acetatemetipranololo
데이터베이스 식별자
- CAS
22664-55-7- PubChem CID
- 31477
- DTXSID
DTXSID4046078
물성
구조 계산 물성
- XLogP
- 2.7
- 극성 표면적
- 67.8 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 5
- 회전 가능 결합 수
- 8
- 무거운 원자 수
- 22
- 형식 전하
- 0
- 복잡도
- 348
실험 및 물리화학적 성질
LogP
2.2
1.95
Solubility1.73e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiglaucoma Agents; Antiarrhythmics
Melting Point
105-107 °C
105 - 107 °C
Physical DescriptionSolid
Dissociation Constants9.54
물리화학적 성질
- 녹는점
- 105 · 105-107℃
- 끓는 점
- 458.7 · 458.7±45.0 °C(Predicted)
- 밀도
- 1.068 · 1.068
- 저장 조건
- 4 °C, · 4°C, protect from light
- 용해도
- 30 mg/ml; · DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:6): 0.14 mg/ml; DMSO: 20 mg/ml; Ethanol: 10 mg/ml
- 물리적 상태
- 결정성 고체
- 산도 계수 (pKa)
- 13.91 · 13.91±0.20(Predicted)
- 색상
- White to off-white
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (100%)
독성 정보
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
안전 데이터
- 독성
- LD50 in mice (mg/kg): 31 i.v. (Bartsch)
화학 및 산업
약리 정보
ATC Code
S - Sensory organs
QS - Sensory organs
Pharmacodynamics
Metipranolol is a beta1 and beta2 (non-selective) adrenergic receptor-blocking agent that does not have significant intrinsic sympathomimetic, direct myocardial depressant, or local anesthetic (membrane-stabilizing) activity. Metipranolol is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Metipranolol, when applied topically to the eye, has the action of reducing elevated, as well as normal, intraocular pressure, whether or not accompanied by glaucoma. Elevated intraocular pressure is a major risk factor in the pathogenesis of glaucomatous visual field loss and optic nerve damage. Metipranolol reduces intraocular pressure with little or no effect on pupil size or accommodation in contrast to the miosis which cholinergic agents are known to produce.
Mechanism of Action
Although it is known that metipranolol binds the beta1 and beta2 adrenergic receptors, the mechanism of metipranolol's action is not known. It has no significant intrinsic sympathomimetic activity, and has only weak local anesthetic (membrane-stabilizing) and myocardial depressant activity. It appears that the ophthalmic beta-adrenergic blocking agents reduce aqueous humor production, as demonstrated by tonography and fluorophotometry. A slight increase in aqueous humor outflow may be an additional mechanism.
FDA Pharmacological Classification
X39AL81KEB
METIPRANOLOL
Mechanisms of Action [MoA] - Adrenergic beta-Antagonists
Established Pharmacologic Class [EPC] - beta-Adrenergic Blocker
Metipranolol is a beta-Adrenergic Blocker. The mechanism of action of metipranolol is as an Adrenergic beta-Antagonist.
MeSH Pharmacological Classification
Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety.
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