기본 정보
- 표준 SMILES
CC(C)(C)NC[C@H](O)COc1cccc2c1CCCC2=O- InChIKey
IXHBTMCLRNMKHZ-LBPRGKRZSA-N- 분자식
- C17H25NO3
- 평균 분자량
- 291.4 g/mol
- 단동위원소 질량
- 291.18344366
개요
Levobunolol is a cyclic ketone that is 3,4-dihydronaphthalen-1-one substituted at position 5 by a 3-(tert-butylamino)-2-hydroxypropoxy group (the S-enantiomer). A non-selective beta-adrenergic antagonist used (as its hydrochloride salt) for treatment of glaucoma. It has a role as a beta-adrenergic antagonist and an antiglaucoma drug. It is a propanolamine, an aromatic ether and a cyclic ketone. It is a conjugate base of a levobunolol(1+). It derives from a hydride of a tetralin.
이름 및 식별자
- 우선 이름
- Levobunolol
- IUPAC
- 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-2H-naphthalen-1-one
- 영어명
- LEVOBUNOLOL
- 분자식
- C17H25NO3
- 분자량
- 291.39
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
47141-42-4- PubChem CID
- 39468
- DTXSID
DTXSID1043833- ChEMBL
CHEMBL1201237- ChEBI
CHEBI:6438- UNII
- G6317AOI7K
- Nikkaji
- J237.992I
물성
구조 계산 물성
- XLogP
- 2.4
- 극성 표면적
- 58.6 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 21
- 형식 전하
- 0
- 복잡도
- 350
실험 및 물리화학적 성질
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiglaucoma Agents; Antiarrhythmics
Pharmaceuticals
Melting Point
209-211 °C
209 - 211 °C
물리화학적 성질
- 녹는점
- 209 · 209-211°C
- 저장 조건
- -20 °C · -20°C Freezer, Under Inert Atmosphere
- 주요 응용
- 의약품(소분자)
- InChI
- 1S/C17H25NO3/c1-17(2,3)18-10-12(19)11-21-16-9-5-6-13-14(16)7-4-8-15(13)20/h5-6,9,12,18-19H,4,7-8,10-11H2,1-3H3/t12-/m0/s1
- InChIKey
- IXHBTMCLRNMKHZ-LBPRGKRZSA-N
- SMILES
- N(C[C@H](O)COc1c2c(ccc1)C(=O)CCC2)C(C)(C)C
화학적 성질
White Solid
안전 및 규제
독성 정보
안전 데이터
- wgk
- WGK 3
- 독성
- LD50 in male, female rats, mice (mg/kg): 700, 800, 1530, 1220 orally; 25, 28, 78, 84 i.v.; LD50 in male, female hamsters, dogs (mg/kg): 435, 500, 100, 100 orally (Kaplan, 1980)
- Hazard Classifications
- Acute Tox. 4 Oral
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
ATC Code
S01ED03
S - Sensory organs
QS - Sensory organs
Pharmacodynamics
Levobunolol is an ophthalmic beta-blocker, equally effective at β(1)- and β(2)-receptor sites. Levobunolol reduces both elevated and normal IOP in patients with or without glaucoma. In patients with elevated IOP, levobunolol reduces mean IOP by approximately 25-40% from baseline. As the drug is a nonselective &beta-adrenergic blocking agent, it can produce both systemic pulmonary and cardiovascular effects following topical application to the eye. These effects include adverse pulmonary effects (eg. bronchoconstriction, increased airway resistance), and a decrease in blood pressure and heart rate.
Mechanism of Action
Levobunolol's mechanism of action in reducing IOP is not clearly defined, but is believed to be due to a reduction of the production of aqueous humor via blockage of endogenous catecholamine-stimulated increases in cyclic adenosine monophosphate (AMP) concentrations within the ciliary processes.
FDA Pharmacological Classification
G6317AOI7K
LEVOBUNOLOL
Mechanisms of Action [MoA] - Adrenergic beta-Antagonists
Established Pharmacologic Class [EPC] - beta-Adrenergic Blocker
Levobunolol is a beta-Adrenergic Blocker. The mechanism of action of levobunolol 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.
Drugs that inhibit the actions of the sympathetic nervous system by any mechanism. The most common of these are the ADRENERGIC ANTAGONISTS and drugs that deplete norepinephrine or reduce the release of transmitters from adrenergic postganglionic terminals (see ADRENERGIC AGENTS). Drugs that act in the central nervous system to reduce sympathetic activity (e.g., centrally acting alpha-2 adrenergic agonists, see ADRENERGIC ALPHA-AGONISTS) are included here.
용도 및 제조
응용 분야
용도As a non-selective adrenoceptor antagonist, Levobunolol is used as an anticonvulsant.
상·하류 제품 정보
상류 원료
공급사14 곳
추가 설명
정의ChEBI: A cyclic ketone that is 3,4-dihydronaphthalen-1-one substituted at position 5 by a 3-(tert-butylamino)-2-hydroxypropoxy group (the S-enantiomer). A non-selective beta-adrenergic antagonist used (as its hydrochlo ide salt) for treatment of glaucoma.
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