CAS 155206-00-1 Bimatoprost (HCID 5311027)

개요

Bimatoprost is a monocarboxylic acid amide. It has a role as an antihypertensive agent and an antiglaucoma drug.

이름 및 식별자

우선 이름: Bimatoprost
IUPAC: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide
현지명: 비마토프로스트
영어명: Bimatoprost
분자식: C25H37NO4
분자량: 415.57

이름 및 동의어

Bimatoprost155206-00-1LumiganLatisseAGN 192024ProstamideAGN-192024bimatoprostum(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamideDURYSTAQXS94885MZ(Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3S)-3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-5-heptenamide

이름 더 보기

비마토프로스트Bimabimatoprost powderN-ETHYL-9ALPHA,11ALPHA,15S-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROSTA-5Z, 13E-DIEN-1-AMIDEbimatoprosBimatoprost (W.S)BiMatoprost HOUSE STANDARD17-phenyl-tri-norprostaglandin f2α-ethyl amide17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA ETHYL AMIDE

CHEBI:51230DTXSID30895042GANFORT COMPONENT BIMATOPROSTAGN1920245-Heptenamide, 7-(3,5-dihydroxy-2-(3-hydrdoxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-, (1R-(1alpha(Z),2beta(1E,3S*),3alpha,5alpha))-(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide(5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide(5Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl)cyclopentyl)-N-ethylhept-5-enamide

데이터베이스 식별자

CAS: 155206-00-1
PubChem CID: 5311027
DTXSID: DTXSID30895042
ChEMBL: CHEMBL1200963
ChEBI: CHEBI:51230
UNII: QXS94885MZ
EC Number: 642-890-9
Nikkaji: J1.596.089B

물성

구조 계산 물성

XLogP: 2.8
극성 표면적: 89.8 Å²
수소 결합 공여자 수: 4
수소 결합 수용자 수: 4
회전 가능 결합 수: 12
무거운 원자 수: 30
형식 전하: 0
복잡도: 541

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15

LogP3.2

Solubility · 2건

soluble in water

1.87e-02 g/L

Human Drugs · 4건

Breast Feeding; Lactation; Milk, Human; Antiglaucoma Agents; Prostaglandins

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Melting Point63-67

Physical DescriptionSolid

물리화학적 성질

녹는점: 66 · 66-68°C
끓는 점: 629.8 · 629.8±55.0 °C(Predicted)
밀도: 1.145 · 1.145±0.06 g/cm3(Predicted)
저장 조건: -20 °C · -20°C
용해도: 클로로포름(약간 용해됨), 디클로로메탄(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태: 고체
산도 계수 (pKa): 14.25 · 14.25±0.20(Predicted)
색상: 흰색에서 황백색까지
BCS Class: 3 · 3
안정성: 감광성
화장품 원료 기능: 속눈썹 컨디셔닝
InChIKey: AQOKCDNYWBIDND-FTOWTWDKSA-N
SMILES: C(NCC)(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1

화학적 성질

Crystalline Solid

안전 및 규제

GHS 분류

GHS Classification · 4건

Danger

H302 (23.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P317, P318, P321, P330, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 21 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (23.8%)

독성 정보

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk: 3
Hazard Classifications: Acute Tox. 4 OralRepr. 1B
스토리지 클래스: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

화학 및 산업

약리 정보

ATC Code · 3건

S01EE03

S - Sensory organs

QS - Sensory organs

Protein BindingBimatoprost is about 88%-90% bound to plasma proteins.

Pharmacodynamics · 1건

High intraocular pressure is a major risk factor for glaucoma-related visual field loss. A linear relationship exists between intraocular pressure and the risk of damaging the optic nerve, which can lead to considerable visual impairment. Therefore, conditions such as ocular hypertension and glaucoma can cause dangerous elevations of intraocular pressure. Bimatoprost rapidly decreases intraocular pressure and reduces the risk for visual field loss from ocular hypertension due to various causes. Other effects of this drug may include gradual changes in eyelid pigmentation, changes in iris pigmentation, changes in eyelash pigmentation, growth and thickness. Patients should be informed of these possible effects, especially if this drug is only administered to one eye, which may noticeably change in appearance with bimatoprost treatment.

Mechanism of Action · 1건

Bimatoprost imitates the effects of prostamides, specifically prostaglandin F2α. Bimatoprost mildly stimulates aqueous humor outflow, relieving elevated intraocular pressure and decreasing the risk of optic nerve damage. It is thought that bimatoprost reduces intraocular pressure (IOP) in humans by causing an increase in outflow of the aqueous humor via the trabecular meshwork and uveoscleral pathways. It achieves the above effects by decreasing tonographic resistance to aqueous humor outflow. Bimatoprost does not affect aqueous humor production.

Biological Half-LifeThe elimination half-life of bimatoprost is approximately 45 minutes.

Metabolism/Metabolites · 1건

Bimatoprost is hydrolyzed to its active form, bimatoprost acid, in the eye. Bimatoprost undergoes oxidation, N-deethylation, and glucuronidation after it is systemically absorbed, and this leads to the production of various metabolites. In vitro studies show that CYP3A4 is an enzyme that participates in the metabolism of bimatoprost. Despite this, many enzymes and pathways metabolize bimatoprost, therefore, no significant drug-drug interactions are likely to occur. Glucuronidated metabolites comprise most of the excreted drug product in the blood, urine, and feces in rats.

응용 분야 · 3건

개요Bimatoprost was first introduced in the US and Brazil as Lumigan, an ophthalmic solution (0.03%) for the reduction of elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension, a proven risk of glaucomatous visual field loss. Bitamoprost is a new agent belonging to the PGF2α analog class of prostamides launched in this indication after latanoprost, the most efficaceous topical medication currently available. This synthetic fatty acid amide can be prepared by esterification of 17- phenyl-18,19,20-trinorprostaglandin F2α followed by ethylamidation. Bimatoprost, as related prostamides, is devoid of typical activities associated with PGF2,, analogs; it exhibits a unique pharmacological profile in contracting the feline iris sphincter with an EC50 of 34 nM without interacting with any known prostanoid receptors. Thus it mimics the action of endogenous prostamides on specific receptors that lower IOP by increasing aqueous humor outflow through both pressure-insensitive and pressure-sensitive pathways without reducing humor formation. In a 3-month controlled clinical trial of efficacy and safety in patients with elevated IOP, bimatoprost demonstrated lower mean intraocular pressures at every time point throughout the study, as well as a good tolerance and systemic safety profile compared to latanoprost.

용도Bimatoprost is a prostaglandin analog used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. It reduces intraocular pressure (IOP) by increasing the outflow of aqueous fluid from the eyes. It ha

일반 설명Bimatoprost (Lumigan) is supplied as a sterile 0.03%ophthalmic solution in 2.5- and 5.0-mL sizes. The recommendeddosage of bimatoprost is limited to one drop intothe affected eye once daily in the evening. Increased usagemay decrease its beneficial effect. If used concurrently withother IOP-lowering drugs, a waiting period of 5 minutesshould separate administrations.