CAS 155206-00-1 Bimatoprost (HCID 5311027)

概要

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

名称と識別子

優先名称: 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
現地名: ビマトプロスト
英語名: Bimatoprost
分子式: C25H37NO4
分子量: 415.57

名称と別名

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

名称をさらに表示

ビマトプロストビマトプロストビマトプロスト (JAN)ルミガン(5Z)-7-[(1R,2R,3R,5S)-3,5-ジヒドロキシ-2-[(1E,3S)-3-ヒドロキシ-5-フェニルペンタ-1-エン-1-イル]シクロペンチル]-N-エチルヘプタ-5-エンアミドグラッシュビスタ(5Z)-N-エチル-7-[(1R,2R,3R,5S)-2-[(1E,3S)-3-ヒドロキシ-5-フェニル-1-ペンテニル]-3,5-ジヒドロキシシクロペンタン-1-イル]-5-ヘプテンアミドプロスタミド(5Z)-N-エチル-7-[2β-[(1E,3S)-3-ヒドロキシ-5-フェニル-1-ペンテニル]-3α,5α-ジヒドロキシシクロペンタン-1α-イル]-5-ヘプテンアミド(5Z)-N-エチル-7-[(1R)-2β-[(1E,3S)-3-ヒドロキシ-5-フェニル-1-ペンテニル]-3α,5α-ジヒドロキシシクロペンタン-1α-イル]-5-ヘプテンアミドBimabimatoprost 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

データベース識別子

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

物性

構造計算による物性

XLogP: 2.8
極性表面積: 89.8 Å²
水素結合供与体数: 4
水素結合受容体数: 4
回転可能結合数: 12
重原子数: 30
形式電荷: 0
複雑度: 541

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

LogP3.2

Solubility · 2 件

soluble in water

1.87e-02 g/L

Human Drugs · 4 件

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

物理化学的性質

融点: 66 · 66-68°C
沸点: 629.8 · 629.8±55.0 °C(Predicted)
比重(密度): 1.145 · 1.145±0.06 g/cm3(Predicted)
貯蔵温度: -20 °C · -20°C
溶解性: クロロホルム（微量）、ジクロロメタン（微量）、メタノール（微量）
外見: 個体
酸解離定数(Pka): 14.25 · 14.25±0.20(Predicted)
色: ホワイトからオフホワイト
BCS Class: 3 · 3
安定性: 光に敏感
化粧品成分の機能: まつ毛コンディショニング
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
CAS データベース: 155206 · 155206-00-1(CAS DataBase Reference)

化学的性質

化学的特性Crystalline Solid

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (23.8%)

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

wgk: 3
Hazard Classifications: Acute Tox. 4 OralRepr. 1B
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

薬理情報

ATC Code · 3 件

S01EE03

S - Sensory organs

QS - Sensory organs

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

Pharmacodynamics · 1 件

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 · 1 件

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 · 1 件

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.

応用分野 · 4 件

用途プロスタマイド受容体（PM 受容体）に作用し、眼房水の排出を促進することで、眼圧低下作用を示します。

説明Bimatoprost 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.

使用Bimatoprost 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

一般的な説明Bimatoprost (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.