CAS 1210344-57-2 Ertugliflozin (HCID 44814423)

部分構造検索類似構造を探す

基本情報

CAS: 1210344-57-2
標準SMILES: CCOc1ccc(Cc2cc([C@]34OC[C@](CO)(O3)[C@@H](O)[C@H](O)[C@H]4O)ccc2Cl)cc1
InChIKey: MCIACXAZCBVDEE-CUUWFGFTSA-N
分子式: C22H25ClO7
平均分子量: 436.9 g/mol
単同位体質量: 436.1288808

概要

Ertugliflozin is a diarylmethane.

名称と識別子

優先名称: Ertugliflozin
IUPAC: (1S,2S,3S,4R,5S)-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
現地名: エルツグリフロジン
英語名: Ertugliflozin
分子式: C22H25ClO7
分子量: 436.88

名称と別名

Ertugliflozin1210344-57-2PF-04971729PF04971729(1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triolertugliflozinaertugliflozine(1S,2S,3S,4R,5S)-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triolMK-8835PF-04971729-006C282481IPDTXSID40153120

名称をさらに表示

エルツグリフロジン(1S,2S,3S,4R,5S)-5-{4-クロロ-3-[(4-エトキシフェニル)メチル]フェニル}-1-(ヒドロキシメチル)-6,8-ジオキサビシクロ[3.2.1]オクタン-2,3,4-トリオール(1S,5S)-1-(ヒドロキシメチル)-5-[3-(4-エトキシベンジル)-4-クロロフェニル]-6,8-ジオキサビシクロ[3.2.1]オクタン-2β,3α,4β-トリオール(1R,2S,3S,4R,5R)-5-{4-クロロ-3-[(4-エトキシフェニル)メチル]フェニル}-1-(ヒドロキシメチル)-6,8-ジオキサビシクロ[3.2.1]オクタン-2,3,4-トリオール5β-(ヒドロキシメチル)-1β-[3-(4-エトキシベンジル)-4-クロロフェニル]-7,8-ジオキサビシクロ[3.2.1]オクタン-2α,3β,4α-トリオール(1S,2S,3S,4R,5S)-(2,3,4-TRIS-BENZYLOXY-5-(4-CHLORO-3-(4-ETHOXY-BENZYL)-PHENYL)-68-DIOXA-BICYCLO(3.2.1)OCT-1-YL)-METHANOLEpagliflozin1,6-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-5-C-(hydroxymethyl)-beta-L-idopyranose PF-04971729(Ertugliflozin)

物性

構造計算による物性

XLogP: 1.7
極性表面積: 109 Å²
水素結合供与体数: 4
水素結合受容体数: 7
回転可能結合数: 6
重原子数: 30
形式電荷: 0
複雑度: 586

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

Human Drugs · 4 件

Breast Feeding; Lactation; Milk, Human; Hypoglycemic Agents; Sodium-Glucose Cotransporter 2 Inhibitors; SGLT2 Inhibitors

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

物理化学的性質

融点: 65 · 65 - 66oC
沸点: 630.5 · 630.5±55.0 °C(Predicted)
比重(密度): 1.455 · 1.455
貯蔵温度: -20 °C · Sealed in dry,Store in freezer, under -20°C
溶解性: DMSO（微量）、メタノール（微量）
酸解離定数(Pka): 12.95 · 12.95±0.70(Predicted)
外見: 個体
色: ホワイトからオフホワイト
InChIKey: MCIACXAZCBVDEE-RDZQEHASNA-N
SMILES: [C@@]12(C3C=CC(Cl)=C(CC4C=CC(OCC)=CC=4)C=3)OC[C@@](CO)([C@@H](O)[C@H](O)[C@H]1O)O2 |&1:0,20,23,25,27,r|

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

危険有害性情報

Hazard Classes and Categories · 2 件

Skin Corr. 1A (100%)

Eye Dam. 1 (100%)

毒性情報

Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Ertugliflozin

vNo-DILI-concern

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

危険有害性情報: コード危険有害性情報危険有害性クラス区分注意喚起語シンボル P コード H314

化学と産業

薬理情報

ATC Code · 2 件

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Protein Binding · 1 件

Ertugliflozin is 93.6% bound to plasma proteins. Plasma protein binding is independent of ertugliflozin plasma concentrations and is not meaningfully altered in patients with renal or hepatic impairment. The blood-to-plasma concentration ratio of ertugliflozin is 0.66.

PharmacodynamicsErtugliflozin causes a dose-dependent increase in urinary glucose excretion and an increase in urinary volume in patients with T2DM.

Mechanism of Action · 1 件

Kidneys play an integral role in glucose homeostasis. After being filtered into urine within the nephron, most of the plasma glucose is reabsorbed through two types of sodium-dependent glucose cotransporters (SGLTs), SGLT1 and SGLT2, expressed in proximal renal tubules. More specifically, SGLT2 is responsible for 80–90% of renal glucose reabsorption while SGLT1 is responsible for the remaining 10-20%. Under physiological conditions, less than one percent of glucose is excreted in urine. In the case of hyperglycemia, SGLTs become saturated and the renal threshold for urinary glucose excretion is increased. Kidneys respond to an elevated threshold for glycosuria by elevating glucose reabsorption and increasing maximum glucose reabsorptive capacity. Ertugliflozin is an inhibitor of SGLT2 that reduces renal reabsorption of filtered glucose and lowers the renal threshold for glucose, thereby increasing urinary glucose excretion.

Biological Half-LifeThe terminal elimination half-life of ertugliflozin ranges from 11 to 17 hours. The mean elimination half-life in T2DM patients with normal renal function was estimated to be 16.6 hours based on the population pharmacokinetic analysis.

Metabolism/Metabolites · 1 件

Ertugliflozin mainly undergoes O-glucuronidation mediated by UGT1A9 and UGT2B7 to form two pharmacologically inactive glucuronides. About 12% of the drug undergoes CYP-mediated oxidative metabolism. Several metabolites have been found in plasma, feces, and urine. In plasma, the unchanged form of ertugliflozin was found to be the major component of the administered dose.