Monomethyl Fumarate (HCID 5369209)

概要

Monomethyl fumarate is a dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1. It has a role as an antioxidant, a drug metabolite and an immunomodulator. It is a methyl ester, a dicarboxylic acid monoester and an enoate ester. It is functionally related to a fumaric acid.

名称と識別子

優先名称: Monomethyl Fumarate
IUPAC: (E)-4-methoxy-4-oxobut-2-enoic acid
現地名: フマル酸1-メチル
英語名: Monomethyl fumarate
分子式: C5H6O4
分子量: 130.1

名称と別名

Monomethyl fumarate2756-87-8Fumaric acid monomethyl esterBafiertam45IUB1PX8RmethylhydrogenfumarateCHEBI:167450NSC-523835DTXSID801016498RefChem:55666DTXCID30209463220-412-6

名称をさらに表示

(E)-2-ブテン二酸1-メチルtrans-エチレン-1,2-ジカルボン酸モノメチルフマル酸モノメチルフマル酸水素1-メチルフマル酸1-メチル(E)-2-ブテン二酸水素1-メチルフマル酸水素メチルMONO-フマル酸メチルTAK438 Impurity 110MethylhydrogenfumaratMonomethylFumarate>Vonoprazan Impurity 110Mono-Methyl fuMarate 97%

Methyl FumaratemonomethylfumarateMethyl hydrogen fumarate4-methoxy-4-oxobut-2-enoic acidmono-Methyl fumarate(E)-4-methoxy-4-oxobut-2-enoic acid(2E)-4-Methoxy-4-oxobut-2-enoic acid2-Butenedioic acid (2E)-, 1-methyl ester

データベース識別子

CAS: 2756-87-8
PubChem CID: 5369209
DTXSID: DTXSID801016498
ChEMBL: CHEMBL589586
ChEBI: CHEBI:167450
UNII: 45IUB1PX8R
EC Number: 220-412-6
Nikkaji: J121.400D、J520.491G

物性

構造計算による物性

XLogP: 0.4
極性表面積: 63.6 Å²
水素結合供与体数: 1
水素結合受容体数: 4
回転可能結合数: 3
重原子数: 9
形式電荷: 0
複雑度: 147

実験および物理化学的性質

DrugsPharmaceuticals -> Metabolite of Dimethyl fumarate

SpringerMaterials PropertiesCrystal structure

Human Drugs · 2 件

FDA approved drugs -> Active ingredient

Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

物理化学的性質

融点: 144 · 144-145 °C (lit.)
沸点: 250 · 250.0±23.0 °C(Predicted)
比重(密度): 1.37 g/cm3 · 1.37 g/cm3
貯蔵温度: 2 · 2-8°C
溶解性: クロロホルム（微量）、DMSO（微量）、メタノール（微量）
酸解離定数(Pka): 3.4 · 3.40±0.10(Predicted)
外見: 個体
色: オフホワイト
InChI: InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+
InChIKey: NKHAVTQWNUWKEO-NSCUHMNNSA-N
SMILES: C(OC)(=O)/C=C/C(O)=O
CAS データベース: 2756 · 2756-87-8(CAS DataBase Reference)

化学的性質

化学的特性Off-White Solid

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 26.2% (37 of 141) of reports.

Danger

H318 (72.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)

Aggregated GHS information provided per 141 reports by companies from 7 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory InformationStatus: Active Update: 23-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/29959

Hazard Classes and CategoriesEye Dam. 1 (72.3%)

毒性情報

Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Monomethyl fumarate

Ambiguous-DILI-concern

4

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

安全データ

wgk: 3
hs_code: 29171900
risk_code: 41
化審法: (2)-1142
hazard_code: Xi
safety_code: 26-39
Hazard Classifications: Eye Irrit. 2
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

ATC CodeL - Antineoplastic and immunomodulating agents

応用分野 · 2 件

説明Monomethyl fumarate (MMF), a bioactive metabolite of fumaric acid ester, is an immunotherapy for psoriasis that causes decreased production of Th1 cytokines and lymphocytopenia. Monomethyl fumarate was shown to decrease DC response to LPS and decreased IL-12p70 and IL-10 production.

使用Monomethyl fumarate is used to treat the relapsing forms of multiple sclerosis (MS), including clinically isolated syndrome, relapsing-remitting disease, and active secondary progressive disease. This medicine will not cure MS, but it may slow some of the disabling effects and decrease the number of relapses of the disease.Fumaric Acid Monomethyl Ester is one of the most bioactive anti-psoriatic fumaric acid ester metabolite. Fumaric Acid Monomethyl Ester is potent nicotinic acid receptor agonist. Fumaric Acid Monomethy l Ester has also been shown to selectively stimulate of T helper 2 cytokine response.

調製方法

製造方法Monomethyl fumarate was synthesized by maleic anhydride and methanol. monomethyl fumarate could inhibit the growth of mold, and the storage time of feed could be prolonged.

サプライヤー50 社

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

合肥翰刚医药科技有限公司+8618062405514 · [email protected]

Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]

補足説明 · 1 件

定義ChEBI: Monomethyl fumarate is a dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1. It has a role as an immunomodulator, an antioxidant and a drug metabolite. It is an enoate ester, a methyl ester and a dicarboxylic acid monoester. It derives from a fumaric acid.