CAS 2756-87-8 Monomethyl Fumarate (HCID 5369209)

개요

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.

이름 및 식별자

우선 이름: Monomethyl Fumarate
IUPAC: (E)-4-methoxy-4-oxobut-2-enoic acid
현지명: 모노메틸푸마르산염
영어명: Monomethyl fumarate
분자식: C5H6O4
분자량: 130.1

이름 및 동의어

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

이름 더 보기

모노메틸푸마르산염TAK438 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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: 0.4
극성 표면적: 63.6 Å²
수소 결합 공여자 수: 1
수소 결합 수용자 수: 4
회전 가능 결합 수: 3
무거운 원자 수: 9
형식 전하: 0
복잡도: 147

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Metabolite of Dimethyl fumarate

SpringerMaterials PropertiesCrystal structure

Human Drugs · 2건

FDA approved drugs -> Active ingredient

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

물리화학적 성질

녹는점: 144 · 144-145 °C (lit.)
끓는 점: 250 · 250.0±23.0 °C(Predicted)
밀도: 1.37 g/cm3 · 1.37 g/cm3
저장 조건: 2 · 2-8°C
용해도: 클로로포름(약간 용해됨), DMSO(약간 용해됨), 메탄올(약간 용해됨)
산도 계수 (pKa): 3.4 · 3.40±0.10(Predicted)
물리적 상태: 고체
색상: 회백색
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

화학적 성질

Off-White Solid

안전 및 규제

GHS 분류

GHS Classification · 5건

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.

유해성 정보

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

Hazard Classes and CategoriesEye Dam. 1 (72.3%)

독성 정보

Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Monomethyl fumarate

Ambiguous-DILI-concern

4

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

안전 데이터

wgk: 3
HS 번호: 29171900
risk_code: 41
hazard_code: Xi
safety_code: 26-39
Hazard Classifications: Eye Irrit. 2
스토리지 클래스: 11 - Combustible Solids

화학 및 산업

약리 정보

ATC CodeL - Antineoplastic and immunomodulating agents

응용 분야 · 2건

개요Monomethyl 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.

용도Monomethyl 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.

제조 방법

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.

공급사100 곳

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]

추가 설명 · 1건

정의ChEBI: 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.