Monomethyl Fumarate (HCID 5369209)

Überblick

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.

Namen und Bezeichner

Bevorzugter Name: Monomethyl Fumarate
IUPAC: (E)-4-methoxy-4-oxobut-2-enoic acid
Lokaler Name: Methylhydrogenfumarat
Englischer Name: Monomethyl fumarate
Summenformel: C5H6O4
Molmasse: 130.1

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 0,4
Polarare Oberfläche (TPSA): 63,6 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 4
Frei drehbare Bindungen: 3
Schwere Atome: 9
Formalladung: 0
Komplexität: 147

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Metabolite of Dimethyl fumarate

SpringerMaterials PropertiesCrystal structure

Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

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

Physikochemische Eigenschaften

Schmelzpunkt: 144 · 144-145 °C (lit.)
Siedepunkt: 250 · 250.0±23.0 °C(Predicted)
Dichte: 1.37 g/cm3 · 1.37 g/cm3
storage temp.: 2 · 2-8°C
Löslichkeit: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka: 3.4 · 3.40±0.10(Predicted)
Aggregatzustand: Solid
Farbe: Off-White
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 Datenbank: 2756 · 2756-87-8(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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.

Gefahrenhinweise

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

Hazard Classes and CategoriesEye Dam. 1 (72.3%)

Toxikologische Informationen

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Monomethyl fumarate

Ambiguous-DILI-concern

4

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Sicherheitsdaten

wgk: 3
hs_code: 29171900
risk_code: 41
hazard_code: Xi
safety_code: 26-39
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Eye Irrit. 2

Chemie und Industrie

Pharmakologische Informationen

ATC CodeL - Antineoplastic and immunomodulating agents

Anwendungen · 2 Einträge

BeschreibungMonomethyl 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.

VerwendenMonomethyl 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.

Darstellung

synthetischeMonomethyl 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.

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

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

Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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.