Methylhydrogenfumarat
Monomethyl Fumarate
Grundinformationen
- CAS
2756-87-8- Standard-SMILES
COC(=O)/C=C/C(=O)O- InChIKey
NKHAVTQWNUWKEO-NSCUHMNNSA-N- Summenformel
- C5H6O4
- Durchschnittliche Molmasse
- 130,1 g/mol
- Monoisotopische Masse
- 130,02660867
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 esterBafiertammethylhydrogenfumarate45IUB1PX8RCHEBI:167450NSC-523835DTXSID801016498RefChem:55666DTXCID30209463220-412-6
Weitere Namen anzeigen
TAK438 Impurity 110MethylhydrogenfumaratMonomethylFumarate>Vonoprazan Impurity 110Mono-Methyl fuMarate 97%
Methyl Fumaratemonomethylfumarate4-methoxy-4-oxobut-2-enoic acidMethyl hydrogen fumaratemono-Methyl fumarate(E)-4-methoxy-4-oxobut-2-enoic acid(2E)-4-Methoxy-4-oxobut-2-enoic acidfumarato de monometilo
Datenbank-Bezeichner
- CAS
2756-87-8- PubChem CID
- 5369209
- DTXSID
DTXSID801016498- ChEMBL
CHEMBL589586- ChEBI
CHEBI:167450- UNII
- 45IUB1PX8R
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,4
- Polarare Oberfläche (TPSA)
- 63,6 Ų
- 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
FDA approved drugs -> Active ingredient
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
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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 InformationREACH registered substance: Methyl hydrogen fumarate (EC: 220-412-6)
Hazard Classes and CategoriesEye Dam. 1 (72.3%)
Toxikologische Informationen
Drug Induced Liver Injury
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 Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Anwendungen
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.
Ergänzende Hinweise
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.
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