diroximel fumarate   Click here for help

GtoPdb Ligand ID: 10525

Synonyms: ALKS-8700 | ALKS8700 | BIIB098 | Vumerity®
Approved drug Immunopharmacology Ligand
diroximel fumarate is an approved drug (FDA (2019), EMA (2021))
Compound class: Synthetic organic
Comment: Diroximel fumarate is a novel oral fumarate prodrug. It is rapidly converted to monomethyl fumarate, which is the same active metabolite of dimethyl fumarate.

diroximel fumarate is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 89.98
Molecular weight 255.07
XLogP -0.81
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC(=O)C=CC(=O)OCCN1C(=O)CCC1=O
Isomeric SMILES COC(=O)/C=C/C(=O)OCCN1C(=O)CCC1=O
InChI InChI=1S/C11H13NO6/c1-17-10(15)4-5-11(16)18-7-6-12-8(13)2-3-9(12)14/h4-5H,2-3,6-7H2,1H3/b5-4+
InChI Key YIMYDTCOUQIDMT-SNAWJCMRSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (2019)  |  EMA (2021)
Is prodrug? Yes
Active form monomethyl fumarate
IUPAC Name Click here for help
4-O-[2-(2,5-dioxopyrrolidin-1-yl)ethyl] 1-O-methyl (E)-but-2-enedioate
International Nonproprietary Names Click here for help
INN number INN
10356 diroximel fumarate
Synonyms Click here for help
ALKS-8700 | ALKS8700 | BIIB098 | Vumerity®
Database Links Click here for help
CAS Registry No. 1577222-14-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL3989944
GtoPdb PubChem SID 387065607
PubChem CID 73330464
Search Google for chemical match using the InChIKey YIMYDTCOUQIDMT-SNAWJCMRSA-N
Search Google for chemicals with the same backbone YIMYDTCOUQIDMT
Search PubMed clinical trials diroximel fumarate
Search PubMed titles diroximel fumarate
Search PubMed titles/abstracts diroximel fumarate
UniChem Compound Search for chemical match using the InChIKey YIMYDTCOUQIDMT-SNAWJCMRSA-N
UniChem Connectivity Search for chemical match using the InChIKey YIMYDTCOUQIDMT-SNAWJCMRSA-N

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MedChemExpress
Diroximel fumarate (links to external site)
Cat. No. HY-100375