Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00202)
Name
Dimethyl fumarate
Synonyms    Click to Show/Hide the Synonyms of This API
Dimethyl fumarate; 624-49-7; Tecfidera; (E)-Dimethyl fumarate; Fumaric acid dimethyl ester; Dimethyl (E)-but-2-enedioate; Fumaric acid, dimethyl ester; trans-Butenedioic acid dimethyl ester; Boletic acid dimethyl ester; Dimethyl trans-ethylenedicarboxylate; Dimethyl 2-butenedioate; Methyl fumarate; BG00012; BG-00012; Fumaderm; Allomaleic acid dimethyl ester; trans-1,2-Ethylenedicarboxylic acid dimethyl ester; BIS-METHYL ESTER; Dimethyl fumar; FAG-201; BG 00012; 2-Butenedioic acid (E)-, dimethyl ester; UNII-FO2303MNI2; (E)-but-2-enedioic acid dimethyl ester; dimethyl (2E)-but-2-enedioate; CHEBI:76004; BG 12 compound; AZL O 211089; AZL-O-211089; MFCD00064438; NSC-25942; NSC-167432; FO2303MNI2; but-2-enedioic acid dimethyl ester; dimethyl (~{E})-but-2-enedioate; LAS41008; FP-187; LAS-41008; AZL-0211089; 1,2-bis(methoxycarbonyl)-trans-ethylene; AZL 0 211089; Dimethyl fumarate, 99%; 23055-10-9; Dimethyl fumarate [USAN]; Dimethylester kyseliny fumarove; 2-Butenedioic acid (2E)-, dimethyl ester; WLN: 1OV1U1VO1 -T; dimethyl (2E)but-2-ene-1,4-dioate; Ethylene,2-bis(methoxycarbonyl)-, trans-; FAG201; FAG 201; BG 12 [Fumarate]; BG-12 [Fumarate]; 2-Butenedioic acid (2E)-, 1,4-dimethyl ester; EINECS 210-849-0; Dimethyl (2e)-2-butenedioate; NSC 25942; TL 353; 1,4-dimethyl but-2-enedioate; NSC 167432; Dimethylester kyseliny fumarove [Czech]; BRN 0774590; Panaclar; AI3-07872; But-2-enedioic acid, dimethyl ester; Ethylene, 1,2-bis(methoxycarbonyl)-, trans-; HSDB 7725; Tecfidera (TN); Fumaric acid dimethyl; Dimethyl fumarate, 97%; dimethyl trans-butenedioate; Fumaric acid-dimethyl ester; SCHEMBL41835; SCHEMBL41836; 4-02-00-02205 (Beilstein Handbook Reference); Dimethyl fumarate (JAN/USAN); GTPL7045; CHEMBL2107333; DTXSID4060787; TIMTEC-BB SBB008222; But-2-enedioic aciddimethyl ester; HMS3264D14; Pharmakon1600-01506154; NSC25942; ZINC3843378; UKRORGSYN-BB BBR-008913; BDBM50504654; NSC167432; NSC760139; SBB008222; STK039379; AKOS000121333; ZINC100509880; AS01220; CCG-213618; CS-0909; DB08908; NE10584; NSC-760139; 2-Butenedioic acid, 1,4-dimethyl ester; AK144836; HY-17363; 2(E)-Butenedioic acid 1,4-dimethyl ester; 2-Butenedioic acid, dimethyl ester, (2E)-; ST50827963; SW219154-1; D03846; W-5060; AB00172980_03; AB00172980_04; Dimethyl fumarate, Vetec(TM) reagent grade, 97%; Q418123; SR-01000944222; SR-01000944222-1; BRD-K31111078-001-01-8; F0001-1675; Fumaric acid-dimethyl ester 1000 microg/mL in Acetonitrile; Dimethyl fumarate, certified reference material, TraceCERT(R); 12287-98-8
Clinical Status
Approved
Disease Indication Multiple sclerosis ICD-11: 8A40 [1]
PubChem CID
637568
Formula
C6H8O4
Canonical SMILES
COC(=O)/C=C/C(=O)OC
InChI
1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
InChIKey
LDCRTTXIJACKKU-ONEGZZNKSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=637568"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 144.12 Topological Polar Surface Area 52.6
XlogP 0.7 Complexity 141
Heavy Atom Count 10 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Dimethyl fumarate 120 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Fd&c blue no. 1; Magnesium stearate; Ferric oxide yellow; Ferrosoferric oxide; Talc; Titanium dioxide; Triethyl citrate; Croscarmellose sodium; Polysorbate 80; Silicon dioxide; Cellulose, microcrystalline; Dimethicone; Gelatin; Methacrylic acid - ethyl acrylate copolymer (1:1) type a; Methacrylic acid - methyl methacrylate copolymer (1:1)
                   Dosage Form Delayed Release Oral Capsule
                   Company Biogen
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Dimethyl fumarate 240 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Fd&c blue no. 1; Magnesium stearate; Ferric oxide yellow; Ferrosoferric oxide; Talc; Titanium dioxide; Triethyl citrate; Croscarmellose sodium; Polysorbate 80; Silicon dioxide; Cellulose, microcrystalline; Dimethicone; Gelatin; Methacrylic acid - ethyl acrylate copolymer (1:1) type a; Methacrylic acid - methyl methacrylate copolymer (1:1)
                   Dosage Form Delayed Release Oral Capsule
                   Company Biogen
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
References
1 FDA label for approved dimethyl fumarate from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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