dimethyl fumarate Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
4757 624-49-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • dimethyl fumarate
  • tecfidera
  • methyl fumarate
  • boletic acid dimethyl ester
  • BG-12
A fumarate derivative that is used as a DERMATOLOGIC AGENT in the treatment of PSORIASIS and SKIN DISEASES. It also may be used as an IMMUNOSUPPRESSIVE AGENT in the treatment of MULTIPLE SCLEROSIS.
  • Molecular weight: 144.13
  • Formula: C6H8O4
  • CLOGP: 0.78
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 0
  • TPSA: 52.60
  • ALOGS: -1.05
  • ROTB: 4

Drug dosage:

DoseUnitRoute
0.48 g O

Approvals:

DateAgencyCompanyOrphan
March 27, 2013 FDA BIOGEN IDEC INC

FDA Adverse Event Reporting System

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Flushing 5383.91 35.42 1299 11620 12814 3360126
Multiple sclerosis relapse 3697.06 35.42 932 11987 10998 3361942
Multiple sclerosis 1844.53 35.42 479 12440 6289 3366651
Prescribed underdose 1722.86 35.42 349 12570 1299 3371641
Nausea 1688.91 35.42 990 11929 128655 3244285
Diarrhoea 1648.88 35.42 905 12014 103443 3269497
Vomiting 1335.21 35.42 749 12170 88782 3284158
Abdominal pain upper 1075.82 35.42 435 12484 24481 3348459
Gastrointestinal disorder 941.96 35.42 315 12604 10254 3362686
Fall 834.16 35.42 478 12441 58405 3314535
Drug intolerance 737.14 35.42 270 12649 11528 3361412
Pruritus 702.29 35.42 395 12524 46438 3326502
Lymphopenia 685.55 35.42 194 12725 3539 3369401
Lymphocyte count decreased 682.56 35.42 198 12721 3961 3368979
Urinary tract infection 657.96 35.42 331 12588 30997 3341943
General symptom 643.62 35.42 151 12768 1241 3371699
Abdominal discomfort 640.16 35.42 278 12641 18606 3354334
Memory impairment 633.69 35.42 258 12661 14680 3358260
Gait disturbance 623.84 35.42 308 12611 27684 3345256
Drug ineffective 579.76 35.42 497 12422 115593 3257347
Abdominal pain 512.04 35.42 321 12598 45904 3327036
Fatigue 508.35 35.42 446 12473 106794 3266146
Hypersensitivity 508.02 35.42 268 12651 27632 3345308
Seizure 499.48 35.42 301 12618 40099 3332841
Gastric disorder 483.36 35.42 149 12770 3689 3369251
Intentional underdose 451.86 35.42 92 12827 349 3372591
Alopecia 434.63 35.42 213 12706 18773 3354167
Central nervous system lesion 428.91 35.42 125 12794 2536 3370404
Muscular weakness 426.58 35.42 215 12704 20126 3352814
Headache 422.17 35.42 376 12543 91604 3281336
Asthenia 416.70 35.42 324 12595 65341 3307599
White blood cell count decreased 412.85 35.42 225 12694 24722 3348218
Balance disorder 404.39 35.42 178 12741 12261 3360679
Maternal exposure during pregnancy 399.88 35.42 167 12752 10104 3362836
Malaise 399.25 35.42 315 12604 64862 3308078
Dehydration 398.32 35.42 244 12675 33405 3339535
Rash 397.18 35.42 325 12594 70496 3302444
Urticaria 393.81 35.42 229 12690 28498 3344442
Hot flush 378.46 35.42 147 12772 7354 3365586
Adverse reaction 344.92 35.42 95 12824 1556 3371384
Hypoaesthesia 344.86 35.42 200 12719 24739 3348201
Burning sensation 340.58 35.42 143 12776 8761 3364179
Paraesthesia 316.21 35.42 196 12723 27352 3345588
Herpes zoster 311.31 35.42 144 12775 11128 3361812
Cognitive disorder 289.57 35.42 123 12796 7751 3365189
Dizziness 288.96 35.42 281 12638 76231 3296709
Underdose 285.77 35.42 117 12802 6717 3366223
Muscle spasms 285.11 35.42 182 12737 26721 3346219
Mobility decreased 283.80 35.42 130 12789 9818 3363122
Erythema 283.44 35.42 186 12733 28624 3344316
Pain 281.86 35.42 269 12650 71288 3301652
Weight decreased 275.96 35.42 208 12711 39903 3333037
Gait inability 261.69 35.42 113 12806 7412 3365528
Pneumonia 248.68 35.42 249 12670 69894 3303046
Dyspepsia 243.84 35.42 124 12795 11788 3361152
Depression 231.75 35.42 187 12732 39583 3333357
Abdominal distension 220.24 35.42 121 12798 13455 3359485
Death 216.92 35.42 342 12577 151982 3220958
Breast cancer 215.66 35.42 101 12818 8016 3364924
Nuclear magnetic resonance imaging abnormal 213.36 35.42 59 12860 980 3371960
Abortion spontaneous 211.24 35.42 109 12810 10676 3362264
Feeling hot 209.72 35.42 98 12821 7738 3365202
Adverse event 192.95 35.42 105 12814 11452 3361488
Loss of control of legs 192.41 35.42 48 12871 521 3372419
Musculoskeletal disorder 168.53 35.42 62 12857 2659 3370281
Feeling abnormal 165.66 35.42 132 12787 27393 3345547
Treatment failure 163.51 35.42 78 12841 6446 3366494
Pyrexia 163.23 35.42 215 12704 80900 3292040
Constipation 162.86 35.42 137 12782 30675 3342265
Dysphagia 150.85 35.42 109 12810 19542 3353398
Stress 147.52 35.42 76 12843 7410 3365530
Adverse drug reaction 145.49 35.42 81 12838 9230 3363710
Optic neuritis 140.89 35.42 51 12868 2087 3370853
Drug dose omission 140.58 35.42 139 12780 38293 3334647
Visual impairment 140.53 35.42 92 12827 14054 3358886
Confusional state 130.83 35.42 133 12786 37865 3335075
Dyspnoea 125.58 35.42 216 12703 102718 3270222
Pain in extremity 120.44 35.42 144 12775 49068 3323872
Hip fracture 118.44 35.42 59 12860 5356 3367584
Lymphocyte count abnormal 116.71 35.42 26 12893 164 3372776
Blindness 113.17 35.42 58 12861 5591 3367349
Road traffic accident 112.98 35.42 62 12857 6864 3366076
Gastrooesophageal reflux disease 111.17 35.42 74 12845 11617 3361323
Migraine 108.98 35.42 69 12850 9947 3362993
Cystitis 107.22 35.42 55 12864 5311 3367629
Tremor 105.10 35.42 103 12816 28041 3344899
Insomnia 104.60 35.42 115 12804 35783 3337157
Urosepsis 104.37 35.42 44 12875 2713 3370227
Decubitus ulcer 102.06 35.42 40 12879 2042 3370898
Back pain 100.91 35.42 116 12803 37889 3335051
Influenza like illness 100.38 35.42 76 12843 14611 3358329
Dysstasia 99.81 35.42 47 12872 3769 3369171
Invasive ductal breast carcinoma 99.69 35.42 30 12889 680 3372260
Mental disorder 96.01 35.42 53 12866 5934 3367006
Decreased appetite 92.70 35.42 116 12803 41374 3331566
Nephrolithiasis 89.46 35.42 53 12866 6783 3366157
Anxiety 88.85 35.42 111 12808 39518 3333422
Infection 87.51 35.42 89 12830 25313 3347627
Chest pain 85.84 35.42 110 12809 40165 3332775
Amnesia 85.70 35.42 61 12858 10665 3362275
Depressed mood 85.63 35.42 51 12868 6590 3366350
Ankle fracture 85.59 35.42 37 12882 2427 3370513
Flatulence 85.38 35.42 49 12870 5910 3367030
CD4 lymphocytes decreased 84.69 35.42 27 12892 745 3372195
Progressive multiple sclerosis 84.49 35.42 21 12898 224 3372716
Cerebrovascular accident 82.57 35.42 101 12818 35187 3337753
Muscle spasticity 81.87 35.42 37 12882 2699 3370241
Peripheral swelling 81.59 35.42 70 12849 16062 3356878
Progressive multifocal leukoencephalopathy 80.37 35.42 38 12881 3074 3369866
Hysterectomy 79.69 35.42 30 12889 1371 3371569
Hemiparesis 77.16 35.42 43 12876 4902 3368038
Decreased immune responsiveness 75.74 35.42 24 12895 649 3372291
Musculoskeletal stiffness 73.54 35.42 62 12857 13888 3359052
Loss of consciousness 73.14 35.42 85 12834 28062 3344878
Urinary incontinence 71.91 35.42 44 12875 5968 3366972
Palpitations 71.50 35.42 70 12849 19013 3353927
Gastroenteritis viral 70.55 35.42 33 12886 2605 3370335
Vertigo 70.34 35.42 56 12863 11576 3361364
Vision blurred 69.95 35.42 70 12849 19519 3353421
Feeding disorder 69.82 35.42 28 12891 1518 3371422
Head injury 68.88 35.42 42 12877 5661 3367279
Chills 68.38 35.42 73 12846 21949 3350991
Dysarthria 68.35 35.42 51 12868 9583 3363357
Caesarean section 66.94 35.42 38 12881 4488 3368452
Secondary progressive multiple sclerosis 66.79 35.42 19 12900 351 3372589
Hepatic enzyme increased 66.62 35.42 58 12861 13567 3359373
Blindness unilateral 66.32 35.42 29 12890 1955 3370985
Speech disorder 66.26 35.42 49 12870 9083 3363857
Influenza 66.24 35.42 56 12863 12590 3360350
Rash generalised 65.45 35.42 50 12869 9732 3363208
Diplopia 65.36 35.42 39 12880 5055 3367885
Drug administered to patient of inappropriate age 64.71 35.42 25 12894 1227 3371713
Pregnancy 63.36 35.42 45 12874 7835 3365105
Malignant melanoma 63.24 35.42 31 12888 2715 3370225
Ill-defined disorder 62.66 35.42 33 12886 3361 3369579
Skin burning sensation 62.07 35.42 28 12891 2033 3370907
Concussion 61.54 35.42 23 12896 1030 3371910
Gastrointestinal pain 61.49 35.42 24 12895 1211 3371729
Viral infection 59.71 35.42 39 12880 5923 3367017
Limb discomfort 59.19 35.42 32 12887 3436 3369504
Impaired self-care 59.03 35.42 18 12901 427 3372513
CD8 lymphocytes decreased 58.35 35.42 13 12906 82 3372858
Intentional product misuse 57.96 35.42 52 12867 12649 3360291
Intentional product use issue 57.68 35.42 26 12893 1884 3371056
Rash pruritic 57.30 35.42 45 12874 9119 3363821
Bipolar disorder 55.61 35.42 25 12894 1800 3371140
Rhinorrhoea 55.20 35.42 41 12878 7648 3365292
Gallbladder operation 54.90 35.42 18 12901 544 3372396
Appendicitis 54.65 35.42 25 12894 1875 3371065
Syncope 54.55 35.42 70 12849 25563 3347377
Mood swings 54.26 35.42 34 12885 4808 3368132
Myocardial infarction 54.12 35.42 93 12826 44040 3328900
Coordination abnormal 53.96 35.42 29 12890 3077 3369863
White blood cell count increased 53.85 35.42 50 12869 12710 3360230
Sepsis 53.19 35.42 78 12841 32295 3340645
Trigeminal neuralgia 53.00 35.42 19 12900 755 3372185
Aphasia 52.45 35.42 38 12881 6823 3366117
Uhthoff's phenomenon 52.19 35.42 13 12906 140 3372800
Surgery 52.06 35.42 38 12881 6902 3366038
Knee arthroplasty 51.83 35.42 28 12891 3002 3369938
Anal incontinence 51.61 35.42 26 12893 2414 3370526
Therapy cessation 51.50 35.42 30 12889 3719 3369221
Hyperhidrosis 51.06 35.42 65 12854 23545 3349395
Relapsing-remitting multiple sclerosis 50.62 35.42 12 12907 103 3372837
Major depression 49.86 35.42 22 12897 1515 3371425
Lower limb fracture 49.79 35.42 25 12894 2305 3370635
Dermatitis allergic 49.46 35.42 25 12894 2338 3370602
Neurogenic bladder 48.91 35.42 17 12902 616 3372324
Swelling face 48.69 35.42 45 12874 11371 3361569
Basal cell carcinoma 47.75 35.42 29 12890 3880 3369060
Arthralgia 47.48 35.42 106 12813 60755 3312185
Cholecystectomy 47.33 35.42 23 12896 1976 3370964
Pulmonary embolism 46.97 35.42 68 12851 27820 3345120
Swelling 46.94 35.42 56 12863 18988 3353952
Agraphia 46.52 35.42 10 12909 52 3372888
Blood count abnormal 46.39 35.42 25 12894 2667 3370273
Diabetes mellitus 46.35 35.42 45 12874 12088 3360852
Mental impairment 46.02 35.42 28 12891 3757 3369183
Generalised erythema 45.63 35.42 23 12896 2138 3370802
Contusion 45.24 35.42 49 12870 14961 3357979
Spinal operation 45.13 35.42 17 12902 778 3372162
Ophthalmic herpes zoster 44.95 35.42 14 12905 357 3372583
Peroneal nerve palsy 43.74 35.42 18 12901 1043 3371897
Kidney infection 43.35 35.42 23 12896 2377 3370563
Intervertebral disc protrusion 42.88 35.42 27 12892 3849 3369091
Cholelithiasis 42.64 35.42 36 12883 8072 3364868
Upper limb fracture 42.43 35.42 24 12895 2814 3370126
Liver function test increased 42.34 35.42 21 12898 1886 3371054
Alanine aminotransferase increased 41.80 35.42 59 12860 23581 3349359
Cellulitis 41.35 35.42 43 12876 12532 3360408
Spinal fracture 40.66 35.42 23 12896 2697 3370243
Temperature intolerance 40.53 35.42 17 12902 1034 3371906
Dry mouth 40.50 35.42 38 12881 9784 3363156
Foot fracture 39.12 35.42 23 12896 2899 3370041
Weight increased 39.04 35.42 61 12858 26679 3346261
Foetal exposure timing unspecified 39.04 35.42 11 12908 196 3372744
Sensory disturbance 38.88 35.42 25 12894 3695 3369245
Squamous cell carcinoma 38.79 35.42 22 12897 2592 3370348
Anaphylactic reaction 38.27 35.42 42 12877 13012 3359928
Night sweats 38.13 35.42 27 12892 4676 3368264
Fear 37.88 35.42 25 12894 3862 3369078
Lip swelling 37.66 35.42 30 12889 6201 3366739
Nasopharyngitis 37.66 35.42 54 12865 21893 3351047
Eosinophilia 37.27 35.42 27 12892 4846 3368094
Blood test abnormal 37.17 35.42 18 12901 1534 3371406
Heart rate increased 36.35 35.42 43 12876 14443 3358497
Gastritis 36.24 35.42 30 12889 6547 3366393
Uterine cancer 36.19 35.42 14 12905 689 3372251
Cervical spinal stenosis 35.62 35.42 12 12907 395 3372545

Pharmacologic Action:

SourceCodeDescription
ATC N07XX09 NERVOUS SYSTEM
OTHER NERVOUS SYSTEM DRUGS
OTHER NERVOUS SYSTEM DRUGS
Other nervous system drugs
CHEBI has role CHEBI:50846 immunomodulator
CHEBI has role CHEBI:50748 antipsoriatic
MeSH PA D003879 Dermatologic Agents
MeSH PA D007155 Immunologic Factors
MeSH PA D007166 Immunosuppressive Agents
MeSH PA D011838 Radiation-Sensitizing Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Plaque psoriasis indication 200965009
Relapsing remitting multiple sclerosis indication 426373005 DOID:2378

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
120MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL 7619001 April 1, 2018 METHOD OF TREATING MULTIPLE SCLEROSIS
120MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL 7803840 April 1, 2018 METHOD OF TREATING AN AUTOIMMUNE DISEASE SELECTED FROM AUTOIMMUNE POLYARTHRITIS AND MULTIPLE SCLEROSIS BUT NOT TREATING PSORIATIC ARTHRITIS
120MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL 8524773 April 1, 2018 METHOD OF TREATING MULTIPLE SCLEROSIS
240MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL 7619001 April 1, 2018 METHOD OF TREATING MULTIPLE SCLEROSIS
240MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL 7803840 April 1, 2018 METHOD OF TREATING AN AUTOIMMUNE DISEASE SELECTED FROM AUTOIMMUNE POLYARTHRITIS AND MULTIPLE SCLEROSIS BUT NOT TREATING PSORIATIC ARTHRITIS
240MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL 8524773 April 1, 2018 METHOD OF TREATING MULTIPLE SCLEROSIS
120MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL 7320999 Oct. 20, 2018 METHOD OF TREATING MULTIPLE SCLEROSIS
240MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL 7320999 Oct. 20, 2018 METHOD OF TREATING MULTIPLE SCLEROSIS
120MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL 8399514 Feb. 7, 2028 METHOD OF TREATING MULTIPLE SCLEROSIS
240MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL 8399514 Feb. 7, 2028 METHOD OF TREATING MULTIPLE SCLEROSIS

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
120MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL March 27, 2018 NEW CHEMICAL ENTITY
240MG TECFIDERA BIOGEN IDEC INC N204063 March 27, 2013 RX CAPSULE, DELAYED RELEASE ORAL March 27, 2018 NEW CHEMICAL ENTITY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Kelch-like ECH-associated protein 1 Cytosolic other INHIBITOR CHEMBL CHEMBL
Hydroxycarboxylic acid receptor 2 GPCR Ki 6.74 CHEMBL

External reference:

IDSource
CHEBI:76004 CHEBI
7045 IUPHAR_LIGAND_ID
D03846 KEGG_DRUG
4032290 VUID
N0000186952 NUI
C0058218 UMLSCUI
1373478 RXNORM
009199 NDDF
29369 MMSL
d08079 MMSL
4032290 VANDF
N0000186952 NDFRT
N0000191910 NDFRT
724035008 SNOMEDCT_US
CHEMBL589586 ChEMBL_ID
DB08908 DRUGBANK_ID
CHEMBL2107333 ChEMBL_ID
FO2303MNI2 UNII
D000069462 MESH_DESCRIPTOR_UI
637568 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Tecfidera HUMAN PRESCRIPTION DRUG LABEL 1 64406-005 CAPSULE 120 mg ORAL NDA 17 sections
Tecfidera HUMAN PRESCRIPTION DRUG LABEL 1 64406-006 CAPSULE 240 mg ORAL NDA 17 sections
Tecfidera HUMAN PRESCRIPTION DRUG LABEL 2 64406-007 KIT 240 mg None NDA 17 sections
Tecfidera HUMAN PRESCRIPTION DRUG LABEL 2 64406-007 KIT 120 mg None NDA 17 sections