rasagiline Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
monoamine oxydase (MAO)-inhibitors type B 3521 136236-51-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • TVP-1022
  • rasagiline hydrochloride
  • rasagiline
  • azilect
  • (R)-(+)-Rasagiline
  • rasagiline mesylate
  • TV-1030
  • rasagiline mesilate
Rasagiline is a selective, irreversible MAO-B inhibitor indicated for the treatment of idiopathic Parkinson's disease. The results of a clinical trial designed to examine the effects of rasagiline tablets on blood pressure when it is administered with increasing doses of tyramine indicates the functional selectivity can be incomplete when healthy subjects ingest large amounts of tyramine while receiving recommended doses of rasagiline tablets. The selectivity for inhibiting MAO-B diminishes in a dose-related manner. One mechanism is believed to be related to its MAO-B inhibitory activity, which causes an increase in extracellular levels of dopamine in the striatum. The elevated dopamine level and subsequent increased dopaminergic activity are likely to mediate rasagiline’s beneficial effects seen in models of dopaminergic motor dysfunction.
  • Molecular weight: 171.24
  • Formula: C12H13N
  • CLOGP: 2.34
  • LIPINSKI: 0
  • HAC: 1
  • HDO: 1
  • TPSA: 12.03
  • ALOGS: -3.84
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 mg O

ADMET properties:

PropertyValueReference
BA (Bioavailability) 36 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
May 16, 2006 FDA TEVA
March 23, 2018 PMDA Takeda Pharmaceutical Company Limited

FDA Adverse Event Reporting System (Female)

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
Hallucination 214.83 23.18 101 4542 53737 53290686
Dyskinesia 192.46 23.18 80 4563 31753 53312670
Hallucination, visual 176.30 23.18 65 4578 18767 53325656
Serotonin syndrome 125.43 23.18 56 4587 26350 53318073
Fall 113.54 23.18 147 4496 358293 52986130
Delusion 71.85 23.18 30 4613 11979 53332444
Pleurothotonus 67.36 23.18 17 4626 1362 53343061
On and off phenomenon 65.60 23.18 19 4624 2559 53341864
Drug interaction 60.01 23.18 84 4559 219245 53125178
Tremor 53.30 23.18 60 4583 125676 53218747
Confusional state 52.52 23.18 74 4569 194147 53150276
Orthostatic hypotension 51.14 23.18 32 4611 29721 53314702
Bradykinesia 48.07 23.18 17 4626 4336 53340087
Gambling disorder 47.85 23.18 13 4630 1387 53343036
Freezing phenomenon 45.60 23.18 13 4630 1654 53342769
Compulsive shopping 44.42 23.18 11 4632 815 53343608
Sudden onset of sleep 41.47 23.18 10 4633 663 53343760
Impulse-control disorder 39.45 23.18 10 4633 815 53343608
Hypersexuality 38.83 23.18 9 4634 503 53343920
Muscle rigidity 36.05 23.18 18 4625 10823 53333600
Coronary artery dissection 34.68 23.18 9 4634 805 53343618
Labelled drug-drug interaction medication error 33.04 23.18 17 4626 10882 53333541
Altered state of consciousness 31.25 23.18 22 4621 24814 53319609
Choking 29.66 23.18 15 4628 9261 53335162
Stoma site extravasation 29.65 23.18 7 4636 424 53343999
Serum serotonin increased 28.99 23.18 6 4637 197 53344226
Gait disturbance 28.25 23.18 50 4593 158792 53185631
Compulsive hoarding 27.65 23.18 5 4638 79 53344344
Psychotic symptom 27.63 23.18 8 4635 1075 53343348
Fracture 25.11 23.18 17 4626 18002 53326421
Dystonia 24.90 23.18 15 4628 13006 53331417
Dementia 23.81 23.18 16 4627 16734 53327689
Parkinsonian gait 23.65 23.18 6 4637 490 53343933
Sleep talking 23.56 23.18 7 4636 1029 53343394
Nocturia 23.38 23.18 12 4631 7638 53336785

FDA Adverse Event Reporting System (Male)

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
Hallucination 456.21 24.50 228 7265 52391 32453642
Impulse-control disorder 279.15 24.50 66 7427 1483 32504550
Dyskinesia 239.08 24.50 114 7379 23489 32482544
Hypersexuality 213.96 24.50 54 7439 1603 32504430
Hallucination, visual 177.09 24.50 84 7409 17075 32488958
Gambling disorder 155.50 24.50 43 7450 1826 32504207
Fall 151.81 24.50 205 7288 195996 32310037
On and off phenomenon 117.05 24.50 40 7453 3461 32502572
Orthostatic hypotension 116.71 24.50 73 7420 25577 32480456
Confusional state 114.18 24.50 152 7341 142963 32363070
Dopamine dysregulation syndrome 113.01 24.50 26 7467 515 32505518
Freezing phenomenon 94.90 24.50 31 7462 2332 32503701
Delusion 90.69 24.50 49 7444 13059 32492974
Serotonin syndrome 73.58 24.50 49 7444 19068 32486965
Abnormal behaviour 72.21 24.50 55 7438 26411 32479622
Resting tremor 68.10 24.50 18 7475 642 32505391
Somnolence 64.49 24.50 98 7395 103699 32402334
Dystonia 60.62 24.50 35 7458 10588 32495445
Compulsive shopping 54.34 24.50 14 7479 451 32505582
Cogwheel rigidity 51.34 24.50 17 7476 1333 32504700
Bradykinesia 50.42 24.50 23 7470 4263 32501770
Tremor 49.39 24.50 76 7417 81201 32424832
Stereotypy 48.47 24.50 14 7479 696 32505337
Muscle rigidity 46.26 24.50 30 7463 11156 32494877
Balance disorder 44.43 24.50 50 7443 39409 32466624
Cognitive disorder 44.07 24.50 41 7452 25853 32480180
Sudden onset of sleep 44.04 24.50 12 7481 481 32505552
Supine hypertension 42.52 24.50 11 7482 360 32505673
Psychomotor hyperactivity 41.75 24.50 26 7467 9013 32497020
Marasmus 40.96 24.50 12 7481 627 32505406
Jealous delusion 40.68 24.50 10 7483 265 32505768
Akinesia 40.28 24.50 17 7476 2616 32503417
Stoma site discharge 38.27 24.50 15 7478 1910 32504123
Oesophageal achalasia 37.42 24.50 10 7483 372 32505661
Anticholinergic syndrome 36.91 24.50 12 7481 888 32505145
Obsessive-compulsive personality disorder 34.01 24.50 8 7485 175 32505858
Sleep disorder 33.75 24.50 36 7457 26716 32479317
Paraphilia 33.25 24.50 7 7486 90 32505943
Gait disturbance 32.76 24.50 63 7430 80345 32425688
Parkinson's disease 32.74 24.50 13 7480 1713 32504320
Dementia 32.54 24.50 26 7467 13360 32492673
Agitation 31.26 24.50 51 7442 57185 32448848
Mesenteric artery thrombosis 31.10 24.50 9 7484 450 32505583
Autonomic nervous system imbalance 30.94 24.50 14 7479 2546 32503487
Psychotic disorder 30.86 24.50 32 7461 22988 32483045
Hyperkinesia 29.24 24.50 13 7480 2269 32503764
Restlessness 28.80 24.50 32 7461 24849 32481184
Hyperthermia 28.59 24.50 22 7471 10706 32495327
Stoma site erythema 28.15 24.50 11 7482 1389 32504644
Blood lactic acid 27.84 24.50 8 7485 390 32505643
Thunderclap headache 27.70 24.50 6 7487 89 32505944
Dysphagia 27.31 24.50 50 7443 61426 32444607
Binge eating 27.22 24.50 6 7487 97 32505936
Therapeutic product effect variable 27.04 24.50 12 7481 2084 32503949
Prescribed underdose 25.83 24.50 19 7474 8640 32497393
Aggression 25.54 24.50 38 7455 39351 32466682
Fracture 25.39 24.50 17 7476 6662 32499371
Disturbance in attention 24.86 24.50 29 7464 23724 32482309
Obsessive-compulsive disorder 24.84 24.50 15 7478 4919 32501114
Nocturia 24.63 24.50 19 7474 9275 32496758

Pharmacologic Action:

SourceCodeDescription
ATC N04BD02 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
DOPAMINERGIC AGENTS
Monoamine oxidase B inhibitors
FDA MoA N0000000184 Monoamine Oxidase Inhibitors
MeSH PA D002491 Central Nervous System Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D008996 Monoamine Oxidase Inhibitors
MeSH PA D018696 Neuroprotective Agents
MeSH PA D020011 Protective Agents
FDA EPC N0000175744 Monoamine Oxidase Inhibitor
CHEBI has role CHEBI:38623 monoamine oxidase inhibitors
CHEBI has role CHEBI:63726 neuroprotective agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Parkinson's disease indication 49049000 DOID:14330
Dyskinesia contraindication 9748009
Bipolar disorder contraindication 13746004 DOID:3312
Orthostatic hypotension contraindication 28651003
Hypertensive disorder contraindication 38341003 DOID:10763
Epilepsy contraindication 84757009 DOID:1826
Disease of liver contraindication 235856003 DOID:409
Pheochromocytoma contraindication 302835009
Malignant melanoma contraindication 372244006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.54 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 0.5MG BASE AZILECT TEVA N021641 May 16, 2006 RX TABLET ORAL 7815942 Aug. 27, 2027 TREATMENT OF PARKINSONS DISEASE
EQ 1MG BASE AZILECT TEVA N021641 May 16, 2006 RX TABLET ORAL 7815942 Aug. 27, 2027 TREATMENT OF PARKINSONS DISEASE

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Amine oxidase [flavin-containing] B Enzyme INHIBITOR Ki 6.15 CHEMBL CHEMBL
Acetylcholinesterase Enzyme IC50 7.72 CHEMBL
Cholinesterase Enzyme IC50 5.32 CHEMBL
Amine oxidase [flavin-containing] A Enzyme Ki 5.01 CHEMBL
Amine oxidase [flavin-containing] B Enzyme IC50 8.36 CHEMBL
Amine oxidase [flavin-containing] A Enzyme IC50 6.39 CHEMBL

External reference:

IDSource
4025261 VUID
N0000179514 NUI
D02562 KEGG_DRUG
136236-50-5 SECONDARY_CAS_RN
4025261 VANDF
4025262 VANDF
C0525678 UMLSCUI
CHEBI:63620 CHEBI
RAU PDB_CHEM_ID
CHEMBL887 ChEMBL_ID
DB01367 DRUGBANK_ID
CHEMBL1201142 ChEMBL_ID
CHEMBL1235738 ChEMBL_ID
3052776 PUBCHEM_CID
7151 INN_ID
C031967 MESH_SUPPLEMENTAL_RECORD_UI
6641 IUPHAR_LIGAND_ID
003N66TS6T UNII
134748 RXNORM
162358 MMSL
20417 MMSL
70623 MMSL
d05612 MMSL
010775 NDDF
010776 NDDF
418734001 SNOMEDCT_US
419010007 SNOMEDCT_US
734664007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 0093-3060 TABLET 0.50 mg ORAL NDA authorized generic 29 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 0093-3061 TABLET 1 mg ORAL NDA authorized generic 29 sections
Rasagiline Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0378-1270 TABLET 0.50 mg ORAL ANDA 30 sections
Rasagiline Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0378-1271 TABLET 1 mg ORAL ANDA 30 sections
Rasagiline Human Prescription Drug Label 1 16714-770 TABLET 0.50 mg ORAL ANDA 29 sections
Rasagiline Human Prescription Drug Label 1 16714-771 TABLET 1 mg ORAL ANDA 29 sections
Rasagiline Mesylate Human Prescription Drug Label 1 23155-746 TABLET 0.50 mg ORAL ANDA 29 sections
Rasagiline Mesylate Human Prescription Drug Label 1 23155-747 TABLET 1 mg ORAL ANDA 29 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 42291-779 TABLET 0.50 mg ORAL NDA authorized generic 29 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 42291-780 TABLET 1 mg ORAL NDA authorized generic 29 sections
RASAGILINE HUMAN PRESCRIPTION DRUG LABEL 1 42571-220 TABLET 0.50 mg ORAL ANDA 29 sections
RASAGILINE HUMAN PRESCRIPTION DRUG LABEL 1 42571-221 TABLET 1 mg ORAL ANDA 29 sections
Azilect HUMAN PRESCRIPTION DRUG LABEL 1 43353-015 TABLET 1 mg ORAL NDA 30 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 47781-683 TABLET 0.50 mg ORAL ANDA 27 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 47781-690 TABLET 1 mg ORAL ANDA 27 sections
Azilect HUMAN PRESCRIPTION DRUG LABEL 1 54868-6206 TABLET 1 mg ORAL NDA 30 sections
Rasagiline Human Prescription Drug Label 1 67877-259 TABLET 0.50 mg ORAL ANDA 29 sections
Rasagiline Human Prescription Drug Label 1 67877-260 TABLET 1 mg ORAL ANDA 29 sections
Azilect HUMAN PRESCRIPTION DRUG LABEL 1 68546-142 TABLET 0.50 mg ORAL NDA 30 sections
Azilect HUMAN PRESCRIPTION DRUG LABEL 1 68546-229 TABLET 1 mg ORAL NDA 30 sections