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
Dyskinesia 109.86 43.31 26 489 4763 2352807
Confusional state 98.29 43.31 34 481 24310 2333260
Serotonin syndrome 90.48 43.31 21 494 3519 2354051
Hallucination, visual 88.62 43.31 20 495 2959 2354611
Drug interaction 77.65 43.31 30 485 29133 2328437
Fall 60.69 43.31 29 486 47070 2310500
Compulsive shopping 58.39 43.31 9 506 160 2357410
Hallucination 55.57 43.31 17 498 8131 2349439
Gambling disorder 54.72 43.31 9 506 245 2357325
Parkinson's disease 50.96 43.31 11 504 1315 2356255
Pleurothotonus 47.32 43.31 8 507 258 2357312
Hypertension 44.97 43.31 20 495 27341 2330229
Hypersexuality 44.61 43.31 7 508 140 2357430
Coronary artery dissection 43.89 43.31 7 508 156 2357414

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
Impulse-control disorder 152.11 44.12 25 635 310 1745811
Dyskinesia 140.03 44.12 35 625 3784 1742337
Orthostatic hypotension 128.51 44.12 32 628 3399 1742722
Hypersexuality 122.19 44.12 21 639 345 1745776
Hallucination 113.68 44.12 35 625 8135 1737986
Gambling disorder 99.88 44.12 18 642 392 1745729
Serotonin syndrome 89.40 44.12 23 637 2765 1743356
On and off phenomenon 86.45 44.12 15 645 260 1745861
Parkinson's disease 84.27 44.12 20 640 1722 1744399
Fall 72.71 44.12 35 625 27179 1718942
Confusional state 71.20 44.12 32 628 21246 1724875
Condition aggravated 68.19 44.12 31 629 21119 1725002
Oesophageal achalasia 67.66 44.12 10 650 57 1746064
Delirium 66.60 44.12 22 638 6340 1739781
Hallucination, visual 62.14 44.12 17 643 2575 1743546
Muscle rigidity 57.97 44.12 15 645 1833 1744288
Compulsive shopping 56.16 44.12 9 651 93 1746028
Dopamine dysregulation syndrome 54.40 44.12 9 651 115 1746006
Stereotypy 54.40 44.12 9 651 115 1746006
Loss of consciousness 51.64 44.12 23 637 14852 1731269
Dizziness 51.27 44.12 30 630 34331 1711790
Abnormal behaviour 50.95 44.12 18 642 6324 1739797
Drug interaction 48.63 44.12 27 633 27931 1718190
Paraphilia 48.46 44.12 7 653 33 1746088
Thunderclap headache 48.35 44.12 6 654 5 1746116
Psychotic disorder 46.97 44.12 16 644 5040 1741081
Akinesia 46.31 44.12 9 651 296 1745825
Neuroleptic malignant syndrome 45.76 44.12 14 646 3134 1742987

Pharmacologic Action:

SourceCodeDescription
ATC N04BD02 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
DOPAMINERGIC AGENTS
Monoamine oxidase B inhibitors
FDA EPC N0000175744 Monoamine Oxidase Inhibitor
CHEBI has role CHEBI:63726 neuroprotective agent
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

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 PARKINSON'S DISEASE
EQ 1MG BASE AZILECT TEVA N021641 May 16, 2006 RX TABLET ORAL 7815942 Aug. 27, 2027 TREATMENT OF PARKINSON'S 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
Amine oxidase [flavin-containing] A Enzyme Ki 5.01 CHEMBL
Amine oxidase [flavin-containing] A Enzyme IC50 6.39 CHEMBL
Amine oxidase [flavin-containing] B Enzyme IC50 8.36 CHEMBL

External reference:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 0093-3060 TABLET 0.50 mg ORAL NDA AUTHORIZED GENERIC 17 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 0093-3061 TABLET 1 mg ORAL NDA AUTHORIZED GENERIC 17 sections
Rasagiline Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0378-1270 TABLET 0.50 mg ORAL ANDA 17 sections
Rasagiline Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0378-1271 TABLET 1 mg ORAL ANDA 17 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 16714-770 TABLET 0.50 mg ORAL ANDA 17 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 16714-771 TABLET 1 mg ORAL ANDA 17 sections
Rasagiline Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 23155-746 TABLET 0.50 mg ORAL ANDA 16 sections
Rasagiline Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 23155-747 TABLET 1 mg ORAL ANDA 16 sections
RASAGILINE HUMAN PRESCRIPTION DRUG LABEL 1 42571-220 TABLET 0.50 mg ORAL ANDA 17 sections
RASAGILINE HUMAN PRESCRIPTION DRUG LABEL 1 42571-221 TABLET 1 mg ORAL ANDA 17 sections
Azilect HUMAN PRESCRIPTION DRUG LABEL 1 43353-015 TABLET 1 mg ORAL NDA 19 sections
Rasagiline Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 47781-138 TABLET 0.50 mg ORAL ANDA 17 sections
Rasagiline Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 47781-139 TABLET 1 mg ORAL ANDA 17 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 47781-683 TABLET 0.50 mg ORAL ANDA 17 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 47781-690 TABLET 1 mg ORAL ANDA 17 sections
Azilect HUMAN PRESCRIPTION DRUG LABEL 1 54868-6206 TABLET 1 mg ORAL NDA 18 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 67877-259 TABLET 0.50 mg ORAL ANDA 17 sections
Rasagiline HUMAN PRESCRIPTION DRUG LABEL 1 67877-260 TABLET 1 mg ORAL ANDA 17 sections
Azilect HUMAN PRESCRIPTION DRUG LABEL 1 68546-142 TABLET 0.50 mg ORAL NDA 17 sections
Azilect HUMAN PRESCRIPTION DRUG LABEL 1 68546-229 TABLET 1 mg ORAL NDA 17 sections