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

Stem definitionDrug idCAS RN
monoamine oxydase (MAO)-inhibitors type B 2429 14611-51-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • selegiline
  • (-)-deprenil
  • (-)-deprenyl
  • (-)-selegiline
  • (r)-(-)-deprenyl
  • (r)-selegiline
  • anipryl
  • l-deprenyl
  • selegina
  • selgene
  • zelapar
  • selegiline hydrochloride
  • selegiline HCl
A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl.
  • Molecular weight: 187.29
  • Formula: C13H17N
  • CLOGP: 2.84
  • LIPINSKI: 0
  • HAC: 1
  • HDO: 0
  • TPSA: 3.24
  • ALOGS: -3.87
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
5 mg O

ADMET properties:

PropertyValueReference
BA (Bioavailability) 4.40 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.89 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 1.90 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 20 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.13 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 5, 1989 FDA SOMERSET

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
Application site erythema 238.43 45.47 37 271 1243 2356534
Application site rash 232.61 45.47 33 275 586 2357191
Application site pruritus 145.18 45.47 23 285 863 2356914
Application site reaction 94.49 45.47 14 294 329 2357448
Application site urticaria 93.19 45.47 12 296 94 2357683
Application site irritation 75.02 45.47 12 296 470 2357307
Dyskinesia 52.56 45.47 13 295 4776 2353001

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
Gambling disorder 112.62 74.90 17 201 393 1746170
Dopamine dysregulation syndrome 106.67 74.90 14 204 110 1746453
Hypersexuality 99.13 74.90 15 203 351 1746212
Application site rash 87.89 74.90 13 205 258 1746305
Hallucination, visual 81.32 74.90 17 201 2575 1743988

Pharmacologic Action:

SourceCodeDescription
ATC N04BD01 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
DOPAMINERGIC AGENTS
Monoamine oxidase B inhibitors
FDA EPC N0000175744 Monoamine Oxidase Inhibitor
FDA EPC N0000175762 Monoamine Oxidase Type B Inhibitor
FDA MoA N0000175761 Monoamine Oxidase-B Inhibitors
MeSH PA D018726 Anti-Dyskinesia Agents
MeSH PA D000928 Antidepressive Agents
MeSH PA D000978 Antiparkinson Agents
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
MeSH PA D011619 Psychotropic Drugs

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Parkinson's disease indication 49049000 DOID:14330
Major depressive disorder indication 370143000
Suicidal thoughts contraindication 6471006
Bipolar disorder contraindication 13746004 DOID:3312
Orthostatic hypotension contraindication 28651003
Conduction disorder of the heart contraindication 44808001
Psychotic disorder contraindication 69322001
Kidney disease contraindication 90708001 DOID:557
Tardive dyskinesia contraindication 102449007
Angina pectoris contraindication 194828000
Mania contraindication 231494001
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 7.6 Basic

Orange Book patent data (new drug applications)

None

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 7.26 CHEMBL CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 6.76 DRUG MATRIX
Amine oxidase [flavin-containing] A Enzyme Ki 5.04 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 6.17 DRUG MATRIX
Amine oxidase [flavin-containing] A Enzyme Ki 4.98 CHEMBL
Amine oxidase [flavin-containing] A Enzyme Ki 5.42 CHEMBL
Amine oxidase [flavin-containing] B Enzyme Ki 6.01 CHEMBL
Amine oxidase [flavin-containing] B Enzyme Ki 5.87 CHEMBL
Monoamine oxidase Enzyme IC50 7.89 CHEMBL

External reference:

IDSource
4019929 VUID
N0000148014 NUI
C0036579 UMLSCUI
D00785 KEGG_DRUG
2K1V7GP655 UNII
4436 INN_ID
14611-52-0 SECONDARY_CAS_RN
108466000 SNOMEDCT_US
4019929 VANDF
21238 MMSL
9639 RXNORM
372497003 SNOMEDCT_US
d00976 MMSL
004599 NDDF
26757 PUBCHEM_CID
CHEBI:50217 CHEBI
CHEMBL972 ChEMBL_ID
DB01037 DRUGBANK_ID
CHEMBL1200904 ChEMBL_ID
D012642 MESH_DESCRIPTOR_UI
6639 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ZELAPAR HUMAN PRESCRIPTION DRUG LABEL 1 0187-0453 TABLET, ORALLY DISINTEGRATING 1.25 mg ORAL NDA 17 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16571-659 CAPSULE 5 mg ORAL ANDA 11 sections
EMSAM HUMAN PRESCRIPTION DRUG LABEL 1 49502-900 PATCH 6 mg TRANSDERMAL NDA 22 sections
EMSAM HUMAN PRESCRIPTION DRUG LABEL 1 49502-901 PATCH 9 mg TRANSDERMAL NDA 22 sections
EMSAM HUMAN PRESCRIPTION DRUG LABEL 1 49502-902 PATCH 12 mg TRANSDERMAL NDA 22 sections
SELEGILINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 60429-019 CAPSULE 5 mg ORAL ANDA 11 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60429-176 TABLET 5 mg ORAL ANDA 11 sections
SELEGILINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 60505-0055 CAPSULE 5 mg ORAL ANDA 11 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60505-3438 TABLET 5 mg ORAL ANDA 11 sections
SELEGILINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 68151-2649 CAPSULE 5 mg ORAL ANDA 11 sections