selegiline 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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
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 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 4.40 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 2.618 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.333 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 49.091 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 57.810 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 33.130 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 28.620 % High 1
herg hERG pIC50 4.737 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 22.594 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 89.950 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 27.920 % High 1
kinase-safety-class ACVR2A,ACVR2B,AKT2,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK2,MAP3K7,MAPK7,MAPKAPK2,MET,NTRK2,PDK2,PDK4,PDPK1,PIK3CB,PIM2,PRKDC,SIK2,SIK3,STK33,TEK,TGFBR1 36
kinase-selectivity-class AXL,BRAF,CAMK2D,EPHB4,GRK2,SIK2,STK33,TEK 8
mdck-mdr1-bcrp-efflux MDCK-MDR1-BCRP efflux ratio 0.592 High 1
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.684 High 1
mh-clint Mouse hepatocyte intrinsic clearance 231.739 High 1
mppb Mouse plasma protein binding (% unbound) 33.900 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.662 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pld-class Phospholipidosis risk class (1 = positive, 0 = negative) 0 High 1
pppb Pig plasma protein binding (% unbound) 57.990 % High 1
rat-kpuu-brain Rat brain Kpuu 0.653 % High 1
rh-clint Rat hepatocyte intrinsic clearance 179.473 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 80.140 % High 1
rppb Rat plasma protein binding (% unbound) 32.620 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 787.046 uM High 1

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
Parkinsonism hyperpyrexia syndrome 262.69 27.32 34 2050 208 90626155
Application site rash 187.47 27.32 35 2049 2634 90623729
Application site erythema 175.58 27.32 37 2047 5171 90621192
Application site pruritus 102.84 27.32 23 2061 4224 90622139
Dyskinesia 100.42 27.32 36 2048 36498 90589865
Application site reaction 91.78 27.32 16 2068 814 90625549
Application site urticaria 79.29 27.32 12 2072 248 90626115
Hallucination 76.65 27.32 35 2049 65924 90560439
Drug interaction 72.80 27.32 56 2028 276397 90349966
Hallucination, visual 68.13 27.32 24 2060 23068 90603295
Application site irritation 60.72 27.32 13 2071 1948 90624415
Serotonin syndrome 40.51 27.32 19 2065 37868 90588495
Rapid eye movement sleep behaviour disorder 39.73 27.32 7 2077 378 90625985
Application site pain 30.89 27.32 9 2075 4711 90621652
Hypertensive crisis 28.99 27.32 12 2072 17772 90608591
Delusion 28.32 27.32 11 2073 13829 90612534
Impulse-control disorder 27.53 27.32 6 2078 976 90625387
Neuroleptic malignant syndrome 27.39 27.32 11 2073 15085 90611278

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 200.97 30.27 91 2796 57416 42561032
Dyskinesia 162.62 30.27 62 2825 25328 42593120
Hallucination, visual 91.77 30.27 39 2848 20981 42597467
Impulse-control disorder 84.85 30.27 20 2867 1555 42616893
Hypersexuality 78.17 30.27 19 2868 1683 42616765
Gambling disorder 77.36 30.27 19 2868 1757 42616691
Dopamine dysregulation syndrome 74.43 30.27 15 2872 558 42617890
On and off phenomenon 73.67 30.27 21 2866 3446 42615002
Application site rash 71.41 30.27 16 2871 993 42617455
Delusion 53.41 30.27 24 2863 14710 42603738
Application site erythema 43.29 30.27 13 2874 2553 42615895
Drug interaction 36.62 30.27 65 2822 266934 42351514
Serotonin syndrome 35.51 30.27 22 2865 25823 42592625
Parkinsonian rest tremor 33.24 30.27 7 2880 324 42618124
Somnolence 32.95 30.27 44 2843 141061 42477387
Parkinsonism hyperpyrexia syndrome 32.67 30.27 7 2880 352 42618096
Binge eating 32.07 30.27 6 2881 150 42618298
Tremor 31.98 30.27 36 2851 96893 42521555
Impulsive behaviour 31.27 30.27 10 2877 2415 42616033
Agitation 30.44 30.27 29 2858 64285 42554163

FDA Adverse Event Reporting System (Geriatric)

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
Parkinsonism hyperpyrexia syndrome 264.76 27.04 41 4216 577 110584465
Hallucination 229.30 27.04 100 4157 101332 110483710
Dyskinesia 211.19 27.04 78 4179 51368 110533674
Application site rash 166.41 27.04 34 4223 2416 110582626
Hallucination, visual 158.61 27.04 59 4198 39546 110545496
Application site erythema 133.31 27.04 33 4224 5577 110579465
Drug interaction 105.48 27.04 112 4145 500071 110084971
Impulse-control disorder 100.52 27.04 22 4235 2172 110582870
Gambling disorder 89.50 27.04 20 4237 2171 110582871
Dopamine dysregulation syndrome 81.53 27.04 15 4242 612 110584430
Hypersexuality 80.84 27.04 18 4239 1922 110583120
Serotonin syndrome 77.09 27.04 40 4217 59113 110525929
Delusion 68.81 27.04 28 4229 23727 110561315
Application site pruritus 62.50 27.04 17 4240 4143 110580899
Application site urticaria 52.66 27.04 9 4248 239 110584803
On and off phenomenon 52.37 27.04 15 4242 4409 110580633
Application site irritation 44.02 27.04 11 4246 1926 110583116
Muscle rigidity 42.44 27.04 20 4237 24011 110561031
Somnolence 41.42 27.04 54 4203 297395 110287647
Neuroleptic malignant syndrome 41.41 27.04 22 4235 34037 110551005
Application site reaction 36.06 27.04 8 4249 839 110584203
Parkinsonian rest tremor 35.86 27.04 7 4250 393 110584649
Orthostatic hypotension 34.68 27.04 25 4232 66224 110518818
Agitation 34.30 27.04 31 4226 113020 110472022
Tremor 33.38 27.04 40 4217 202192 110382850
Rapid eye movement sleep behaviour disorder 32.59 27.04 7 4250 632 110584410
Sudden onset of sleep 31.87 27.04 7 4250 701 110584341
Psychotic disorder 28.45 27.04 20 4237 50917 110534125
Sleep talking 27.82 27.04 7 4250 1261 110583781
Binge eating 27.10 27.04 6 4251 624 110584418

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N04BD01 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
DOPAMINERGIC AGENTS
Monoamine oxidase B inhibitors
FDA MoA N0000000184 Monoamine Oxidase Inhibitors
MeSH PA D000928 Antidepressive Agents
MeSH PA D000978 Antiparkinson Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D008996 Monoamine Oxidase Inhibitors
MeSH PA D011619 Psychotropic Drugs
MeSH PA D018696 Neuroprotective Agents
MeSH PA D018726 Anti-Dyskinesia Agents
MeSH PA D020011 Protective Agents
FDA EPC N0000175744 Monoamine Oxidase Inhibitor
FDA MoA N0000175761 Monoamine Oxidase-B Inhibitors
FDA EPC N0000175762 Monoamine Oxidase Type B Inhibitor
CHEBI has role CHEBI:176497 geroprotector
CHEBI has role CHEBI:38623 EC 1.4.3.4 (monoamine oxidase) inhibitor
CHEBI has role CHEBI:48407 antiparkinson drug
CHEBI has role CHEBI:48560 dopaminergic agent

Related Drugs by ATC class:

N04BD Monoamine oxidase B inhibitors 2 drugs
rasagilinesafinamide

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

SpeciesUseRelation
Dogs Cognitive dysfunction syndrome (CDS) Indication
Dogs Pituitary dependent hyperadrenocorticism (PDH) Indication

🐶 Veterinary products

ProductApplicantIngredients
Anipryl Zoetis Inc. 1

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
Alpha-synuclein Transporter IC50 6.57 CHEMBL
Amine oxidase [flavin-containing] B Enzyme Ki 5.87 CHEMBL
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
Monoamine oxidase Enzyme IC50 7.89 CHEMBL

External reference:

IDSource
4019929 VUID
N0000148014 NUI
D00785 KEGG_DRUG
14611-52-0 SECONDARY_CAS_RN
4019485 VANDF
4019929 VANDF
C0036579 UMLSCUI
CHEBI:9086 CHEBI
CHEMBL972 ChEMBL_ID
DB01037 DRUGBANK_ID
CHEMBL1200904 ChEMBL_ID
D012642 MESH_DESCRIPTOR_UI
26757 PUBCHEM_CID
6639 IUPHAR_LIGAND_ID
4436 INN_ID
2K1V7GP655 UNII
203137 RXNORM
1551 MMSL
21238 MMSL
53269 MMSL
5448 MMSL
63129 MMSL
d00976 MMSL
003465 NDDF
004599 NDDF
108466000 SNOMEDCT_US
108467009 SNOMEDCT_US
372497003 SNOMEDCT_US
2K1V7GP655 INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ZELAPAR HUMAN PRESCRIPTION DRUG LABEL 1 0187-0453 TABLET, ORALLY DISINTEGRATING 1.25 mg ORAL NDA 25 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-737 CAPSULE 5 mg ORAL ANDA 20 sections
Selegiline Hydrochloride Human Prescription Drug Label 1 16571-659 CAPSULE 5 mg ORAL ANDA 19 sections
EMSAM HUMAN PRESCRIPTION DRUG LABEL 1 49502-900 PATCH 6 mg TRANSDERMAL NDA 31 sections
EMSAM HUMAN PRESCRIPTION DRUG LABEL 1 49502-901 PATCH 9 mg TRANSDERMAL NDA 31 sections
EMSAM HUMAN PRESCRIPTION DRUG LABEL 1 49502-902 PATCH 12 mg TRANSDERMAL NDA 31 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-2918 TABLET 5 mg ORAL ANDA 19 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60429-176 TABLET 5 mg ORAL ANDA 20 sections
SELEGILINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 60505-0055 CAPSULE 5 mg ORAL ANDA 13 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60505-3438 TABLET 5 mg ORAL ANDA 20 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 62135-694 TABLET 5 mg ORAL ANDA 20 sections
SELEGILINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 68151-2649 CAPSULE 5 mg ORAL ANDA 19 sections
Selegiline Hydrochloride Human Prescription Drug Label 1 70954-504 CAPSULE 5 mg ORAL ANDA 20 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 71205-888 CAPSULE 5 mg ORAL ANDA 19 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 71335-2673 CAPSULE 5 mg ORAL ANDA 19 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 71335-2676 CAPSULE 5 mg ORAL ANDA 20 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 72319-006 TABLET 5 mg ORAL ANDA 15 sections
Selegiline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 73141-006 TABLET 5 mg ORAL ANDA 15 sections