Selegiline

Identification

Summary

Selegiline is a monoamine oxidase inhibitor used to treat major depressive disorder and Parkinson's.

Brand Names
Emsam, Zelapar
Generic Name
Selegiline
DrugBank Accession Number
DB01037
Background

A selective, irreversible inhibitor of Type B monoamine oxidase. It is used in newly diagnosed patients with Parkinson's disease. It may slow progression of the clinical disease and delay the requirement for levodopa therapy. It also may be given with levodopa upon onset of disability. (From AMA Drug Evaluations Annual, 1994, p385) The compound without isomeric designation is Deprenyl.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Weight
Average: 187.286
Monoisotopic: 187.136099551
Chemical Formula
C13H17N
Synonyms
  • (−)-selegiline
  • L-Deprenalin
  • Selegilina
  • Selegiline
  • Selegilinum

Pharmacology

Indication

Monotherapy for initial treatment of Parkinson's disease, as well as an adjunct therapy in patients with a decreased response to levodopa/carbadopa. Also used for the palliative treatment of mild to moderate Alzheimer's disease and at higher doses, for the treatment of depression.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAdhd••• •••••
Treatment ofMajor depressive disorder••••••••••••
Adjunct therapy in management ofParkinson's disease••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Dopamine is an essential chemical that occurs in many parts of the body. It is the premature degradation of dopamine that results in the symptoms of Parkinson's disease. Monoamine oxidase (MAO) is an enzyme which accelerates the breakdown of dopamine. Selegiline can prolong the effects of dopamine in the brain by preventing its breakdown through seletively blocking MAO-B. It also may prevent the removal of dopamine between nerve endings and enhance release of dopamine from nerve cells.

Mechanism of action

Although the mechanisms for selegiline's beneficial action in the treatment of Parkinson's disease are not fully understood, the selective, irreversible inhibition of monoamine oxidase type B (MAO-B) is thought to be of primary importance. MAO-B is involved in the oxidative deamination of dopamine in the brain. Selegiline binds to MAO-B within the nigrostriatal pathways in the central nervous system, thus blocking microsomal metabolism of dopamine and enhancing the dopaminergic activity in the substantial nigra. Selegiline may also increase dopaminergic activity through mechanisms other than inhibition of MAO-B. At higher doses, selegiline can also inhibit monozmine oxidase type A (MAO-A), allowing it to be used for the treatment of depression.

TargetActionsOrganism
AAmine oxidase [flavin-containing] B
inhibitor
Humans
NAmine oxidase [flavin-containing] A
inhibitor
Humans
Absorption

Rapidly absorbed from the gastrointestinal tract.

Volume of distribution

Not Available

Protein binding

> 99.5%

Metabolism

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

1.2-2 hours

Clearance

Not Available

Adverse Effects
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Toxicity

LD50=63 mg/kg (rats, IV)

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Selegiline is combined with 1,2-Benzodiazepine.
AbaloparatideSelegiline may increase the orthostatic hypotensive activities of Abaloparatide.
AbametapirThe serum concentration of Selegiline can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Selegiline can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Selegiline is combined with Abciximab.
Food Interactions
  • Avoid tyramine-containing foods and supplements. Consuming foods containing tyramine such as yogurt, aged cheese, ripe bananas, wine, and sourdough bread may increase the risk of having an uncontrolled hypertensive reaction.
  • Take before a meal. Take selegiline oral disintegrating tablets before breakfast and at least 5 minutes before or after any food or drink. Taking selegiline with food reduces the AUC by approximately 60%.
  • Take with food. Take selegiline capsules or tablets with breakfast and lunch. Food can increase the exposure to selegiline by 3-4 fold.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Selegiline hydrochloride6W731X367Q14611-52-0IYETZZCWLLUHIJ-UTONKHPSSA-N
Product Images
International/Other Brands
Carbex / Jumex
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EldeprylTablet5 mg/1OralSomerset Pharmaceuticals Inc.1989-06-052010-01-01US flag
EldeprylCapsule5 mg/1OralMylan Specialty L.P.1996-05-152015-03-31US flag
Eldepryl - 5mg TabTablet5 mgOralDraxis Health Inc.1997-09-022004-09-23Canada flag
Eldepryl Tab 5mgTablet5 mgOralDeprenyl Research Ltd.1990-12-311997-07-10Canada flag
EmsamPatch9 mg/24hTransdermalMylan Specialty L.P.2006-02-27Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dom-selegilineTablet5 mgOralDominion Pharmacal1998-09-172016-10-25Canada flag
EldeprylCapsule5 mg/1OralSomerset Pharmaceuticals Inc.1996-05-152014-01-31US flag
Med SelegilineTablet5 mgOralMedican Pharma Incorporated1999-06-302011-03-29Canada flag
Mylan-selegilineTablet5 mgOralMylan Pharmaceuticals1997-04-092017-08-02Canada flag
Nu-selegilineTablet5 mgOralNu Pharm Inc1997-05-282012-09-04Canada flag

Categories

ATC Codes
N04BD01 — Selegiline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Aralkylamines / Trialkylamines / Acetylides / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Acetylide / Amine / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenylpropane
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
terminal acetylenic compound, selegiline (CHEBI:9086)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
2K1V7GP655
CAS number
14611-51-9
InChI Key
MEZLKOACVSPNER-GFCCVEGCSA-N
InChI
InChI=1S/C13H17N/c1-4-10-14(3)12(2)11-13-8-6-5-7-9-13/h1,5-9,12H,10-11H2,2-3H3/t12-/m1/s1
IUPAC Name
methyl[(2R)-1-phenylpropan-2-yl](prop-2-yn-1-yl)amine
SMILES
C[C@H](CC1=CC=CC=C1)N(C)CC#C

References

Synthesis Reference

Silvia Ott-Dembrowski, Richard Cyrus, Jorg Schmidt, Hans Waiblinger, "Preparation of selegiline." U.S. Patent US5847216, issued March, 1962.

US5847216
General References
  1. Engberg G, Elebring T, Nissbrandt H: Deprenyl (selegiline), a selective MAO-B inhibitor with active metabolites; effects on locomotor activity, dopaminergic neurotransmission and firing rate of nigral dopamine neurons. J Pharmacol Exp Ther. 1991 Nov;259(2):841-7. [Article]
  2. Macleod AD, Counsell CE, Ives N, Stowe R: Monoamine oxidase B inhibitors for early Parkinson's disease. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD004898. [Article]
  3. Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. [Article]
  4. Heinonen EH, Anttila MI, Lammintausta RA: Pharmacokinetic aspects of l-deprenyl (selegiline) and its metabolites. Clin Pharmacol Ther. 1994 Dec;56(6 Pt 2):742-9. [Article]
  5. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [Article]
  6. Culpepper L, Kovalick LJ: A review of the literature on the selegiline transdermal system: an effective and well-tolerated monoamine oxidase inhibitor for the treatment of depression. Prim Care Companion J Clin Psychiatry. 2008;10(1):25-30. [Article]
  7. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [Article]
Human Metabolome Database
HMDB15171
KEGG Drug
D03731
KEGG Compound
C07245
PubChem Compound
26757
PubChem Substance
46507655
ChemSpider
24930
BindingDB
15579
RxNav
9639
ChEBI
9086
ChEMBL
CHEMBL972
ZINC
ZINC000019632633
Therapeutic Targets Database
DAP000579
PharmGKB
PA451316
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Selegiline
FDA label
Download (189 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableHealthy Volunteers (HV)1
4CompletedDiagnosticHealthy Volunteers (HV)1
4CompletedTreatmentMajor Depressive Disorder (MDD)1
4CompletedTreatmentParkinson's Disease (PD)3
4TerminatedTreatmentDepression, Bipolar1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Alphapharm Party Ltd.
  • Apotex Inc.
  • Bristol-Myers Squibb Co.
  • Catalent Pharma Solutions
  • DAHI Animal Health Inc.
  • DAVA Pharmaceuticals
  • Dey Pharma LP
  • Draxis Specialty Pharmaceuticals Inc.
  • Endo Pharmaceuticals Inc.
  • Heartland Repack Services LLC
  • Legacy Pharmaceuticals Packaging LLC
  • Major Pharmaceuticals
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Novopharm Ltd.
  • Par Pharmaceuticals
  • Physicians Total Care Inc.
  • Resource Optimization and Innovation LLC
  • Somerset Pharmaceuticals Inc.
  • Standard Chem and Pharm Co. Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • Torpharm Inc.
  • Ultratab Labs Inc.
  • Valeant Ltd.
Dosage Forms
FormRouteStrength
CapsuleOral5 mg/1
PatchTransdermal12 mg/24h
PatchTransdermal6 mg/24h
PatchTransdermal9 mg/24h
TabletOral5.000 mg
SolutionOral
Tablet, coated
TabletOral10 MG
TabletOral
TabletOral5 mg/1
Tablet, orally disintegratingOral1.25 mg/1
TabletOral5 mg
Prices
Unit descriptionCostUnit
Emsam 30 12 mg/24hr Patches Box627.1USD box
Emsam 30 6 mg/24hr Patches Box627.1USD box
Emsam 30 9 mg/24hr Patches Box627.1USD box
Selegiline hcl powder127.3USD g
Eldepryl 30 5 mg capsule Box89.55USD box
Emsam 12 mg/24 hours patch20.1USD patch
Emsam 6 mg/24 hours patch20.1USD patch
Emsam 9 mg/24 hours patch20.1USD patch
Zelapar 1.25 mg odt tablet8.33USD tablet
Selegiline HCl 5 mg capsule2.4USD capsule
Selegiline hcl 5 mg tablet2.1USD tablet
Apo-Selegiline 5 mg Tablet1.33USD tablet
Mylan-Selegiline 5 mg Tablet1.33USD tablet
Novo-Selegiline 5 mg Tablet1.33USD tablet
Nu-Selegiline 5 mg Tablet1.33USD tablet
Pms-Selegiline 5 mg Tablet1.33USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5648093No1997-07-152014-07-15US flag
US7150881No2006-12-192018-06-12US flag
US7070808No2006-07-042018-05-10US flag
US7638140No2009-12-292018-05-10US flag
US6423342No2002-07-232016-03-01US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)141-142 °CNot Available
logP2.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0254 mg/mLALOGPS
logP3.08ALOGPS
logP2.85Chemaxon
logS-3.9ALOGPS
pKa (Strongest Basic)8.67Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area3.24 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity61.35 m3·mol-1Chemaxon
Polarizability22.69 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9788
Blood Brain Barrier+0.9809
Caco-2 permeable+0.8453
P-glycoprotein substrateNon-substrate0.543
P-glycoprotein inhibitor INon-inhibitor0.9632
P-glycoprotein inhibitor IINon-inhibitor0.9779
Renal organic cation transporterInhibitor0.5327
CYP450 2C9 substrateNon-substrate0.7993
CYP450 2D6 substrateSubstrate0.6987
CYP450 3A4 substrateNon-substrate0.5671
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9341
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9285
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9285
Ames testNon AMES toxic0.889
CarcinogenicityNon-carcinogens0.6567
BiodegradationNot ready biodegradable0.9767
Rat acute toxicity2.9199 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8869
hERG inhibition (predictor II)Non-inhibitor0.8269
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9400000000-ce456dc803e548082459
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-4444efe7769d7f4a171c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-babf742e5f2551dddf85
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-6900000000-db429e5eec5668a1c489
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gbi-9600000000-1f9d38bbaea2ea455dc6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kf-9000000000-4ea2d0328413a0db3c28
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-147.6223748
predicted
DarkChem Lite v0.1.0
[M-H]-139.17693
predicted
DeepCCS 1.0 (2019)
[M+H]+148.3809748
predicted
DarkChem Lite v0.1.0
[M+H]+141.5725
predicted
DeepCCS 1.0 (2019)
[M+Na]+148.1253748
predicted
DarkChem Lite v0.1.0
[M+Na]+148.95412
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Chrisp P, Mammen GJ, Sorkin EM: Selegiline. A review of its pharmacology, symptomatic benefits and protective potential in Parkinson's disease. Drugs Aging. 1991 May;1(3):228-48. [Article]
  3. Heinonen EH, Myllyla V: Safety of selegiline (deprenyl) in the treatment of Parkinson's disease. Drug Saf. 1998 Jul;19(1):11-22. [Article]
  4. Authors unspecified: Selegiline: a second look. Six years later: too risky in Parkinson's disease. Prescrire Int. 2002 Aug;11(60):108-11. [Article]
  5. Macleod AD, Counsell CE, Ives N, Stowe R: Monoamine oxidase B inhibitors for early Parkinson's disease. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD004898. [Article]
  6. Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. [Article]
  7. Heinonen EH, Anttila MI, Lammintausta RA: Pharmacokinetic aspects of l-deprenyl (selegiline) and its metabolites. Clin Pharmacol Ther. 1994 Dec;56(6 Pt 2):742-9. [Article]
  8. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [Article]
  9. Patkar AA, Pae CU, Masand PS: Transdermal selegiline: the new generation of monoamine oxidase inhibitors. CNS Spectr. 2006 May;11(5):363-75. [Article]
  10. Azzaro AJ, Ziemniak J, Kemper E, Campbell BJ, VanDenBerg C: Pharmacokinetics and absolute bioavailability of selegiline following treatment of healthy subjects with the selegiline transdermal system (6 mg/24 h): a comparison with oral selegiline capsules. J Clin Pharmacol. 2007 Oct;47(10):1256-67. Epub 2007 Aug 22. [Article]
  11. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [Article]
  12. Baker GB, Sowa B, Todd KG: Amine oxidases and their inhibitors: what can they tell us about neuroprotection and the development of drugs for neuropsychiatric disorders? J Psychiatry Neurosci. 2007 Sep;32(5):313-5. [Article]
  13. Andoh T, Chock PB, Murphy DL, Chiueh CC: Role of the redox protein thioredoxin in cytoprotective mechanism evoked by (-)-deprenyl. Mol Pharmacol. 2005 Nov;68(5):1408-14. doi: 10.1124/mol.105.012302. Epub 2005 Aug 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Patkar AA, Pae CU, Masand PS: Transdermal selegiline: the new generation of monoamine oxidase inhibitors. CNS Spectr. 2006 May;11(5):363-75. [Article]
  2. Azzaro AJ, Ziemniak J, Kemper E, Campbell BJ, VanDenBerg C: Pharmacokinetics and absolute bioavailability of selegiline following treatment of healthy subjects with the selegiline transdermal system (6 mg/24 h): a comparison with oral selegiline capsules. J Clin Pharmacol. 2007 Oct;47(10):1256-67. Epub 2007 Aug 22. [Article]
  3. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [Article]
  4. Baker GB, Sowa B, Todd KG: Amine oxidases and their inhibitors: what can they tell us about neuroprotection and the development of drugs for neuropsychiatric disorders? J Psychiatry Neurosci. 2007 Sep;32(5):313-5. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Culpepper L, Kovalick LJ: A review of the literature on the selegiline transdermal system: an effective and well-tolerated monoamine oxidase inhibitor for the treatment of depression. Prim Care Companion J Clin Psychiatry. 2008;10(1):25-30. [Article]
  2. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [Article]
  3. Benetton SA, Fang C, Yang YO, Alok R, Year M, Lin CC, Yeh LT: P450 phenotyping of the metabolism of selegiline to desmethylselegiline and methamphetamine. Drug Metab Pharmacokinet. 2007 Apr;22(2):78-87. [Article]
  4. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [Article]
  5. Nirogi R, Palacharla RC, Mohammed AR, Manoharan A, Ponnamaneni RK, Bhyrapuneni G: Evaluation of metabolism dependent inhibition of CYP2B6 mediated bupropion hydroxylation in human liver microsomes by monoamine oxidase inhibitors and prediction of potential as perpetrators of drug interaction. Chem Biol Interact. 2015 Mar 25;230:9-20. doi: 10.1016/j.cbi.2015.01.028. Epub 2015 Feb 3. [Article]
  6. Sridar C, Kenaan C, Hollenberg PF: Inhibition of bupropion metabolism by selegiline: mechanism-based inactivation of human CYP2B6 and characterization of glutathione and peptide adducts. Drug Metab Dispos. 2012 Dec;40(12):2256-66. doi: 10.1124/dmd.112.046979. Epub 2012 Aug 30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Benetton SA, Fang C, Yang YO, Alok R, Year M, Lin CC, Yeh LT: P450 phenotyping of the metabolism of selegiline to desmethylselegiline and methamphetamine. Drug Metab Pharmacokinet. 2007 Apr;22(2):78-87. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [Article]
  2. Benetton SA, Fang C, Yang YO, Alok R, Year M, Lin CC, Yeh LT: P450 phenotyping of the metabolism of selegiline to desmethylselegiline and methamphetamine. Drug Metab Pharmacokinet. 2007 Apr;22(2):78-87. [Article]
  3. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  4. Siu EC, Tyndale RF: Selegiline is a mechanism-based inactivator of CYP2A6 inhibiting nicotine metabolism in humans and mice. J Pharmacol Exp Ther. 2008 Mar;324(3):992-9. Epub 2007 Dec 7. [Article]
  5. Di YM, Chow VD, Yang LP, Zhou SF: Structure, function, regulation and polymorphism of human cytochrome P450 2A6. Curr Drug Metab. 2009 Sep;10(7):754-80. [Article]
  6. Tanner JA, Tyndale RF: Variation in CYP2A6 Activity and Personalized Medicine. J Pers Med. 2017 Dec 1;7(4). pii: jpm7040018. doi: 10.3390/jpm7040018. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Taavitsainen P, Anttila M, Nyman L, Karnani H, Salonen JS, Pelkonen O: Selegiline metabolism and cytochrome P450 enzymes: in vitro study in human liver microsomes. Pharmacol Toxicol. 2000 May;86(5):215-21. [Article]
  2. Salonen JS, Nyman L, Boobis AR, Edwards RJ, Watts P, Lake BG, Price RJ, Renwick AB, Gomez-Lechon MJ, Castell JV, Ingelman-Sundberg M, Hidestrand M, Guillouzo A, Corcos L, Goldfarb PS, Lewis DF, Taavitsainen P, Pelkonen O: Comparative studies on the cytochrome p450-associated metabolism and interaction potential of selegiline between human liver-derived in vitro systems. Drug Metab Dispos. 2003 Sep;31(9):1093-102. doi: 10.1124/dmd.31.9.1093. [Article]
  3. CYP1A2 document, cancer.gov [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Salonen JS, Nyman L, Boobis AR, Edwards RJ, Watts P, Lake BG, Price RJ, Renwick AB, Gomez-Lechon MJ, Castell JV, Ingelman-Sundberg M, Hidestrand M, Guillouzo A, Corcos L, Goldfarb PS, Lewis DF, Taavitsainen P, Pelkonen O: Comparative studies on the cytochrome p450-associated metabolism and interaction potential of selegiline between human liver-derived in vitro systems. Drug Metab Dispos. 2003 Sep;31(9):1093-102. doi: 10.1124/dmd.31.9.1093. [Article]
  2. Hidestrand M, Oscarson M, Salonen JS, Nyman L, Pelkonen O, Turpeinen M, Ingelman-Sundberg M: CYP2B6 and CYP2C19 as the major enzymes responsible for the metabolism of selegiline, a drug used in the treatment of Parkinson's disease, as revealed from experiments with recombinant enzymes. Drug Metab Dispos. 2001 Nov;29(11):1480-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Salonen JS, Nyman L, Boobis AR, Edwards RJ, Watts P, Lake BG, Price RJ, Renwick AB, Gomez-Lechon MJ, Castell JV, Ingelman-Sundberg M, Hidestrand M, Guillouzo A, Corcos L, Goldfarb PS, Lewis DF, Taavitsainen P, Pelkonen O: Comparative studies on the cytochrome p450-associated metabolism and interaction potential of selegiline between human liver-derived in vitro systems. Drug Metab Dispos. 2003 Sep;31(9):1093-102. doi: 10.1124/dmd.31.9.1093. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Nomoto M, Nakatsuka A, Nagai M, Yabe H, Moritoyo T, Moritoyo H, Nisikawa N: [Inter- and intraindividual pharmacokinetic variations in the treatment of Parkinson's disease]. Rinsho Shinkeigaku. 2005 Nov;45(11):895-8. [Article]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48