Identification

Name
Selegiline
Accession Number
DB01037  (APRD00525)
Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Description

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.

Structure
Thumb
Synonyms
  • (−)-selegiline
  • L-Deprenalin
  • Selegilina
  • Selegilinum
Product Ingredients
IngredientUNIICASInChI Key
Selegiline hydrochloride6W731X367Q14611-52-0IYETZZCWLLUHIJ-UTONKHPSSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EldeprylTablet5 mg/1OralSomerset Pharmaceuticals Inc.1989-06-052010-01-01Us
EldeprylCapsule5 mg/1OralMylan Specialty1996-05-152018-09-25Us
Eldepryl - 5mg TabTablet5 mgOralDraxis Health Inc.1997-09-022004-09-23Canada
Eldepryl Tab 5mgTablet5 mgOralDeprenyl Research Ltd.1990-12-311997-07-10Canada
EmsamPatch12 mg/24hTransdermalMylan Specialty L.P.2006-02-27Not applicableUs
EmsamPatch6 mg/24hTransdermalMylan Specialty L.P.2006-02-27Not applicableUs
EmsamPatch6 mg/24hTransdermalSomerset Pharmaceuticals Inc.2010-12-132010-12-31Us
EmsamPatch12 mg/24hTransdermalSomerset Pharmaceuticals Inc.2010-12-132010-12-31Us
EmsamPatch9 mg/24hTransdermalMylan Specialty L.P.2006-02-27Not applicableUs
EmsamPatch9 mg/24hTransdermalSomerset Pharmaceuticals Inc.2010-12-132010-12-31Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-selegilineTablet5 mgOralApotex Corporation1997-02-13Not applicableCanada
Dom-selegilineTablet5 mgOralDominion Pharmacal1998-09-172016-10-25Canada
EldeprylCapsule5 mg/1OralSomerset Pharmaceuticals Inc.1996-05-152014-01-31Us
Mylan-selegilineTablet5 mgOralMylan Pharmaceuticals1997-04-09Not applicableCanada
Nu-selegilineTablet5 mgOralNu Pharm Inc1997-05-282012-09-04Canada
PMS-selegilineTablet5 mgOralPharmascience Inc1998-06-042016-10-28Canada
Selegiline HydrochlorideCapsule5 mg/1OralApotex Corporation1997-07-15Not applicableUs
Selegiline HydrochlorideTablet5 mg/1OralApotex Corporation1997-07-06Not applicableUs
Selegiline HydrochlorideCapsule5 mg/1OralA-S Medication Solutions1997-07-15Not applicableUs
Selegiline HydrochlorideTablet5 mg/1OralA-S Medication Solutions1997-07-06Not applicableUs
International/Other Brands
Carbex / Jumex
Categories
UNII
2K1V7GP655
CAS number
14611-51-9
Weight
Average: 187.286
Monoisotopic: 187.136099551
Chemical Formula
C13H17N
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

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.

Associated Conditions
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
Human
NAmine oxidase [flavin-containing] A
inhibitor
Human
Absorption

Rapidly absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding

> 99.5%

Metabolism
Route of elimination
Not Available
Half life

1.2-2 hours

Clearance
Not Available
Toxicity

LD50=63 mg/kg (rats, IV)

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Selegiline is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Selegiline is combined with (S)-Warfarin.
2,4-thiazolidinedioneSelegiline may increase the hypoglycemic activities of 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Selegiline.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Selegiline.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Selegiline.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Selegiline.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Selegiline.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Selegiline.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Selegiline.
Food Interactions
  • Food increases the oral bioavailability by 3-5 fold.

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. [PubMed:1658311]
  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. [PubMed:16034956]
  3. Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. [PubMed:6441926]
  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. [PubMed:7995016]
  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. [PubMed:11978145]
  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. [PubMed:18311418]
  7. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [PubMed:19300583]
External Links
Human Metabolome Database
HMDB15171
KEGG Drug
D03731
KEGG Compound
C07245
PubChem Compound
26757
PubChem Substance
46507655
ChemSpider
24930
BindingDB
15579
ChEBI
9086
ChEMBL
CHEMBL972
Therapeutic Targets Database
DAP000579
PharmGKB
PA451316
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Selegiline
ATC Codes
N04BD01 — Selegiline
AHFS Codes
  • 28:36.32 — Monoamine Oxidase B Inhibitors
FDA label
Download (189 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentSchizophrenic Disorders1
1CompletedTreatmentCocaine-Related Disorders1
1Unknown StatusTreatmentAmphetamine-Related Disorders1
2CompletedTreatmentCocaine Use Disorders1
2CompletedTreatmentCocaine-Related Disorders3
2CompletedTreatmentCognition Disorders / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentCognitive Disorders / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentMarijuana Abuse1
2CompletedTreatmentNicotine Dependence1
2CompletedTreatmentTobacco Use Cessation1
2CompletedTreatmentTobacco Use Disorders1
3CompletedTreatmentBorderline Personality Disorder (BPD)1
3CompletedTreatmentCocaine-Related Disorders1
4CompletedDiagnosticHealthy Volunteers1
4CompletedTreatmentMajor Depressive Disorder (MDD)1
4CompletedTreatmentParkinson's Disease (PD)2
4RecruitingTreatmentErectile Dysfunction (ED) / Parkinson's Disease (PD)1
4TerminatedTreatmentDepression, Bipolar1
Not AvailableCompletedTreatmentCognitive Disorders / Human Immunodeficiency Virus (HIV) Infections1

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
TabletOral5 mg
CapsuleOral5 mg/1
PatchTransdermal12 mg/24h
PatchTransdermal6 mg/24h
PatchTransdermal9 mg/24h
TabletOral5 mg/1
Tablet, orally disintegratingOral1.25 mg/1
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)
US5648093No1994-07-152014-07-15Us
US7150881No1998-06-122018-06-12Us
US7070808No1998-05-102018-05-10Us
US7638140No1998-05-102018-05-10Us
US6423342No1996-03-012016-03-01Us

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
Not Available

Taxonomy

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
Amphetamine or derivatives / Phenylpropane / Aralkylamine / Tertiary aliphatic amine / Tertiary amine / Acetylide / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
terminal acetylenic compound, selegiline (CHEBI:9086)

Targets

Kind
Protein
Organism
Human
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. [PubMed:11752352]
  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. [PubMed:1794016]
  3. Heinonen EH, Myllyla V: Safety of selegiline (deprenyl) in the treatment of Parkinson's disease. Drug Saf. 1998 Jul;19(1):11-22. [PubMed:9673855]
  4. Authors unspecified: Selegiline: a second look. Six years later: too risky in Parkinson's disease. Prescrire Int. 2002 Aug;11(60):108-11. [PubMed:12199263]
  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. [PubMed:16034956]
  6. Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. [PubMed:6441926]
  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. [PubMed:7995016]
  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. [PubMed:11978145]
  9. Patkar AA, Pae CU, Masand PS: Transdermal selegiline: the new generation of monoamine oxidase inhibitors. CNS Spectr. 2006 May;11(5):363-75. [PubMed:16641841]
  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. [PubMed:17715422]
  11. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [PubMed:19300583]
  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. [PubMed:17823646]
Kind
Protein
Organism
Human
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. [PubMed:16641841]
  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. [PubMed:17715422]
  3. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [PubMed:19300583]
  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. [PubMed:17823646]

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:18311418]
  2. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [PubMed:19300583]
  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. [PubMed:17495414]
  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. [PubMed:17101742]
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  6. 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. [PubMed:25656918]
  7. 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. [PubMed:22936314]
Kind
Protein
Organism
Human
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. [PubMed:17495414]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. [PubMed:19300583]
  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. [PubMed:17495414]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  4. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:10862503]
  3. 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. [PubMed:12920164]
  4. CYP1A2 document, cancer.gov [File]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  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. [PubMed:11996015]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  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. [PubMed:11996015]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:12438524]

Drug created on June 13, 2005 07:24 / Updated on November 13, 2018 07:55