Banner
targets (2)
for drugs
Identification
Name Pargyline
Accession Number DB01626
Type small molecule
Groups approved
Description

A monoamine oxidase inhibitor with antihypertensive properties. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Benzyl-methyl-2-propinylamin
Methylbenzylpropynylamine
Methylbenzylpropynylamine hydrochloride
N-Benzyl-N-methyl-2-propyn-1-amine
N-Benzyl-N-methyl-2-propynylamine
N-Benzyl-N-methyl-2-propynylamine hydrochloride
N-Methyl-N-2-propynylbenzylamine
Paragyline
Pargylamine
Pargylin
Pargyline chloride
Pargyline hydrochloride
First Prev Next Last
Salts Not Available
Brand names
Name Company
Eudatin
Eutonyl
Eutonyl-ten
Lopac-P-8013
Supirdyl
Brand mixtures Not Available
Categories
  • Antihypertensive Agents
  • Monoamine Oxidase Inhibitors
CAS number 555-57-7
Weight Average: 159.2276
Monoisotopic: 159.104799421
Chemical Formula C11H13N
InChI Key InChIKey=DPWPWRLQFGFJFI-UHFFFAOYSA-N
InChI
InChI=1S/C11H13N/c1-3-9-12(2)10-11-7-5-4-6-8-11/h1,4-8H,9-10H2,2H3
Plain Text
IUPAC Name
benzyl(methyl)(prop-2-yn-1-yl)amine
SMILES
CN(CC#C)CC1=CC=CC=C1
Plain Text
Mass Spec show (10 KB)
Taxonomy
Kingdom Organic
Classes
  • Benzene and Derivatives
Substructures
  • Alkynes
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Aromatic compounds
Pharmacology
Indication For the treatment of moderate to severe hypertension.
Pharmacodynamics Pargyline is a monoamine oxidase B (MAO-B) inhibitor with antihypertensive properties. Patients taking pargyline must avoid concurrent consumption of tyramine-containing foods such as bleu cheese and beer, as this can lead to a hypertensive crisis.
Mechanism of action MAOIs act by inhibiting the activity of monoamine oxidase, thus preventing the breakdown of monoamine neurotransmitters and thereby increasing their availability. There are two isoforms of monoamine oxidase, MAO-A and MAO-B. MAO-A preferentially deaminates serotonin, melatonin, epinephrine and norepinephrine. MAO-B preferentially deaminates phenylethylamine and trace amines. Pargyline functions by inhibiting the metabolism of catecholamines and tyramine within presynaptic nerve terminals. Catecholamines cause general physiological changes that prepare the body for physical activity (fight-or-flight response). Some typical effects are increases in heart rate, blood pressure, blood glucose levels, and a general reaction of the sympathetic nervous system.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Abbott laboratories pharmaceutical products div
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 9.98e-02 g/l ALOGPS
logP 2.05 ALOGPS
logP 2.14 ChemAxon
logS -3.2 ALOGPS
pKa (strongest basic) 8.13 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 3.24 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 52.18 ChemAxon
polarizability 18.78 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07414 Link_out
PubChem Compound 4688 Link_out
PubChem Substance 46507368 Link_out
ChemSpider 4526 Link_out
BindingDB 50172756 Link_out
Therapeutic Targets Database DAP000580 Link_out
PharmGKB PA450797 Link_out
Wikipedia http://en.wikipedia.org/wiki/Pargyline Link_out
ATC Codes
  • C02KC01
  • C02LL01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Epinephrine Increased arterial pressure
Fenoterol Increased arterial pressure
Guanethidine Pargyline may decrease the effect of guanethidine.
Methotrimeprazine Possible severe adverse reaction with this combination
Milnacipran Increase serotonin levels. Combination therapy is contraindicated.
Orciprenaline Increased arterial pressure
Phenylephrine Increased arterial pressure
Phenylpropanolamine Increased arterial pressure
Pseudoephedrine Increased arterial pressure
Terbutaline Increased arterial pressure
Food Interactions
  • Food increases the oral bioavailability by 3-5 fold.
Targets

1. Amine oxidase [flavin-containing] B

Pharmacological action: yes
Actions: inhibitor

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 tissues. MAOB preferentially degrades benzylamine and phenylethylamine

Organism class: human
UniProt ID: P27338 Link_out
Gene: MAOB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. Heinonen EH, Myllyla V: Safety of selegiline (deprenyl) in the treatment of Parkinson’s disease. Drug Saf. 1998 Jul;19(1):11-22. Pubmed
  3. Selegiline: a second look. Six years later: too risky in Parkinson’s disease. Prescrire Int. 2002 Aug;11(60):108-11. Pubmed
  4. 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# Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. Pubmed
  5. 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
  6. 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
  7. Patkar AA, Pae CU, Masand PS: Transdermal selegiline: the new generation of monoamine oxidase inhibitors. CNS Spectr. 2006 May;11(5):363-75. Pubmed
  8. 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
  9. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. Pubmed
  10. 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
  11. Villeneuve C, Caudrillier A, Ordener C, Pizzinat N, Parini A, Mialet-Perez J: Dose-dependent activation of distinct hypertrophic pathways by serotonin in cardiac cells. Am J Physiol Heart Circ Physiol. 2009 Aug;297(2):H821-8. Epub 2009 Jun 19. Pubmed
  12. Murphy DL, Karoum F, Pickar D, Cohen RM, Lipper S, Mellow AM, Tariot PN, Sunderland T: Differential trace amine alterations in individuals receiving acetylenic inhibitors of MAO-A (clorgyline) or MAO-B (selegiline and pargyline). J Neural Transm Suppl. 1998;52:39-48. Pubmed
  13. Fuentes JA, Ordaz A, Neff NH: Central mediation of the antihypertensive effect of pargyline in spontaneously hypertensive rats. Eur J Pharmacol. 1979 Jul 15;57(1):21-7. Pubmed

2. Amine oxidase [flavin-containing] A

Pharmacological action: unknown
Actions: inhibitor

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 tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine

Organism class: human
UniProt ID: P21397 Link_out
Gene: MAOA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  3. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. Pubmed
  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
  5. Murphy DL, Karoum F, Pickar D, Cohen RM, Lipper S, Mellow AM, Tariot PN, Sunderland T: Differential trace amine alterations in individuals receiving acetylenic inhibitors of MAO-A (clorgyline) or MAO-B (selegiline and pargyline). J Neural Transm Suppl. 1998;52:39-48. Pubmed
  6. Fuentes JA, Ordaz A, Neff NH: Central mediation of the antihypertensive effect of pargyline in spontaneously hypertensive rats. Eur J Pharmacol. 1979 Jul 15;57(1):21-7. Pubmed
Comments
Drug created on August 29, 2007 15:04 / Updated on February 08, 2013 16:20