Identification
- Generic Name
- Pargyline
- DrugBank Accession Number
- DB01626
- Background
Pargyline is a monoamine oxidase inhibitor with antihypertensive properties.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pargyline (DB01626)
- Weight
- Average: 159.2276
Monoisotopic: 159.104799421 - Chemical Formula
- C11H13N
- Synonyms
- Pargilina
- Pargyline
- Pargylinum
- External IDs
- A 19120
- Lopac-P-8013
- MO 911
Pharmacology
- Indication
For the treatment of moderate to severe hypertension.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AAmine oxidase [flavin-containing] B inhibitorHumans UAmine oxidase [flavin-containing] A inhibitorHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Pargyline is combined with 1,2-Benzodiazepine. Abaloparatide Pargyline may increase the orthostatic hypotensive activities of Abaloparatide. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Pargyline is combined with Abciximab. Acarbose Pargyline may increase the hypoglycemic activities of Acarbose. Acebutolol Pargyline may increase the hypotensive activities of Acebutolol. - Food Interactions
- Avoid tyramine-containing foods and supplements. Foods that contain tyramine include yogurt, aged cheese, ripe bananas, wine, and sourdough bread.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pargyline hydrochloride W70V6I2OMY 306-07-0 BCXCABRDBBWWGY-UHFFFAOYSA-N - International/Other Brands
- Eutonyl / Eutron
Categories
- ATC Codes
- C02LL01 — Pargyline and diuretics
- C02LL — MAO inhibitors and diuretics
- C02L — ANTIHYPERTENSIVES AND DIURETICS IN COMBINATION
- C02 — ANTIHYPERTENSIVES
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Agents that produce hypertension
- Agents that reduce seizure threshold
- Amines
- Antidepressive Agents
- Antihypertensive Agents
- Benzene Derivatives
- Benzyl Compounds
- Benzylamines
- Cardiovascular Agents
- Central Nervous System Depressants
- Enzyme Inhibitors
- MAO Inhibitors and Diuretics
- Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates
- Monoamine Oxidase Inhibitors
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylmethylamines
- Direct Parent
- Phenylmethylamines
- Alternative Parents
- Benzylamines / Aralkylamines / Trialkylamines / Acetylides / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Acetylide / Amine / Aralkylamine / Aromatic homomonocyclic compound / Benzylamine / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenylmethylamine
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- aromatic amine (CHEBI:7930) / a small molecule (CPD-13898)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 9MV14S8G3E
- CAS number
- 555-57-7
- InChI Key
- 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
- IUPAC Name
- benzyl(methyl)(prop-2-yn-1-yl)amine
- SMILES
- CN(CC#C)CC1=CC=CC=C1
References
- General References
- Not Available
- External Links
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- 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 0.0998 mg/mL ALOGPS logP 2.05 ALOGPS logP 2.14 Chemaxon logS -3.2 ALOGPS pKa (Strongest Basic) 8.05 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 3.24 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 52.18 m3·mol-1 Chemaxon Polarizability 18.78 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9504 Blood Brain Barrier + 0.9568 Caco-2 permeable + 0.8188 P-glycoprotein substrate Non-substrate 0.6641 P-glycoprotein inhibitor I Non-inhibitor 0.9864 P-glycoprotein inhibitor II Non-inhibitor 0.9357 Renal organic cation transporter Non-inhibitor 0.5518 CYP450 2C9 substrate Non-substrate 0.8061 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6977 CYP450 1A2 substrate Non-inhibitor 0.7981 CYP450 2C9 inhibitor Non-inhibitor 0.9213 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.945 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7826 Ames test Non AMES toxic 0.9413 Carcinogenicity Non-carcinogens 0.5475 Biodegradation Not ready biodegradable 0.9459 Rat acute toxicity 2.6935 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7258 hERG inhibition (predictor II) Non-inhibitor 0.8819
Spectra
- Mass Spec (NIST)
- Download (10 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 142.5676373 predictedDarkChem Lite v0.1.0 [M-H]- 128.35893 predictedDeepCCS 1.0 (2019) [M+H]+ 143.1499373 predictedDarkChem Lite v0.1.0 [M+H]+ 131.53827 predictedDeepCCS 1.0 (2019) [M+Na]+ 143.3057373 predictedDarkChem Lite v0.1.0 [M+Na]+ 140.80678 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- 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]
- Heinonen EH, Myllyla V: Safety of selegiline (deprenyl) in the treatment of Parkinson's disease. Drug Saf. 1998 Jul;19(1):11-22. [Article]
- Authors unspecified: Selegiline: a second look. Six years later: too risky in Parkinson's disease. Prescrire Int. 2002 Aug;11(60):108-11. [Article]
- 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]
- Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. [Article]
- 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]
- 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]
- Patkar AA, Pae CU, Masand PS: Transdermal selegiline: the new generation of monoamine oxidase inhibitors. CNS Spectr. 2006 May;11(5):363-75. [Article]
- 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]
- Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [Article]
- 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]
- 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. doi: 10.1152/ajpheart.00345.2009. Epub 2009 Jun 19. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Patkar AA, Pae CU, Masand PS: Transdermal selegiline: the new generation of monoamine oxidase inhibitors. CNS Spectr. 2006 May;11(5):363-75. [Article]
- 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]
- Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [Article]
- 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]
- 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. [Article]
- 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. [Article]
Drug created at August 29, 2007 21:04 / Updated at January 02, 2024 23:50