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Identification
Name Phenylpropanolamine
Accession Number DB00397 (APRD00457)
Type small molecule
Groups approved, withdrawn
Description

Phenylpropanolamine has been withdrawn in Canada. In November 2000, the Food and Drug Administration (FDA) issued a public health advisory against the use of the drug.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(+-)-Phenylpropanolamine
(+/-)-Norephedrin
Salts Not Available
Brand names
Name Company
Acutrim
Ami-Tex
Codimal
Conex
Contuss
Despec
Dexatrim
Dura-Vent
Gentab
Guaipax
Myminic
Nolex
Partuss
Phenoxine
Phenyldrine
Phenylfenesin
Propagest
Rhindecon
Rhymed
Snaplets
ULR
Vanex
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Brand mixtures
Brand Name Ingredients
Alka Seltzer Plus Cold Medicine Evt Acetylsalicylic Acid + Chlorpheniramine Maleate + Phenylpropanolamine Bitartrate
Alka-Seltzer Plus Cold Medicine - Evt Acetylsalicylic Acid + Chlorpheniramine Maleate + Phenylpropanolamine Bitartrate
Antitussive Decong Antihistamine Syr Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Bronchodex D Cap Chlorpheniramine Maleate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride
Bronchosirum Pour Enfants Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Caldomine Dh Adulte Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Caldomine Dh Enfant Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Centracol DM - Syr Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Chlor Tripolon Decongest Syr Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Cold & Allergy Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Cold & Allergy Relief - Liq Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Cold Decongestant Long Acting Cap Chlorpheniramine Maleate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride
Cold Relief Brompheniramine Maleate + Phenylpropanolamine Hydrochloride
Cold Relief DM Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Coltalin Tablet Acetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Contac Cold Capsules Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Contac Cold Extra Strength Capsules Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Contac Cough Cold and Flu Caplets Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Contact C Src Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Coricidin D Long Acting Tab Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Coricidin D Tab Acetylsalicylic Acid + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Coricidin Nd Tab Acetylsalicylic Acid + Phenylpropanolamine Hydrochloride
Coricidin Sinus Headache Tab Acetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Corsym Suspension Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Cough, Cold & Allergy Relief Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Counteract Sinus and Allergy Acetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Decongestant Antihistaminic Syrup Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dilotab Acetaminophen + Phenylpropanolamine Hydrochloride
Dimetane Expectorant Liq Brompheniramine Maleate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetane Expectorant-C Syr Brompheniramine Maleate + Codeine Phosphate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetane Expectorant-Dc Syr Brompheniramine Maleate + Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp Chewable Tablets Brompheniramine Maleate + Phenylpropanolamine Hydrochloride
Dimetapp Children's Cold & Allergy Tablets Brompheniramine Maleate + Phenylpropanolamine Hydrochloride
Dimetapp Children's Cold & Fever Acetaminophen + Brompheniramine Maleate + Phenylpropanolamine Hydrochloride
Dimetapp Clear Brompheniramine Maleate + Phenylpropanolamine Hydrochloride
Dimetapp Cold & Sinus Acetaminophen + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp Cough & Cold Liqui-Gels - Cap Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Dimetapp Cough, Cold & Flu Acetaminophen + Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Dimetapp DM Elixir Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp DM Tab Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp Elixir Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp Extentabs Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp Liqui-Gels Cap Brompheniramine Maleate + Phenylpropanolamine Hydrochloride
Dimetapp Oral Infant Drops Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp Tab Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp-C Syr Brompheniramine Maleate + Codeine Phosphate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dristan Capsules Acetylsalicylic Acid + Caffeine + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Emercidin D Tab Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Emertabs Tab Acetaminophen + Caffeine + Phenylpropanolamine Hydrochloride
Entex La Guaifenesin + Phenylpropanolamine Hydrochloride
Entex La Tablets Srt Guaifenesin + Phenylpropanolamine Hydrochloride
Extra Strength Contac C - Src Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Oradrine 2 Tab Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Oradrine Tablets Acetaminophen + Caffeine + Codeine Phosphate + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Oradrine-2 Tab Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Ornade Af Liquid Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Ornade Af Spansule Src Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Ornade DM 10 Liq Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Ornade DM 15 Liq Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Ornade DM 30 Liq Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Ornade Expectorant Cough Formula Chlorpheniramine Maleate + Guaifenesin + Phenylpropanolamine Hydrochloride
Ornade Liquid Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Ornade Spansule Src Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Pharmacol DM Syr Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Pharmetapp Elixir Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Pharminicol DM Syrup Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Sine Off Nd Extra Strength Caplet Acetaminophen + Phenylpropanolamine Hydrochloride
Sine-Off Allergy Tab Acetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Sine-Off N.D. Tab Acetaminophen + Phenylpropanolamine Hydrochloride
Sine-Off N.D. Tablet Acetaminophen + Phenylpropanolamine Hydrochloride
Sinutab Sa Tab Acetaminophen + Phenylpropanolamine Hydrochloride + Phenyltoloxamine Citrate
Tantacol DM Syr Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Tantapp Elixir Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Tavist-D Tablets Clemastine (Clemastine Hydrogen Fumarate) + Phenylpropanolamine Hydrochloride
Tri-Anamine Cold Syrup Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Tri-Anamine Expect Antihist Decong Syrup Guaifenesin + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Triaminic Cold and Allergy Syrup Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Triaminic DM Daytime Syr Dextromethorphan Hydrobromide + Guaifenesin + Phenylpropanolamine Hydrochloride
Triaminic Expectorant Dh Syrup Guaifenesin + Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Triaminic Time Release Tab Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Triaminicin Colds & Flu Caplets Acetaminophen + Caffeine + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Trisulfaminic Sus Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate + Sulfadiazine + Sulfamerazine + Sulfamethazine
Trisulfaminic Tab Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate + Sulfadiazine + Sulfamerazine + Sulfamethazine
Tussaminic C Forte Syrup Codeine Phosphate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Tussaminic C Pediatric Syrup Codeine Phosphate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Tussaminic Dh Forte Syrup Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Tussaminic DH Pediatric Syrup Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
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Categories
  • Sympathomimetics
  • Appetite Depressants
  • Adrenergic alpha-Agonists
  • Nasal Decongestants
CAS number 14838-15-4
Weight Average: 151.2056
Monoisotopic: 151.099714043
Chemical Formula C9H13NO
InChI Key InChIKey=DLNKOYKMWOXYQA-VXNVDRBHSA-N
InChI
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m1/s1
Plain Text
IUPAC Name
(1S,2R)-2-amino-1-phenylpropan-1-ol
SMILES
C[C@@H](N)[C@@H](O)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Amphetamines
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Amino Alcohols
  • Phenethylamines
  • Aromatic compounds
  • Alcohols and Polyols
  • Amphetamines
Pharmacology
Indication For the treatment of nasal congestion, control of urinary incontinence, priapism and obesity.
Pharmacodynamics Phenylpropanolamine (PPA), a sympathomimetic agent structurally similar to pseudoephedrine, is used to treat nasal congestion. Phenylpropanolamine is found in appetite suppressant formulations and with guaifenesinin in cough-cold formulations. In 2000, the FDA requested that all drug companies discontinue marketing products containing phenylpropanolamine, due to an increased risk of hemorrhagic stroke in women who used phenylpropanolamine.
Mechanism of action Phenylpropanolamine acts directly on alpha- and, to a lesser degree, beta-adrenergic receptors in the mucosa of the respiratory tract. Stimulation of alpha-adrenergic receptors produces vasoconstriction, reduces tissue hyperemia, edema, and nasal congestion, and increases nasal airway patency. PPA indirectly stimulates beta-receptors, producing tachycardia and a positive inotropic effect.
Absorption Reduced bioavailability (about 38%) from gastrointestinal tract because of first pass metabolism by monoamine oxidase in the stomach and liver.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Hepatic
Route of elimination Not Available
Half life 2.1 to 3.4 hours.
Clearance Not Available
Toxicity May induce ventricular extrasystoles and short paroxysms of ventricular tachycardia, a sensation of fullness in the head and tingling of the extremities; LD50=1490mg/kg (orally in rat)
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Naldecon Senior EX 200 mg/5ml Syrup 118ml Bottle 15.99 USD bottle
Entex ER 10-300 mg 12 Hour Capsule 1.14 USD capsule
Codimal la capsule 0.7 USD capsule
Despec-dm tablet 0.61 USD tablet
Despec-tab tablet 0.47 USD tablet
Triaminic allergy thin strip 0.35 USD strip
Triaminic cold-stuff nose strip 0.35 USD strip
Conex tablet 0.33 USD tablet
Triaminic cgh-runny nose strip 0.3 USD strip
Triaminic cough strips 0.3 USD strip
Triaminic cough-cold chew 0.27 USD each
Triaminic softchew tablet 0.27 USD tablet
Triaminic softchews tablet 0.25 USD tablet
Childrens triaminic decon spray 0.24 USD ml
Triaminicin tablet 0.23 USD tablet
Dexatrim natural caplet 0.19 USD caplet
Codimal DH 5-8.33-1.66 mg/5ml Syrup 0.18 USD ml
Despec-exp syrup 0.18 USD ml
Codimal dm syrup 0.16 USD ml
Naldecon-dx senior 0.06 USD ml
Apap allergy sinus caplet 0.05 USD caplet
Triaminic chest-nasal cong liq 0.04 USD ml
Triaminic cold & cough liquid 0.04 USD ml
Triaminic cold-allergy pe liq 0.04 USD ml
Triaminic cough-nasal cong liquid 0.04 USD ml
Triaminic cough-sore throat liquid 0.04 USD ml
Triaminic flu cough-fever suspension 0.04 USD ml
Triaminic flu-cough-fever liquid 0.04 USD ml
Triaminic-d syrup 0.04 USD ml
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 190-194 °C Not Available
water solubility Freely soluble Not Available
logP 0.67 SANGSTER (1994)
pKa 9.44 (at 20 °C) PERRIN,DD (1965)
Predicted Properties
Property Value Source
water solubility 2.06e+01 g/l ALOGPS
logP 0.57 ALOGPS
logP 0.89 ChemAxon
logS -0.87 ALOGPS
pKa (strongest acidic) 13.9 ChemAxon
pKa (strongest basic) 9.37 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 46.25 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 44.91 ChemAxon
polarizability 16.98 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07911 Link_out
PubChem Compound 26934 Link_out
PubChem Substance 46508087 Link_out
ChemSpider 25082 Link_out
Therapeutic Targets Database DNC001144 Link_out
PharmGKB PA164748965 Link_out
Drug Product Database 2247031 Link_out
Drugs.com http://www.drugs.com/mtm/phenylpropanolamine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Phenylpropanolamine Link_out
ATC Codes
  • R01BA01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (52.4 KB)
Interactions
Drug Interactions
Drug Interaction
Acetophenazine Decreased anorexic effect, may increase psychotic symptoms
Alseroxylon Increased arterial pressure
Amitriptyline The tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of phenylpropanolamine.
Amoxapine The tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of phenylpropanolamine.
Bromocriptine The sympathomimetic, phenylpropanolamine, increases the toxicity of bromocriptine.
Chlorpromazine Decreased anorexic effect, may increase psychotic symptoms
Clomipramine The tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of phenylpropanolamine.
Deserpidine Increased arterial pressure
Desipramine The tricyclic antidepressant, desipramine, increases the sympathomimetic effect of phenylpropanolamine.
Doxepin The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of phenylpropanolamine.
Ethopropazine Decreased anorexic effect, may increase psychotic symptoms
Fluoxetine Risk of serotoninergic syndrome
Fluphenazine Decreased anorexic effect, may increase psychotic symptoms
Fluvoxamine Risk of serotoninergic syndrome
Guanethidine Phenylpropanolamine may decrease the effect of guanethidine.
Imipramine The tricyclic antidepressant, imipramine, increases the sympathomimetic effect of phenylpropanolamine.
Iobenguane Sympathomimetic that increase chances of producing a false negative imaging result
Isocarboxazid Increased arterial pressure
Linezolid Possible increase of arterial pressure
Mesoridazine Decreased anorexic effect, may increase psychotic symptoms
Methdilazine Decreased anorexic effect, may increase psychotic symptoms
Methotrimeprazine Decreased anorexic effect, may increase psychotic symptoms
Methyldopa Increased arterial pressure
Midodrine Increased arterial pressure
Moclobemide Moclobemide increases the sympathomimetic effect of phenylpropanolamine.
Nortriptyline The tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of phenylpropanolamine.
Pargyline Increased arterial pressure
Paroxetine Risk of serotoninergic syndrome
Perphenazine Decreased anorexic effect, may increase psychotic symptoms
Phenelzine Increased arterial pressure
Prochlorperazine Decreased anorexic effect, may increase psychotic symptoms.
Promazine Decreased anorexic effect, may increase psychotic symptoms
Promethazine Decreased anorexic effect, may increase psychotic symptoms.
Propericiazine Decreased anorexic effect, may increase psychotic symptoms.
Propiomazine Decreased anorexic effect, may increase psychotic symptoms
Protriptyline The tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of phenylpropanolamine.
Rasagiline Increased arterial pressure
Reserpine Increased arterial pressure
Thiethylperazine Decreased anorexic effect, may increase psychotic symptoms
Thioridazine Decreased anorexic effect, may increase psychotic symptoms
Tranylcypromine Increased arterial pressure
Trifluoperazine Decreased anorexic effect, may increase psychotic symptoms
Triflupromazine Decreased anorexic effect, may increase psychotic symptoms
Trimeprazine Decreased anorexic effect, may increase psychotic symptoms
Trimipramine The tricyclic antidepressant, trimipramine, increases the sympathomimetic effect of phenylpropanolamine.
Venlafaxine Risk of serotoninergic syndrome
Food Interactions
  • Limit caffeine intake.
  • Take without regard to meals.
Targets

1. Alpha-1A adrenergic receptor

Pharmacological action: yes
Actions: agonist

This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins

Organism class: human
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  2. Wellman PJ, McMahon LR, Green T, Tole A: Effects of the alpha 1a-adrenoceptor antagonist RS-17053 on phenylpropanolamine-induced anorexia in rats. Pharmacol Biochem Behav. 1997 May-Jun;57(1-2):281-4. Pubmed
  3. Buckner SA, Milicic I, Daza AV, Meyer MD, Altenbach RJ, Williams M, Sullivan JP, Brioni JD: ABT-866, a novel alpha(1A)-adrenoceptor agonist with antagonist properties at the alpha(1B)- and alpha(1D)-adrenoceptor subtypes. Eur J Pharmacol. 2002 Aug 2;449(1-2):159-65. Pubmed
  4. Altenbach RJ, Khilevich A, Kolasa T, Rohde JJ, Bhatia PA, Patel MV, Searle XB, Yang F, Bunnelle WH, Tietje K, Bayburt EK, Carroll WA, Meyer MD, Henry R, Buckner SA, Kuk J, Daza AV, Milicic IV, Cain JC, Kang CH, Ireland LM, Carr TL, Miller TR, Hancock AA, Nakane M, Esbenshade TA, Brune ME, O’Neill AB, Gauvin DM, Katwala SP, Holladay MW, Brioni JD, Sullivan JP: Synthesis and structure-activity studies on N-[5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonami de, an imidazole-containing alpha(1A)-adrenoceptor agonist. J Med Chem. 2004 Jun 3;47(12):3220-35. Pubmed
  5. Moya-Huff FA, Maher TJ: Adrenergic receptor subtype activation by ()-, (-)- and (/-)-norephedrine in the pithed rat. J Pharm Pharmacol. 1987 Feb;39(2):108-12. Pubmed

2. Alpha-2A adrenergic receptor

Pharmacological action: yes
Actions: agonist

Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol

Organism class: human
UniProt ID: P08913 Link_out
Gene: ADRA2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Flavahan NA: Phenylpropanolamine constricts mouse and human blood vessels by preferentially activating alpha2-adrenoceptors. J Pharmacol Exp Ther. 2005 Apr;313(1):432-9. Epub 2004 Dec 17. Pubmed

3. D(1A) dopamine receptor

Pharmacological action: unknown
Actions: partial agonist

This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase

Organism class: human
UniProt ID: P21728 Link_out
Gene: DRD1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Cheng JT, Kuo DY: Both alpha1-adrenergic and D(1)-dopaminergic neurotransmissions are involved in phenylpropanolamine-mediated feeding suppression in mice. Neurosci Lett. 2003 Aug 21;347(2):136-8. Pubmed

4. Beta-1 adrenergic receptor

Pharmacological action: unknown
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Thomas SH, Clark KL, Allen R, Smith SE: A comparison of the cardiovascular effects of phenylpropanolamine and phenylephrine containing proprietary cold remedies. Br J Clin Pharmacol. 1991 Dec;32(6):705-11. Pubmed
  2. Moya-Huff FA, Maher TJ: Adrenergic receptor subtype activation by ()-, (-)- and (/-)-norephedrine in the pithed rat. J Pharm Pharmacol. 1987 Feb;39(2):108-12. Pubmed
Enzymes

1. Amine oxidase [flavin-containing] A

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

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

References:
  1. Yu PH: Inhibition of monoamine oxidase activity by phenylpropanolamine, an anorectic agent. Res Commun Chem Pathol Pharmacol. 1986 Feb;51(2):163-71. Pubmed

2. Cytochrome P450 1A2

Actions: inhibitor

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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19