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Identification
NamePhenylpropanolamine
Accession NumberDB00397  (APRD00457)
TypeSmall Molecule
GroupsApproved, Withdrawn
Description

Phenylpropanolamine has been withdrawn in Canada and the United States. In November 2000, the Food and Drug Administration (FDA) issued a public health advisory against the use of the drug.

Structure
Thumb
Synonyms
SynonymLanguageCode
2-amino-1-phenylpropan-1-olNot AvailableIUPAC
FenilpropanolaminaSpanishINN
NorephedrinNot AvailableWHO
NorephedrineNot AvailableNot Available
PhenylpropanolaminGermanINN
PhénylpropanolamineFrenchINN
PhenylpropanolaminumLatinINN
PPANot AvailableNot Available
β-hydroxyamphetamine)Not AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AcutrimNot Available
BoxogettenCheplapharm
DexatrimNot Available
DisudrinPediatrica
NaldecIAE
NasadecMedlink
NasatheraMorishita-Seggs
PropagestNot Available
Recatol monoRiemser
RhindeconNot Available
RinexinMeda
Brand mixtures
Brand NameIngredients
Alka Seltzer Plus Cold Medicine EvtAcetylsalicylic Acid + Chlorpheniramine Maleate + Phenylpropanolamine Bitartrate
Bronchodex D CapChlorpheniramine Maleate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride
Bronchosirum Pour EnfantsDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Caldomine DHHydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Centracol DMDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Chlor Tripolon DecongestChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Cold & AllergyBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Cold & Allergy ReliefBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Cold Decongestant Long ActingChlorpheniramine Maleate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride
Cold ReliefBrompheniramine Maleate + Phenylpropanolamine Hydrochloride
Cold Relief DMBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Coltalin TabletAcetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Contac Cold CapsulesChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Contac Cold Extra Strength CapsulesChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Contac Cough Cold and Flu CapletsAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Contact CChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Coricidin DAcetylsalicylic Acid + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Coricidin NDAcetylsalicylic Acid + Phenylpropanolamine Hydrochloride
Coricidin Sinus HeadacheAcetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Corsym SuspensionChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Cough, Cold & Allergy ReliefBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Counteract Sinus and AllergyAcetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Decongestant Antihistaminic SyrupBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
DilotabAcetaminophen + Phenylpropanolamine Hydrochloride
Dimetane ExpectorantBrompheniramine Maleate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetane Expectorant-CBrompheniramine Maleate + Codeine Phosphate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetane Expectorant-DCBrompheniramine Maleate + Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
DimetappBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp Chewable TabletsBrompheniramine Maleate + Phenylpropanolamine Hydrochloride
Dimetapp Children's Cold & Allergy TabletsBrompheniramine Maleate + Phenylpropanolamine Hydrochloride
Dimetapp Children's Cold & FeverAcetaminophen + Brompheniramine Maleate + Phenylpropanolamine Hydrochloride
Dimetapp ClearBrompheniramine Maleate + Phenylpropanolamine Hydrochloride
Dimetapp Cold & SinusAcetaminophen + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp Cough & Cold Liqui-GelsBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Dimetapp Cough, Cold & FluAcetaminophen + Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Dimetapp DMBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp ElixirBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp ExtentabsBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp Liqui-GelsBrompheniramine Maleate + Phenylpropanolamine Hydrochloride
Dimetapp Oral Infant DropsBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp-CBrompheniramine Maleate + Codeine Phosphate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dristan CapsulesAcetylsalicylic Acid + Caffeine + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Emercidin DAcetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
EmertabsAcetaminophen + Caffeine + Phenylpropanolamine Hydrochloride
Entex LAGuaifenesin + Phenylpropanolamine Hydrochloride
Extra Strength Contac CChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Oradrine 2Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Oradrine TabletsAcetaminophen + Caffeine + Codeine Phosphate + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Ornade AF LiquidChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Ornade AF SpansuleChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Ornade DMChlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Ornade Expectorant Cough FormulaChlorpheniramine Maleate + Guaifenesin + Phenylpropanolamine Hydrochloride
Ornade LiquidChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Ornade SpansuleChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Partuss-LAGuaifenesin + Phenylpropanolamine Hydrochloride
Pharmacol DMDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Pharmetapp ElixirBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Pharminicol DM SyrupDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Sine Off NDAcetaminophen + Phenylpropanolamine Hydrochloride
Sine-Off AllergyAcetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Sinutab SAAcetaminophen + Phenylpropanolamine Hydrochloride + Phenyltoloxamine Citrate
Tantacol DMDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Tantapp ElixirBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Tavist-DClemastine (Clemastine Hydrogen Fumarate) + Phenylpropanolamine Hydrochloride
Tri-Anamine Cold SyrupChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Tri-Anamine Expect AntihistGuaifenesin + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Triaminic Cold and Allergy SyrupChlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Triaminic DM DaytimeDextromethorphan Hydrobromide + Guaifenesin + Phenylpropanolamine Hydrochloride
Triaminic Expectorant DH SyrupGuaifenesin + Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Triaminic Time ReleasePheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Triaminicin Colds & Flu CapletsAcetaminophen + Caffeine + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
TrisulfaminicPheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate + Sulfadiazine + Sulfamerazine + Sulfamethazine
Tussaminic C Forte SyrupCodeine Phosphate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Tussaminic C Pediatric SyrupCodeine Phosphate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Tussaminic Dh Forte SyrupHydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Tussaminic DH Pediatric SyrupHydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Salts
Name/CASStructureProperties
Phenylpropanolamine hydrochloride
ThumbNot applicableDBSALT000996
Categories
CAS number14838-15-4
WeightAverage: 151.2056
Monoisotopic: 151.099714043
Chemical FormulaC9H13NO
InChI KeyDLNKOYKMWOXYQA-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
IUPAC Name
(1S,2R)-2-amino-1-phenylpropan-1-ol
SMILES
C[C@@H](N)[C@@H](O)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Aralkylamine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of nasal congestion, control of urinary incontinence, priapism and obesity.
PharmacodynamicsPhenylpropanolamine (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 actionPhenylpropanolamine 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.
AbsorptionReduced bioavailability (about 38%) from gastrointestinal tract because of first pass metabolism by monoamine oxidase in the stomach and liver.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half life2.1 to 3.4 hours.
ClearanceNot Available
ToxicityMay 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9871
Blood Brain Barrier+0.5843
Caco-2 permeable+0.7568
P-glycoprotein substrateNon-substrate0.7276
P-glycoprotein inhibitor INon-inhibitor0.9849
P-glycoprotein inhibitor IINon-inhibitor0.9917
Renal organic cation transporterNon-inhibitor0.9113
CYP450 2C9 substrateNon-substrate0.8077
CYP450 2D6 substrateNon-substrate0.8418
CYP450 3A4 substrateNon-substrate0.8063
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-inhibitor0.9261
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9096
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6929
BiodegradationNot ready biodegradable0.6917
Rat acute toxicity2.0244 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9446
hERG inhibition (predictor II)Non-inhibitor0.937
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Naldecon Senior EX 200 mg/5ml Syrup 118ml Bottle15.99USD bottle
Entex ER 10-300 mg 12 Hour Capsule1.14USD capsule
Codimal la capsule0.7USD capsule
Despec-dm tablet0.61USD tablet
Despec-tab tablet0.47USD tablet
Triaminic allergy thin strip0.35USD strip
Triaminic cold-stuff nose strip0.35USD strip
Conex tablet0.33USD tablet
Triaminic cgh-runny nose strip0.3USD strip
Triaminic cough strips0.3USD strip
Triaminic cough-cold chew0.27USD each
Triaminic softchew tablet0.27USD tablet
Triaminic softchews tablet0.25USD tablet
Childrens triaminic decon spray0.24USD ml
Triaminicin tablet0.23USD tablet
Dexatrim natural caplet0.19USD caplet
Codimal DH 5-8.33-1.66 mg/5ml Syrup0.18USD ml
Despec-exp syrup0.18USD ml
Codimal dm syrup0.16USD ml
Naldecon-dx senior0.06USD ml
Apap allergy sinus caplet0.05USD caplet
Triaminic chest-nasal cong liq0.04USD ml
Triaminic cold & cough liquid0.04USD ml
Triaminic cold-allergy pe liq0.04USD ml
Triaminic cough-nasal cong liquid0.04USD ml
Triaminic cough-sore throat liquid0.04USD ml
Triaminic flu cough-fever suspension0.04USD ml
Triaminic flu-cough-fever liquid0.04USD ml
Triaminic-d syrup0.04USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point190-194 °CNot Available
water solubilityFreely solubleNot Available
logP0.67SANGSTER (1994)
pKa9.44 (at 20 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility20.6 mg/mLALOGPS
logP0.57ALOGPS
logP0.89ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)13.9ChemAxon
pKa (Strongest Basic)9.37ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.91 m3·mol-1ChemAxon
Polarizability16.98 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS/MS1D NMR2D NMR
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesR01BA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (52.4 KB)
Interactions
Drug Interactions
Drug
AminophyllineMay enhance the adverse/toxic effect of other Sympathomimetics.
AmphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
ArformoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
armodafinilMay enhance the adverse/toxic effect of other Sympathomimetics.
ArticaineMay enhance the adverse/toxic effect of other Sympathomimetics.
AtomoxetineAtoMOXetine may enhance the hypertensive effect of Sympathomimetics. AtoMOXetine may enhance the tachycardic effect of Sympathomimetics.
BenzphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
CaffeineMay enhance the adverse/toxic effect of other Sympathomimetics.
CocaineMay enhance the adverse/toxic effect of other Sympathomimetics.
DexmethylphenidateMay enhance the adverse/toxic effect of other Sympathomimetics.
DextroamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DiethylpropionMay enhance the adverse/toxic effect of other Sympathomimetics.
DihydrocodeineMay enhance the adverse/toxic effect of other Sympathomimetics.
DipivefrinMay enhance the adverse/toxic effect of other Sympathomimetics.
DobutamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DopamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DoxapramMay enhance the adverse/toxic effect of other Sympathomimetics.
DronabinolCannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
FenoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
Fluticasone furoateMay enhance the adverse/toxic effect of other Sympathomimetics.
FormoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
IndacaterolMay enhance the adverse/toxic effect of other Sympathomimetics.
IobenguaneMay diminish the therapeutic effect of Iobenguane I 123.
Ipratropium bromideMay enhance the adverse/toxic effect of other Sympathomimetics.
IsomethepteneMay enhance the adverse/toxic effect of other Sympathomimetics.
LevonordefrinMay enhance the adverse/toxic effect of other Sympathomimetics.
LinezolidLinezolid may enhance the hypertensive effect of Sympathomimetics.
LisdexamfetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethylphenidateMay enhance the adverse/toxic effect of other Sympathomimetics.
MidodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
ModafinilMay enhance the adverse/toxic effect of other Sympathomimetics.
NabiloneCannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
NaphazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
NorepinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
OrciprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
OxymetazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhendimetrazineMay enhance the adverse/toxic effect of other Sympathomimetics.
PheniramineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PirbuterolMay enhance the adverse/toxic effect of other Sympathomimetics.
PropylhexedrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PseudoephedrineMay enhance the adverse/toxic effect of other Sympathomimetics.
SalbutamolMay enhance the adverse/toxic effect of other Sympathomimetics.
SalmeterolMay enhance the adverse/toxic effect of other Sympathomimetics.
Tedizolid PhosphateTedizolid may enhance the hypertensive effect of Sympathomimetics. Tedizolid may enhance the tachycardic effect of Sympathomimetics.
TerbutalineMay enhance the adverse/toxic effect of other Sympathomimetics.
TheophyllineMay enhance the adverse/toxic effect of other Sympathomimetics.
TriprolidineMay enhance the adverse/toxic effect of other Sympathomimetics.
Food Interactions
  • Limit caffeine intake.
  • Take without regard to meals.

Targets

1. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-2A adrenergic receptor P08913 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: partial agonist

Components

Name UniProt ID Details
D(1A) dopamine receptor P21728 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

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

5. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

References:

  1. 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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] A P21397 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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

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Drug created on June 13, 2005 07:24 / Updated on March 13, 2014 11:46