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Identification
NamePhenylpropanolamine
Accession NumberDB00397  (APRD00457)
TypeSmall Molecule
GroupsApproved, Vet Approved, Withdrawn
DescriptionPhenylpropanolamine has been withdrawn in Canada and the United States.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
2-amino-1-phenylpropan-1-ol
Fenilpropanolamina
Norephedrin
Norephedrine
Phenylpropanolamin
Phénylpropanolamine
Phenylpropanolaminum
PPA
β-hydroxyamphetamine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AcutrimNot Available
BoxogettenCheplapharm
DexatrimNot Available
DisudrinPediatrica
NaldecIAE
NasadecMedlink
NasatheraMorishita-Seggs
PropagestNot Available
Recatol monoRiemser
RhindeconNot Available
RinexinMeda
Brand mixtures
NameLabellerIngredients
Antitussive Decong Antihistamine SyrProdemdis Enr.
Bronchodex D CapProdemdis Enr.
Bronchosirum Pour EnfantsBronchosirum Inc.
Caldomine Dh AdulteTechnilab Pharma Inc.
Caldomine Dh EnfantTechnilab Pharma Inc.
Centracol DM - SyrPrometic Pharma Inc.
Chlor Tripolon Decongest SyrSchering Plough Canada Inc
Cold & Allergy Relief - LiqStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Cold Decongestant Long Acting CapNovopharm Limited
Cold ReliefPerrigo International
Cold Relief DMPerrigo International
Contac Cold CapsulesSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Contac Cold Extra Strength CapsulesSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Contac Cough Cold and Flu CapletsSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Contact C SrcSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Coricidin D Long Acting TabSchering Plough Canada Inc
Coricidin D TabSchering Plough Canada Inc
Coricidin Nd TabSchering Plough Canada Inc
Coricidin Sinus Headache TabSchering Plough Canada Inc
Corsym SuspensionCiba Self Medication
Cough, Cold & Allergy ReliefStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Counteract Sinus and AllergyMelaleuca Of Canada Inc.
Decongestant Antihistaminic SyrupPharmascience Inc
DilotabZee Medical Inc
Dimetane Expectorant LiqWhitehall Robins Inc.
Dimetane Expectorant-C SyrWhitehall Robins Inc.
Dimetane Expectorant-DC SyrWhitehall Robins Inc.
Dimetapp Chewable TabletsWhitehall Robins Inc.
Dimetapp Children's Cold & Allergy TabletsWhitehall Robins Inc.
Dimetapp Children's Cold & FeverWhitehall Robins Inc.
Dimetapp ClearWhitehall Robins Inc.
Dimetapp Cold & SinusWhitehall Robins Inc.
Dimetapp Cough & Cold Liqui-gels - CapWhitehall Robins Inc.
Dimetapp Cough, Cold & FluWhitehall Robins Inc.
Dimetapp DM ElixirWhitehall Robins Inc.
Dimetapp DM TabWhitehall Robins Inc.
Dimetapp ElixirWhitehall Robins Inc.
Dimetapp ExtentabsWhitehall Robins Inc.
Dimetapp Liqui-gels CapWhitehall Robins Inc.
Dimetapp Oral Infant DropsWhitehall Robins Inc.
Dimetapp TabWhitehall Robins Inc.
Dimetapp-C SyrWhitehall Robins Inc.
Dristan CapsulesWhitehall Robins Inc.
Emertabs TabPharmetics (2011) Inc
Entex LAPurdue Pharma
Entex LA Tablets SrtProcter & Gamble Pharmaceuticals Canada Inc
Extra Strength Contac C - SrcSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Oradrine 2 TabNutribon (1986) Inc.
Oradrine TabletsPharmavite Laboratories (1987) Inc.
Oradrine-2 TabPharmetics (2011) Inc
Ornade AF LiquidSmithkline Beecham Pharma Division Of Smithkline Beecham Inc
Ornade AF Spansule SrcSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Ornade DM 10 LiqSmithkline Beecham Pharma Division Of Smithkline Beecham Inc
Ornade DM 15 LiqSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Ornade DM 30 LiqSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Ornade Expectorant Cough FormulaSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Ornade LiquidSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Ornade Spansule SrcSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Pharmacol DM SyrTherapex Division De E Z Em Canada Inc
Pharmetapp ElixirTherapex Division De E Z Em Canada Inc
Pharminicol DM SyrupTherapex Division De E Z Em Canada Inc
Sine Off Nd Extra Strength CapletSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Sine-off Allergy TabSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Sine-off N.D. TabSmithkline Consumer Products
Sine-off N.D. TabletSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.
Sinutab Sa TabWarner Lambert Canada Inc.
Tantacol DM SyrTanta Pharmaceuticals Inc
Tantapp ElixirTanta Pharmaceuticals Inc
Tavist-D TabletsNovartis Consumer Health Canada Inc.
Triaminic Cold and Allergy SyrupNovartis Consumer Health Canada Inc.
Triaminic DM Daytime SyrNovartis Consumer Health Canada Inc.
Triaminic Expectorant Dh SyrupNovartis Consumer Health Canada Inc.
Triaminic Time Release TabNovartis Consumer Health Canada Inc.
Triaminicin Colds & Flu CapletsNovartis Consumer Health Canada Inc.
Trisulfaminic SusShepherd Pharmaceuticals Inc.
Trisulfaminic TabShepherd Pharmaceuticals Inc.
Tussaminic C Forte SyrupNovartis Consumer Health Canada Inc.
Tussaminic C Pediatric SyrupNovartis Consumer Health Canada Inc.
Tussaminic Dh Forte SyrupNovartis Consumer Health Canada Inc.
Tussaminic Dh Pediatric SyrupNovartis Consumer Health Canada Inc.
Salts
Name/CASStructureProperties
Phenylpropanolamine hydrochloride
ThumbNot applicableDBSALT000996
Categories
UNII33RU150WUN
CAS number14838-15-4
WeightAverage: 151.2056
Monoisotopic: 151.099714043
Chemical FormulaC9H13NO
InChI KeyInChIKey=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
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.
Related Articles
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 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Suspensionoral
Syruporal
Elixiroral
Tablet (extended-release)oral
Capsuleoral
Dropsoral
Tabletoral
Liquidoral
Capsule (sustained-release)oral
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
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000j-0900000000-1599181977614a0d00ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05ox-4900000000-3ee623f48a8306bcaf2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ugi-9600000000-afe25efb2c27bc61ad3aView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesR01BA51R01BA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (52.4 KB)
Interactions
Drug Interactions
Drug
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINEThe risk or severity of adverse effects can be increased when 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE is combined with Phenylpropanolamine.
AcebutololThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Acebutolol.
AlprenololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Alprenolol.
AlprenololAlprenolol may decrease the bronchodilatory activities of Phenylpropanolamine.
AmineptineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Amineptine.
AmitriptylineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Amitriptyline.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Phenylpropanolamine.
ArotinololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Arotinolol.
AtenololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Atenolol.
AtenololAtenolol may decrease the bronchodilatory activities of Phenylpropanolamine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Phenylpropanolamine.
AtosibanThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Atosiban.
BefunololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Befunolol.
BendroflumethiazidePhenylpropanolamine may increase the hypokalemic activities of Bendroflumethiazide.
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Phenylpropanolamine.
BenzphetamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Benzphetamine.
BetahistineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Betahistine.
BetaxololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Betaxolol.
BetaxololBetaxolol may decrease the bronchodilatory activities of Phenylpropanolamine.
BevantololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bevantolol.
BisoprololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bisoprolol.
BisoprololBisoprolol may decrease the bronchodilatory activities of Phenylpropanolamine.
BopindololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bopindolol.
BopindololBopindolol may decrease the bronchodilatory activities of Phenylpropanolamine.
BufuralolPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bufuralol.
BumetanidePhenylpropanolamine may increase the hypokalemic activities of Bumetanide.
BupranololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bupranolol.
BupranololBupranolol may decrease the bronchodilatory activities of Phenylpropanolamine.
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Phenylpropanolamine.
CarteololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Carteolol.
CarteololCarteolol may decrease the bronchodilatory activities of Phenylpropanolamine.
CarvedilolPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Carvedilol.
CeliprololThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Celiprolol.
ChlorothiazidePhenylpropanolamine may increase the hypokalemic activities of Chlorothiazide.
ChlorphentermineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Chlorphentermine.
ChlorthalidonePhenylpropanolamine may increase the hypokalemic activities of Chlorthalidone.
ClenbuterolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Clenbuterol.
ClomipramineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Clomipramine.
CyclobenzaprineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Cyclobenzaprine.
DesipramineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Desipramine.
DesvenlafaxineDesvenlafaxine may decrease the antihypertensive activities of Phenylpropanolamine.
DobutamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Dobutamine.
DopamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Dopamine.
DosulepinThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Dosulepin.
DoxepinThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Doxepin.
DoxofyllineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Phenylpropanolamine.
DuloxetineDuloxetine may decrease the antihypertensive activities of Phenylpropanolamine.
EphedrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Phenylpropanolamine.
EsmirtazapineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Esmirtazapine.
EsmololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Esmolol.
EsmololEsmolol may decrease the bronchodilatory activities of Phenylpropanolamine.
Etacrynic acidPhenylpropanolamine may increase the hypokalemic activities of Etacrynic acid.
EtilefrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Etilefrine.
FenoterolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Fenoterol.
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Phenylpropanolamine.
FurosemidePhenylpropanolamine may increase the hypokalemic activities of Furosemide.
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Phenylpropanolamine.
HydrochlorothiazidePhenylpropanolamine may increase the hypokalemic activities of Hydrochlorothiazide.
HydroflumethiazidePhenylpropanolamine may increase the hypokalemic activities of Hydroflumethiazide.
Hydroxyamphetamine hydrobromideThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Hydroxyamphetamine hydrobromide.
ImipramineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Imipramine.
IndapamidePhenylpropanolamine may increase the hypokalemic activities of Indapamide.
IndenololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Indenolol.
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Phenylpropanolamine.
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Phenylpropanolamine.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Phenylpropanolamine.
IsoprenalineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Isoprenaline.
IsoxsuprineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Isoxsuprine.
LabetalolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Labetalol.
LevomilnacipranLevomilnacipran may decrease the antihypertensive activities of Phenylpropanolamine.
LinezolidLinezolid may increase the hypertensive activities of Phenylpropanolamine.
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Phenylpropanolamine.
MephentermineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Mephentermine.
MetaraminolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Metaraminol.
MethamphetamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Methamphetamine.
MethoxamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Methoxamine.
MethyclothiazidePhenylpropanolamine may increase the hypokalemic activities of Methyclothiazide.
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Phenylpropanolamine.
MetolazonePhenylpropanolamine may increase the hypokalemic activities of Metolazone.
MetoprololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Metoprolol.
MetoprololMetoprolol may decrease the bronchodilatory activities of Phenylpropanolamine.
MianserinThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Mianserin.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Phenylpropanolamine.
MilnacipranMilnacipran may decrease the antihypertensive activities of Phenylpropanolamine.
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Phenylpropanolamine.
MirtazapineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Mirtazapine.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Phenylpropanolamine.
NabiloneNabilone may increase the tachycardic activities of Phenylpropanolamine.
NadololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Nadolol.
NadololNadolol may decrease the bronchodilatory activities of Phenylpropanolamine.
NebivololNebivolol may decrease the bronchodilatory activities of Phenylpropanolamine.
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Phenylpropanolamine.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Phenylpropanolamine.
NortriptylineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Nortriptyline.
NylidrinThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Nylidrin.
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Phenylpropanolamine.
OrciprenalineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Orciprenaline.
OxprenololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Oxprenolol.
OxprenololOxprenolol may decrease the bronchodilatory activities of Phenylpropanolamine.
OxymetazolineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Oxymetazoline.
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Phenylpropanolamine.
PenbutololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Penbutolol.
PenbutololPenbutolol may decrease the bronchodilatory activities of Phenylpropanolamine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Phenylpropanolamine.
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Phenylpropanolamine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Phenmetrazine.
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Phenylpropanolamine.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Phenylpropanolamine.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Phenylpropanolamine.
PindololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Pindolol.
PindololPindolol may decrease the bronchodilatory activities of Phenylpropanolamine.
PiretanidePhenylpropanolamine may increase the hypokalemic activities of Piretanide.
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Phenylpropanolamine.
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Phenylpropanolamine.
PolythiazidePhenylpropanolamine may increase the hypokalemic activities of Polythiazide.
PractololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Practolol.
ProcaterolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Procaterol.
PropranololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Propranolol.
PropranololPropranolol may decrease the bronchodilatory activities of Phenylpropanolamine.
ProtriptylineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Protriptyline.
PseudoephedrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Pseudoephedrine.
QuinethazonePhenylpropanolamine may increase the hypokalemic activities of Quinethazone.
RacepinephrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Racepinephrine.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Phenylpropanolamine.
RitodrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Ritodrine.
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Phenylpropanolamine.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Phenylpropanolamine.
SotalolPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Sotalol.
SotalolSotalol may decrease the bronchodilatory activities of Phenylpropanolamine.
SynephrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Synephrine.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Phenylpropanolamine.
TerbutalineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Terbutaline.
TetryzolineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Tetryzoline.
TianeptineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Tianeptine.
TimololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Timolol.
TimololTimolol may decrease the bronchodilatory activities of Phenylpropanolamine.
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Phenylpropanolamine.
TorasemidePhenylpropanolamine may increase the hypokalemic activities of Torasemide.
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Phenylpropanolamine.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Phenylpropanolamine.
TrichlormethiazidePhenylpropanolamine may increase the hypokalemic activities of Trichlormethiazide.
TrimipramineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Trimipramine.
TyramineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Tyramine.
VenlafaxineVenlafaxine may decrease the antihypertensive activities of Phenylpropanolamine.
Food Interactions
  • Limit caffeine intake.
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein heterodimerization activity
Specific Function:
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. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
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:17016423 ]
  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:9164583 ]
  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:12163120 ]
  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]methanesulfonamide, an imidazole-containing alpha(1A)-adrenoceptor agonist. J Med Chem. 2004 Jun 3;47(12):3220-35. [PubMed:15163201 ]
  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:2881994 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Thioesterase binding
Specific Function:
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 = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular Weight:
48956.275 Da
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:17139284 ]
  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:17016423 ]
  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:15608085 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
partial agonist
General Function:
G-protein coupled amine receptor activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular Weight:
49292.765 Da
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:12873745 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Receptor signaling protein activity
Specific Function:
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. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
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:1722692 ]
  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:2881994 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
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:2881994 ]

Enzymes

Kind
Protein
Organism
Human
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 tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular Weight:
59681.27 Da
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:3961266 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
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 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 N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23