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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GroupsApproved, Vet Approved, Withdrawn
DescriptionPhenylpropanolamine has been withdrawn in Canada and the United States.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
154-41-6
Thumb
  • InChI Key: DYWNLSQWJMTVGJ-KUSKTZOESA-N
  • Monoisotopic Mass: 187.0763918
  • Average Mass: 187.67
DBSALT000996
Categories
UNII33RU150WUN
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
Pharmacology
IndicationFor the treatment of nasal congestion, control of urinary incontinence, priapism and obesity.
Structured Indications Not Available
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Alpha-1A adrenergic receptorProteinyes
agonist
HumanP35348 details
Alpha-2A adrenergic receptorProteinyes
agonist
HumanP08913 details
D(1A) dopamine receptorProteinunknown
partial agonist
HumanP21728 details
Beta-1 adrenergic receptorProteinunknown
agonist
HumanP08588 details
Beta-2 adrenergic receptorProteinunknown
agonist
HumanP07550 details
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
Interactions
Drug Interactions
DrugInteractionDrug group
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.Experimental
AcebutololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Acebutolol.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Phenylpropanolamine.Approved, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved, Withdrawn
AmineptineAmineptine may decrease the antihypertensive activities of Phenylpropanolamine.Illicit, Withdrawn
AmitriptylineAmitriptyline may decrease the antihypertensive activities of Phenylpropanolamine.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Phenylpropanolamine.Approved, Illicit
Aop200704Phenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Aop200704.Investigational
ArotinololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Arotinolol.Approved
AtenololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Atenolol.Approved
AtomoxetineAtomoxetine may increase the hypertensive activities of Phenylpropanolamine.Approved
AtosibanThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Atosiban.Approved
BefunololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Befunolol.Experimental
BendroflumethiazidePhenylpropanolamine may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Phenylpropanolamine.Withdrawn
BenzphetamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Benzphetamine.Approved, Illicit
Benzylpenicilloyl PolylysinePhenylpropanolamine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Betahistine.Approved
BetaxololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Betaxolol.Approved
BevantololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bevantolol.Approved
BisoprololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bisoprolol.Approved
BopindololBopindolol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved
BromocriptineBromocriptine may increase the hypertensive activities of Phenylpropanolamine.Approved, Investigational
BucindololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bucindolol.Investigational
BufuralolPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bufuralol.Experimental, Investigational
BumetanidePhenylpropanolamine may increase the hypokalemic activities of Bumetanide.Approved
BupranololBupranolol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved
CabergolineCabergoline may increase the hypertensive activities of Phenylpropanolamine.Approved
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Phenylpropanolamine.Withdrawn
CarteololCarteolol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved
CarvedilolPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Carvedilol.Approved, Investigational
CeliprololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Celiprolol.Approved, Investigational
ChlorothiazidePhenylpropanolamine may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorphentermineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Chlorphentermine.Illicit, Withdrawn
ChlorthalidonePhenylpropanolamine may increase the hypokalemic activities of Chlorthalidone.Approved
ClenbuterolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Clenbuterol.Approved, Vet Approved
ClomipramineClomipramine may decrease the antihypertensive activities of Phenylpropanolamine.Approved, Vet Approved
CyclobenzaprineCyclobenzaprine may decrease the antihypertensive activities of Phenylpropanolamine.Approved
DesipramineDesipramine may decrease the antihypertensive activities of Phenylpropanolamine.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Phenylpropanolamine.Approved
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Phenylpropanolamine.Approved
DobutamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Dobutamine.Approved
DopamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Dopamine.Approved
DosulepinDosulepin may decrease the antihypertensive activities of Phenylpropanolamine.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Phenylpropanolamine.Approved
DoxepinDoxepin may decrease the antihypertensive activities of Phenylpropanolamine.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Doxofylline.Approved
DronabinolDronabinol may increase the tachycardic activities of Phenylpropanolamine.Approved, Illicit
DuloxetineDuloxetine may increase the tachycardic activities of Phenylpropanolamine.Approved
EphedrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Ephedrine.Approved
EpinephrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Epinephrine.Approved, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Phenylpropanolamine.Approved
ErgonovineErgonovine may increase the hypertensive activities of Phenylpropanolamine.Approved
ErgotamineErgotamine may increase the hypertensive activities of Phenylpropanolamine.Approved
EsmirtazapineEsmirtazapine may decrease the antihypertensive activities of Phenylpropanolamine.Investigational
EsmololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Esmolol.Approved
Etacrynic acidPhenylpropanolamine may increase the hypokalemic activities of Etacrynic acid.Approved
EtilefrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Etilefrine.Withdrawn
FenoterolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Fenoterol.Approved
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Phenylpropanolamine.Approved, Vet Approved
FurosemidePhenylpropanolamine may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Phenylpropanolamine.Approved, Investigational
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Phenylpropanolamine.Approved
HydrochlorothiazidePhenylpropanolamine may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazidePhenylpropanolamine may increase the hypokalemic activities of Hydroflumethiazide.Approved
Hydroxyamphetamine hydrobromideThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Hydroxyamphetamine hydrobromide.Approved
ImipramineImipramine may decrease the antihypertensive activities of Phenylpropanolamine.Approved
IndapamidePhenylpropanolamine may increase the hypokalemic activities of Indapamide.Approved
IndenololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Indenolol.Withdrawn
IndoraminIndoramin may decrease the vasoconstricting activities of Phenylpropanolamine.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Phenylpropanolamine.Approved
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Phenylpropanolamine.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Phenylpropanolamine.Withdrawn
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Phenylpropanolamine.Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Isoprenaline.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Isoxsuprine.Approved, Withdrawn
LabetalolPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Labetalol.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Phenylpropanolamine.Approved
LinezolidLinezolid may increase the hypertensive activities of Phenylpropanolamine.Approved, Investigational
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Phenylpropanolamine.Withdrawn
MephentermineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Mephentermine.Approved
MetaraminolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Metaraminol.Approved, Investigational
MethamphetamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Methamphetamine.Approved, Illicit
MethoxamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Methoxamine.Approved
MethyclothiazidePhenylpropanolamine may increase the hypokalemic activities of Methyclothiazide.Approved
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Phenylpropanolamine.Investigational
MetolazonePhenylpropanolamine may increase the hypokalemic activities of Metolazone.Approved
MetoprololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Metoprolol.Approved, Investigational
MianserinThe therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Mianserin.Approved
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Phenylpropanolamine.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Phenylpropanolamine.Approved
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Phenylpropanolamine.Approved
MirtazapineMirtazapine may decrease the antihypertensive activities of Phenylpropanolamine.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Phenylpropanolamine.Approved
NabiloneNabilone may increase the tachycardic activities of Phenylpropanolamine.Approved, Investigational
NadololNadolol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved
NebivololNebivolol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved, Investigational
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Phenylpropanolamine.Withdrawn
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Phenylpropanolamine.Approved
NortriptylineNortriptyline may decrease the antihypertensive activities of Phenylpropanolamine.Approved
NylidrinThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Nylidrin.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Phenylpropanolamine.Withdrawn
OpipramolOpipramol may decrease the antihypertensive activities of Phenylpropanolamine.Investigational
OrciprenalineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Orciprenaline.Approved
OxprenololOxprenolol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved
OxymetazolineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Oxymetazoline.Approved
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Phenylpropanolamine.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved, Investigational
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Phenylpropanolamine.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Phenylpropanolamine.Withdrawn
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Phenmetrazine.Approved, Illicit
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Phenylpropanolamine.Withdrawn
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Phenylpropanolamine.Approved, Illicit
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Phenylpropanolamine.Approved
PindololPindolol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved
PiretanidePhenylpropanolamine may increase the hypokalemic activities of Piretanide.Experimental
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Phenylpropanolamine.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Phenylpropanolamine.Withdrawn
PolythiazidePhenylpropanolamine may increase the hypokalemic activities of Polythiazide.Approved
PractololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Practolol.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Phenylpropanolamine.Approved
ProcaterolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Procaterol.Approved
PropranololPropranolol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved, Investigational
ProtriptylineProtriptyline may decrease the antihypertensive activities of Phenylpropanolamine.Approved
PseudoephedrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Pseudoephedrine.Approved
QuinethazonePhenylpropanolamine may increase the hypokalemic activities of Quinethazone.Approved
RacepinephrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Racepinephrine.Approved
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Phenylpropanolamine.Approved
RitodrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Ritodrine.Approved
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Phenylpropanolamine.Withdrawn
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Phenylpropanolamine.Approved, Investigational, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Phenylpropanolamine.Approved
SotalolSotalol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Phenylpropanolamine.Approved
SynephrineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Synephrine.Experimental
TamsulosinTamsulosin may decrease the vasoconstricting activities of Phenylpropanolamine.Approved, Investigational
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Phenylpropanolamine.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Phenylpropanolamine.Approved
TerbutalineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Terbutaline.Approved
TetryzolineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Tetryzoline.Approved
TianeptineTianeptine may decrease the antihypertensive activities of Phenylpropanolamine.Approved
TimololTimolol may decrease the bronchodilatory activities of Phenylpropanolamine.Approved
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Phenylpropanolamine.Approved
TorasemidePhenylpropanolamine may increase the hypokalemic activities of Torasemide.Approved
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Phenylpropanolamine.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Phenylpropanolamine.Approved
TrichlormethiazidePhenylpropanolamine may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Phenylpropanolamine.Experimental
TrimipramineTrimipramine may decrease the antihypertensive activities of Phenylpropanolamine.Approved
TyramineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Tyramine.Investigational, Nutraceutical
VenlafaxineVenlafaxine may increase the tachycardic activities of Phenylpropanolamine.Approved
Food Interactions
  • Limit caffeine intake.
  • Take without regard to meals.
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesR01BA51R01BA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (52.4 KB)
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 releaseOral
CapsuleOral
Solution / dropsOral
TabletOral
LiquidOral
Capsule, extended releaseOral
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
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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
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

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 December 08, 2016 11:46