Identification
NamePhenylpropanolamine
Accession NumberDB00397  (APRD00457, DB09441)
TypeSmall Molecule
GroupsApproved, Vet Approved, Withdrawn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Phenylpropanolamine has been withdrawn in Canada and the United States.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
2-amino-1-phenylpropan-1-ol
Fenilpropanolamina
Norephedrin
Norephedrine
Phenylpropanolamin
Phénylpropanolamine
Phenylpropanolaminum
PPA
β-hydroxyamphetamine
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Phenylpropanolamine hydrochloride8D5I63UE1Q 154-41-6DYWNLSQWJMTVGJ-KUSKTZOESA-NDetails
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
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Antitussive Decong Antihistamine SyrSyrupOralProdemdis Enr.1992-12-312001-04-26Canada
Bronchodex D CapCapsule, extended releaseOralProdemdis Enr.1981-12-312001-04-26Canada
Bronchosirum Pour EnfantsSyrupOralBronchosirum Inc.1987-12-311997-08-05Canada
Caldomine Dh AdulteLiquidOralTechnilab Pharma Inc.1981-12-312001-04-04Canada
Caldomine Dh EnfantLiquidOralTechnilab Pharma Inc.1982-12-312001-04-04Canada
Centracol DM - SyrSyrupOralPrometic Pharma Inc.1994-12-311999-08-12Canada
Chlor Tripolon Decongest SyrSyrupOralSchering Plough1981-12-312000-07-11Canada
Cold & Allergy Relief - LiqLiquidOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1996-12-312001-04-09Canada
Cold Decongestant Long Acting CapCapsule, extended releaseOralNovopharm Limited1969-12-312001-04-12Canada
Cold ReliefLiquidOralPerrigo International1997-11-302001-03-07Canada
Cold Relief DMLiquidOralPerrigo International1998-08-072001-03-07Canada
Contac Cold CapsulesCapsule, extended releaseOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1997-07-082000-11-06Canada
Contac Cold Extra Strength CapsulesCapsule, extended releaseOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1997-07-082000-11-06Canada
Contac Cough Cold and Flu CapletsTabletOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1994-12-312000-11-06Canada
Contact C SrcCapsule, extended releaseOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1991-12-311997-08-15Canada
Coricidin D Long Acting TabTablet, extended releaseOralSchering Plough1985-12-312001-04-02Canada
Coricidin D TabTabletOralSchering Plough1981-12-312001-04-02Canada
Coricidin Nd TabTabletOralSchering Plough1991-12-312001-04-02Canada
Coricidin Sinus Headache TabTabletOralSchering Plough1993-12-312001-04-02Canada
Corsym SuspensionSuspensionOralCiba Self Medication1994-04-211998-07-06Canada
Cough, Cold & Allergy ReliefLiquidOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1997-09-172001-04-09Canada
Counteract Sinus and AllergyTabletOralMelaleuca, Inc.1997-09-262000-12-15Canada
Decongestant Antihistaminic SyrupElixirOralPharmascience Inc1984-12-312001-03-30Canada
DilotabTabletOralZee Medical Inc1990-12-312001-04-12Canada
Dimetane Expectorant LiqLiquidOralWhitehall Robins Inc.1964-12-312001-04-10Canada
Dimetane Expectorant-C SyrSyrupOralWhitehall Robins Inc.1993-12-312001-04-10Canada
Dimetane Expectorant-DC SyrSyrupOralWhitehall Robins Inc.1993-12-312001-04-10Canada
Dimetapp Chewable TabletsTabletOralWhitehall Robins Inc.1993-12-312001-04-10Canada
Dimetapp Children's Cold & Allergy TabletsTabletOralWhitehall Robins Inc.1997-10-022001-04-10Canada
Dimetapp Children's Cold & FeverLiquidOralWhitehall Robins Inc.2000-07-212001-04-10Canada
Dimetapp ClearLiquidOralWhitehall Robins Inc.1994-12-312001-04-10Canada
Dimetapp Cold & SinusTabletOralWhitehall Robins Inc.1993-12-312001-04-10Canada
Dimetapp Cough & Cold Liqui-gels - CapCapsuleOralWhitehall Robins Inc.1996-10-222001-04-10Canada
Dimetapp Cough, Cold & FluLiquidOralWhitehall Robins Inc.2000-07-212001-04-10Canada
Dimetapp DM ElixirElixirOralWhitehall Robins Inc.1992-12-312001-04-10Canada
Dimetapp DM TabTabletOralWhitehall Robins Inc.1993-12-312001-04-10Canada
Dimetapp ElixirElixirOralWhitehall Robins Inc.1992-12-312001-04-10Canada
Dimetapp ExtentabsTablet, extended releaseOralWhitehall Robins Inc.1966-12-312001-04-10Canada
Dimetapp Liqui-gels CapCapsuleOralWhitehall Robins Inc.1993-12-312001-04-10Canada
Dimetapp Oral Infant DropsSolution / dropsOralWhitehall Robins Inc.1992-12-312001-04-10Canada
Dimetapp TabTabletOralWhitehall Robins Inc.1964-12-312001-04-10Canada
Dimetapp-C SyrSyrupOralWhitehall Robins Inc.1993-12-312001-04-10Canada
Dristan CapsulesCapsuleOralWhitehall Robins Inc.1993-12-311999-08-04Canada
Emercidin D TabTabletOralPharmetics (2011) Inc.1989-12-312001-03-30Canada
Emertabs TabTabletOralPharmetics (2011) Inc.1989-12-311999-08-13Canada
Entex LATablet, extended releaseOralPurdue Pharma1997-09-252000-11-07Canada
Entex LA Tablets SrtTablet, extended releaseOralProcter And Gamble1993-12-311997-10-31Canada
Extra Strength Contac C - SrcCapsule, extended releaseOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1995-12-311997-08-15Canada
Oradrine 2 TabTabletOralNutribon (1986) Inc.1995-12-312001-03-30Canada
Oradrine TabletsTabletOralPharmavite Laboratories (1987) Inc.1989-12-312001-03-30Canada
Ornade AF LiquidLiquidOralSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1993-12-311997-08-15Canada
Ornade AF Spansule SrcCapsule, extended releaseOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1965-12-312000-11-06Canada
Ornade DM 10 LiqLiquidOralSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1993-12-311997-08-15Canada
Ornade DM 15 LiqLiquidOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1965-12-311997-08-15Canada
Ornade DM 30 LiqLiquidOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1994-12-311997-08-15Canada
Ornade Expectorant Cough FormulaLiquidOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1994-12-311997-08-15Canada
Ornade LiquidLiquidOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1965-12-311997-08-15Canada
Ornade Spansule SrcCapsule, extended releaseOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1995-12-312000-11-06Canada
Pharmacol DM SyrSyrupOralTherapex Division De E Z Em Canada Inc1985-12-312001-04-05Canada
Pharmetapp ElixirLiquidOralTherapex Division De E Z Em Canada Inc1986-12-311997-07-22Canada
Pharminicol DM SyrupSyrupOralTherapex Division De E Z Em Canada Inc1985-12-311997-07-22Canada
Sine Off Nd Extra Strength CapletTabletOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1992-12-312000-11-06Canada
Sine-off Allergy TabTabletOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1993-12-312000-11-06Canada
Sine-off N.D. TabTabletOralSmithkline Consumer Products1988-12-311997-08-15Canada
Sine-off N.D. TabletTabletOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1996-09-242000-11-06Canada
Sinutab Sa TabTablet, extended releaseOralWarner Lambert Canada Inc.1992-12-312000-11-09Canada
Tantacol DM SyrSyrupOralTanta Pharmaceuticals Inc1992-12-312001-03-29Canada
Tantapp ElixirElixirOralTanta Pharmaceuticals Inc1994-12-312001-03-29Canada
Tavist-D TabletsTablet, extended releaseOralNovartis1992-12-312001-04-24Canada
Triaminic Cold and Allergy SyrupSyrupOralNovartis1991-12-312001-04-06Canada
Triaminic DM Daytime SyrSyrupOralNovartis1994-12-312001-04-06Canada
Triaminic Expectorant Dh SyrupSyrupOralNovartis1993-12-312001-04-06Canada
Triaminic Time Release TabTablet, extended releaseOralNovartis1992-12-311999-07-21Canada
Triaminicin Colds & Flu CapletsTabletOralNovartis1992-12-312000-07-19Canada
Trisulfaminic SusSuspensionOralShepherd Pharmaceuticals Inc.1959-12-312001-04-11Canada
Trisulfaminic TabTabletOralShepherd Pharmaceuticals Inc.1959-12-312001-04-11Canada
Tussaminic C Forte SyrupSyrupOralNovartis1992-12-312001-04-06Canada
Tussaminic C Pediatric SyrupSyrupOralNovartis1993-12-312000-07-19Canada
Tussaminic Dh Forte SyrupSyrupOralNovartis1992-12-312001-04-06Canada
Tussaminic Dh Pediatric SyrupSyrupOralNovartis1993-12-312001-04-06Canada
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
Indication

For the treatment of nasal congestion, control of urinary incontinence, priapism and obesity.

Structured Indications Not Available
Pharmacodynamics

Phenylpropanolamine (PPA), a sympathomimetic agent structurally similar to pseudoephedrine, is used to treat nasal congestion. Phenylpropanolamine is found in appetite suppressant formulations and with guaifenesinin in cough-cold formulations. In 2000, the FDA requested that all drug companies discontinue marketing products containing phenylpropanolamine, due to an increased risk of hemorrhagic stroke in women who used phenylpropanolamine.

Mechanism of action

Phenylpropanolamine acts directly on alpha- and, to a lesser degree, beta-adrenergic receptors in the mucosa of the respiratory tract. Stimulation of alpha-adrenergic receptors produces vasoconstriction, reduces tissue hyperemia, edema, and nasal congestion, and increases nasal airway patency. PPA indirectly stimulates beta-receptors, producing tachycardia and a positive inotropic effect.

TargetKindPharmacological actionActionsOrganismUniProt ID
D(1A) dopamine receptorProteinunknown
partial agonist
HumanP21728 details
Beta-1 adrenergic receptorProteinunknown
agonist
HumanP08588 details
Beta-2 adrenergic receptorProteinunknown
agonist
HumanP07550 details
Alpha-2 adrenergic receptorsProtein groupunknownNot AvailableHumannot applicabledetails
Related Articles
Absorption

Reduced 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 life

2.1 to 3.4 hours.

ClearanceNot Available
Toxicity

May induce ventricular extrasystoles and short paroxysms of ventricular tachycardia, a sensation of fullness in the head and tingling of the extremities; LD50=1490mg/kg (orally in rat)

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not 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
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
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.Experimental
HydrochlorothiazidePhenylpropanolamine may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazidePhenylpropanolamine may increase the hypokalemic activities of Hydroflumethiazide.Approved
HydroxyamphetamineThe 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
LandiololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Aop200704.Investigational
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
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
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 CodesR01BA51 — Phenylpropanolamine, combinationsR01BA01 — Phenylpropanolamine
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (52.4 KB)
Clinical Trials
Clinical Trials Not Available
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
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)190-194 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 )
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00lr-1900000000-033f74cd4a3197c7510bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-6f806bd0a58cb073b571View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylpropanes
Alternative ParentsAralkylamines / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives / Aromatic alcohols
SubstituentsPhenylpropane / Aralkylamine / 1,2-aminoalcohol / Secondary alcohol / Organic nitrogen compound / Hydrocarbon derivative / Aromatic alcohol / Organopnictogen compound / Primary amine / Organic oxygen compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptorsamphetamines (CHEBI:36 )

Targets

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
Uniprot Name:
D(1A) dopamine receptor
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
Uniprot Name:
Beta-1 adrenergic receptor
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
Uniprot Name:
Beta-2 adrenergic receptor
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 ]
Kind
Protein group
Organism
Human
Pharmacological action
unknown
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 = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol.
Components:
NameUniProt IDDetails
Alpha-2A adrenergic receptorP08913 Details
Alpha-2B adrenergic receptorP18089 Details
Alpha-2C adrenergic receptorP18825 Details
References
  1. 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 ]

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
Uniprot Name:
Amine oxidase [flavin-containing] A
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
Uniprot Name:
Cytochrome P450 1A2
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 ]
Drug created on June 13, 2005 07:24 / Updated on August 02, 2017 16:23