Identification

Name
Phenylpropanolamine
Accession Number
DB00397  (APRD00457, DB09441)
Type
Small Molecule
Groups
Approved, Vet Approved, Withdrawn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Phenylpropanolamine has been withdrawn in Canada and the United States.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
Product Ingredients
IngredientUNIICASInChI Key
Phenylpropanolamine hydrochloride8D5I63UE1Q154-41-6DYWNLSQWJMTVGJ-KUSKTZOESA-N
International/Other Brands
Acutrim / Boxogetten (Cheplapharm) / Dexatrim / Disudrin (Pediatrica) / Naldec (IAE) / Nasadec (Medlink) / Nasathera (Morishita-Seggs) / Propagest / Recatol mono (Riemser) / Rhindecon / Rinexin (Meda)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Antitussive Decong Antihistamine SyrPhenylpropanolamine hydrochloride (13 mg) + Dextromethorphan hydrobromide (15 mg) + Pyrilamine maleate (6.5 mg) + Pheniramine maleate (6.5 mg)SyrupOralProdemdis Enr.1992-12-312001-04-26Canada
Bronchodex D CapPhenylpropanolamine hydrochloride (50 mg) + Chlorpheniramine maleate (1 mg) + Pheniramine maleate (12.5 mg)Capsule, extended releaseOralProdemdis Enr.1981-12-312001-04-26Canada
Bronchosirum Pour EnfantsPhenylpropanolamine hydrochloride (12.5 mg) + Dextromethorphan hydrobromide (15 mg) + Pyrilamine maleate (6.25 mg) + Pheniramine maleate (6.25 mg)SyrupOralBronchosirum Inc.1987-12-311997-08-05Canada
Caldomine Dh AdultePhenylpropanolamine hydrochloride (25 mg) + Hydrocodone bitartrate (5 mg) + Pyrilamine maleate (12.5 mg) + Pheniramine maleate (12.5 mg)LiquidOralTechnilab Pharma Inc.1981-12-312001-04-04Canada
Caldomine Dh EnfantPhenylpropanolamine hydrochloride (12.5 mg) + Hydrocodone bitartrate (1.667 mg) + Pyrilamine maleate (6.25 mg) + Pheniramine maleate (6.25 mg)LiquidOralTechnilab Pharma Inc.1982-12-312001-04-04Canada
Centracol DM - SyrPhenylpropanolamine hydrochloride (12.5 mg) + Dextromethorphan hydrobromide (15 mg) + Pyrilamine maleate (6.25 mg) + Pheniramine maleate (6.25 mg)SyrupOralPrometic Pharma Inc.1994-12-311999-08-12Canada
Chlor Tripolon Decongest SyrPhenylpropanolamine hydrochloride (2.5 mg) + Chlorpheniramine maleate (.4 mg)SyrupOralSchering Plough1981-12-312000-07-11Canada
Cold & Allergy Relief - LiqPhenylpropanolamine hydrochloride (5 mg) + Brompheniramine maleate (4 mg) + Phenylephrine hydrochloride (5 mg)LiquidOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1996-12-312001-04-09Canada
Cold Decongestant Long Acting CapPhenylpropanolamine hydrochloride (50 mg) + Chlorpheniramine maleate (1 mg) + Pheniramine maleate (12.5 mg)Capsule, extended releaseOralNovopharm Limited1969-12-312001-04-12Canada
Cold ReliefPhenylpropanolamine hydrochloride (12.5 mg) + Brompheniramine maleate (2 mg)LiquidOralPerrigo International1997-11-302001-03-07Canada
Categories
UNII
7875H6443P
CAS number
14838-15-4
Weight
Average: 151.2056
Monoisotopic: 151.099714043
Chemical Formula
C9H13NO
InChI Key
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[[email protected]@H](N)[[email protected]@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.

TargetActionsOrganism
UD(1A) dopamine receptor
partial agonist
Human
UBeta-1 adrenergic receptor
agonist
Human
UBeta-2 adrenergic receptor
agonist
Human
UAlpha-2 adrenergic receptorsNot AvailableHuman
Absorption

Reduced bioavailability (about 38%) from gastrointestinal tract because of first pass metabolism by monoamine oxidase in the stomach and liver.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic

Route of elimination
Not Available
Half life

2.1 to 3.4 hours.

Clearance
Not Available
Toxicity

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

Affected organisms
  • Humans and other mammals
Pathways
Not Available
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
AlprenololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Alprenolol.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 Phenylpropanolamine is combined with Amphetamine.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
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
BopindololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bopindolol.Approved
BrofaromineThe risk or severity of adverse effects can be increased when Brofaromine is combined with Phenylpropanolamine.Experimental
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
BunazosinBunazosin may decrease the vasoconstricting activities of Phenylpropanolamine.Investigational
BupranololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Bupranolol.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
CarteololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Carteolol.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
CloranololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Cloranolol.Experimental
CyclobenzaprineCyclobenzaprine may decrease the antihypertensive activities of Phenylpropanolamine.Approved
CyclopenthiazidePhenylpropanolamine may increase the hypokalemic activities of Cyclopenthiazide.Experimental
DesipramineDesipramine may decrease the antihypertensive activities of Phenylpropanolamine.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Phenylpropanolamine.Approved
DibenzepinDibenzepin may decrease the antihypertensive activities of Phenylpropanolamine.Experimental
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
EpanololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Epanolol.Experimental
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
FenozoloneThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Fenozolone.Experimental
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
HarmalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Phenylpropanolamine.Experimental
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.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
IprindoleIprindole may decrease the antihypertensive activities of Phenylpropanolamine.Experimental
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 Landiolol.Investigational
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Phenylpropanolamine.Approved
LinezolidLinezolid may increase the hypertensive activities of Phenylpropanolamine.Approved, Investigational
LofepramineLofepramine may decrease the antihypertensive activities of Phenylpropanolamine.Experimental
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Phenylpropanolamine.Withdrawn
MefenorexThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Mefenorex.Experimental
MephentermineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Mephentermine.Approved
MepindololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Mepindolol.Experimental
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
MethylergometrineMethylergometrine may increase the hypertensive activities of Phenylpropanolamine.Approved
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 Phenylpropanolamine is combined with Midodrine.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
NadololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Nadolol.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 Phenylpropanolamine is combined with Norepinephrine.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
OxprenololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Oxprenolol.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
PenbutololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Penbutolol.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 Phenylpropanolamine is combined with Phentermine.Approved, Illicit
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Phenylpropanolamine.Approved
PindololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Pindolol.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
PrenalterolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Prenalterol.Experimental
ProcaterolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Procaterol.Approved
PropranololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Propranolol.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
SotalolPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Sotalol.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
TalinololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Talinolol.Investigational
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
TertatololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Tertatolol.Experimental
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
TimololPhenylpropanolamine may increase the atrioventricular blocking (AV block) activities of Timolol.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
TramazolineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Tramazoline.Investigational
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
TretoquinolThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Tretoquinol.Experimental
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
UrapidilUrapidil may decrease the vasoconstricting activities of Phenylpropanolamine.Investigational
VenlafaxineVenlafaxine may increase the tachycardic activities of Phenylpropanolamine.Approved
Food Interactions
  • Limit caffeine intake.
  • Take without regard to meals.

References

Synthesis Reference
Not Available
General References
Not Available
External Links
Human Metabolome Database
HMDB01942
KEGG Compound
C02343
PubChem Compound
26934
PubChem Substance
46508087
ChemSpider
25082
BindingDB
50405613
ChEBI
36
ChEMBL
CHEMBL2092846
Therapeutic Targets Database
DNC001144
PharmGKB
PA164748965
Drugs.com
Drugs.com Drug Page
Wikipedia
Phenylpropanolamine
ATC Codes
R01BA51 — Phenylpropanolamine, combinationsR01BA01 — Phenylpropanolamine
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Download (52.4 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not 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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Patents
Not Available

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000j-0900000000-1599181977614a0d00dd
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-05ox-4900000000-3ee623f48a8306bcaf2c
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0ugi-9600000000-afe25efb2c27bc61ad3a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00lr-1900000000-033f74cd4a3197c7510b
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-001i-0900000000-6f806bd0a58cb073b571
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
Alternative Parents
Aralkylamines / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives / Aromatic alcohols
Substituents
Phenylpropane / Aralkylamine / 1,2-aminoalcohol / Secondary alcohol / Organic nitrogen compound / Hydrocarbon derivative / Aromatic alcohol / Organopnictogen compound / Primary amine / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
amphetamines (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 e...
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 ...
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 oxymetazo...

Components:
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...
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 un...
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 October 02, 2017 04:36