Identification
- Summary
Phenylpropanolamine is a sympathomimetic that was previously used in nasal decongestants and weight loss products, but has been withdrawn by the FDA due to safety risks and lack of efficacy.
- Generic Name
- Phenylpropanolamine
- DrugBank Accession Number
- DB00397
- Background
Phenylpropanolamine is a sympathomimetic agent that acts as a nonselective adrenergic receptor agonist and norepinephrine reuptake inhibitor. It has been used as a decongestant and appetite suppressant. Currently, it is withdrawn from the market in Canada and the United States due to the risk for hemorrahgic strokes.
- Type
- Small Molecule
- Groups
- Approved, Vet approved, Withdrawn
- Structure
Structure for Phenylpropanolamine (DB00397)
- Weight
- Average: 151.209
Monoisotopic: 151.099714043 - Chemical Formula
- C9H13NO
- Synonyms
- (+-)-Norephedrine
- (+-)-Phenylpropanolamine
- Fenilpropanolamina
- Norephedrine
- Phenylpropanolamin
- Phenylpropanolamina
- Phénylpropanolamine
- Phenylpropanolamine
- Phenylpropanolaminum
- PPA
Pharmacology
- Indication
For the treatment of nasal congestion, control of urinary incontinence, priapism and obesity.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Allergy-induced respiratory symptoms Combination Product in combination with: Brompheniramine (DB00835), Phenylephrine (DB00388) ••• ••• ••••••••• ••••• Used in combination for symptomatic treatment of Bronchitis Combination Product in combination with: Guaifenesin (DB00874), Dextromethorphan (DB00514), Chlorpheniramine (DB01114) •••••••••••• ••••• Used in combination for symptomatic treatment of Common cold Combination Product in combination with: Dextromethorphan (DB00514), Diphenhydramine (DB01075) ••• ••• •••••• Used in combination to treat Coughing Combination Product in combination with: Guaifenesin (DB00874) •••••••••••• ••••• Treatment of Coughing •••••••••••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism UDopamine D1 receptor partial agonistHumans UBeta-1 adrenergic receptor agonistHumans UBeta-2 adrenergic receptor agonistHumans UAlpha-2 adrenergic receptors Not Available Humans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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)
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Phenylpropanolamine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Phenylpropanolamine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Phenylpropanolamine is combined with Acemetacin. Acetazolamide The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Phenylpropanolamine. Aclidinium The risk or severity of Tachycardia can be increased when Phenylpropanolamine is combined with Aclidinium. - Food Interactions
- Limit caffeine intake.
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Phenylpropanolamine hydrochloride 8D5I63UE1Q 154-41-6 DYWNLSQWJMTVGJ-UHFFFAOYSA-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
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antitussive Decong Antihistamine Syr Phenylpropanolamine hydrochloride (13 mg / 5 mL) + Dextromethorphan hydrobromide (15 mg / 5 mL) + Mepyramine maleate (6.5 mg / 5 mL) + Pheniramine maleate (6.5 mg / 5 mL) Syrup Oral Prodemdis Enr. 1992-12-31 2001-04-26 Canada 
Bronchodex D Cap Phenylpropanolamine hydrochloride (50 mg) + Chlorpheniramine maleate (1 mg) + Pheniramine maleate (12.5 mg) Capsule, extended release Oral Prodemdis Enr. 1981-12-31 2001-04-26 Canada Bronchosirum Pour Enfants Phenylpropanolamine hydrochloride (12.5 mg / 5 mL) + Dextromethorphan hydrobromide (15 mg / 5 mL) + Mepyramine maleate (6.25 mg / 5 mL) + Pheniramine maleate (6.25 mg / 5 mL) Syrup Oral Bronchosirum Inc. 1987-12-31 1997-08-05 Canada Caldomine Dh Adulte Phenylpropanolamine hydrochloride (25 mg / 5 mL) + Hydrocodone bitartrate (5 mg / 5 mL) + Mepyramine maleate (12.5 mg / 5 mL) + Pheniramine maleate (12.5 mg / 5 mL) Liquid Oral Technilab Pharma Inc. 1981-12-31 2001-04-04 Canada Caldomine Dh Enfant Phenylpropanolamine hydrochloride (12.5 mg / 5 mL) + Hydrocodone bitartrate (1.667 mg / 5 mL) + Mepyramine maleate (6.25 mg / 5 mL) + Pheniramine maleate (6.25 mg / 5 mL) Liquid Oral Technilab Pharma Inc. 1982-12-31 2001-04-04 Canada
Categories
- ATC Codes
- R01BA51 — Phenylpropanolamine, combinations
- R01BA — Sympathomimetics
- R01B — NASAL DECONGESTANTS FOR SYSTEMIC USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic alpha-Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Agents that reduce seizure threshold
- Alcohols
- Amines
- Amino Alcohols
- Anti-Obesity Agents
- Appetite Depressants
- Autonomic Agents
- Cardiovascular Agents
- Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates
- Nasal Decongestants
- Nasal Decongestants for Systemic Use
- Nasal Preparations
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Propanolamines
- Propanols
- Respiratory System Agents
- Sympathomimetics
- Vasoconstrictor Agents
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 33RU150WUN
- CAS number
- 14838-15-4
- InChI Key
- DLNKOYKMWOXYQA-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3
- IUPAC Name
- 2-amino-1-phenylpropan-1-ol
- SMILES
- CC(N)C(O)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0243518
- KEGG Compound
- C16719
- PubChem Compound
- 26934
- PubChem Substance
- 46508087
- ChemSpider
- 4622
- BindingDB
- 50022722
- 8175
- ChEBI
- 80680
- ChEMBL
- CHEMBL61006
- ZINC
- ZINC000000157545
- Therapeutic Targets Database
- DNC001144
- PharmGKB
- PA164748965
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Phenylpropanolamine
- MSDS
- Download (52.4 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Peripheral Arterial Disease (PAD) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Amerisource Health Services Corp.
- Boca Pharmacal
- Breckenridge Pharmaceuticals
- Bristol-Myers Squibb Co.
- C.O. Truxton Inc.
- Carlisle Laboratories Inc.
- Century Pharmaceuticals Inc.
- Chattem Chemicals Inc.
- Corvit Pharmaceuticals
- DHHS Program Support Center Supply Service Center
- Direct Dispensing Inc.
- Duramed
- Econolab Inc.
- Equipharm Inc.
- Farmaquimia SA de CV
- Generics Puerto Rico Inc.
- Gm Pharmaceuticals Inc.
- Golden State Medical Supply Inc.
- H and H Laboratories
- Hi Tech Pharmacal Co. Inc.
- International Ethical Labs Inc.
- Iopharm Laboratories Inc.
- Kaiser Foundation Hospital
- Kraft Pharmaceutical Co. Inc.
- Lark Pharmaceuticals Inc.
- Llorens Pharmaceutical
- Long Island Pharmacal
- Major Pharmaceuticals
- Mallinckrodt Inc.
- Mcgregor Pharmaceuticals Inc.
- Midland Pharmaceutical LLC
- Murfreesboro Pharmaceutical Nursing Supply
- Nexgen Pharma Inc.
- Norega Laboratories Inc.
- Novartis AG
- Pamlab LLC
- Patient First Corp.
- PD-Rx Pharmaceuticals Inc.
- Pecos Pharmaceutical Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmedix
- Physicians Total Care Inc.
- Prometic Pharma Inc.
- Qualitest
- Respa Pharmaceuticals Inc.
- Sandhills Packaging Inc.
- Sanofi-Aventis Inc.
- Seatrace Pharmaceuticals Inc.
- Southwood Pharmaceuticals
- St Mary's Medical Park Pharmacy
- Talbert Medical Management Corp.
- Topco
- Tri Med Laboratories Inc.
- United Research Laboratories Inc.
- Veratex Corp.
- Vista Pharmaceuticals Inc.
- Dosage Forms
Form Route Strength Tablet, sugar coated Oral Capsule Oral 15 MG Tablet Oral 15 mg Capsule Elixir Oral Capsule Oral Solution / drops Oral Tablet Oral 10 mg Capsule, coated Oral Syrup Oral Tablet Oral 8 mg Tablet, film coated Oral Liquid Oral Capsule, extended release Oral Tablet Oral Tablet, extended release Oral Suspension Oral Tablet Syrup - Prices
Unit description Cost Unit Naldecon Senior EX 200 mg/5ml Syrup 118ml Bottle 15.99USD bottle Entex ER 10-300 mg 12 Hour Capsule 1.14USD capsule Codimal la capsule 0.7USD capsule Despec-dm tablet 0.61USD tablet Despec-tab tablet 0.47USD tablet Triaminic allergy thin strip 0.35USD strip Triaminic cold-stuff nose strip 0.35USD strip Conex tablet 0.33USD tablet Triaminic cgh-runny nose strip 0.3USD strip Triaminic cough strips 0.3USD strip Triaminic cough-cold chew 0.27USD each Triaminic softchew tablet 0.27USD tablet Triaminic softchews tablet 0.25USD tablet Childrens triaminic decon spray 0.24USD ml Triaminicin tablet 0.23USD tablet Dexatrim natural caplet 0.19USD caplet Codimal DH 5-8.33-1.66 mg/5ml Syrup 0.18USD ml Despec-exp syrup 0.18USD ml Codimal dm syrup 0.16USD ml Naldecon-dx senior 0.06USD ml Apap allergy sinus caplet 0.05USD caplet Triaminic chest-nasal cong liq 0.04USD ml Triaminic cold & cough liquid 0.04USD ml Triaminic cold-allergy pe liq 0.04USD ml Triaminic cough-nasal cong liquid 0.04USD ml Triaminic cough-sore throat liquid 0.04USD ml Triaminic flu cough-fever suspension 0.04USD ml Triaminic flu-cough-fever liquid 0.04USD ml Triaminic-d syrup 0.04USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 190-194 °C Not Available water solubility Freely soluble Not Available logP 0.67 SANGSTER (1994) pKa 9.44 (at 20 °C) PERRIN,DD (1965) - Predicted Properties
Property Value Source Water Solubility 20.6 mg/mL ALOGPS logP 0.57 ALOGPS logP 0.89 Chemaxon logS -0.87 ALOGPS pKa (Strongest Acidic) 13.9 Chemaxon pKa (Strongest Basic) 9.37 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 46.25 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 44.91 m3·mol-1 Chemaxon Polarizability 17 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9871 Blood Brain Barrier + 0.5843 Caco-2 permeable + 0.7568 P-glycoprotein substrate Non-substrate 0.7276 P-glycoprotein inhibitor I Non-inhibitor 0.9849 P-glycoprotein inhibitor II Non-inhibitor 0.9917 Renal organic cation transporter Non-inhibitor 0.9113 CYP450 2C9 substrate Non-substrate 0.8077 CYP450 2D6 substrate Non-substrate 0.8418 CYP450 3A4 substrate Non-substrate 0.8063 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9261 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9096 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.6929 Biodegradation Not ready biodegradable 0.6917 Rat acute toxicity 2.0244 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9446 hERG inhibition (predictor II) Non-inhibitor 0.937
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0159-0900000000-ffa84cc0fde2af9e0ad9 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-4900000000-36001f01c83ff9d73502 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0aou-2900000000-14d85667698155ac6f63 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00kf-9200000000-fbc0780420b307fd5edb Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9500000000-d363ce0590ab9ff2aa56 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05r3-9700000000-9fc127f1616542285f45 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 130.57143 predictedDeepCCS 1.0 (2019) [M+H]+ 133.79355 predictedDeepCCS 1.0 (2019) [M+Na]+ 143.1107 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein group
- Organism
- Humans
- 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:
| Name | UniProt ID |
|---|---|
| Alpha-2A adrenergic receptor | P08913 |
| Alpha-2B adrenergic receptor | P18089 |
| Alpha-2C adrenergic receptor | P18825 |
References
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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
- Yu PH: Inhibition of monoamine oxidase activity by phenylpropanolamine, an anorectic agent. Res Commun Chem Pathol Pharmacol. 1986 Feb;51(2):163-71. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 07:00