Identification

Name
Pseudoephedrine
Accession Number
DB00852  (APRD00634)
Type
Small Molecule
Groups
Approved
Description

An alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used in the treatment of several disorders including asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.

Structure
Thumb
Synonyms
  • (+) threo-2-(methylamino)-1-phenyl-1-propanol
  • (+)-(1S,2S)-Pseudoephedrine
  • (+)-Pseudoephedrine
  • (+)-psi-Ephedrine
  • (+)-threo-Ephedrine
  • d-Isoephedrine
  • d-Pseudoephedrine
  • d-psi-2-Methylamino-1-phenyl-1-propanol
  • d-psi-Ephedrine
  • Isoephedrine
  • L-(+)-Pseudoephedrine
  • L(+)-psi-Ephedrine
  • Pseudoefedrina
  • pseudoéphédrine
  • Pseudoephedrine D-form
  • Pseudoephedrinum
  • Psi-ephedrin
  • Psi-ephedrine
  • trans-Ephedrine
  • ψ-ephedrine
Product Ingredients
IngredientUNIICASInChI Key
Pseudoephedrine hydrochloride6V9V2RYJ8N345-78-8BALXUFOVQVENIU-KXNXZCPBSA-N
Pseudoephedrine sulfateY9DL7QPE6B7460-12-0XVPDSDYVNYOVMP-KXNXZCPBSA-N
Active Moieties
NameKindUNIICASInChI Key
EphedrineunknownGN83C131XS299-42-3KWGRBVOPPLSCSI-WPRPVWTQSA-N
Product Images
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
12 Hour DecongestantTablet, film coated, extended release120 mg/1OralKroger1999-12-14Not applicableUs
12 Hour DecongestantTablet, film coated, extended release120 mg/1OralL. Perrigo Company2011-10-04Not applicableUs
12 Hour DecongestantTablet, film coated, extended release120 mg/1OralMeijer Distribution1999-11-05Not applicableUs
12 Hour Nasal DecongestantTablet, film coated, extended release120 mg/1OralCVS Health1999-12-01Not applicableUs
12 Hour Nasal Decongestant Non DrowsyTablet, film coated, extended release120 mg/1OralSafeway2000-05-252017-08-25Us
Balminil Decongestionnant Sirop 30mg/5mlSyrup30 mgOralRougier Pharma Division Of Ratiopharm Inc1988-12-312000-09-07Canada
Benylin D for InfantsSyrup7.5 mgOralPfizer Canada Inc., Consumer Healthcare Division2004-08-092006-08-03Canada
Care One Suphedrine Nasal Decongestant Non DrowsyTablet, film coated30 mg/1OralAmerican Sales Company2003-12-01Not applicableUs
CareOne Nasal and Sinus DecongestantTablet, film coated, extended release120 mg/1OralAmerican Sales Company2016-09-15Not applicableUs
CareOne Nasal and Sinus DecongestantTablet, film coated30 mg/1OralAmerican Sales Company2017-09-25Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
12 Hour Allergy and CongestionPseudoephedrine sulfate (120 mg/1) + Loratadine (5 mg/1)Tablet, film coated, extended releaseOralWalgreen2018-05-05Not applicableUs
12 Hour Allergy DPseudoephedrine hydrochloride (120 mg/1) + Cetirizine hydrochloride (5 mg/1)Tablet, extended releaseOralMeijer Distribution1988-07-15Not applicableUs
A.M. Cold Relief FormulaPseudoephedrine hydrochloride (30.0 mg) + Acetaminophen (325.0 mg) + Dextromethorphan hydrobromide (15.0 mg)CapsuleOralIvax Pharmaceuticals IncorporatedNot applicableNot applicableCanada
Abanatuss PedPseudoephedrine hydrochloride (60 mg/5mL) + Chlophedianol hydrochloride (25 mg/5mL) + Dexchlorpheniramine maleate (2 mg/5mL)SolutionOralKramer Novis.2015-07-01Not applicableUs
Abanatuss Ped DropsPseudoephedrine hydrochloride (15 mg/1mL) + Chlophedianol hydrochloride (6.25 mg/1mL) + Dexchlorpheniramine maleate (0.5 mg/1mL)SolutionOralKramer Novis.2015-08-05Not applicableUs
Abatuss DmxPseudoephedrine hydrochloride (30 mg/5mL) + Dexchlorpheniramine maleate (1 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL)LiquidOralKramer Novis.2014-05-25Not applicableUs
Acetaminophen/dextromethorphan/pseudoephedrinePseudoephedrine hydrochloride (30 mg) + Acetaminophen (325 mg) + Dextromethorphan hydrobromide (15 mg)CapsuleOralApotex CorporationNot applicableNot applicableCanada
Acetaminophen/pseudoephedrine/dextromethorphan/doxylaminePseudoephedrine hydrochloride (30 mg) + Acetaminophen (325 mg) + Dextromethorphan hydrobromide (15 mg) + Doxylamine succinate (6.25 mg)CapsuleOralApotex CorporationNot applicableNot applicableCanada
ActiconPseudoephedrine hydrochloride (60 mg/1) + Dexbrompheniramine maleate (2 mg/1)TabletOralActipharma, Inc2015-08-13Not applicableUs
ActiconPseudoephedrine hydrochloride (30 mg/5mL) + Dexbrompheniramine maleate (1 mg/5mL)LiquidOralActipharma, Inc2016-07-14Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AlleRx Dose PackPseudoephedrine hydrochloride (120 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Phenylephrine hydrochloride (10 mg/1)KitOralCornerstone Therapeutics Inc.2008-02-012012-10-31Us
AlleRx-DPseudoephedrine hydrochloride (120 mg/1) + Methscopolamine nitrate (2.5 mg/1)TabletOralCornerstone Therapeutics Inc.2008-07-012012-11-30Us
Atuss DS Tannate SuspensionPseudoephedrine hydrochloride (30 mg/5mL) + Chlorpheniramine maleate (4 mg/5mL) + Dextromethorphan hydrobromide monohydrate (30 mg/5mL)SuspensionOralAtley Pharmaceuticals2006-11-21Not applicableUs
Atuss HS TannatePseudoephedrine hydrochloride (30 mg/5mL) + Chlorpheniramine maleate (4 mg/5mL) + Hydrocodone bitartrate (5 mg/5mL)SuspensionOralAtley Pharmaceuticals2006-11-212009-08-03Us
Bromdex DPseudoephedrine hydrochloride (50 mg/5mL) + Brompheniramine maleate (3 mg/5mL) + Dextromethorphan hydrobromide monohydrate (30 mg/5mL)SyrupOralBreckenridge Pharmaceutical, Inc.2009-07-212011-05-31Us
Brompheniramine Maleate Pseudoephedrine HClPseudoephedrine hydrochloride (7.5 mg/1mL) + Dexbrompheniramine maleate (1 mg/1mL)LiquidOralRiver's Edge Pharmaceuticals, LLC2008-06-012010-10-31Us
Brompheniramine Maleate, Pseudoephedrine Hydrochloride, Dextromethorphan HydrobromidePseudoephedrine hydrochloride (20 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Dextromethorphan hydrobromide monohydrate (20 mg/5mL)LiquidOralRiver's Edge Pharmaceuticals, LLC2010-01-182012-01-31Us
Carbinoxamine/Pseudoephedrine/DMPseudoephedrine hydrochloride (15 mg/1mL) + Carbinoxamine Maleate (1 mg/1mL) + Dextromethorphan hydrobromide monohydrate (4 mg/1mL)LiquidOralPhysicians Total Care, Inc.2003-01-152007-08-08Us
Carbofed DMPseudoephedrine hydrochloride (45 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL)SyrupOralHi Tech Pharmacal Co., Inc.2001-09-032011-11-03Us
Chlorphen Mal Dex HBr Pseudoeph HClPseudoephedrine hydrochloride (9 mg/1mL) + Chlorpheniramine maleate (.8 mg/1mL) + Dextromethorphan hydrobromide monohydrate (3 mg/1mL)Solution / dropsOralRiver's Edge Pharmaceuticals2010-02-152011-01-31Us
International/Other Brands
Afrinol / Benylin Decongestant / Cenafed / Decofed / Dimetapp Decongestant / Eltor 120 / Genaphed / Maxenal / Myfedrine / Novafed / Robidrine / Sudafed Decongestant
Categories
UNII
7CUC9DDI9F
CAS number
90-82-4
Weight
Average: 165.2322
Monoisotopic: 165.115364107
Chemical Formula
C10H15NO
InChI Key
KWGRBVOPPLSCSI-WCBMZHEXSA-N
InChI
InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1
IUPAC Name
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
SMILES
CN[C@@H](C)[C@@H](O)C1=CC=CC=C1

Pharmacology

Indication

For the treatment of nasal congestion, sinus congestion, Eustachian tube congestion, and vasomotor rhinitis, and as an adjunct to other agents in the optimum treatment of allergic rhinitis, croup, sinusitis, otitis media, and tracheobronchitis. Also used as first-line therapy of priapism.

Associated Conditions
Pharmacodynamics

Pseudoephedrine is a sympathomimetic agent, structurally similar to ephedrine, used to relieve nasal and sinus congestion and reduce air-travel-related otalgia in adults. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations either as single-ingredient preparations, or more commonly in combination with antihistamines and/or paracetamol/ibuprofen. Unlike antihistamines, which modify the systemic histamine-mediated allergic response, pseudoephedrine only serves to relieve nasal congestion commonly associated with colds or allergies. The advantage of oral pseudoephedrine over topical nasal preparations, such as oxymetazoline, is that it does not cause rebound congestion (rhinitis medicamentosa).

Mechanism of action

Pseudoephedrine acts directly on both alpha- and, to a lesser degree, beta-adrenergic receptors. Through direct action on alpha-adrenergic receptors in the mucosa of the respiratory tract, pseudoephedrine produces vasoconstriction. Pseudoephedrine relaxes bronchial smooth muscle by stimulating beta2-adrenergic receptors. Like ephedrine, pseudoephedrine releasing norepinephrine from its storage sites, an indirect effect. This is its main and direct mechanism of action. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the postsynaptic adrenergic receptors.

TargetActionsOrganism
ASodium-dependent noradrenaline transporter
inhibitor
Human
ASodium-dependent dopamine transporter
inhibitor
Human
AAlpha-1A adrenergic receptor
agonist
Human
AAlpha-2A adrenergic receptor
agonist
Human
ASodium-dependent serotonin transporter
inhibitor
Human
UBeta-2 adrenergic receptor
partial agonist
Human
UBeta-1 adrenergic receptor
agonist
partial agonist
Human
UNuclear factor of activated T-cells, cytoplasmic 1
inhibitor
Human
UTumor necrosis factor
inhibitor
Human
UNuclear factor kappa-light-chain-enhancer of activated B cells
inhibitor
Human
Uactivator protein 1
inhibitor
Human
UInterleukin-2
inhibitor
Human
Absorption

Pseudoephedrine is readily and almost completely absorbed from the GI tract and there is no evidence of first-pass metabolism.

Volume of distribution
Not Available
Protein binding

Pseudoephedrine does not bind to human plasma proteins over the concentration range of 50 to 2000 ng/mL

Metabolism

Hepatic.

Route of elimination
Not Available
Half life

9-16 hours

Clearance
Not Available
Toxicity

Common adverse reactions include nervousness, restlessness, and insomnia. Rare adverse reactions include difficult/painful urination, dizziness/lightheadedness, heart palpitations, headache, increased sweating, nausea/vomiting, trembling, troubled breathing, unusual paleness, and weakness.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Pseudoephedrine.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Pseudoephedrine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Pseudoephedrine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Pseudoephedrine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Pseudoephedrine is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe therapeutic efficacy of Pseudoephedrine can be increased when used in combination with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Pseudoephedrine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Pseudoephedrine is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Pseudoephedrine is combined with 6-O-benzylguanine.
7-DeazaguanineThe risk or severity of adverse effects can be increased when Pseudoephedrine is combined with 7-Deazaguanine.
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

Andrew G. Myers, "Synthesis of l-azatyrosine using pseudoephedrine as a chiral auxiliary." U.S. Patent US5760237, issued June, 1991.

US5760237
General References
Not Available
External Links
Human Metabolome Database
HMDB0001943
KEGG Drug
D08449
KEGG Compound
C02765
PubChem Compound
7028
PubChem Substance
46508190
ChemSpider
6761
ChEBI
51209
ChEMBL
CHEMBL1590
Therapeutic Targets Database
DAP000195
PharmGKB
PA451170
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pseudoephedrine
ATC Codes
R01BA02 — PseudoephedrineR01BA52 — Pseudoephedrine, combinations
AHFS Codes
  • 12:12.12 — Alpha-and Beta-adrenergic Agonists
  • 12:12.00 — Sympathomimetic (Adrenergic) Agents
MSDS
Download (52.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingOtherMultiple System Atrophy (MSA) / Shy-Drager Syndrome1
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1CompletedDiagnosticBMI >30 kg/m2 / High Blood Pressure (Hypertension) / Progressive autonomic failure / Shy-Drager Syndrome1
1CompletedTreatmentHealthy Volunteers6
1RecruitingBasic ScienceHealthy Volunteers1
2CompletedTreatmentAllergic Rhinitis (AR)3
2CompletedTreatmentSeasonal Allergic Rhinitis (SAR)1
2RecruitingTreatmentAcute Gouty Arthritis1
2Unknown StatusTreatmentRhinitis, Seasonal, Allergic1
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Sinusitis1
3CompletedTreatmentNasal Congestion Associated With the Common Cold1
3CompletedTreatmentNasal Congestion and Inflammations / Rhinitis1
3CompletedTreatmentPerennial Allergic Rhinitis (PAR)1
3CompletedTreatmentAcute Rhinitis / Pharyngitis1
3CompletedTreatmentRhinitis, Allergic, Perennial1
3CompletedTreatmentRhinitis, Allergic, Seasonal1
3CompletedTreatmentRhinitis / Sleep1
3CompletedTreatmentSeasonal Rhinitis1
3CompletedTreatmentVasomotor Rhinitis1
3CompletedTreatmentAcute Rhinitis1
3Unknown StatusTreatmentViral Infections of the Upper Respiratory Tract1
3WithdrawnTreatmentCoughing / Inflammatory Reaction / Rhinitis1
4CompletedPreventionAcute Upper Respiratory Track Infection1
4CompletedTreatmentAcute Rhinosinusitis / Respiratory Infections, Acute1
4CompletedTreatmentAcute maxillary sinusitis caused by M. catarrhalis / Bronchitis / Respiratory Infections, Acute1
4CompletedTreatmentAcute Rhinitis / Headaches / Nasal Stuffiness1
4CompletedTreatmentNasal Stuffiness1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailableSeasonal Allergic Rhinitis (SAR) / Sinusitis1
Not AvailableCompletedBasic ScienceUrethral Sphincter Activity1
Not AvailableCompletedTreatmentAtopics / Rhinitis1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Sinusitis1
Not AvailableCompletedTreatmentSeasonal Allergic Rhinitis (SAR)1
Not AvailableRecruitingBasic ScienceMiddle Ear Disease / Nasal Allergies1
Not AvailableUnknown StatusTreatmentCoughing1

Pharmacoeconomics

Manufacturers
  • Ucb inc
  • Schering plough healthcare products inc
Packagers
  • Actavis Group
  • AG Marin Pharmaceuticals
  • Alaven Pharmaceutical
  • Allaire Pharmaceuticals
  • Allegis Pharmaceuticals
  • Alphagen Laboratories Inc.
  • Ambi Pharmaceuticals Inc.
  • Amend
  • Anip Acquisition Co.
  • Apotheca Inc.
  • Aristos Pharmaceuticals
  • A-S Medication Solutions LLC
  • Athlon Pharmaceuticals Inc.
  • Atlantic Biologicals Corporation
  • Atley Pharmaceuticals
  • Auriga Pharmaceuticals LLC
  • Ballay Pharmaceuticals
  • Banner Pharmacaps Inc.
  • Bayer Healthcare
  • Bergen Brunswig
  • Bio Pharm Inc.
  • Blansett Pharmacal Co. Inc.
  • Boca Pharmacal
  • Bradley Pharmaceuticals Inc.
  • Breckenridge Pharmaceuticals
  • Bryant Ranch Prepack
  • BTA Pharmaceuticals
  • Burel Pharmaceuticals Inc.
  • C.O. Truxton Inc.
  • Capellon Pharmaceuticals LLC
  • Cardinal Health
  • Caremark LLC
  • Carwin Associates Inc.
  • Centrix Pharmaceuticals
  • Centurion Labs
  • Century Pharmaceuticals Inc.
  • Contract Pharm
  • Cornerstone Pharmacy
  • CVS Pharmacy
  • Cypress Pharmaceutical Inc.
  • Dartmouth Pharmaceuticals Inc.
  • Dayton Pharmaceuticals
  • Deliz Pharmaceutical Corp.
  • Deltex Pharmaceuticals Inc.
  • Denison Pharmaceuticals Inc.
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DSC Laboratories
  • DSM Corp.
  • Dunhall Pharmaceuticals Inc.
  • Duramed
  • Econolab Inc.
  • ECR Pharmaceuticals
  • Elite Laboratories Inc.
  • Emrex Economed Pharmaceuticals Inc.
  • Eon Labs
  • Ethex Corp.
  • Everett Laboratories Inc.
  • Gil Pharmaceutical Corp.
  • Gm Pharmaceuticals Inc.
  • Great Southern Laboratories
  • H.J. Harkins Co. Inc.
  • Hawthorn Pharmaceuticals
  • Health Care Products
  • Heartland Repack Services LLC
  • Hi Tech Pharmacal Co. Inc.
  • Huckaby Pharmaceuticals Inc.
  • International Ethical Labs Inc.
  • Iopharm Laboratories Inc.
  • Irisys Inc.
  • Ivax Pharmaceuticals
  • Jaymac Pharmaceuticals LLC
  • Kaiser Foundation Hospital
  • Kowa Pharmaceuticals America Inc.
  • Kroger Co.
  • KV Pharmaceutical Co.
  • Lake Erie Medical and Surgical Supply
  • Lark Pharmaceuticals Inc.
  • Larken Laboratories Inc.
  • Laser Pharmaceuticals
  • Liberty Pharmaceuticals
  • Llorens Pharmaceutical
  • Macoven Pharmaceuticals LLC
  • Major Pharmaceuticals
  • Marnel Pharmaceuticals Inc.
  • Mckesson Corp.
  • McNeil Laboratories
  • MCR American Pharmaceuticals Inc.
  • Med Tek Pharmaceuticals Inc.
  • Meda AB
  • Medicine Shop
  • Merrell Pharmaceuticals Inc.
  • Midland Pharmaceutical LLC
  • Midlothian Labs
  • Murfreesboro Pharmaceutical Nursing Supply
  • Neilgen Pharma Inc.
  • Nexgen Pharma Inc.
  • Norega Laboratories Inc.
  • Nucare Pharmaceuticals Inc.
  • Numark Laboratories Inc.
  • Pa Benjamin Manufacturing Co. Ltd.
  • Palmetto Pharmaceuticals Inc.
  • Pamlab LLC
  • Patheon Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pell Tech Health Care Private Limited
  • Perrigo Co.
  • Pfizer Inc.
  • Pharma Medica Research Inc.
  • Pharmaceutical Generic Developers Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Poly Pharmaceuticals Inc.
  • Prasco Labs
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Propharma Inc.
  • Provident Pharmaceuticals LLC
  • Qualitest
  • Reckitt Benckiser Inc.
  • Redpharm Drug
  • Remedy Repack
  • Respa Pharmaceuticals Inc.
  • Rij Pharmaceutical Corp.
  • River's Edge Pharmaceuticals
  • Roxane Labs
  • Rx Formulations Corp.
  • S&P Healthcare
  • Sage Pharmaceuticals Inc.
  • Sanofi-Aventis Inc.
  • Schering Corp.
  • Schering-Plough Inc.
  • Schwarz Pharma Inc.
  • Sciele Pharma Inc.
  • Scientific Laboratories Inc.
  • SDA Laboratories Inc.
  • Seatrace Pharmaceuticals Inc.
  • Seneca Pharmaceuticals Inc.
  • Seyer Pharmatec Inc.
  • Silarx Pharmaceuticals
  • SJ Pharmaceuticals LLC
  • Southwood Pharmaceuticals
  • Sovereign Pharmaceuticals Ltd.
  • Stat Rx Usa
  • Stewart Jackson Pharmacal Inc.
  • Taro Pharmaceuticals USA
  • Teamm Pharmaceuticals Inc.
  • Teva Pharmaceutical Industries Ltd.
  • TG United Inc.
  • Tiber Pharmaceuticals LLC
  • Time-Cap Labs
  • Tri Med Laboratories Inc.
  • Trigen Laboratories Inc.
  • Tya Pharmaceuticals
  • UCB Pharma
  • United Research Laboratories Inc.
  • UPM Pharmaceuticals Inc.
  • US Pharmaceutical Group
  • Varsity Laboratories
  • Verum Pharmaceuticals Inc.
  • Vintage Pharmaceuticals Inc.
  • Vision Pharma LLC
  • Walgreen Co.
  • Warner Lambert Company LLC
  • Watson Pharmaceuticals
  • Winthrop Us
  • Wockhardt Ltd.
  • Wyeth Pharmaceuticals
  • Zyber Pharmaceuticals
Dosage forms
FormRouteStrength
CapsuleOral
Tablet, film coatedOral
Tablet, extended releaseOral
KitOral
SyrupOral
SyrupOral7.5 mg
SuspensionOral
SolutionOral15 mg/5mL
Solution / dropsOral
Tablet, multilayer, extended releaseOral
Capsule; kitOral
Kit; tabletOral
SolutionOral
TabletOral30 mg
Capsule, extended releaseOral120 mg
Solution / dropsNasal
PillOral30 mg/1
Kit; powder, for solutionOral
Tablet; tablet, extended releaseOral
Tablet, extended releaseOral120 mg
LiquidOral60 mg/60mL
Kit; powderOral
Powder, for solutionOral
Tablet, film coated, extended releaseOral
Tablet, film coated, extended releaseOral120 mg/1
PowderOral
Capsule, liquid filledOral
Tablet, coatedOral
Tablet, sugar coatedOral
Tablet, chewableOral
TabletOral120 mg
Capsule, extended releaseOral240 mg
Tablet, sugar coatedOral30 mg/1
Capsule, extended releaseOral
Tablet, coatedOral30 mg/1
Tablet, extended releaseOral120 mg/1
Tablet, film coatedOral120 mg/1
TabletOral60 mg
ElixirOral
LiquidOral
LiquidOral30 mg/5mL
TabletOral
Tablet, extended releaseOral240 mg/1
TabletOral15 mg
SyrupOral30 mg
LiquidOral15 mg/5mL
TabletOral30 mg/1
TabletOral60 mg/1
Tablet, film coatedOral60 mg/1
Tablet, film coatedOral30 mg/1
Tablet, multilayerOral
LiquidOral30 mg
LiquidOral7.5 mg
Kit
Capsule, gelatin coatedOral30 mg/1
Prices
Unit descriptionCostUnit
Sudafed 24 hour tablet0.84USD tablet
Pseudoephedrine hcl crystal0.67USD g
Afrin 0.05% nose spray0.62USD ml
Sudafed 12 hr sinus-pain caplet0.53USD caplet
Drixoral cold & allergy tablet sa0.4USD tablet
Sudafed om sinus nasal spray0.4USD ml
Afrin no drip sinus pump mist0.38USD ml
Sudafed pe cold & cough caplet0.34USD caplet
Afrin sinus spray0.33USD ml
Chlor-trimeton allergy0.31USD each
Sudafed pe severe cold caplet0.28USD caplet
Guaifenesin-phenylephrine tablet0.27USD tablet
Dimetapp cold-allergy tablet chew0.25USD tablet
Sudafed pe 10 mg tablet0.25USD tablet
Chlor-trimeton 8 mg repetab0.24USD tablet
Sudafed pe day & night tablet0.24USD tablet
Sudafed triple action caplet0.23USD caplet
Sudafed pe nighttime cold caplet0.22USD caplet
Sudafed non-drying sinus caplet0.2USD caplet
Sudafed pe sinus & allergy tablet0.2USD tablet
Sudafed pe sinus headache caplet0.2USD caplet
Sudafed 30 mg tablet0.19USD tablet
Wal-phed 30 mg tablet0.17USD tablet
Suphedrin 30 mg tablet0.15USD tablet
CVS Pharmacy decongestant 30 mg tablet0.12USD tablet
Sudogest 60 mg tablet0.12USD tablet
Medi-phedrine 30 mg tablet0.1USD tablet
Nasal decongestant 30 mg tablet0.1USD tablet
Genaphed plus tablet0.09USD tablet
CVS Pharmacy nasal decongest 30 mg tablet0.07USD tablet
Genaphed 30 mg tablet0.07USD tablet
Pseudoephedrine gg syrup0.07USD ml
Pseudoephedrine 60 mg tablet0.06USD tablet
Children's sudafed pe liquid0.05USD ml
Pseudoephedrine 30 mg tablet0.05USD tablet
Dimetapp cold & cough liquid0.04USD ml
Dimetapp dm cold & cough elix0.04USD ml
Dimetapp long-acting cough liquid0.04USD ml
Suphedrine 30 mg tablet0.04USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6037353Yes2000-03-142017-09-14Us
US6039974No2000-03-212018-07-31Us
US6211246No2001-04-032019-06-10Us
US6469009No2002-10-222019-07-13Us
US7226614No2007-06-052022-06-10Us
US6489329No2002-12-032016-04-08Us
US7014867No2006-03-212022-06-10Us
US6100274Yes2000-08-082020-01-07Us
US6372252No2002-04-162020-04-28Us
US6955821No2005-10-182020-04-28Us
US7838032No2010-11-232020-04-28Us
US7618649Yes2009-11-172021-06-19Us
US6709676No2004-03-232021-02-18Us
US8187630No2012-05-292020-12-19Us
US7863287No2011-01-042027-02-28Us
US6979463No2005-12-272022-03-28Us
US7820199Yes2010-10-262022-09-28Us
US6613357No2003-09-022020-12-25Us
USRE39069No2006-04-182018-05-29Us
US6113942Yes2000-09-052015-08-28Us
US5855912Yes1999-01-052015-08-28Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)119 °CPhysProp
water solubility7 mg/LNot Available
logP0.89KRIL,MB & FUNG,HL (1990)
pKa10.3 (at 0 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility8.26 mg/mLALOGPS
logP1ALOGPS
logP1.32ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.69 m3·mol-1ChemAxon
Polarizability18.83 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9645
Blood Brain Barrier+0.5638
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.7182
P-glycoprotein inhibitor INon-inhibitor0.9795
P-glycoprotein inhibitor IINon-inhibitor0.984
Renal organic cation transporterNon-inhibitor0.8965
CYP450 2C9 substrateNon-substrate0.8001
CYP450 2D6 substrateNon-substrate0.7839
CYP450 3A4 substrateNon-substrate0.7235
CYP450 1A2 substrateNon-inhibitor0.5595
CYP450 2C9 inhibitorNon-inhibitor0.7209
CYP450 2D6 inhibitorInhibitor0.5846
CYP450 2C19 inhibitorNon-inhibitor0.5737
CYP450 3A4 inhibitorNon-inhibitor0.9431
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.907
Ames testNon AMES toxic0.9517
CarcinogenicityNon-carcinogens0.7739
BiodegradationNot ready biodegradable0.7807
Rat acute toxicity2.3882 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9329
hERG inhibition (predictor II)Non-inhibitor0.9277
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.24 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-9000000000-8f0484f72b48017f1f2e
MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)LC-MS/MSsplash10-016s-3900000000-868bf4bba93d8b4be696
MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)LC-MS/MSsplash10-0159-2900000000-6c55fc67b7576cb42a8a
MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)LC-MS/MSsplash10-0006-9700000000-459686cbaf7d3b59c202
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
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 / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
Phenylpropane / Aralkylamine / 1,2-aminoalcohol / Secondary alcohol / Secondary aliphatic amine / Secondary amine / Alcohol / Organopnictogen compound / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary alcohol, secondary amine (CHEBI:51209) / Phenylalanine derived alkaloids (C02765)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Wee S, Ordway GA, Woolverton WL: Reinforcing effect of pseudoephedrine isomers and the mechanism of action. Eur J Pharmacol. 2004 Jun 16;493(1-3):117-25. [PubMed:15189772]
  2. Foley KF, Van Dort ME, Sievert MK, Ruoho AE, Cozzi NV: Stereospecific inhibition of monoamine uptake transporters by meta-hydroxyephedrine isomers. J Neural Transm (Vienna). 2002 Oct;109(10):1229-40. [PubMed:12373557]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Wee S, Ordway GA, Woolverton WL: Reinforcing effect of pseudoephedrine isomers and the mechanism of action. Eur J Pharmacol. 2004 Jun 16;493(1-3):117-25. [PubMed:15189772]
  2. Foley KF, Van Dort ME, Sievert MK, Ruoho AE, Cozzi NV: Stereospecific inhibition of monoamine uptake transporters by meta-hydroxyephedrine isomers. J Neural Transm (Vienna). 2002 Oct;109(10):1229-40. [PubMed:12373557]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Wellington K, Jarvis B: Cetirizine/pseudoephedrine. Drugs. 2001;61(15):2231-40; discussion 2241-2. [PubMed:11772135]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Wee S, Ordway GA, Woolverton WL: Reinforcing effect of pseudoephedrine isomers and the mechanism of action. Eur J Pharmacol. 2004 Jun 16;493(1-3):117-25. [PubMed:15189772]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Partial 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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Vansal SS, Feller DR: Direct effects of ephedrine isomers on human beta-adrenergic receptor subtypes. Biochem Pharmacol. 1999 Sep 1;58(5):807-10. [PubMed:10449190]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
Partial 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. Vansal SS, Feller DR: Direct effects of ephedrine isomers on human beta-adrenergic receptor subtypes. Biochem Pharmacol. 1999 Sep 1;58(5):807-10. [PubMed:10449190]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transcriptional activator activity, rna polymerase ii distal enhancer sequence-specific binding
Specific Function
Plays a role in the inducible expression of cytokine genes in T-cells, especially in the induction of the IL-2 or IL-4 gene transcription. Also controls gene expression in embryonic cardiac cells. ...
Gene Name
NFATC1
Uniprot ID
O95644
Uniprot Name
Nuclear factor of activated T-cells, cytoplasmic 1
Molecular Weight
101241.73 Da
References
  1. Fiebich BL, Collado JA, Stratz C, Valina C, Hochholzer W, Munoz E, Bellido LM: Pseudoephedrine inhibits T-cell activation by targeting NF-kappaB, NFAT and AP-1 signaling pathways. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):98-106. doi: 10.3109/08923973.2011.582118. Epub 2011 Jun 2. [PubMed:21631396]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Tumor necrosis factor receptor binding
Specific Function
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...
Gene Name
TNF
Uniprot ID
P01375
Uniprot Name
Tumor necrosis factor
Molecular Weight
25644.15 Da
References
  1. Wu Z, Kong X, Zhang T, Ye J, Fang Z, Yang X: Pseudoephedrine/ephedrine shows potent anti-inflammatory activity against TNF-alpha-mediated acute liver failure induced by lipopolysaccharide/D-galactosamine. Eur J Pharmacol. 2014 Feb 5;724:112-21. doi: 10.1016/j.ejphar.2013.11.032. Epub 2013 Dec 21. [PubMed:24365491]
  2. Fiebich BL, Collado JA, Stratz C, Valina C, Hochholzer W, Munoz E, Bellido LM: Pseudoephedrine inhibits T-cell activation by targeting NF-kappaB, NFAT and AP-1 signaling pathways. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):98-106. doi: 10.3109/08923973.2011.582118. Epub 2011 Jun 2. [PubMed:21631396]
10. Nuclear factor kappa-light-chain-enhancer of activated B cells
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
References
  1. Fiebich BL, Collado JA, Stratz C, Valina C, Hochholzer W, Munoz E, Bellido LM: Pseudoephedrine inhibits T-cell activation by targeting NF-kappaB, NFAT and AP-1 signaling pathways. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):98-106. doi: 10.3109/08923973.2011.582118. Epub 2011 Jun 2. [PubMed:21631396]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transcriptional activator activity, rna polymerase ii transcription regulatory region sequence-specific binding
Specific Function
This protein binds the cAMP response element (CRE) (consensus: 5'-GTGACGT[AC][AG]-3'), a sequence present in many viral and cellular promoters. Binds to the Tax-responsive element (TRE) of HTLV-I. ...

Components:
References
  1. Fiebich BL, Collado JA, Stratz C, Valina C, Hochholzer W, Munoz E, Bellido LM: Pseudoephedrine inhibits T-cell activation by targeting NF-kappaB, NFAT and AP-1 signaling pathways. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):98-106. doi: 10.3109/08923973.2011.582118. Epub 2011 Jun 2. [PubMed:21631396]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Kinase activator activity
Specific Function
Produced by T-cells in response to antigenic or mitogenic stimulation, this protein is required for T-cell proliferation and other activities crucial to regulation of the immune response. Can stimu...
Gene Name
IL2
Uniprot ID
P60568
Uniprot Name
Interleukin-2
Molecular Weight
17627.52 Da
References
  1. Fiebich BL, Collado JA, Stratz C, Valina C, Hochholzer W, Munoz E, Bellido LM: Pseudoephedrine inhibits T-cell activation by targeting NF-kappaB, NFAT and AP-1 signaling pathways. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):98-106. doi: 10.3109/08923973.2011.582118. Epub 2011 Jun 2. [PubMed:21631396]

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. Ulus IH, Maher TJ, Wurtman RJ: Characterization of phentermine and related compounds as monoamine oxidase (MAO) inhibitors. Biochem Pharmacol. 2000 Jun 15;59(12):1611-21. [PubMed:10799660]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 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]
  2. Update on mapping the landscape of genetic tests for non-cancer diseases/conditions. (2012). Raman G., Chang L., Gaylor J. et al.. FDA.

Drug created on June 13, 2005 07:24 / Updated on December 12, 2018 03:40