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Identification
NamePseudoephedrine
Accession NumberDB00852  (APRD00634)
TypeSmall Molecule
GroupsApproved
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. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(+)-(1S,2S)-PseudoephedrineNot AvailableNot Available
(+)-PseudoephedrineNot AvailableNot Available
(+)-Psi-ephedrineNot AvailableNot Available
(+)-threo-EphedrineNot AvailableNot Available
D-IsoephedrineNot AvailableNot Available
D-PseudoephedrineNot AvailableNot Available
D-Psi-2-methylamino-1-phenyl-1-propanolNot AvailableNot Available
D-Psi-ephedrineNot AvailableNot Available
IsoephedrineNot AvailableNot Available
L-(+)-PseudoephedrineNot AvailableNot Available
L(+)-Psi-ephedrineNot AvailableNot Available
PseudoefedrinaNot AvailableNot Available
PseudoephedrineNot AvailableNot Available
PseudoephedrinumNot AvailableNot Available
Psi-ephedrinNot AvailableNot Available
Psi-ephedrineNot AvailableNot Available
trans-EphedrineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Suphedrinetablet, film coated, extended release120 mgoralRite Aid Corporation2002-08-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated, extended release120 mgoralSafeway Inc.2006-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated, extended release120 mgoralShopko Stores Operating Co., LLC2006-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated, extended release120 mgoralHEB2006-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated, extended release120 mgoralMeijer Distribution, Inc.2006-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated, extended release120 mgoralPerrigo New York Inc2014-05-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated30 mgoralPerrigo New York Inc2008-10-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated, extended release120 mgoralAmerisource Bergen2006-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated120 mgoralOhm Laboratories Inc.2006-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, extended release120 mgoralOhm Laboratories Inc.2006-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated60 mgoralPhysicians Total Care, Inc.2002-11-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated, extended release120 mgoralPublix Super Markets Inc2006-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, coated30 mgoralAAA Pharmaceutical, Inc.2012-12-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated, extended release120 mgoralCVS Pharmacy2006-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated, extended release120 mgoralChain Drug Marketing Association Inc.2006-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ephed 60liquid60 mg/60mLoralDickey Consumer Products DBA DMD2011-10-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pseudoephedrine Hydrochloridetablet, film coated, extended release120 mgoralPremier Value2006-04-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
International Brands
NameCompany
AfrinolNot Available
Benylin DecongestantNot Available
CenafedNot Available
DecofedNot Available
Dimetapp DecongestantNot Available
Eltor 120Not Available
GenaphedNot Available
MaxenalNot Available
MyfedrineNot Available
NovafedNot Available
RobidrineNot Available
Sudafed DecongestantNot Available
Brand mixtures
Brand NameIngredients
Actifed DM SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride + Triprolidine Hydrochloride
Actifed DM TabletsDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride + Triprolidine Hydrochloride
Actifed Plus CapletAcetaminophen + Pseudoephedrine Hydrochloride + Triprolidine Hydrochloride
Actifed SyrupPseudoephedrine Hydrochloride + Triprolidine Hydrochloride
Actifed TabletsPseudoephedrine Hydrochloride + Triprolidine Hydrochloride
Allergy Sinus Medication - CapletAcetaminophen + Chlorpheniramine Maleate + Pseudoephedrine Hydrochloride
Benadryl Decongestant TabletsDiphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
Benylin 4 Flu - SyrupAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Benylin Codeine 3.3mg de SyrCodeine Phosphate + Guaifenesin + Pseudoephedrine Hydrochloride
BromfedDMDextromethorphan + Brompheniramine + Pseudoephedrine
Bronchodex PediatriqueDextromethorphan Hydrobromide + Guaifenesin + Pheniramine Maleate + Pseudoephedrine Hydrochloride
Calmylin #2 SyrDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Calmylin #3 SyrDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Calmylin Codeine D-E SyrCodeine Phosphate + Guaifenesin + Pseudoephedrine Hydrochloride
Calmylin Cough and Flu LiqAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Calmylin Pediatric SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Centracol Pediatrique - SyrDextromethorphan Hydrobromide + Guaifenesin + Pheniramine Maleate + Pseudoephedrine Hydrochloride
Children's Tussin Cough Medicine DM Antitussive DecongestantDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Children's Tylenol Allergy - D Chewable TabletsAcetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
Children's Tylenol Allergy-D SuspensionAcetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
Children's Tylenol Cold LiquidAcetaminophen + Chlorpheniramine Maleate + Pseudoephedrine Hydrochloride
Children's Tylenol Cold Liquid with DMAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Children's Tylenol Sinus Chewable TabletAcetaminophen + Pseudoephedrine Hydrochloride
Clarinex-D 12 Hour Extended Release Tabletsdesloratadine + pseudoephedrine
Claritin Allergy + Sinus Extra StrengthLoratadine + Pseudoephedrine Sulfate
Cold/Flu ReliefAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Contac Day & Night Sinus/Allergy CapletAcetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
Contac-C Ext.Stren.Night Time Cough,Cold&FluAcetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
CotrifedCodeine Phosphate + Pseudoephedrine Hydrochloride + Triprolidine Hydrochloride
Cough and Flu SyrupAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Cough Syr W.Cod. Pseudoephed.Hcl GuaifenesinCodeine Phosphate + Guaifenesin + Pseudoephedrine Hydrochloride
Cough Syrup DM DecongestantDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Cough Syrup DM Decongestant ExpectorantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Cough Syrup DM Decongestant for ChildrenDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Cough Syrup DM-D-EDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Demdec SyrDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Dimetapp Children's Cough and Cold LiquidDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Dimetapp Cold and Sinus CapletsIbuprofen + Pseudoephedrine Hydrochloride
DM Cough Syrup DecongestantDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
DM Plus Decongestant Cough SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
DM Plus Decongestant Plus Expector.Ex.St.SyrDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
DM Plus Decongestant Plus Expectorant Cough SyrupDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
DM-D-Expectorant Cough and Cold SyrupDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Dristan Sinus CapletsIbuprofen + Pseudoephedrine Hydrochloride
Entre-SDextromethorphan + Pseudoephedrine + Chlorphenamine
Extra Strength Allergy Plus Sinus ReliefAcetaminophen + Chlorpheniramine Maleate + Pseudoephedrine Hydrochloride
Extra Strength Allergy Sinus MedicationAcetaminophen + Chlorpheniramine Maleate + Pseudoephedrine Hydrochloride
Extra Strength Cold Medication Daytime RlfAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Extra Strength Daytime Cold Relief-CapletAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Extra Strength Nighttime Cold Relief-CapletAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Extra Strength Sinus Medication-CapletAcetaminophen + Pseudoephedrine Hydrochloride
Extra Strength Sinus Relief-CapletAcetaminophen + Pseudoephedrine Hydrochloride
Extra Strength Tylenol Cold and Flu PowderAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Extra Strength Tylenol Sinus Nighttime CapletAcetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Ibuprofen and PseudoephedrineIbuprofen + Pseudoephedrine Hydrochloride
Koffex DM + Decongestant + ExpectorantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Koffex DM + Decongestant + Expectorant Extra StrengthDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Koffex DM + Decongestant SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Koffex DM-D-E - LiqDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Medicament Sinus Personnel Ex-Fort CapletAcetaminophen + Pseudoephedrine Hydrochloride
Medicament Sinus Personnel Reg CapletAcetaminophen + Pseudoephedrine Hydrochloride
Nasal Decongestant AntihistaminePseudoephedrine Hydrochloride + Triprolidine Hydrochloride
Neo Citran Daycaps Extra Strength - CapletAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Nighttime Cold and Flu Liquid CapsulesAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nighttime Cold and Flu ReliefAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nitetime Cold MedicineAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Novahistex DM Expectorant with DecongestantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Novahistex DM with DecongestantDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Novahistex Expectorant with DecongestantGuaifenesin + Pseudoephedrine Hydrochloride
Novahistine DM Expectorant with DecongestantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Novahistine DM with Decongestant - LiqDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Nyquil LiquicapsAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Once-a-Day Benylin Cold CapChlorpheniramine Maleate + Pseudoephedrine Hydrochloride
Pediatric Cough SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Personnelle DM SyrDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Promatussin DM Adult Formula SyrDextromethorphan Hydrobromide + Promethazine Hydrochloride + Pseudoephedrine Hydrochloride
Promatussin DM Children FormulaDextromethorphan Hydrobromide + Promethazine Hydrochloride + Pseudoephedrine Hydrochloride
Pulmosirum Decongestionnant SiropBeechwood Creosote + Cocillana + Eucalyptus + Guaiacol + Ipecac + Lobelia Inflata + Menthol + Myroxylon Balsamum + Pseudoephedrine Hydrochloride + White Pine
Reg.Str.Cold Medic.Night Time Relief)Caplet (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Regular Strength Cold MedicationDaytime R.) (Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Regular Strength Sinus MedicationAcetaminophen + Pseudoephedrine Hydrochloride
Regular Strength Sinus Medication-CapletAcetaminophen + Pseudoephedrine Hydrochloride
Regular Strength Tylenol Cold and Flu PowderAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Regular Strength Tylenol Cold Chest CongestionAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Regular Strength Tylenol Cough Suspension with DecongestantAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Robitussin Honey Cough and ColdDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Robitussin Honey FluAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Sinus, Pain & Nasal Congest Relief CapletAcetaminophen + Pseudoephedrine Hydrochloride
Sinutab N.T. Regular Strength CapletsAcetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride
Sudafed Cold and Cough Extra Strength CapletAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Sudafed Cold and Flu Gel CapsAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Sudafed DMDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Sudafed Head Cold and Sinus Extra Strength CapletsAcetaminophen + Pseudoephedrine Hydrochloride
Sudafed Sinus Extra StrengthAcetaminophen + Pseudoephedrine Hydrochloride
Theraflu Flu Cold and Cough MedicineAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Triacin-CCodeine + Triprolidine + Pseudoephedrine
Triaminic Cold and AllergyChlorpheniramine Maleate + Pseudoephedrine Hydrochloride
Triaminic Decongest+Expect Liqui-Gels CapGuaifenesin + Pseudoephedrine Hydrochloride
Triaminic DM Expectorant SyrChlorpheniramine Maleate + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Triaminic DM Plus Decongestant SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Triaminic DM+Decongestant Liqui-Gels CapsulesDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Triaminic Expectorant SyrChlorpheniramine Maleate + Guaifenesin + Pseudoephedrine Hydrochloride
Triaminicol DM SyrupChlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Triprofed TabPseudoephedrine Hydrochloride + Triprolidine Hydrochloride
Tussin Cough Medicine DM Antitussive Expectorant DecongestantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
ZUTRIPROPseudoephedrine + Hydrocodone + Chlorphenamine
Salts
Name/CASStructureProperties
Pseudoephedrine hydrochloride
345-78-8
Thumb
  • InChI Key: BALXUFOVQVENIU-KXNXZCPBSA-N
  • Monoisotopic Mass: 201.092041846
  • Average Mass: 201.693
DBSALT000149
Pseudoephedrine sulfate
Thumb
  • InChI Key: XVPDSDYVNYOVMP-KXNXZCPBSA-N
  • Monoisotopic Mass: 263.082743349
  • Average Mass: 263.311
DBSALT000150
CategoriesNot Available
CAS number90-82-4
WeightAverage: 165.2322
Monoisotopic: 165.115364107
Chemical FormulaC10H15NO
InChI KeyKWGRBVOPPLSCSI-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Aralkylamine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsPseudoephedrine 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 actionPseudoephedrine 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.
AbsorptionPseudoephedrine is readily and almost completely absorbed from the GI tract and there is no evidence of first-pass metabolism.
Volume of distributionNot Available
Protein bindingPseudoephedrine does not bind to human plasma proteins over the concentration range of 50 to 2000 ng/mL
Metabolism

Hepatic.

Route of eliminationNot Available
Half life9-16 hours
ClearanceNot Available
ToxicityCommon 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.7209
CYP450 2D6 substrateInhibitor0.5846
CYP450 2C19 substrateNon-inhibitor0.5737
CYP450 3A4 substrateNon-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
Pharmacoeconomics
Manufacturers
  • Ucb inc
  • Schering plough healthcare products inc
Packagers
Dosage forms
FormRouteStrength
Liquidoral60 mg/60mL
Tablet, coatedoral30 mg
Tablet, extended releaseoral120 mg
Tablet, film coatedoral120 mg
Tablet, film coatedoral30 mg
Tablet, film coatedoral60 mg
Tablet, film coated, extended releaseoral120 mg
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point119 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.24 KB)
SpectraMS/MSMS1D NMR2D NMR
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 ReferenceNot Available
External Links
ATC CodesR01BA02
AHFS Codes
  • 12:12.12
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (52.7 KB)
Interactions
Drug Interactions
Drug
AlseroxylonIncreased arterial pressure
AmitriptylineThe tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of pseudoephedrine.
AmoxapineThe tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of pseudoephedrine.
BromocriptineThe sympathomimetic, pseudoephedrine, increases the toxicity of bromocriptine.
ClomipramineThe tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of pseudoephedrine.
DeserpidineIncreased arterial pressure
DesipramineThe tricyclic antidepressant, desipramine, increases the sympathomimetic effect of pseudoephedrine.
DesvenlafaxineDesvenlafaxine may increase the tachycardic and vasopressor effects of pseudoephedrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
DoxepinThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of pseudoephedrine.
GuanethidinePseudoephedrine may decrease the effect of guanethidine.
ImipramineThe tricyclic antidepressant, imipramine, increases the sympathomimetic effect of pseudoephedrine.
IobenguaneSympathomimetic that increase chances of producing a false negative imaging result
IsocarboxazidIncreased arterial pressure
LinezolidPossible increase of arterial pressure
MethyldopaIncreased arterial pressure
MidodrineIncreased arterial pressure
MoclobemideMoclobemide increases the sympathomimetic effect of pseudoephedrine.
NortriptylineThe tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of pseudoephedrine.
PargylineIncreased arterial pressure
PhenelzineIncreased arterial pressure
ProtriptylineThe tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of pseudoephedrine.
RasagilineIncreased arterial pressure
ReserpineIncreased arterial pressure
TranylcypromineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of Pseudoephedrine. Concomitant therapy should be avoided.
TrimipramineThe tricyclic antidepressant, trimipramine, increases the sympathomimetic effect of pseudoephedrine.
VenlafaxineVenlafaxine may increase the tachycardic and vasopressor effects of Pseudoephedrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
Food Interactions
  • Take without regard to meals.

Targets

1. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

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
  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. 2002 Oct;109(10):1229-40. Pubmed

2. Sodium-dependent dopamine transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

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
  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. 2002 Oct;109(10):1229-40. Pubmed

3. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

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
  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
  3. Wellington K, Jarvis B: Cetirizine/pseudoephedrine. Drugs. 2001;61(15):2231-40; discussion 2241-2. Pubmed

4. Alpha-2A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-2A adrenergic receptor P08913 Details

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
  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

5. Sodium-dependent serotonin transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent serotonin transporter P31645 Details

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

6. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: partial agonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

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
  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
  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

7. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist partial agonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

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

8. Nuclear factor of activated T-cells, cytoplasmic 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Nuclear factor of activated T-cells, cytoplasmic 1 O95644 Details

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

9. Tumor necrosis factor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tumor necrosis factor P01375 Details

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
  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

10. Nuclear factor kappa-light-chain-enhancer of activated B cells

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details

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

11. activator protein 1

Kind: protein group

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cyclic AMP-dependent transcription factor ATF-1 P18846 Details
Cyclic AMP-dependent transcription factor ATF-2 P15336 Details
Cyclic AMP-dependent transcription factor ATF-3 P18847 Details
Cyclic AMP-dependent transcription factor ATF-4 P18848 Details
Cyclic AMP-dependent transcription factor ATF-5 Q9Y2D1 Details
Cyclic AMP-dependent transcription factor ATF-6 alpha P18850 Details
Cyclic AMP-dependent transcription factor ATF-7 P17544 Details
Jun dimerization protein 2 Q8WYK2 Details
Proto-oncogene c-Fos P01100 Details
Transcription factor AP-1 P05412 Details

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

12. Interleukin-2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Interleukin-2 P60568 Details

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

Enzymes

1. Amine oxidase [flavin-containing] A

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] A P21397 Details

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

2. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12