Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H15NO.BrH |
| Molecular Weight | 246.144 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.CN[C@@H](C)[C@@H](O)C1=CC=CC=C1
InChI
InChIKey=VGBAPRQRVHQDMK-KXNXZCPBSA-N
InChI=1S/C10H15NO.BrH/c1-8(11-2)10(12)9-6-4-3-5-7-9;/h3-8,10-12H,1-2H3;1H/t8-,10+;/m0./s1
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12373557 | http://www.mayoclinic.org/drugs-supplements/ephedra--ma-huang/background/hrb-20059270 | https://www.sudafed.com/adult-products/congestion/sudafed-24-hour#uses-and-directions | https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0011888 | https://www.ncbi.nlm.nih.gov/pubmed/11772135 | https://www.ncbi.nlm.nih.gov/pubmed/10449190 | https://www.ncbi.nlm.nih.gov/pubmed/12954796
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12373557 | http://www.mayoclinic.org/drugs-supplements/ephedra--ma-huang/background/hrb-20059270 | https://www.sudafed.com/adult-products/congestion/sudafed-24-hour#uses-and-directions | https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0011888 | https://www.ncbi.nlm.nih.gov/pubmed/11772135 | https://www.ncbi.nlm.nih.gov/pubmed/10449190 | https://www.ncbi.nlm.nih.gov/pubmed/12954796
Pseudoephedrine is a sympathomimetic drug. Pseudoephedrine acts as an adrenomimetic and inhibitor of monoamine transporters. Ephedra sinica, a species of ephedra (ma huang), contains ephedrine and pseudoephedrine. Ephedra has been found to stimulate the nervous system, increase airflow into the lungs and constrict blood vessels. In combination with caffeine, ephedra appears to cause weight loss. Pseudoephedrine is a decongestant that shrinks blood vessels in the nasal passages. Pseudoephedrine is used to relieve nasal or sinus congestion caused by the common cold, sinusitis, and hay fever and other respiratory allergies.
Originator
Sources: A. Ladenburg, C. Oelschlägel, Ber. 22, 1823 (1889).
Curator's Comment: (+)-threo-isomer of ephedrine, q.v. Isoln from E. vulgaris: A. Ladenburg, C. Oelschlägel, Ber. 22, 1823 (1889). Synthesis: E. Späth, R. Göhring, Monatsh. Chem. 41, 319 (1920). reference retrieved from http://www.drugfuture.com/chemdata/pseudoephedrine.html
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL238 |
5.6 µM [IC50] | ||
| 1.18 µM [IC50] | |||
Target ID: CHEMBL2095203 |
|||
Target ID: CHEMBL2094118 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | SUDAFED 24 HOUR Approved Usetemporarily relieves nasal congestion due to the common cold, hay fever or other upper respiratory allergies; reduces swelling of nasal passages; relieves sinus pressure Launch Date1992 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
292 ng/mL |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PSEUDOEPHEDRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4346 ng × h/mL |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PSEUDOEPHEDRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.3 h |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PSEUDOEPHEDRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1500 mg single, oral Overdose |
unknown, 16 years n = 1 Health Status: unknown Age Group: 16 years Sex: F Population Size: 1 Sources: |
Other AEs: Rhabdomyolysis, Creatine kinase increased... Other AEs: Rhabdomyolysis (1 patient) Sources: Creatine kinase increased (1 patient) Blood myoglobin increased (1 patient) |
150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
Other AEs: Tension, Dry mouth... Other AEs: Tension (10 patients) Sources: Dry mouth (6 patients) Tachycardia (9 patients) Palpitations (10 patients) Anxiety (13 patients) Insomnia (12 patients) Anorexia (7 patients) Restlessness (10 patients) |
90 mg 1 times / day multiple, oral Overdose Dose: 90 mg, 1 times / day Route: oral Route: multiple Dose: 90 mg, 1 times / day Sources: |
unhealthy, 3 years n = 1 Health Status: unhealthy Age Group: 3 years Sex: M Population Size: 1 Sources: |
Disc. AE: Urinary retention... AEs leading to discontinuation/dose reduction: Urinary retention (acute, 1 patient) Sources: |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: sinusitis Age Group: 37 years Sex: F Population Size: 1 Sources: |
Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Sources: Abdominal pain (acute, 1 patient) |
720 mg 1 times / day multiple, oral Highest studied dose Dose: 720 mg, 1 times / day Route: oral Route: multiple Dose: 720 mg, 1 times / day Sources: |
unhealthy, 38.8 years n = 38 Health Status: unhealthy Age Group: 38.8 years Sex: M+F Population Size: 38 Sources: |
|
30 mg 3 times / day multiple, oral Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
unhealthy, 44 years n = 1 Health Status: unhealthy Condition: upper airway infection Age Group: 44 years Sex: F Population Size: 1 Sources: |
Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Sources: Abdominal pain (acute, 1 patient) |
120 mg 1 times / day multiple, oral Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: |
unhealthy, 46 years n = 1 Health Status: unhealthy Condition: chronic sinusitis | allergic rhinitis Age Group: 46 years Sex: F Population Size: 1 Sources: |
Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Sources: Abdominal pain (acute, 1 patient) |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: chlorpheniramine maleate(2 mg; twice daily, oral) |
unhealthy, 50 years n = 1 Health Status: unhealthy Condition: rhinitis Age Group: 50 years Sex: F Population Size: 1 Sources: |
Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Sources: Abdominal pain (acute, 1 patient) |
720 mg single, oral Overdose |
unhealthy, 87 years n = 1 Health Status: unhealthy Age Group: 87 years Sex: M Population Size: 1 Sources: |
Other AEs: Hypertension... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Blood myoglobin increased | 1 patient | 1500 mg single, oral Overdose |
unknown, 16 years n = 1 Health Status: unknown Age Group: 16 years Sex: F Population Size: 1 Sources: |
| Creatine kinase increased | 1 patient | 1500 mg single, oral Overdose |
unknown, 16 years n = 1 Health Status: unknown Age Group: 16 years Sex: F Population Size: 1 Sources: |
| Rhabdomyolysis | 1 patient | 1500 mg single, oral Overdose |
unknown, 16 years n = 1 Health Status: unknown Age Group: 16 years Sex: F Population Size: 1 Sources: |
| Palpitations | 10 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
| Restlessness | 10 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
| Tension | 10 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
| Insomnia | 12 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
| Anxiety | 13 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
| Dry mouth | 6 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
| Anorexia | 7 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
| Tachycardia | 9 patients | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: |
| Urinary retention | acute, 1 patient Disc. AE |
90 mg 1 times / day multiple, oral Overdose Dose: 90 mg, 1 times / day Route: oral Route: multiple Dose: 90 mg, 1 times / day Sources: |
unhealthy, 3 years n = 1 Health Status: unhealthy Age Group: 3 years Sex: M Population Size: 1 Sources: |
| Ischemic colitis | 1 patient Disc. AE |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: sinusitis Age Group: 37 years Sex: F Population Size: 1 Sources: |
| Abdominal pain | acute, 1 patient Disc. AE |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: |
unhealthy, 37 years n = 1 Health Status: unhealthy Condition: sinusitis Age Group: 37 years Sex: F Population Size: 1 Sources: |
| Ischemic colitis | 1 patient Disc. AE |
30 mg 3 times / day multiple, oral Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
unhealthy, 44 years n = 1 Health Status: unhealthy Condition: upper airway infection Age Group: 44 years Sex: F Population Size: 1 Sources: |
| Abdominal pain | acute, 1 patient Disc. AE |
30 mg 3 times / day multiple, oral Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
unhealthy, 44 years n = 1 Health Status: unhealthy Condition: upper airway infection Age Group: 44 years Sex: F Population Size: 1 Sources: |
| Ischemic colitis | 1 patient Disc. AE |
120 mg 1 times / day multiple, oral Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: |
unhealthy, 46 years n = 1 Health Status: unhealthy Condition: chronic sinusitis | allergic rhinitis Age Group: 46 years Sex: F Population Size: 1 Sources: |
| Abdominal pain | acute, 1 patient Disc. AE |
120 mg 1 times / day multiple, oral Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: |
unhealthy, 46 years n = 1 Health Status: unhealthy Condition: chronic sinusitis | allergic rhinitis Age Group: 46 years Sex: F Population Size: 1 Sources: |
| Ischemic colitis | 1 patient Disc. AE |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: chlorpheniramine maleate(2 mg; twice daily, oral) |
unhealthy, 50 years n = 1 Health Status: unhealthy Condition: rhinitis Age Group: 50 years Sex: F Population Size: 1 Sources: |
| Abdominal pain | acute, 1 patient Disc. AE |
30 mg 2 times / day multiple, oral Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Co-administed with:: acetominophen(500 mg twice daily, oral) Sources: chlorpheniramine maleate(2 mg; twice daily, oral) |
unhealthy, 50 years n = 1 Health Status: unhealthy Condition: rhinitis Age Group: 50 years Sex: F Population Size: 1 Sources: |
| Hypertension | 1 patient | 720 mg single, oral Overdose |
unhealthy, 87 years n = 1 Health Status: unhealthy Age Group: 87 years Sex: M Population Size: 1 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cetirizine/pseudoephedrine. | 2001 |
|
| Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures. | 2001 Apr |
|
| Mass spectrometric quantitation of chiral drugs by the kinetic method. | 2001 Apr 15 |
|
| Hypokalemic metabolic acidosis attributed to cough mixture abuse. | 2001 Aug |
|
| Aziridine ring-opening reactions with chiral enolates. Stereocontrolled synthesis of 5-substituted-3-methyl-pyrrolidin-2-ones. | 2001 Aug 24 |
|
| Stereocontrolled Mannich reaction with enolizable imines using (S,S)-(+)-pseudoephedrine as chiral auxiliary. Asymmetric synthesis of alpha,beta-disubstituted beta-aminoesters and beta-lactams. | 2001 Dec 28 |
|
| Human islet transplantation network for the treatment of Type I diabetes: first data from the Swiss-French GRAGIL consortium (1999-2000). Groupe de Recherche Rhin Rhĵne Alpes Genève pour la transplantation d'Ilots de Langerhans. | 2001 Jul |
|
| New observations on the secondary chemistry of world Ephedra (Ephedraceae). | 2001 Jul |
|
| Cold-syrup induced movement disorder. | 2001 Jun |
|
| Asymmetric synthesis of beta-substituted alpha-methyl-beta-amino esters by Mannich reaction of (S,S)-(+)-pseudoephedrine acetamide derived enolate with imines. | 2001 Mar 8 |
|
| Comparative oral and topical decongestant effects of phenylpropanolamine and d-pseudoephedrine. | 2001 Mar-Apr |
|
| Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man. | 2001 May |
|
| Epinephrine analogues. | 2001 Nov |
|
| [Separation and determination of pseudoephedrine in bufferin cold tablet by capillary electrophoresis with hydropropyl-beta-cyclodextrin as chiral selective reagent]. | 2001 Nov |
|
| Desloratadine reduces nasal congestion in patients with intermittent allergic rhinitis. | 2001 Nov |
|
| Biotransformation of benzaldehyde into (R)-phenylacetylcarbinol by filamentous fungi or their extracts. | 2001 Oct |
|
| Acute psychosis due to the interaction of legal compounds--ephedra alkaloids in 'vigueur fit' tablets, caffeine in 'red bull' and alcohol. | 2001 Oct |
|
| Cathinone (Khat) and methcathinone (CAT) in urine specimens: a gas chromatographic-mass spectrometric detection procedure. | 2001 Oct |
|
| Relationship between expansion of the CAG repeat in exon 1 of the androgen receptor gene and idiopathic male infertility. | 2001 Oct |
|
| Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry. | 2001 Sep |
|
| [An open label multi-center clinical trial to evaluate the efficacy of compound pseudoephedrine [corrected] hydrochloride sustained release capsules in patients with nasal symptoms associated with common cold]. | 2002 Aug |
|
| Evaluation of a pseudoephedrine linker for asymmetric alkylations on solid phase. | 2002 Dec 26 |
|
| Linezolid: its role in the treatment of gram-positive, drug-resistant bacterial infections. | 2002 Feb 15 |
|
| Acoustic rhinometry in the dog: a novel large animal model for studies of nasal congestion. | 2002 Jan-Feb |
|
| Modifying the bitterness of selected oral pharmaceuticals with cation and anion series of salts. | 2002 Jul |
|
| Erythrodermia to pseudoephedrine in a patient with contact allergy to phenylephrine. | 2002 Jul-Aug |
|
| A comparative study of the side effects between pseudoephedrine in Loratadine plus Pseudoephedrine Sulfate Repetabs Tables and loratadine + pseudoephedrine tablet in treatment of allergic rhinitis in Thai patients. | 2002 Jun |
|
| Pseudoephedrine as a chiral auxiliary for asymmetric Michael reactions: synthesis of 3-aryl-delta-lactones. | 2002 May 30 |
|
| [Bacteremia caused by coagulase-negative staphylococci: incidence, frequency of teicoplanin resistance and molecular epidemiology]. | 2002 Nov |
|
| A moderate dose of pseudoephedrine does not alter muscle contraction strength or anaerobic power. | 2002 Nov |
|
| Quantitative and structural determination of pseudoephedrine sulfate and its related compounds in pharmaceutical preparations using high-performance liquid chromatography. | 2002 Nov 7 |
|
| Severe adverse drug reactions due to pseudoephedrine from over-the-counter medications. | 2002 Sep |
|
| [Toxic dermatitis caused by pseudoephedrine: apropos of a case]. | 2002 Sep |
|
| Efficacy of once-daily desloratadine/pseudoephedrine for relief of nasal congestion. | 2002 Sep-Oct |
|
| Pharmacokinetic interaction study of a fixed combination of 500 mg acetylsalicylic acid/30 mg pseudoephedrine versus each of the single active ingredients in healthy male volunteers. | 2003 |
|
| Baboon syndrome due to pseudoephedrine. | 2003 Apr |
|
| [Improving the medical treatment of minors who are victims of sexual assault or physical abuse: a receiving center and partnership between a psychiatric hospital and university hospital]. | 2003 Apr |
|
| Sensitive determination of ephedrine and pseudoephedrine by capillary electrophoresis with laser-induced fluorescence detection. | 2003 Apr |
|
| Nonpigmenting solitary fixed drug eruption caused by a Chinese traditional herbal medicine, ma huang (Ephedra Hebra), mainly containing pseudoephedrine and ephedrine. | 2003 Apr |
|
| Controlled porosity osmotic pump-based controlled release systems of pseudoephedrine. I. Cellulose acetate as a semipermeable membrane. | 2003 Apr 14 |
|
| Stroke associated with sympathomimetics contained in over-the-counter cough and cold drugs. | 2003 Jul |
|
| Development and validation of a capillary zone electrophoresis method for the determination of ephedrine and related compounds in urine without extraction. | 2003 Jul 5 |
|
| Chiral analysis of amphetamine-type stimulants using reversed-polarity capillary electrophoresis/positive ion electrospray ionization tandem mass spectrometry. | 2003 Jun |
|
| [Tobacco: knowledge, reasoning and opinion of high school students in Doubs. Reflections on prevention]. | 2003 Mar |
|
| Safety of selegiline with cold medications. | 2003 Mar |
|
| Adrenaline given outside the context of life threatening allergic reactions. | 2003 Mar 15 |
|
| In vitro evaluation of apical microleakage following canal filling with a coated carrier system compared with lateral and thermomechanical Gutta-Percha condensation techniques. | 2003 May |
|
| A comparative study of root canal preparation using FlexMaster and HERO 642 rotary Ni-Ti instruments. | 2003 May |
|
| Exemption of chemical mixtures containing the List I chemicals ephedrine, N-methylephedrine, N-methylpseudoephedrine, norpseudoephedrine, phenylpropanolamine, and pseudoephedrine. Final rule. | 2003 May 1 |
|
| Press-coating of immediate release powders onto coated controlled release tablets with adhesives. | 2003 May 20 |
Sample Use Guides
SUDAFED® 24 HOUR TABLET, EXTENDED RELEASE; ORAL (PSEUDOEPHEDRINE HYDROCHLORIDE) 240MG
adults and children 12 years and older: a tablet with water every 24 hours
children under 12 years: do not use this product in children under 12 years of age
Route of Administration:
Oral
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60706-27-6
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67679722
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X7TX4R5VWL
Created by
admin on Sat Dec 16 19:27:40 GMT 2023 , Edited by admin on Sat Dec 16 19:27:40 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD
