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
Molecular Formula | C10H15NO |
Molecular Weight | 165.2322 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | BrH |
Molecular Weight | 80.912 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.drugs.com/pseudoephedrine.htmlCurator'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
Sources: https://www.drugs.com/pseudoephedrine.html
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] | ||
Target ID: CHEMBL222 |
1.18 µM [IC50] | ||
Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796 |
|||
Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10449190 |
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 |
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 |
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 |
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 Sources: |
unhealthy, 37 years |
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 Health Status: unhealthy Age Group: 38.8 years Sex: M+F 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 |
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 |
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 Sources: |
unhealthy, 50 years |
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 |
Other AEs: Hypertension... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Blood myoglobin increased | 1 patient | 1500 mg single, oral Overdose |
unknown, 16 years |
Creatine kinase increased | 1 patient | 1500 mg single, oral Overdose |
unknown, 16 years |
Rhabdomyolysis | 1 patient | 1500 mg single, oral Overdose |
unknown, 16 years |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 Sources: |
unhealthy, 37 years |
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 Sources: |
unhealthy, 37 years |
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 |
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 |
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 |
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 |
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 Sources: |
unhealthy, 50 years |
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 Sources: |
unhealthy, 50 years |
Hypertension | 1 patient | 720 mg single, oral Overdose |
unhealthy, 87 years |
PubMed
Title | Date | PubMed |
---|---|---|
Cetirizine/pseudoephedrine. | 2001 |
|
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 |
|
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 |
|
Chloroephedrine: contaminant of methamphetamine synthesis with cardiovascular activity. | 2001 Nov 1 |
|
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 |
|
Small-cell carcinoma of the esophagus: report of three cases and review of the literature with emphasis on therapy. | 2001 Sep |
|
Community pharmacists' experience of over-the-counter medicine misuse in Scotland. | 2001 Sep |
|
Analysis of enantiomers giving partially overlapped peaks by using different treatments of the chromatographic ultraviolet signals: quantification of pseudoephedrine enantiomers. | 2001 Sep 28 |
|
Myocardial infarction temporally related to ephedra--a possible role for the coronary microcirculation. | 2002 |
|
Liquid chromatography/tandem mass spectrometric bioanalysis using normal-phase columns with aqueous/organic mobile phases - a novel approach of eliminating evaporation and reconstitution steps in 96-well SPE. | 2002 |
|
[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 |
|
Pseudoephedrine causing mania-like symptoms. | 2002 Feb 22 |
|
Immediate hypersensitivity due to pseudoephedrine. | 2002 Jan |
|
Maternal medication use and risks of gastroschisis and small intestinal atresia. | 2002 Jan 1 |
|
Rapid determination of pseudoephedrine in human plasma by high-performance liquid chromatography. | 2002 Jan 25 |
|
Cerebral vasoconstriction and stroke after use of serotonergic drugs. | 2002 Jan 8 |
|
Pharmacological characterization of a noninvasive, chronic, experimental dog model of nasal congestion. | 2002 Jan-Feb |
|
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 |
|
Rapid simultaneous determination of amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine, 3,4-methylenedioxymethamphetamine, and 3,4-methylenedioxyethylamphetamine in urine by solid-phase extraction and GC-MS: a method optimized for high-volume laboratories. | 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 |
|
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use. | 2002 Jun |
|
Implementation of the Comprehensive Methamphetamine Control Act of 1996; regulation of pseudoephedrine, phenylpropanolamine, and combination ephedrine drug products and reports of certain transactions to nonregulated persons. Final rule. | 2002 Mar 28 |
|
Pigmented purpuric dermatosis due to pseudoephedrine. | 2002 May |
|
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 |
|
Enantiomeric separation of methamphetamine and related analogs by capillary zone electrophoresis: intelligence study in routine methamphetamine seizures. | 2002 Nov |
|
Enhanced enantio- and diastereoselectivity via confinement and cation binding: yang photocyclization of 2-benzoyladamantane derivatives within zeolites. | 2002 Nov 29 |
|
Quantitative and structural determination of pseudoephedrine sulfate and its related compounds in pharmaceutical preparations using high-performance liquid chromatography. | 2002 Nov 7 |
|
[Blood supply of the lips]. | 2002 Oct |
|
[Cutaneous complications following liver transplantation: epidemiologic and clinical study in 86 patients]. | 2002 Oct |
|
Enzymatic (R)-phenylacetylcarbinol production in benzaldehyde emulsions. | 2002 Oct |
|
Stereospecific inhibition of monoamine uptake transporters by meta-hydroxyephedrine isomers. | 2002 Oct |
|
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 |
|
Separation and determination of ephedrine and pseudoephedrine by combination of flow injection with capillary electrophoresis. | 2003 Jan |
|
Physiological, subjective and performance effects of pseudoephedrine and phenylpropanolamine during endurance running exercise. | 2003 Jan |
|
Efficacy and safety of clemastine-pseudoephedrine-acetaminophen versus pseudoephedrine-acetaminophen in the treatment of seasonal allergic rhinitis in a 1-day, placebo-controlled park study. | 2003 Jan |
|
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 |
|
Canine model of nasal congestion and allergic rhinitis. | 2003 May |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21631396
Curator's Comment: Pseudoephedrine inhibits interleukin-2 (IL-2) and tumor necrosis factor (TNF) alpha-gene transcription in stimulated Jurkat cells, a human T-cell leukemia cell line.
Unknown
Substance Class |
Chemical
Created
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admin
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Edited
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Record UNII |
X7TX4R5VWL
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Record Status |
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Record Version |
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