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 |
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 |
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 |
|---|---|---|
| Development and validation of a capillary zone electrophoresis method for the determination of ephedrine and related compounds in urine without extraction. | 2003-07-05 |
|
| Stroke associated with sympathomimetics contained in over-the-counter cough and cold drugs. | 2003-07 |
|
| Chiral analysis of amphetamine-type stimulants using reversed-polarity capillary electrophoresis/positive ion electrospray ionization tandem mass spectrometry. | 2003-06 |
|
| Press-coating of immediate release powders onto coated controlled release tablets with adhesives. | 2003-05-20 |
|
| Exemption of chemical mixtures containing the List I chemicals ephedrine, N-methylephedrine, N-methylpseudoephedrine, norpseudoephedrine, phenylpropanolamine, and pseudoephedrine. Final rule. | 2003-05-01 |
|
| In vitro evaluation of apical microleakage following canal filling with a coated carrier system compared with lateral and thermomechanical Gutta-Percha condensation techniques. | 2003-05 |
|
| A comparative study of root canal preparation using FlexMaster and HERO 642 rotary Ni-Ti instruments. | 2003-05 |
|
| Canine model of nasal congestion and allergic rhinitis. | 2003-05 |
|
| Controlled porosity osmotic pump-based controlled release systems of pseudoephedrine. I. Cellulose acetate as a semipermeable membrane. | 2003-04-14 |
|
| Baboon syndrome due to pseudoephedrine. | 2003-04 |
|
| [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]. | 2003-04 |
|
| Sensitive determination of ephedrine and pseudoephedrine by capillary electrophoresis with laser-induced fluorescence detection. | 2003-04 |
|
| Surfing, self-medicating and safety: buying non-prescription and complementary medicines via the internet. | 2003-04 |
|
| Nonpigmenting solitary fixed drug eruption caused by a Chinese traditional herbal medicine, ma huang (Ephedra Hebra), mainly containing pseudoephedrine and ephedrine. | 2003-04 |
|
| Spectrophotometric determination of binary mixtures of pseudoephedrine with some histamine H1-receptor antagonists using derivative ratio spectrum method. | 2003-03-26 |
|
| Adrenaline given outside the context of life threatening allergic reactions. | 2003-03-15 |
|
| [Tobacco: knowledge, reasoning and opinion of high school students in Doubs. Reflections on prevention]. | 2003-03 |
|
| Safety of selegiline with cold medications. | 2003-03 |
|
| Separation and determination of ephedrine and pseudoephedrine by combination of flow injection with capillary electrophoresis. | 2003-01 |
|
| Physiological, subjective and performance effects of pseudoephedrine and phenylpropanolamine during endurance running exercise. | 2003-01 |
|
| 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. | 2003-01 |
|
| 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 |
|
| Evaluation of a pseudoephedrine linker for asymmetric alkylations on solid phase. | 2002-12-26 |
|
| Efficacy of once-daily desloratadine/pseudoephedrine for relief of nasal congestion. | 2002-12-13 |
|
| Enhanced enantio- and diastereoselectivity via confinement and cation binding: yang photocyclization of 2-benzoyladamantane derivatives within zeolites. | 2002-11-29 |
|
| Quantitative and structural determination of pseudoephedrine sulfate and its related compounds in pharmaceutical preparations using high-performance liquid chromatography. | 2002-11-07 |
|
| [Bacteremia caused by coagulase-negative staphylococci: incidence, frequency of teicoplanin resistance and molecular epidemiology]. | 2002-11 |
|
| A moderate dose of pseudoephedrine does not alter muscle contraction strength or anaerobic power. | 2002-11 |
|
| Enantiomeric separation of methamphetamine and related analogs by capillary zone electrophoresis: intelligence study in routine methamphetamine seizures. | 2002-11 |
|
| Pharmacological characterization of a noninvasive, chronic, experimental dog model of nasal congestion. | 2002-10-22 |
|
| [Blood supply of the lips]. | 2002-10 |
|
| [Cutaneous complications following liver transplantation: epidemiologic and clinical study in 86 patients]. | 2002-10 |
|
| Enzymatic (R)-phenylacetylcarbinol production in benzaldehyde emulsions. | 2002-10 |
|
| Stereospecific inhibition of monoamine uptake transporters by meta-hydroxyephedrine isomers. | 2002-10 |
|
| Severe adverse drug reactions due to pseudoephedrine from over-the-counter medications. | 2002-09 |
|
| [Toxic dermatitis caused by pseudoephedrine: apropos of a case]. | 2002-09 |
|
| Erythrodermia to pseudoephedrine in a patient with contact allergy to phenylephrine. | 2002-08-30 |
|
| 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. | 2002-08-09 |
|
| [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]. | 2002-08 |
|
| Generalized dermatitis due to pseudoephedrine. | 2002-08 |
|
| Modifying the bitterness of selected oral pharmaceuticals with cation and anion series of salts. | 2002-07 |
|
| Onset of action, efficacy, and safety of fexofenadine 60 mg/pseudoephedrine 120 mg versus placebo in the Atlanta allergen exposure unit. | 2002-07 |
|
| 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. | 2002-06 |
|
| Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use. | 2002-06 |
|
| Pseudoephedrine as a chiral auxiliary for asymmetric Michael reactions: synthesis of 3-aryl-delta-lactones. | 2002-05-30 |
|
| Pigmented purpuric dermatosis due to pseudoephedrine. | 2002-05 |
|
| 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 |
|
| Epinephrine analogues. | 2001-11 |
|
| [Separation and determination of pseudoephedrine in bufferin cold tablet by capillary electrophoresis with hydropropyl-beta-cyclodextrin as chiral selective reagent]. | 2001-11 |
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
| 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 |
Validated (UNII)
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| Record Version |
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ACTIVE MOIETY |
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