PSEUDOEPHEDRINE

US Approved OTC

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H15NO
Molecular Weight	165.2322
Optical Activity	( + )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN[C@@H](C)[C@@H](O)C1=CC=CC=C1

InChI

InChIKey=KWGRBVOPPLSCSI-WCBMZHEXSA-N

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

HIDE SMILES / InChI

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

Description
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine transporter 180 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15189772 \| https://www.ncbi.nlm.nih.gov/pubmed/12373557	Inhibitor 8297	5.6 µM [IC50]
Norepinephrine transporter 191 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15189772 \| https://www.ncbi.nlm.nih.gov/pubmed/12373557	Inhibitor 8297	1.18 µM [IC50]
Adrenergic receptor alpha 64 Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796	Agonist 2678
Adrenergic receptor beta 87 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10449190	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nasal congestion 26 Sources: https://www.drugs.com/ppa/pseudoephedrine.html	Primary		Approved 8429	SUDAFED 24 HOUR Approved Use temporarily relieves nasal congestion due to the common cold, hay fever or other upper respiratory allergies; reduces swelling of nasal passages; relieves sinus pressure Launch Date 1992

C_max

Value	Dose	Co-administered	Analyte	Population
292 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/073585Orig1s000.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/073585Orig1s000.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.3 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/073585Orig1s000.pdf	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 Dose: 1500 mg Route: oral Route: single Dose: 1500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/19006543	unknown, 16 years n = 1 Health Status: unknown Age Group: 16 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/19006543	Other AEs: Rhabdomyolysis, Creatine kinase increased... Other AEs: Rhabdomyolysis (1 patient) Creatine kinase increased (1 patient) Blood myoglobin increased (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/19006543
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: https://pubmed.ncbi.nlm.nih.gov/729619	healthy, 24 years n = 17 Health Status: healthy Age Group: 24 years Sex: M Population Size: 17 Sources: https://pubmed.ncbi.nlm.nih.gov/729619	Other AEs: Tension, Dry mouth... Other AEs: Tension (10 patients) Dry mouth (6 patients) Tachycardia (9 patients) Palpitations (10 patients) Anxiety (13 patients) Insomnia (12 patients) Anorexia (7 patients) Restlessness (10 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/729619
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: https://pubmed.ncbi.nlm.nih.gov/18365604	unhealthy, 3 years n = 1 Health Status: unhealthy Age Group: 3 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/18365604	Disc. AE: Urinary retention... AEs leading to discontinuation/dose reduction: Urinary retention (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18365604
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: https://pubmed.ncbi.nlm.nih.gov/10484004	unhealthy, 37 years n = 1 Health Status: unhealthy Condition: sinusitis Age Group: 37 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Abdominal pain (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/10484004
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: https://pubmed.ncbi.nlm.nih.gov/23918202	unhealthy, 38.8 years n = 38 Health Status: unhealthy Age Group: 38.8 years Sex: M+F Population Size: 38 Sources: https://pubmed.ncbi.nlm.nih.gov/23918202	Sources: https://pubmed.ncbi.nlm.nih.gov/23918202
30 mg 3 times / day multiple, oral Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	unhealthy, 44 years n = 1 Health Status: unhealthy Condition: upper airway infection Age Group: 44 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Abdominal pain (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/10484004
120 mg 1 times / day multiple, oral Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	unhealthy, 46 years n = 1 Health Status: unhealthy Condition: chronic sinusitis \| allergic rhinitis Age Group: 46 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Abdominal pain (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/10484004
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) chlorpheniramine maleate(2 mg; twice daily, oral) Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	unhealthy, 50 years n = 1 Health Status: unhealthy Condition: rhinitis Age Group: 50 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/10484004	Disc. AE: Ischemic colitis, Abdominal pain... AEs leading to discontinuation/dose reduction: Ischemic colitis (1 patient) Abdominal pain (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/10484004
720 mg single, oral Overdose Dose: 720 mg Route: oral Route: single Dose: 720 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18608273	unhealthy, 87 years n = 1 Health Status: unhealthy Age Group: 87 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/18608273	Other AEs: Hypertension... Other AEs: Hypertension (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18608273

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51209	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51209
ZINC	ZINC000000020259	http://zinc15.docking.org/substances/ZINC000000020259
eMolecules	494893	https://www.emolecules.com/cgi-bin/more?vid=494893

PubMed

Title	Date	PubMed
Dextromethorphan- and pseudoephedrine-induced agitated psychosis and ataxia: case report.	1999 Mar-Apr	10195488
Cetirizine/pseudoephedrine.	2001	11772135
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
A fast and efficient determination of amines and preservatives in cough and cold liquid and suspension formulations using a single isocratic ion-pairing high performance [correction of power] liquid chromatography method.	2001 Aug	11451651
Cost-effectiveness of urinary dipsticks to screen asymptomatic catheter-associated urinary infections in an intensive care unit.	2001 Dec	11797017
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	11749640
[Cost effectiveness of GM-CSF in the treatment of acute myeloblastic leukemia in aged patients: protocol of GOELAM Sa3].	2001 Mar-Apr	11471363
Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man.	2001 May	11381283
Desloratadine reduces nasal congestion in patients with intermittent allergic rhinitis.	2001 Nov	11703222
Acute psychosis due to the interaction of legal compounds--ephedra alkaloids in 'vigueur fit' tablets, caffeine in 'red bull' and alcohol.	2001 Oct	11693229
Small-cell carcinoma of the esophagus: report of three cases and review of the literature with emphasis on therapy.	2001 Sep	11697847
Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations.	2001 Sep	11593992
Toxicity of over-the-counter cough and cold medications.	2001 Sep	11533370
Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations.	2001 Sep	11470203
Rapid chiral on-chip separation with simplified amperometric detection.	2001 Sep 14	11587341
Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes.	2001 Sep 5	11530984
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	12362389
Evaluation of a pseudoephedrine linker for asymmetric alkylations on solid phase.	2002 Dec 26	12489935
Pseudoephedrine causing mania-like symptoms.	2002 Feb 22	11913943
Immediate hypersensitivity due to pseudoephedrine.	2002 Jan	11991291
Maternal medication use and risks of gastroschisis and small intestinal atresia.	2002 Jan 1	11772781
Cerebral vasoconstriction and stroke after use of serotonergic drugs.	2002 Jan 8	11781419
Pharmacological characterization of a noninvasive, chronic, experimental dog model of nasal congestion.	2002 Jan-Feb	12387934
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	12322847
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use.	2002 Jun	12087345
Pigmented purpuric dermatosis due to pseudoephedrine.	2002 May	12084086
Enantiomeric separation of methamphetamine and related analogs by capillary zone electrophoresis: intelligence study in routine methamphetamine seizures.	2002 Nov	12455645
Enhanced enantio- and diastereoselectivity via confinement and cation binding: yang photocyclization of 2-benzoyladamantane derivatives within zeolites.	2002 Nov 29	12444610
Quantitative and structural determination of pseudoephedrine sulfate and its related compounds in pharmaceutical preparations using high-performance liquid chromatography.	2002 Nov 7	12408905
[Blood supply of the lips].	2002 Oct	12449862
Enzymatic (R)-phenylacetylcarbinol production in benzaldehyde emulsions.	2002 Oct	12382047
Stereospecific inhibition of monoamine uptake transporters by meta-hydroxyephedrine isomers.	2002 Oct	12373557
Severe adverse drug reactions due to pseudoephedrine from over-the-counter medications.	2002 Sep	12492550
[Toxic dermatitis caused by pseudoephedrine: apropos of a case].	2002 Sep	12389444
Efficacy of once-daily desloratadine/pseudoephedrine for relief of nasal congestion.	2002 Sep-Oct	12476542
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	12785122
Surfing, self-medicating and safety: buying non-prescription and complementary medicines via the internet.	2003 Apr	12679503
Stroke associated with sympathomimetics contained in over-the-counter cough and cold drugs.	2003 Jul	12791938
Chiral analysis of amphetamine-type stimulants using reversed-polarity capillary electrophoresis/positive ion electrospray ionization tandem mass spectrometry.	2003 Jun	12783454
Safety of selegiline with cold medications.	2003 Mar	12639177
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	12752651
A comparative study of root canal preparation using FlexMaster and HERO 642 rotary Ni-Ti instruments.	2003 May	12752650

Patents

Sample Use Guides

In Vivo Use Guide

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

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:21:38 GMT 2023` Edited by `admin` on `Fri Dec 15 15:21:38 GMT 2023`
Record UNII	7CUC9DDI9F
Record Status	`Validated (UNII)`
Record Version

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Related Record	Type

Name

Type

Language

PSEUDOEPHEDRINE

Official Name

English

(1S,2S)-(+)-PSEUDOEPHEDRINE

Common Name

English

(.ALPHA.S)-.ALPHA.-((1R)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL

Systematic Name

English

(+)-(1S,2S)-PSEUDOEPHEDRINE

Common Name

English

PSEUDOEPHEDRINE [VANDF]

Common Name

English

EPHEDRINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]

Common Name

English

ACUNASO

Brand Name

English

1-(S),2-(R)-ERYTHRO-(+)-EPHEDRINE

Common Name

English

BENZENEMETHANOL, .ALPHA.-((1S)-1-(METHYLAMINO)ETHYL)-, (.ALPHA.S)-

Systematic Name

English

pseudoephedrine [INN]

Common Name

English

PSEUDOEPHEDRINE [HSDB]

Common Name

English

(+)-THREO-EPHEDRINE

Common Name

English

PSEUDOEPHEDRINE [MI]

Common Name

English

PSEUDOEPHEDRINE [MART.]

Common Name

English

Pseudoephedrine [WHO-DD]

Common Name

English

ISOEPHEDRINE, D-

Common Name

English

BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (S-(R*,R*))-

Systematic Name

English

(+)-PSEUDOEPHEDRINE

Common Name

English

PSEUDOEPHEDRINE, (+)-

Common Name

English

NEODURASINA

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QR01BA02