PSEUDOEPHEDRINE

US Approved OTC

First approved in 1961

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H15NO
Molecular Weight	165.2326
Optical Activity	( + )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]([H])([C@]([H])(c1ccccc1)O)NC

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	165.2326
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 164 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15189772 \| https://www.ncbi.nlm.nih.gov/pubmed/12373557	Inhibitor 7728	5.6 µM [IC50]
Norepinephrine transporter 175 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15189772 \| https://www.ncbi.nlm.nih.gov/pubmed/12373557	Inhibitor 7728	1.18 µM [IC50]
Adrenergic receptor alpha 63 Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796	Agonist 2470
Adrenergic receptor beta 86 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10449190	Agonist 2470

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nasal congestion 25 Sources: https://www.drugs.com/ppa/pseudoephedrine.html	Primary		Approved 8043	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 7.2429122E11

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
Cetirizine/pseudoephedrine.	2001	11772135
Ischaemic colitis on pseudoephedrine.	2001 Aug	11718182
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
Epinephrine analogues.	2001 Nov	12806441
Desloratadine reduces nasal congestion in patients with intermittent allergic rhinitis.	2001 Nov	11703222
Chloroephedrine: contaminant of methamphetamine synthesis with cardiovascular activity.	2001 Nov 1	11672944
Biotransformation of benzaldehyde into (R)-phenylacetylcarbinol by filamentous fungi or their extracts.	2001 Oct	11759677
Acute psychosis due to the interaction of legal compounds--ephedra alkaloids in 'vigueur fit' tablets, caffeine in 'red bull' and alcohol.	2001 Oct	11693229
Cathinone (Khat) and methcathinone (CAT) in urine specimens: a gas chromatographic-mass spectrometric detection procedure.	2001 Oct	11599595
Relationship between expansion of the CAG repeat in exon 1 of the androgen receptor gene and idiopathic male infertility.	2001 Oct	11591412
Small-cell carcinoma of the esophagus: report of three cases and review of the literature with emphasis on therapy.	2001 Sep	11697847
Community pharmacists' experience of over-the-counter medicine misuse in Scotland.	2001 Sep	11688306
Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations.	2001 Sep	11593992
Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry.	2001 Sep	11565946
Toxicity of over-the-counter cough and cold medications.	2001 Sep	11533370
Rapid chiral on-chip separation with simplified amperometric detection.	2001 Sep 14	11587341
Analysis of enantiomers giving partially overlapped peaks by using different treatments of the chromatographic ultraviolet signals: quantification of pseudoephedrine enantiomers.	2001 Sep 28	11681584
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
Generalized dermatitis due to pseudoephedrine.	2002 Aug	12121199
Linezolid: its role in the treatment of gram-positive, drug-resistant bacterial infections.	2002 Feb 15	11871684
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
Acoustic rhinometry in the dog: a novel large animal model for studies of nasal congestion.	2002 Jan-Feb	11895194
Onset of action, efficacy, and safety of fexofenadine 60 mg/pseudoephedrine 120 mg versus placebo in the Atlanta allergen exposure unit.	2002 Jul	12141718
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use.	2002 Jun	12087345
Oral medications.	2002 Mar	12012745
Pseudoephedrine as a chiral auxiliary for asymmetric Michael reactions: synthesis of 3-aryl-delta-lactones.	2002 May 30	12027658
A moderate dose of pseudoephedrine does not alter muscle contraction strength or anaerobic power.	2002 Nov	12466695
[Blood supply of the lips].	2002 Oct	12449862
Severe adverse drug reactions due to pseudoephedrine from over-the-counter medications.	2002 Sep	12492550
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
Baboon syndrome due to pseudoephedrine.	2003 Apr	12786741
[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	12784493
Sensitive determination of ephedrine and pseudoephedrine by capillary electrophoresis with laser-induced fluorescence detection.	2003 Apr	12741643
Nonpigmenting solitary fixed drug eruption caused by a Chinese traditional herbal medicine, ma huang (Ephedra Hebra), mainly containing pseudoephedrine and ephedrine.	2003 Apr	12664035
Physiological, subjective and performance effects of pseudoephedrine and phenylpropanolamine during endurance running exercise.	2003 Jan	12582945
Stroke associated with sympathomimetics contained in over-the-counter cough and cold drugs.	2003 Jul	12791938
Development and validation of a capillary zone electrophoresis method for the determination of ephedrine and related compounds in urine without extraction.	2003 Jul 5	12798180
Chiral analysis of amphetamine-type stimulants using reversed-polarity capillary electrophoresis/positive ion electrospray ionization tandem mass spectrometry.	2003 Jun	12783454
[Tobacco: knowledge, reasoning and opinion of high school students in Doubs. Reflections on prevention].	2003 Mar	12806810
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
Canine model of nasal congestion and allergic rhinitis.	2003 May	12547842
Exemption of chemical mixtures containing the List I chemicals ephedrine, N-methylephedrine, N-methylpseudoephedrine, norpseudoephedrine, phenylpropanolamine, and pseudoephedrine. Final rule.	2003 May 1	12725239
Press-coating of immediate release powders onto coated controlled release tablets with adhesives.	2003 May 20	12737841

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 `Sat Jun 26 09:17:56 UTC 2021` Edited by `admin` on `Sat Jun 26 09:17:56 UTC 2021`
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

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 [WHO-DD]

Common Name

English

PSEUDOEPHEDRINE [MI]

Common Name

English

PSEUDOEPHEDRINE [MART.]

Common Name

English

EPHEDRINE HYDROCHLORIDE IMPURITY B [EP]

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