PSEUDOEPHEDRINE SULFATE

US Approved OTC

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C10H15NO.H2O4S
Molecular Weight	428.543
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.CN[C@@H](C)[C@@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@@H](O)C2=CC=CC=C2

InChI

InChIKey=CAVQBDOACNULDN-NRCOEFLKSA-N

InChI=1S/2C10H15NO.H2O4S/c2*1-8(11-2)10(12)9-6-4-3-5-7-9;1-5(2,3)4/h2*3-8,10-12H,1-2H3;(H2,1,2,3,4)/t2*8-,10+;/m00./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

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
A Double-blind crossover trial of pseudoephedrine and triprolidine, alone and in combination, for the treatment of allergenic rhinitis.	1975 Jan	1098524
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
Angle closure risk from proprietary medicines.	2001 Apr	11339612
Mass spectrometric quantitation of chiral drugs by the kinetic method.	2001 Apr 15	11338581
Ischaemic colitis on pseudoephedrine.	2001 Aug	11718182
Hypokalemic metabolic acidosis attributed to cough mixture abuse.	2001 Aug	11479167
Cost-effectiveness of urinary dipsticks to screen asymptomatic catheter-associated urinary infections in an intensive care unit.	2001 Dec	11797017
Effect of organic cations on the renal tubular secretion of pseudoephedrine in the rat.	2001 Jan-Feb	11153535
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	11508270
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	11259059
[Cost effectiveness of GM-CSF in the treatment of acute myeloblastic leukemia in aged patients: protocol of GOELAM Sa3].	2001 Mar-Apr	11471363
Cardiovascular sympathomimetic amine interactions in rats treated with monoamine oxidase inhibitors and the novel oxazolidinone antibiotic linezolid.	2001 May	11336106
Epinephrine analogues.	2001 Nov	12806441
Chloroephedrine: contaminant of methamphetamine synthesis with cardiovascular activity.	2001 Nov 1	11672944
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
Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry.	2001 Sep	11565946
Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes.	2001 Sep 5	11530984
Myocardial infarction temporally related to ephedra--a possible role for the coronary microcirculation.	2002	12426924
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
Evaluation of a pseudoephedrine linker for asymmetric alkylations on solid phase.	2002 Dec 26	12489935
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
Modifying the bitterness of selected oral pharmaceuticals with cation and anion series of salts.	2002 Jul	12180534
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	11922057
Enhanced enantio- and diastereoselectivity via confinement and cation binding: yang photocyclization of 2-benzoyladamantane derivatives within zeolites.	2002 Nov 29	12444610
[Cutaneous complications following liver transplantation: epidemiologic and clinical study in 86 patients].	2002 Oct	12442126
Enzymatic (R)-phenylacetylcarbinol production in benzaldehyde emulsions.	2002 Oct	12382047
Stereospecific inhibition of monoamine uptake transporters by meta-hydroxyephedrine isomers.	2002 Oct	12373557
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
Sensitive determination of ephedrine and pseudoephedrine by capillary electrophoresis with laser-induced fluorescence detection.	2003 Apr	12741643
Surfing, self-medicating and safety: buying non-prescription and complementary medicines via the internet.	2003 Apr	12679503
Nonpigmenting solitary fixed drug eruption caused by a Chinese traditional herbal medicine, ma huang (Ephedra Hebra), mainly containing pseudoephedrine and ephedrine.	2003 Apr	12664035
Separation and determination of ephedrine and pseudoephedrine by combination of flow injection with capillary electrophoresis.	2003 Jan	12597588
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
[Tobacco: knowledge, reasoning and opinion of high school students in Doubs. Reflections on prevention].	2003 Mar	12806810
Safety of selegiline with cold medications.	2003 Mar	12639177
Adrenaline given outside the context of life threatening allergic reactions.	2003 Mar 15	12637407
Spectrophotometric determination of binary mixtures of pseudoephedrine with some histamine H1-receptor antagonists using derivative ratio spectrum method.	2003 Mar 26	12644207
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

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 15:09:28 GMT 2023` Edited by `admin` on `Fri Dec 15 15:09:28 GMT 2023`
Record UNII	Y9DL7QPE6B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PSEUDOEPHEDRINE SULFATE

Official Name

English

D-PSEUDOEPHEDRINE SULFATE

Common Name

English

PSEUDOEPHEDRINE SULFATE COMPONENT OF CLARINEX-D

Common Name

English

PSEUDOEPHEDRINE SULFATE COMPONENT OF DRIXORAL PLUS

Common Name

English

DISOBROM COMPONENT PSEUDOEPHEDRINE SULFATE

Common Name

English

BROMPHERIL COMPONENT PSEUDOEPHEDRINE SULFATE

Common Name

English

PSEUDOEPHEDRINE SULFATE COMPONENT OF DRIXORAL

Common Name

English

PSEUDOEPHEDRINE SULFATE [MI]

Common Name

English

PSEUDOEPHEDRINE SULFATE COMPONENT OF DISOPHROL

Common Name

English

PSEUDOEPHEDRINE SULFATE [USP-RS]

Common Name

English

RESPORAL COMPONENT PSEUDOEPHEDRINE SULFATE

Common Name

English

PSEUDOEPHEDRINE SULFATE COMPONENT OF RESPORAL

Common Name

English

PSEUDOEPHEDRINE SULFATE [MART.]

Common Name

English

TRINALIN COMPONENT PSEUDOEPHEDRINE SULFATE

Common Name

English

PSEUDOEPHEDRINE SULFATE COMPONENT OF CLARITIN-D

Common Name

English

(+)-PSEUDOEPHEDRINE SULPHATE

Common Name

English

DISOPHROL COMPONENT PSEUDOEPHEDRINE SULFATE

Common Name

English

Pseudoephedrine sulfate [WHO-DD]

Common Name

English

PSEUDOEPHEDRINE SULFATE COMPONENT OF DISOBROM

Common Name

English

PSEUDOEPHEDRINE SULFATE [ORANGE BOOK]

Common Name

English

CLARINEX-D COMPONENT PSEUDOEPHEDRINE SULFATE

Common Name

English

CLARITIN-D COMPONENT PSEUDOEPHEDRINE SULFATE

Common Name

English

SCH-4855

Code

English

(+)-PSEUDOEPHEDRINE SULFATE

Common Name

English

SCH 4855

Code

English

PSEUDOEPHEDRINE SULFATE [USP MONOGRAPH]

Common Name

English

PSEUDOEPHEDRINE SULFATE [USAN]

Common Name

English

PSEUDOEPHEDRINE SULPHATE

Common Name

English

DRIXORAL COMPONENT PSEUDOEPHEDRINE SULFATE

Common Name

English

PSEUDOEPHEDRINE SULFATE COMPONENT OF TRINALIN

Common Name

English

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

Common Name

English

PSEUDOEPHEDRINE SULFATE [VANDF]

Common Name

English

PSEUDOEPHEDRINE SULFATE COMPONENT OF BROMPHERIL

Common Name

English

DRIXORAL PLUS COMPONENT PSEUDOEPHEDRINE SULFATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29709