U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula 2C9H13NO.H2O4S
Molecular Weight 400.49
Optical Activity ( + / - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLPROPANOLAMINE SULFATE

SMILES

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

InChI

InChIKey=QSGAFDSLNHRMIQ-SMBKYJPPSA-N
InChI=1S/2C9H13NO.H2O4S/c2*1-7(10)9(11)8-5-3-2-4-6-8;1-5(2,3)4/h2*2-7,9,11H,10H2,1H3;(H2,1,2,3,4)/t2*7-,9-;/m00./s1

HIDE SMILES / InChI

Molecular Formula C9H13NO
Molecular Weight 151.2056
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
Curator's Comment: Description was created based on several sources, including http://www.druginfosys.com/drug.aspx?drugcode=569&type=1 | https://www.drugs.com/dosage/phenylpropanolamine.html | https://www.petcarerx.com/medication-guides/about-the-proin-dosage-for-urinary-incontinence/1086?page=all | https://www.federalregister.gov/documents/2014/02/20/2014-03596/phenylpropanolamine-withdrawal-of-approval-of-13-new-drug-applications-and-7-abbreviated-new-drug

Phenylpropanolamine belongs to the sympathomimetic amine class of drugs and is structurally related to ephedrine. The effects of phenylpropanolamine are largely the result of alpha-adrenergic agonist activity resulting from both direct stimulation of adrenergic receptors and release of neuronal norepinephrine. Phenylpropanolamine is mainly used as a nasal decongestant. Phenylpropanolamine is also used as anorexiant in obesity and to treat urinary incontinence in veteranary. Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.

Originator

Sources: C. Mannich and W. Jacobsohn, Ber., 43, 189 (1910).
Curator's Comment: reference retrieved from http://www.sciencedirect.com/science/article/pii/S0099542808601719?via%3Dihub

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
PHENYLPROPANOLAMINE

Approved Use

Phenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity
Primary
PHENYLPROPANOLAMINE

Approved Use

Phenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity
Primary
CODAMINE

Approved Use

Unknown

Launch Date

2000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
107 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLPROPANOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1104 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLPROPANOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLPROPANOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Co-administed with::
brompheniramine, p.o(36 mg, single)
Sources: Page: p.825
healthy, 14
n = 1
Health Status: healthy
Age Group: 14
Sex: F
Population Size: 1
Sources: Page: p.825
Disc. AE: Cardiomyopathy...
AEs leading to
discontinuation/dose reduction:
Cardiomyopathy
Sources: Page: p.825
25 mg 2 times / day multiple, oral
Recommended
Dose: 25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 25 mg, 2 times / day
Sources: Page: p.100
healthy, 25
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 25
Sex: F
Population Size: 1
Sources: Page: p.100
Disc. AE: Myocardial infarction...
AEs leading to
discontinuation/dose reduction:
Myocardial infarction
Sources: Page: p.100
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Co-administed with::
caffeine, p.o(8 g, single)
Sources: Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources: Page: p.52
Disc. AE: Vomiting, Hypertension...
AEs leading to
discontinuation/dose reduction:
Vomiting
Hypertension
Sources: Page: p.52
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: Page: p.510
Disc. AE: Headache, Vomiting...
AEs leading to
discontinuation/dose reduction:
Headache (severe)
Vomiting
Intracranial hemorrhage
Sources: Page: p.510
AEs

AEs

AESignificanceDosePopulation
Cardiomyopathy Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Co-administed with::
brompheniramine, p.o(36 mg, single)
Sources: Page: p.825
healthy, 14
n = 1
Health Status: healthy
Age Group: 14
Sex: F
Population Size: 1
Sources: Page: p.825
Myocardial infarction Disc. AE
25 mg 2 times / day multiple, oral
Recommended
Dose: 25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 25 mg, 2 times / day
Sources: Page: p.100
healthy, 25
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 25
Sex: F
Population Size: 1
Sources: Page: p.100
Hypertension Disc. AE
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Co-administed with::
caffeine, p.o(8 g, single)
Sources: Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources: Page: p.52
Vomiting Disc. AE
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Co-administed with::
caffeine, p.o(8 g, single)
Sources: Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources: Page: p.52
Intracranial hemorrhage Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: Page: p.510
Vomiting Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: Page: p.510
Headache severe
Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: Page: p.510
PubMed

PubMed

TitleDatePubMed
Nifedipine therapy of phenylpropanolamine-induced hypertension.
1987 Feb
Alpha and beta adrenergic receptor involvement in catecholamine-induced growth of gram-negative bacteria.
1993 Jan 29
Phenylpropanolamine-induced psychosis. Potential predisposing factors.
1994 Sep
Dystonic reaction following recommended use of a cold syrup.
1995 Dec
Analysis of multicomponent formulations containing phenylpropanolamine hydrochloride, caffeine and diazepam by using LC.
2001 Jun
Clarification--Drug risk in patients with glaucoma.
2001 Jun 11
Tolterodine once-daily: superior efficacy and tolerability in the treatment of the overactive bladder.
2001 Mar
Tolterodine: an overview.
2001 Nov
Pharmacological properties of A-204176, a novel and selective alpha1A adrenergic agonist, in in vitro and in vivo models of urethral function.
2001 Nov 30
Intense and recurrent déjà vu experiences related to amantadine and phenylpropanolamine in a healthy male.
2001 Sep
Effect of tolterodine on the anticoagulant actions and pharmacokinetics of single-dose warfarin in healthy volunteers.
2002
Maternal medication use and risks of gastroschisis and small intestinal atresia.
2002 Jan 1
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
Different responses to drugs against overactive bladder in detrusor muscle of pig, guinea pig and mouse.
2002 Nov 1
Treatment of overactive bladder: the Antimuscarinic Clinical Effectiveness Trial.
2002 Oct
A randomized controlled trial of tolterodine and oxybutynin on tolerability and clinical efficacy for treating Chinese women with an overactive bladder.
2002 Sep
Adrenergic drugs for urinary incontinence in adults.
2003
Quantifying errors without random sampling.
2003 Jun 12
Cerebral infarcts in a pediatric patient secondary to phenylpropanolamine, a recalled medication.
2004 Apr
Hidden amphetamines: from smoking cessation to diabetes.
2004 Feb
Fatal pulmonary arterial hypertension associated with phenylpropanolamine exposure.
2004 Jul
A validated chiral HPLC method for the enantiomeric separation of tolterodine tartarate.
2004 Sep 3
Pharmacological management of overactive bladder : a systematic and critical review of published economic evaluations.
2005
Antimuscarinic agents exhibit local inhibitory effects on muscarinic receptors in bladder-afferent pathways.
2005 Feb
Should we switch over to tolterodine in every child with non-neurogenic daytime urinary incontinence in whom oxybutynin failed?
2005 Feb
[Therapy of bladder weakness].
2005 Jan 21
Comparison of symptom severity and treatment response in patients with incontinent and continent overactive bladder.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Juvenile pig detrusor: effects of propiverine and three of its metabolites.
2005 Nov 7
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.
2005 Oct 15
Effects of bladder training and/or tolterodine in female patients with overactive bladder syndrome: a prospective, randomized study.
2006 Dec
[Comment on the STAR study: Comparison of the efficacy and tolerance of solifenacin and tolterodine retard in the treatment of overactive bladder].
2006 Jul
Tolterodine extended release improves patient-reported outcomes in overactive bladder: results from the IMPACT trial.
2006 Jun
Tolterodine.
2006 Jun 6-12
Using anticholinergics to treat overactive bladder: the issue of treatment tolerability.
2006 Mar
Mass spectrometric data characteristics of commonly abused amphetamines with sequential derivatization at two active sites.
2006 Sep 12
[Stroke and phenylpropanolamine: what risk factors and what recommendations in request?].
2007
Protracted 'pro-addictive' phenotype produced in mice by pre-adolescent phenylpropanolamine.
2007 Aug
Mixed urinary incontinence: continuing to confound?
2007 Dec
Treatment of men with lower urinary tract symptoms and overactive bladder.
2007 Mar 21
Efficacy and safety of combined therapy with terazosin and tolteradine for patients with lower urinary tract symptoms associated with benign prostatic hyperplasia: a prospective study.
2007 Mar 5
The nonmedical use of prescription ADHD medications: results from a national Internet panel.
2007 Oct 31
Transcriptional interruption of cAMP response element binding protein modulates superoxide dismutase and neuropeptide Y-mediated feeding behavior in freely moving rats.
2008 May
Extended-release tolterodine with or without tamsulosin in men with lower urinary tract symptoms and overactive bladder: effects on urinary symptoms assessed by the International Prostate Symptom Score.
2008 Nov
How many drugs for LUTS due to BPH are too many?
2008 Sep
Transdermal delivery of tolterodine by O-acylmenthol: In vitro/in vivo correlation.
2009 Jun 5
Ephedra alkaloids inhibit platelet aggregation.
2010 Apr
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Cystoscopic diagnosis and treatment of ectopic ureters in female dogs: 16 cases (2005-2008).
2010 Jul 15
Targeting oxidative stress in the hypothalamus: the effect of transcription factor STAT3 knockdown on endogenous antioxidants-mediated appetite control.
2015 Jan
Patents

Sample Use Guides

Usual Adult Dose for Nasal Congestion 25 mg (Phenylpropanolamine) orally every 4 hours
Route of Administration: Nasal
In Vitro Use Guide
Curator's Comment: phenylpropanolamine inhibits platelet aggregation
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 14:32:27 GMT 2023
Edited
by admin
on Sat Dec 16 14:32:27 GMT 2023
Record UNII
TQA3O9M79V
Record Status Validated (UNII)
Record Version
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Name Type Language
PHENYLPROPANOLAMINE SULFATE
WHO-DD  
Common Name English
Phenylpropanolamine sulfate [WHO-DD]
Common Name English
PHENYLPROPANOLAMINE SULPHATE
Common Name English
Code System Code Type Description
SMS_ID
300000035981
Created by admin on Sat Dec 16 14:32:27 GMT 2023 , Edited by admin on Sat Dec 16 14:32:27 GMT 2023
PRIMARY
ECHA (EC/EINECS)
214-457-0
Created by admin on Sat Dec 16 14:32:27 GMT 2023 , Edited by admin on Sat Dec 16 14:32:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID40920970
Created by admin on Sat Dec 16 14:32:27 GMT 2023 , Edited by admin on Sat Dec 16 14:32:27 GMT 2023
PRIMARY
PUBCHEM
76966052
Created by admin on Sat Dec 16 14:32:27 GMT 2023 , Edited by admin on Sat Dec 16 14:32:27 GMT 2023
PRIMARY
CAS
1130-06-9
Created by admin on Sat Dec 16 14:32:27 GMT 2023 , Edited by admin on Sat Dec 16 14:32:27 GMT 2023
PRIMARY
FDA UNII
TQA3O9M79V
Created by admin on Sat Dec 16 14:32:27 GMT 2023 , Edited by admin on Sat Dec 16 14:32:27 GMT 2023
PRIMARY
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