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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO.ClH
Molecular Weight 187.667
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLPROPANOLAMINE HYDROCHLORIDE, (+)-

SMILES

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

InChI

InChIKey=DYWNLSQWJMTVGJ-PRCZDLBKSA-N
InChI=1S/C9H13NO.ClH/c1-7(10)9(11)8-5-3-2-4-6-8;/h2-7,9,11H,10H2,1H3;1H/t7-,9-;/m1./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 ClH
Molecular Weight 36.461
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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.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

9.700992E11
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
Positive phentolamine test in hypertension induced by a nasal decongestant.
1969 Apr 17
Phenylpropanolamine-associated headache.
1985 Apr
Failure of tolterodine to treat clozapine-induced nocturnal enuresis.
2001 Jul-Aug
Clarification--Drug risk in patients with glaucoma.
2001 Jun 11
Tolterodine: an overview.
2001 Nov
The effect of tolterodine on the pharmacokinetics and pharmacodynamics of a combination oral contraceptive containing ethinyl estradiol and levonorgestrel.
2001 Nov
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
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
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
Both alpha1-adrenergic and D(1)-dopaminergic neurotransmissions are involved in phenylpropanolamine-mediated feeding suppression in mice.
2003 Aug 21
Implementation of the Methamphetamine Anti-Proliferation Act; thresholds for retailers and for distributors required to submit mail order reports; changes to mail order reporting requirements. Final rule.
2003 Oct 7
Impact of a health education intervention in overactive bladder patients.
2004 Dec
The fitness of copings constructed over UCLA abutments and the implant, constructed by different techniques: casting and casting with laser welding.
2004 Dec
Examination of aqueous oxidized cellulose dispersions as a potential drug carrier. I. Preparation and characterization of oxidized cellulose-phenylpropanolamine complexes.
2004 Oct 8
A validated chiral HPLC method for the enantiomeric separation of tolterodine tartarate.
2004 Sep 3
Tolterodine for the treatment of overactive bladder: a review.
2005 Apr
Should we switch over to tolterodine in every child with non-neurogenic daytime urinary incontinence in whom oxybutynin failed?
2005 Feb
Medical costs after initiation of drug treatment for overactive bladder: effects of selection bias on cost estimates.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Validation of the urgency perception scale.
2005 Mar
Tolterodinium (+)-(2R,3R)-hydrogen tartrate.
2005 Mar
Nighttime dosing with tolterodine reduces overactive bladder-related nocturnal micturitions in patients with overactive bladder and nocturia.
2006 Apr
Tolterodine extended release improves patient-reported outcomes in overactive bladder: results from the IMPACT trial.
2006 Jun
Using anticholinergics to treat overactive bladder: the issue of treatment tolerability.
2006 Mar
Protracted 'pro-addictive' phenotype produced in mice by pre-adolescent phenylpropanolamine.
2007 Aug
Efficacy of combined anticholinergic treatment and behavioral modification as a first line treatment for nonneurogenic and nonanatomical voiding dysfunction in children: a randomized controlled trial.
2007 Jun
The nonmedical use of prescription ADHD medications: results from a national Internet panel.
2007 Oct 31
Comparison of fesoterodine and tolterodine in patients with overactive bladder.
2008 Nov
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
Cost-effectiveness analysis of solifenacin flexible dosing in patients with overactive bladder symptoms in four Nordic countries.
2009
Keep an eye on the pupil: developing countries under chemical attack.
2009 Jun
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
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.
2010 Feb 25
Proof of principle: The effect of antimuscarinics on bladder filling sensations in healthy subjects--a placebo controlled double blind investigation using 4 and 8 mg tolterodine extended release.
2010 Mar
Syndrome of inappropriate antidiuretic hormone associated with tolterodine therapy.
2010 May
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 10:59:35 UTC 2023
Edited
by admin
on Sat Dec 16 10:59:35 UTC 2023
Record UNII
184M412SJH
Record Status Validated (UNII)
Record Version
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Name Type Language
PHENYLPROPANOLAMINE HYDROCHLORIDE, (+)-
Common Name English
D-PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
PHENYLPROPANOLAMINE (+)-FORM HYDROCHLORIDE [MI]
Common Name English
(1S,2R)-NOREPHEDRINE HYDROCHLORIDE
Common Name English
(+)-PHENYLPROPANOLAMINE HYDROCHLORIDE
Common Name English
(1S,2R)-(+)-NOREPHEDRINE HYDROCHLORIDE
Common Name English
BENZENEMETHANOL, .ALPHA.-((1R)-1-AMINOETHYL)-, HYDROCHLORIDE (1:1), (.ALPHA.S)-
Systematic Name English
(+)-NOREPHEDRINE HYDROCHLORIDE
Common Name English
Code System Code Type Description
MERCK INDEX
m8687
Created by admin on Sat Dec 16 10:59:35 UTC 2023 , Edited by admin on Sat Dec 16 10:59:35 UTC 2023
PRIMARY Merck Index
FDA UNII
184M412SJH
Created by admin on Sat Dec 16 10:59:35 UTC 2023 , Edited by admin on Sat Dec 16 10:59:35 UTC 2023
PRIMARY
CAS
40626-29-7
Created by admin on Sat Dec 16 10:59:35 UTC 2023 , Edited by admin on Sat Dec 16 10:59:35 UTC 2023
PRIMARY
PUBCHEM
6433169
Created by admin on Sat Dec 16 10:59:35 UTC 2023 , Edited by admin on Sat Dec 16 10:59:35 UTC 2023
PRIMARY
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ENANTIOMER -> ENANTIOMER
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