PHENYLPROPANOLAMINE HYDROCHLORIDE, (-)-

US Previously Marketed

First approved in 1941

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, (-)-

Structure Search

SMILES

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

InChI

InChIKey=DYWNLSQWJMTVGJ-KUSKTZOESA-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-;/m0./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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8381276 | https://www.google.com/patents/US5260073http://www.sciencedirect.com/science/article/pii/S0099542808601719?via%3Dihub
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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Adrenergic receptor alpha-1 169 Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8381276	Agonist 2678
Adrenergic receptor alpha 64 Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954796 \| https://www.ncbi.nlm.nih.gov/pubmed/15608085	Agonist 2678
Alpha-1a adrenergic receptor 66 Target ID: CHEMBL319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918	Agonist 2678	9.8 µM [Ki]
Alpha-1b adrenergic receptor 44 Target ID: CHEMBL315 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918	Agonist 2678	280.0 µM [EC50]
Alpha-1d adrenergic receptor 36 Target ID: CHEMBL326 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918	Agonist 2678	8.4 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Sinusitis 26 Sources: https://www.google.com/patents/US5260073	Primary	Not Provided 504	Unknown Approved Use Unknown
Otitis 40 Sources: https://www.google.com/patents/US5260073	Primary	Not Provided 504	Unknown Approved Use Unknown
Nasal congestion 26 Sources: https://www.drugs.com/dosage/phenylpropanolamine.html http://www.druginfosys.com/drug.aspx?drugcode=569&type=1	Primary	Withdrawn	PHENYLPROPANOLAMINE Approved Use Phenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity
Obesity 203 Sources: https://www.drugs.com/dosage/phenylpropanolamine.html http://www.druginfosys.com/drug.aspx?drugcode=569&type=1	Primary	Withdrawn	PHENYLPROPANOLAMINE Approved Use Phenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity
Nasal congestion 26 Sources: https://www.drugs.com/comments/phenylpropanolamine/	Primary	Withdrawn	CODAMINE Approved Use Unknown Launch Date 2000

C_max

Value	Dose	Co-administered	Analyte	Population
107 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11361053/	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

Value	Dose	Co-administered	Analyte	Population
1104 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11361053/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11361053/	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/7901355 Page: p.825	healthy, 14 n = 1 Health Status: healthy Age Group: 14 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7901355 Page: p.825	Disc. AE: Cardiomyopathy... AEs leading to discontinuation/dose reduction: Cardiomyopathy Sources: https://pubmed.ncbi.nlm.nih.gov/7901355 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: https://pubmed.ncbi.nlm.nih.gov/12734532 Page: p.100	healthy, 25 n = 1 Health Status: healthy Condition: Weight control Age Group: 25 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/12734532 Page: p.100	Disc. AE: Myocardial infarction... AEs leading to discontinuation/dose reduction: Myocardial infarction Sources: https://pubmed.ncbi.nlm.nih.gov/12734532 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: https://pubmed.ncbi.nlm.nih.gov/7055513 Page: p.52	unhealthy, 31 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 31 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7055513 Page: p.52	Disc. AE: Vomiting, Hypertension... AEs leading to discontinuation/dose reduction: Vomiting Hypertension Sources: https://pubmed.ncbi.nlm.nih.gov/7055513 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: https://pubmed.ncbi.nlm.nih.gov/4002267 Page: p.510	healthy, 56 n = 1 Health Status: healthy Condition: Weight control Age Group: 56 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4002267 Page: p.510	Disc. AE: Headache, Vomiting... AEs leading to discontinuation/dose reduction: Headache (severe) Vomiting Intracranial hemorrhage Sources: https://pubmed.ncbi.nlm.nih.gov/4002267 Page: p.510

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/7901355 Page: p.825	healthy, 14 n = 1 Health Status: healthy Age Group: 14 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7901355 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: https://pubmed.ncbi.nlm.nih.gov/12734532 Page: p.100	healthy, 25 n = 1 Health Status: healthy Condition: Weight control Age Group: 25 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/12734532 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: https://pubmed.ncbi.nlm.nih.gov/7055513 Page: p.52	unhealthy, 31 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 31 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7055513 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: https://pubmed.ncbi.nlm.nih.gov/7055513 Page: p.52	unhealthy, 31 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 31 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7055513 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: https://pubmed.ncbi.nlm.nih.gov/4002267 Page: p.510	healthy, 56 n = 1 Health Status: healthy Condition: Weight control Age Group: 56 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4002267 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: https://pubmed.ncbi.nlm.nih.gov/4002267 Page: p.510	healthy, 56 n = 1 Health Status: healthy Condition: Weight control Age Group: 56 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4002267 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: https://pubmed.ncbi.nlm.nih.gov/4002267 Page: p.510	healthy, 56 n = 1 Health Status: healthy Condition: Weight control Age Group: 56 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4002267 Page: p.510

Sourcing

Vendor/Aggregator	ID	URL
ChemIDplus	67244900	https://chem.nlm.nih.gov/chemidplus/id/0067244900
PubChem	118984428	https://pubchem.ncbi.nlm.nih.gov/compound/118984428
Wikidata	Q27274344

PubMed

Title	Date	PubMed
Positive phentolamine test in hypertension induced by a nasal decongestant.	1969 Apr 17	4180300
Phenylpropanolamine-associated headache.	1985 Apr	3976619
Intracerebral hemorrhage and phenylpropanolamine use.	1987 Mar	3822132
[Cerebral hemorrhage associated with the use of phenylpropanolamine. Clinical cases].	1996 Dec	9334487
Detrol LA and Diropan XL for overactive bladder.	2001 Apr 2	11283473
Failure of tolterodine to treat clozapine-induced nocturnal enuresis.	2001 Jul-Aug	11485135
Analysis of multicomponent formulations containing phenylpropanolamine hydrochloride, caffeine and diazepam by using LC.	2001 Jun	11377029
Tolterodine once-daily: superior efficacy and tolerability in the treatment of the overactive bladder.	2001 Mar	11248608
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.	2001 May	11361053
The effect of tolterodine on the pharmacokinetics and pharmacodynamics of a combination oral contraceptive containing ethinyl estradiol and levonorgestrel.	2001 Nov	11768839
A TLC visualisation reagent for dimethylamphetamine and other abused tertiary amines.	2001 Oct-Dec	11793881
Intense and recurrent déjà vu experiences related to amantadine and phenylpropanolamine in a healthy male.	2001 Sep	11535020
Different responses to drugs against overactive bladder in detrusor muscle of pig, guinea pig and mouse.	2002 Nov 1	12409006
Treatment of overactive bladder: the Antimuscarinic Clinical Effectiveness Trial.	2002 Oct	12354340
HPLC determination of phenylpropanolamine in pharmaceutical OTC preparations.	2002 Oct	12378559
Use of Ephedra-containing products and risk for hemorrhagic stroke.	2003 Jan 14	12525737
Quantifying errors without random sampling.	2003 Jun 12	12892568
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	14535265
The fitness of copings constructed over UCLA abutments and the implant, constructed by different techniques: casting and casting with laser welding.	2004 Dec	20976410
Hidden amphetamines: from smoking cessation to diabetes.	2004 Feb	15055218
Examination of aqueous oxidized cellulose dispersions as a potential drug carrier. I. Preparation and characterization of oxidized cellulose-phenylpropanolamine complexes.	2004 Oct 8	15760066
A validated chiral HPLC method for the enantiomeric separation of tolterodine tartarate.	2004 Sep 3	15336373
Effects of solifenacin succinate (YM905) on detrusor overactivity in conscious cerebral infarcted rats.	2005 Apr 4	15814091
Should we switch over to tolterodine in every child with non-neurogenic daytime urinary incontinence in whom oxybutynin failed?	2005 Feb	15708055
[Therapy of bladder weakness].	2005 Jan 21	15650964
Economic impact of extended-release tolterodine versus immediate- and extended-release oxybutynin among commercially insured persons with overactive bladder.	2005 Jul	16161387
Comparison of symptom severity and treatment response in patients with incontinent and continent overactive bladder.	2005 Jul	15967259
Medical costs after initiation of drug treatment for overactive bladder: effects of selection bias on cost estimates.	2005 Jul	16161386
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Determination of ephedrine and related compounds in pharmaceutical preparations by ion chromatography with direct conductivity detection.	2005 May	15651083
[Comment on the STAR study: Comparison of the efficacy and tolerance of solifenacin and tolterodine retard in the treatment of overactive bladder].	2006 Jul	16816976
Efficacy and tolerability of tolterodine extended-release in men with overactive bladder and urgency urinary incontinence.	2006 May	16643482
[Stroke and phenylpropanolamine: what risk factors and what recommendations in request?].	2007	19102094
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	17509350
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	17376305
The nonmedical use of prescription ADHD medications: results from a national Internet panel.	2007 Oct 31	17974020
Development and evaluation of oral controlled release chlorpheniramine-ion exchange resinate suspension.	2008 Jul-Aug	20046790
Effects of serum PSA on efficacy of tolterodine extended release with or without tamsulosin in men with LUTS, including OAB.	2008 Nov	18817961
Cost-effectiveness analysis of solifenacin flexible dosing in patients with overactive bladder symptoms in four Nordic countries.	2009	19384673
Asymmetric conjugate reductions of coumarins. A new route to tolterodine and related coumarin derivatives.	2009 Dec 3	19877705
Mean arterial pressure: therapeutic goals and pharmacologic support.	2010 Apr	20381720
Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography.	2010 Feb 25	20047807
Cystoscopic diagnosis and treatment of ectopic ureters in female dogs: 16 cases (2005-2008).	2010 Jul 15	20632793

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Nasal Congestion 25 mg (Phenylpropanolamine) orally every 4 hours

Route of Administration: Nasal

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:46:44 GMT 2023` Edited by `admin` on `Sat Dec 16 14:46:44 GMT 2023`
Record UNII	B4HG4K9HF5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENYLPROPANOLAMINE HYDROCHLORIDE, (-)-

Common Name

English

BENZENEMETHANOL, .ALPHA.-((1S)-1-AMINOETHYL)-, HYDROCHLORIDE (1:1), (.ALPHA.R)-

Systematic Name

English

(1R,2S)-(-)-NOREPHEDRINE HYDROCHLORIDE

Common Name

English

L-NOREPHEDRINE HYDROCHLORIDE

Common Name

English

(1R,2S)-NOREPHEDRINE HYDROCHLORIDE

Common Name

English

NOREPHEDRINE HYDROCHLORIDE, (-)-

Common Name

English

NSC-24522

Code

English

L-PHENYLPROPANOLAMINE HYDROCHLORIDE

Common Name

English

D-(-)-NOREPHEDRINE HYDROCHLORIDE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID80891190