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Details

Stereochemistry MIXED
Molecular Formula C9H13NO.C4H6O6
Molecular Weight 301.2925
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0
Stereo Comments Phenylpropanolamine is racemic and Tartaric acid chiral

SHOW SMILES / InChI
Structure of PHENYLPROPANOLAMINE BITARTRATE

SMILES

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

InChI

InChIKey=NCHHVLCKEUNWNJ-IOJVUJSNSA-N
InChI=1S/C9H13NO.C4H6O6/c1-7(10)9(11)8-5-3-2-4-6-8;5-1(3(7)8)2(6)4(9)10/h2-7,9,11H,10H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t7-,9-;1-,2-/m01/s1

HIDE SMILES / InChI
Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C9H13NO
Molecular Weight 151.2056
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.

CNS Activity

Originator

Mannich, C.|Jacobsohn, W.
9
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

1941
158
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Agonist
2678
Agonist
2678
 9.8 µM [Ki]
Agonist
2678
 280.0 µM [EC50]
Agonist
2678
 8.4 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
504
Unknown

Approved Use

Unknown
Primary
Not Provided
504
Unknown

Approved Use

Unknown
Primary
Withdrawn
PHENYLPROPANOLAMINE

Approved Use

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Withdrawn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

Approved Use

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Withdrawn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

Approved Use

Unknown

Launch Date

2000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

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:
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

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:
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

Sourcing

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

PubMed

TitleDatePubMed
Intracranial hemorrhages due to phenylpropanolamine.
1985 May-Jun
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
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
Don't be so quick to ban medications.
2002 Jan 8
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
Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing.
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
Both alpha1-adrenergic and D(1)-dopaminergic neurotransmissions are involved in phenylpropanolamine-mediated feeding suppression in mice.
2003 Aug 21
Simplified bladder training augments the effectiveness of tolterodine in patients with an overactive bladder.
2003 Jan
Use of Ephedra-containing products and risk for hemorrhagic stroke.
2003 Jan 14
Intracellular signaling pathways for norepinephrine- and endothelin-1-mediated regulation of myocardial cell apoptosis.
2004 Apr
Impact of a health education intervention in overactive bladder patients.
2004 Dec
Intramolecular chiral relay at stereogenic nitrogen. Synthesis and application of a new chiral auxiliary derived from (1R,2S)-norephedrine and acetone.
2004 Feb 6
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
Tolterodine for the treatment of overactive bladder: a review.
2005 Apr
[Therapy of bladder weakness].
2005 Jan 21
Economic impact of extended-release tolterodine versus immediate- and extended-release oxybutynin among commercially insured persons with overactive bladder.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Validation of the urgency perception scale.
2005 Mar
Juvenile pig detrusor: effects of propiverine and three of its metabolites.
2005 Nov 7
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
Comparative evaluation of efficacy of use of tamsulosin and/or tolterodine for medical treatment of distal ureteral stones.
2007 Apr
Protracted 'pro-addictive' phenotype produced in mice by pre-adolescent phenylpropanolamine.
2007 Aug
Treatment of men with lower urinary tract symptoms and overactive bladder.
2007 Mar 21
Transcriptional interruption of cAMP response element binding protein modulates superoxide dismutase and neuropeptide Y-mediated feeding behavior in freely moving rats.
2008 May
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
How many drugs for LUTS due to BPH are too many?
2008 Sep
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
Khat use and neurobehavioral functions: suggestions for future studies.
2010 Dec 1
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
Targeting oxidative stress in the hypothalamus: the effect of transcription factor STAT3 knockdown on endogenous antioxidants-mediated appetite control.
2015 Jan
Patents

Patents

JP2000516204A
66
JP2001335473A
9
JP2003511458A
17
JP2007513168A
10
JPH02133A
9
JPH10203971A
9
JPS59184168A
9

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
Curator's Comment: phenylpropanolamine inhibits platelet aggregation
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:16:41 GMT 2023
Edited
by admin
on Fri Dec 15 15:16:41 GMT 2023
Record UNII
B48FTC099P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYLPROPANOLAMINE BITARTRATE
USP   USP-RS   WHO-DD  
Common Name English
(R*,S*)-(±)-.ALPHA.-(1-AMINOETHYL)BENZENEMETHANOL BITARTRATE
Systematic Name English
Phenylpropanolamine bitartrate [WHO-DD]
Common Name English
PHENYLPROPANOLAMINE BITARTRATE [USP IMPURITY]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C87053
Created by admin on Fri Dec 15 15:16:41 GMT 2023 , Edited by admin on Fri Dec 15 15:16:41 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
266-617-4
Created by admin on Fri Dec 15 15:16:41 GMT 2023 , Edited by admin on Fri Dec 15 15:16:41 GMT 2023
PRIMARY
SMS_ID
100000085299
Created by admin on Fri Dec 15 15:16:41 GMT 2023 , Edited by admin on Fri Dec 15 15:16:41 GMT 2023
PRIMARY
NCI_THESAURUS
C84053
Created by admin on Fri Dec 15 15:16:41 GMT 2023 , Edited by admin on Fri Dec 15 15:16:41 GMT 2023
PRIMARY
EVMPD
SUB03781MIG
Created by admin on Fri Dec 15 15:16:41 GMT 2023 , Edited by admin on Fri Dec 15 15:16:41 GMT 2023
PRIMARY
CAS
67244-90-0
Created by admin on Fri Dec 15 15:16:41 GMT 2023 , Edited by admin on Fri Dec 15 15:16:41 GMT 2023
PRIMARY
ChEMBL
CHEMBL61006
Created by admin on Fri Dec 15 15:16:41 GMT 2023 , Edited by admin on Fri Dec 15 15:16:41 GMT 2023
PRIMARY
FDA UNII
B48FTC099P
Created by admin on Fri Dec 15 15:16:41 GMT 2023 , Edited by admin on Fri Dec 15 15:16:41 GMT 2023
PRIMARY
PUBCHEM
118984428
Created by admin on Fri Dec 15 15:16:41 GMT 2023 , Edited by admin on Fri Dec 15 15:16:41 GMT 2023
PRIMARY
RXCUI
221140
Created by admin on Fri Dec 15 15:16:41 GMT 2023 , Edited by admin on Fri Dec 15 15:16:41 GMT 2023
PRIMARY RxNorm
Related Record Type Details
Structure of PHENYLPROPANOLAMINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PHENYLPROPANOLAMINE
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