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Details

Stereochemistry RACEMIC
Molecular Formula C9H13NO.C4H4O4
Molecular Weight 267.2778
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PHENYLPROPANOLAMINE MALEATE

SMILES

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

InChI

InChIKey=PMRCIPUNYJFMII-LBTDPVFMSA-N
InChI=1S/C9H13NO.C4H4O4/c1-7(10)9(11)8-5-3-2-4-6-8;5-3(6)1-2-4(7)8/h2-7,9,11H,10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/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 C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
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 is an enantiomer of propanolamine. The substance has low adrenergic activity and exerts measurable physiological effect only at high doses, which were lethal to experimental animals tested. 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 Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.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
Intracranial hemorrhages due to phenylpropanolamine.
1985 May-Jun
Nifedipine therapy of phenylpropanolamine-induced hypertension.
1987 Feb
Failure of tolterodine to treat clozapine-induced nocturnal enuresis.
2001 Jul-Aug
Analysis of multicomponent formulations containing phenylpropanolamine hydrochloride, caffeine and diazepam by using LC.
2001 Jun
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.
2001 May
Tolterodine: an overview.
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
Treatment of overactive bladder: the Antimuscarinic Clinical Effectiveness Trial.
2002 Oct
HPLC determination of phenylpropanolamine in pharmaceutical OTC preparations.
2002 Oct
Use of Ephedra-containing products and risk for hemorrhagic stroke.
2003 Jan 14
The fitness of copings constructed over UCLA abutments and the implant, constructed by different techniques: casting and casting with laser welding.
2004 Dec
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
Nocturnal enuresis in children. A four-year experience in outpatient clinics of pediatric urology.
2005
[Therapy of bladder weakness].
2005 Jan 21
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
Determination of ephedrine and related compounds in pharmaceutical preparations by ion chromatography with direct conductivity detection.
2005 May
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
Efficacy and tolerability of tolterodine extended-release in men with overactive bladder and urgency urinary incontinence.
2006 May
Relationships among symptoms, bother, and treatment satisfaction in overactive bladder patients.
2007
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
Effect of tolterodine on sleep structure modulated by CYP2D6 genotype.
2008 Jul
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
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
Transobturator vaginal tape inside out for treatment of urethral sphincter mechanism incompetence: preliminary results in 7 female dogs.
2010 Dec
Cystoscopic diagnosis and treatment of ectopic ureters in female dogs: 16 cases (2005-2008).
2010 Jul 15
Patents

Sample Use Guides

Usual Adult Dose for Nasal Congestion 25 mg orally every 4 hours. -or- 75 mg orally extended release every 12 hours. Not to exceed 150 mg/day. Usual Adult Dose for Weight Loss 25 mg orally 3 times a day, one-half hour before meals. -or- 75 mg orally extended release once a day in the morning. The use of phenylpropanolamine for weight loss should be limited to 12 weeks.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: phenylpropanolamine inhibits platelet aggregation
Unknown
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:02:06 UTC 2023
Edited
by admin
on Wed Jul 05 23:02:06 UTC 2023
Record UNII
86ILV507ZN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYLPROPANOLAMINE MALEATE
Common Name English
Code System Code Type Description
PUBCHEM
76960503
Created by admin on Wed Jul 05 23:02:06 UTC 2023 , Edited by admin on Wed Jul 05 23:02:06 UTC 2023
PRIMARY
FDA UNII
86ILV507ZN
Created by admin on Wed Jul 05 23:02:06 UTC 2023 , Edited by admin on Wed Jul 05 23:02:06 UTC 2023
PRIMARY
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