Details
Stereochemistry | RACEMIC |
Molecular Formula | C9H13NO.ClH |
Molecular Weight | 187.667 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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
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 |
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/8381276 | https://www.google.com/patents/US5260073http://www.sciencedirect.com/science/article/pii/S0099542808601719?via%3DihubCurator'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
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8381276 |
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Target ID: CHEMBL2095203 |
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Target ID: CHEMBL319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918 |
9.8 µM [Ki] | ||
Target ID: CHEMBL315 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918 |
280.0 µM [EC50] | ||
Target ID: CHEMBL326 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918 |
8.4 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.google.com/patents/US5260073 |
Primary | Unknown Approved UseUnknown |
||
Sources: https://www.google.com/patents/US5260073 |
Primary | Unknown Approved UseUnknown |
||
Primary | PHENYLPROPANOLAMINE Approved UsePhenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity |
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Primary | PHENYLPROPANOLAMINE Approved UsePhenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity |
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Primary | CODAMINE Approved UseUnknown Launch Date2000 |
Cmax
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 |
T1/2
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: 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 Sources: Page: p.52Hypertension |
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) Sources: Page: p.510Vomiting Intracranial hemorrhage |
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: 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
Title | Date | PubMed |
---|---|---|
Phenylpropanolamine-associated headache. | 1985 Apr |
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Alpha and beta adrenergic receptor involvement in catecholamine-induced growth of gram-negative bacteria. | 1993 Jan 29 |
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Phenylpropanolamine-induced psychosis. Potential predisposing factors. | 1994 Sep |
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Dystonic reaction following recommended use of a cold syrup. | 1995 Dec |
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[Cerebral hemorrhage associated with the use of phenylpropanolamine. Clinical cases]. | 1996 Dec |
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The overactive bladder in children: a potential future indication for tolterodine. | 2001 Apr |
|
Analysis of multicomponent formulations containing phenylpropanolamine hydrochloride, caffeine and diazepam by using LC. | 2001 Jun |
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Tolterodine: an overview. | 2001 Nov |
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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 |
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Intense and recurrent déjà vu experiences related to amantadine and phenylpropanolamine in a healthy male. | 2001 Sep |
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Effect of tolterodine on the anticoagulant actions and pharmacokinetics of single-dose warfarin in healthy volunteers. | 2002 |
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Maternal medication use and risks of gastroschisis and small intestinal atresia. | 2002 Jan 1 |
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Don't be so quick to ban medications. | 2002 Jan 8 |
|
Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing. | 2002 Oct |
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Treatment of overactive bladder: the Antimuscarinic Clinical Effectiveness Trial. | 2002 Oct |
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A randomized controlled trial of tolterodine and oxybutynin on tolerability and clinical efficacy for treating Chinese women with an overactive bladder. | 2002 Sep |
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Both alpha1-adrenergic and D(1)-dopaminergic neurotransmissions are involved in phenylpropanolamine-mediated feeding suppression in mice. | 2003 Aug 21 |
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Simplified bladder training augments the effectiveness of tolterodine in patients with an overactive bladder. | 2003 Jan |
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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 |
|
Hidden amphetamines: from smoking cessation to diabetes. | 2004 Feb |
|
Intramolecular chiral relay at stereogenic nitrogen. Synthesis and application of a new chiral auxiliary derived from (1R,2S)-norephedrine and acetone. | 2004 Feb 6 |
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Examination of aqueous oxidized cellulose dispersions as a potential drug carrier. I. Preparation and characterization of oxidized cellulose-phenylpropanolamine complexes. | 2004 Oct 8 |
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A validated chiral HPLC method for the enantiomeric separation of tolterodine tartarate. | 2004 Sep 3 |
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Tolterodine for the treatment of overactive bladder: a review. | 2005 Apr |
|
Antimuscarinic agents exhibit local inhibitory effects on muscarinic receptors in bladder-afferent pathways. | 2005 Feb |
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Economic impact of extended-release tolterodine versus immediate- and extended-release oxybutynin among commercially insured persons with overactive bladder. | 2005 Jul |
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Comparison of symptom severity and treatment response in patients with incontinent and continent overactive bladder. | 2005 Jul |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches. | 2005 Oct 15 |
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Tolterodine extended release improves patient-reported outcomes in overactive bladder: results from the IMPACT trial. | 2006 Jun |
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Tolterodine. | 2006 Jun 6-12 |
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Comparative evaluation of efficacy of use of tamsulosin and/or tolterodine for medical treatment of distal ureteral stones. | 2007 Apr |
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Protracted 'pro-addictive' phenotype produced in mice by pre-adolescent phenylpropanolamine. | 2007 Aug |
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Mixed urinary incontinence: continuing to confound? | 2007 Dec |
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Treatment of men with lower urinary tract symptoms and overactive bladder. | 2007 Mar 21 |
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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 |
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Effect of tolterodine on sleep structure modulated by CYP2D6 genotype. | 2008 Jul |
|
Transcriptional interruption of cAMP response element binding protein modulates superoxide dismutase and neuropeptide Y-mediated feeding behavior in freely moving rats. | 2008 May |
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Comparison of fesoterodine and tolterodine in patients with overactive bladder. | 2008 Nov |
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How many drugs for LUTS due to BPH are too many? | 2008 Sep |
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Asymmetric conjugate reductions of coumarins. A new route to tolterodine and related coumarin derivatives. | 2009 Dec 3 |
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Keep an eye on the pupil: developing countries under chemical attack. | 2009 Jun |
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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 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:21:18 GMT 2023
by
admin
on
Fri Dec 15 16:21:18 GMT 2023
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Record UNII |
8D5I63UE1Q
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C87053
Created by
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205-826-7
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DBSALT000996
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C66379
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8D5I63UE1Q
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154-41-6
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CHEMBL61006
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62943
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3266
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m8687
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8D5I63UE1Q
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SUB14842MIG
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100000091354
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1534005
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DTXSID2025896
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23798
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE |
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PARENT -> SALT/SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE | |||
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BASIS OF STRENGTH->SUBSTANCE | |||
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ENANTIOMER -> RACEMATE |
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BASIS OF STRENGTH->SUBSTANCE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
IMPURITY (UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |