phenylpropanolamine indications/contra

Stem definitionDrug idCAS RN
2149 14838-15-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • phenylpropanolamine
  • norephedrine
  • propadrine
  • (+/-)-phenylpropanolamine
  • phenylpropanolamine hydrochloride
  • phenylpropanolamine HCl
  • phenylpropanolamine polistirex
A sympathomimetic that acts mainly by causing release of NOREPINEPHRINE but also has direct agonist activity at some adrenergic receptors. It is most commonly used as a nasal vasoconstrictor and an appetite depressant.
  • Molecular weight: 151.21
  • Formula: C9H13NO
  • CLOGP: 0.58
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 2
  • TPSA: 46.25
  • ALOGS: -0.87
  • ROTB: 2

Drug dosage:

DoseUnitRoute
0.10 g O
0.10 g O

Approvals:

DateAgencyCompanyOrphan
Sept. 29, 2000 FDA ALPHARMA US PHARMS

FDA Adverse Event Reporting System

None

Pharmacologic Action:

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SourceCodeDescription
ATC R01BA01 RESPIRATORY SYSTEM
NASAL PREPARATIONS
NASAL DECONGESTANTS FOR SYSTEMIC USE
Sympathomimetics
ATC R01BA51 RESPIRATORY SYSTEM
NASAL PREPARATIONS
NASAL DECONGESTANTS FOR SYSTEMIC USE
Sympathomimetics
MeSH PA D018663 Adrenergic Agents
MeSH PA D000322 Adrenergic Agonists
MeSH PA D000316 Adrenergic alpha-Agonists
MeSH PA D019440 Anti-Obesity Agents
MeSH PA D001067 Appetite Depressants
MeSH PA D001337 Autonomic Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D014663 Nasal Decongestants
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D019141 Respiratory System Agents
MeSH PA D013566 Sympathomimetics
MeSH PA D014662 Vasoconstrictor Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Sinus headache indication 4969004
Vasomotor rhinitis indication 8229003 DOID:4730
Cough indication 49727002
Allergic rhinitis indication 61582004
Nasal discharge indication 64531003
Nasal congestion indication 68235000
Rhinitis indication 70076002 DOID:4483
Sneezing indication 76067001
Common cold indication 82272006 DOID:10459
Influenza-like symptoms indication 315642008
Seasonal allergic rhinitis indication 367498001
Allergic conjunctivitis indication 473460002 DOID:11204
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005 DOID:8677
Ocular hypertension contraindication 4210003 DOID:9282
Suicidal thoughts contraindication 6471006
Dependent drug abuse contraindication 6525002
Alcoholism contraindication 7200002
Alcohol withdrawal delirium contraindication 8635005
Peptic ulcer contraindication 13200003 DOID:750
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Asthenia contraindication 13791008
Constipation contraindication 14760008 DOID:2089
Primary hyperoxaluria contraindication 17901006 DOID:2977
Mood swings contraindication 18963009
Myocardial infarction contraindication 22298006 DOID:5844
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Ventricular tachycardia contraindication 25569003
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Hypercapnia contraindication 29596007
Dehydration contraindication 34095006
Hyperthyroidism contraindication 34486009 DOID:7998
Acute hepatitis contraindication 37871000
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Gastrointestinal ulcer contraindication 40845000
Hypothyroidism contraindication 40930008 DOID:1459
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Acidosis contraindication 51387008
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Ulcerative colitis contraindication 64766004 DOID:8577
Arterial thrombosis contraindication 65198009
Substance abuse contraindication 66214007
Benign intracranial hypertension contraindication 68267002 DOID:11459
Poisoning by acetaminophen contraindication 70273001
Agoraphobia contraindication 70691001 DOID:593
Arteriosclerotic vascular disease contraindication 72092001 DOID:2349
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Gastrointestinal hemorrhage contraindication 74474003
Urethral stricture contraindication 76618002
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Chronic idiopathic constipation contraindication 82934008
Cor pulmonale contraindication 83291003 DOID:8515
Pulmonary emphysema contraindication 87433001
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:2527
Hemophilia contraindication 90935002
Anemia due to enzyme deficiency contraindication 111577008
Acute abdominal pain contraindication 116290004
Gastrointestinal obstruction contraindication 126765001
Neoplasm of brain contraindication 126952004 DOID:1319
Hb SS disease contraindication 127040003 DOID:10923
von Willebrand disorder contraindication 128105004 DOID:12531
Seizure disorder contraindication 128613002 DOID:1826
Drug-induced psychosis contraindication 191483003 DOID:1742
Obsessive-compulsive disorder contraindication 191736004 DOID:10933
Insomnia contraindication 193462001
Partial atrioventricular block contraindication 195039008
Acute pancreatitis contraindication 197456007 DOID:2913
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Benign prostatic hyperplasia contraindication 266569009 DOID:2883
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Exacerbation of asthma contraindication 281239006
Pregnancy, function contraindication 289908002
Lesion of brain contraindication 301766008
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Panic disorder contraindication 371631005 DOID:594
Coma contraindication 371632003
Primary adrenocortical insufficiency contraindication 373662000 DOID:13774
Operation on gastrointestinal tract contraindication 386621005
Hypoxia contraindication 389086002
Angle-closure glaucoma contraindication 392291006 DOID:13550
Hemochromatosis contraindication 399187006 DOID:2352
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Myocardial infarction in recovery phase contraindication 418044006
Central nervous system depression contraindication 418072004
Dysfunction of sphincter of Oddi contraindication 430887001
Hypertensive urgency contraindication 443482000
Acute erosive gastritis contraindication 444926003
Urinary incontinence off-label use 165232002
Obesity off-label use 414916001 DOID:9970

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.86 acidic
pKa2 8.89 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Alpha-1A adrenergic receptor GPCR AGONIST CHEMBL CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 6.56 WOMBAT-PK
Sodium-dependent noradrenaline transporter Transporter Ki 7.82 PDSP
Sodium-dependent dopamine transporter Transporter Ki 7.17 PDSP
Alpha-2C adrenergic receptor GPCR Ki 6.58 PDSP
Alpha-2B adrenergic receptor GPCR Ki 6.40 PDSP
Muscarinic acetylcholine receptor M1 GPCR Ki 5.17 PDSP
5-hydroxytryptamine receptor 7 GPCR Ki 5.15 PDSP
Potassium voltage-gated channel subfamily H member 2 Ion channel WOMBAT-PK
Alpha-1B adrenergic receptor GPCR Ki 5.02 CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 5.07 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 5.01 CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 6.58 CHEMBL

External reference:

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IDSource
CHEBI:8104 CHEBI
DB00397 DRUGBANK_ID
4019893 VUID
N0000147978 NUI
C0031495 UMLSCUI
D01224 KEGG_DRUG
33RU150WUN UNII
4955 INN_ID
CHEMBL61006 ChEMBL_ID
4019893 VANDF
7196 MMSL
8175 RXNORM
387464001 SNOMEDCT_US
80127003 SNOMEDCT_US
5286 MMSL
d00767 MMSL
N0000006004 NDFRT
N0000147978 NDFRT
004434 NDDF
154-41-6 SECONDARY_CAS_RN
CHEMBL1200695 ChEMBL_ID
CHEMBL1201535 ChEMBL_ID
D010665 MESH_DESCRIPTOR_UI
26934 PUBCHEM_CID
NPU PDB_CHEM_ID

Pharmaceutical products:

None