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Identification
NamePropylhexedrine
Accession NumberDB06714
Typesmall molecule
Groupsapproved
Description

Propylhexedrine is an alpha-adrenergic agonist often used in nasal decongestant inhalers. It is used to give temporary relief for nasal congestion from colds, allergic rhinitis, or allergies.

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand names
NameCompany
BenzedrexNot Available
ObesinNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number3595-11-7
WeightAverage: 155.2804
Monoisotopic: 155.167399677
Chemical FormulaC10H21N
InChI KeyJCRIVQIOJSSCQD-UHFFFAOYSA-N
InChI
InChI=1S/C10H21N/c1-9(11-2)8-10-6-4-3-5-7-10/h9-11H,3-8H2,1-2H3
IUPAC Name
(1-cyclohexylpropan-2-yl)(methyl)amine
SMILES
CNC(C)CC1CCCCC1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassAmines
SubclassPolyamines
Direct parentPolyamines
Alternative parentsDialkylamines
SubstituentsNot Available
Classification descriptionThis compound belongs to the polyamines. These are compounds containing more than one amine group.
Pharmacology
IndicationIt is used to provide temporary symptomatic relief of nasal congestion due to colds, allergies and allergic rhinitis.
PharmacodynamicsLike other monoamine releasing stimulants propylhexedrine is active as a norepinephrine and dopamine releaser in the central nervous system. The acute effects of the drug closely resemble the physiological and psychological effects of an epinephrine-provoked fight-or-flight response, including increased heart rate and blood pressure, vasoconstriction (constriction of the arterial walls), bronchodilation, and hyperglycemia (increased blood sugar).
Mechanism of actionPropylhexidrine causes the norepinephrine, dopamine, and serotonin (5HT) transporters to reverse their direction of flow. This inversion leads to a release of these transmitters from the vesicles to the cytoplasm and from the cytoplasm to the synapse. It also antagonizes the action of VMAT2, causing the release of more neurotransmitters.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityThe signs and symptoms that are produced after the acute overdosage of Propylhexidrine include Psychosis, Burning sensation.
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9657
Blood Brain Barrier + 0.9829
Caco-2 permeable + 0.7226
P-glycoprotein substrate Non-substrate 0.6278
P-glycoprotein inhibitor I Non-inhibitor 0.8635
P-glycoprotein inhibitor II Non-inhibitor 0.9148
Renal organic cation transporter Non-inhibitor 0.6
CYP450 2C9 substrate Non-substrate 0.7991
CYP450 2D6 substrate Substrate 0.7284
CYP450 3A4 substrate Non-substrate 0.6368
CYP450 1A2 substrate Non-inhibitor 0.7982
CYP450 2C9 substrate Non-inhibitor 0.9671
CYP450 2D6 substrate Non-inhibitor 0.7367
CYP450 2C19 substrate Non-inhibitor 0.8882
CYP450 3A4 substrate Non-inhibitor 0.9827
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8718
Ames test Non AMES toxic 0.9178
Carcinogenicity Non-carcinogens 0.8877
Biodegradation Not ready biodegradable 0.8187
Rat acute toxicity 3.2412 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8496
hERG inhibition (predictor II) Non-inhibitor 0.7482
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
AerosolNasal
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility9.04e-02 g/lALOGPS
logP3.37ALOGPS
logP2.7ChemAxon
logS-3.2ALOGPS
pKa (strongest basic)10.61ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area12.03ChemAxon
rotatable bond count3ChemAxon
refractivity49.54ChemAxon
polarizability20.27ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US2454746
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD05637
PubChem Compound7558
PubChem Substance99443266
PharmGKBPA165958387
WikipediaPropylhexedrine
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Synaptic vesicular amine transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Components

Name UniProt ID Details
Synaptic vesicular amine transporter Q05940 Details

References:

  1. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. Pubmed
  2. Docherty JR: Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA). Br J Pharmacol. 2008 Jun;154(3):606-22. doi: 10.1038/bjp.2008.124. Pubmed

2. Trace amine-associated receptor 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Trace amine-associated receptor 1 Q96RJ0 Details

References:

  1. Reese EA, Bunzow JR, Arttamangkul S, Sonders MS, Grandy DK: Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine. J Pharmacol Exp Ther. 2007 Apr;321(1):178-86. Epub 2007 Jan 11. Pubmed
  2. Xie Z, Westmoreland SV, Bahn ME, Chen GL, Yang H, Vallender EJ, Yao WD, Madras BK, Miller GM: Rhesus monkey trace amine-associated receptor 1 signaling: enhancement by monoamine transporters and attenuation by the D2 autoreceptor in vitro. J Pharmacol Exp Ther. 2007 Apr;321(1):116-27. Epub 2007 Jan 18. Pubmed
  3. Wolinsky TD, Swanson CJ, Smith KE, Zhong H, Borowsky B, Seeman P, Branchek T, Gerald CP: The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia. Genes Brain Behav. 2007 Oct;6(7):628-39. Epub 2006 Dec 21. Pubmed
  4. Xie Z, Miller GM: Trace amine-associated receptor 1 is a modulator of the dopamine transporter. J Pharmacol Exp Ther. 2007 Apr;321(1):128-36. Epub 2007 Jan 18. Pubmed
  5. Miller GM, Verrico CD, Jassen A, Konar M, Yang H, Panas H, Bahn M, Johnson R, Madras BK: Primate trace amine receptor 1 modulation by the dopamine transporter. J Pharmacol Exp Ther. 2005 Jun;313(3):983-94. Epub 2005 Mar 11. Pubmed

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Drug created on May 16, 2010 12:30 / Updated on October 08, 2013 14:25