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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
Synonyms
SynonymLanguageCode
Dristan inhalerNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Benzedrex 09-19-2014inhalant250 mgnasalBF ASCHER AND CO INC2014-09-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
International Brands
NameCompany
BenzedrexNot Available
ObesinNot Available
Brand mixturesNot Available
SaltsNot 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
Taxonomy
ClassificationNot classified
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
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9657
Blood Brain Barrier+0.9829
Caco-2 permeable+0.7226
P-glycoprotein substrateNon-substrate0.6278
P-glycoprotein inhibitor INon-inhibitor0.8635
P-glycoprotein inhibitor IINon-inhibitor0.9148
Renal organic cation transporterNon-inhibitor0.6
CYP450 2C9 substrateNon-substrate0.7991
CYP450 2D6 substrateSubstrate0.7284
CYP450 3A4 substrateNon-substrate0.6368
CYP450 1A2 substrateNon-inhibitor0.7982
CYP450 2C9 substrateNon-inhibitor0.9671
CYP450 2D6 substrateNon-inhibitor0.7367
CYP450 2C19 substrateNon-inhibitor0.8882
CYP450 3A4 substrateNon-inhibitor0.9827
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8718
Ames testNon AMES toxic0.9178
CarcinogenicityNon-carcinogens0.8877
BiodegradationNot ready biodegradable0.8187
Rat acute toxicity3.2412 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8496
hERG inhibition (predictor II)Non-inhibitor0.7482
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Inhalantnasal250 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0904 mg/mLALOGPS
logP3.37ALOGPS
logP2.7ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)10.61ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.54 m3·mol-1ChemAxon
Polarizability20.27 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US2454746
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololMay enhance the adverse/toxic effect of other Sympathomimetics.
AmphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
AtomoxetineMay enhance the hypertensive effect of Sympathomimetics. AtoMOXetine may enhance the tachycardic effect of Sympathomimetics.
BenzphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
ChlorphentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
ClenbuterolMay enhance the adverse/toxic effect of other Sympathomimetics.
DobutamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DopamineMay enhance the adverse/toxic effect of other Sympathomimetics.
EpinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
FenoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
FentanylAlpha1-Agonists may decrease the serum concentration of FentaNYL. Specifically, fentanyl nasal spray serum concentrations may decrease and onset of effect may be delayed.
FormoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
IsoprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
LabetalolMay enhance the adverse/toxic effect of other Sympathomimetics.
LinezolidMay enhance the hypertensive effect of Sympathomimetics.
MephentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
MetaraminolMay enhance the adverse/toxic effect of other Sympathomimetics.
MethamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethoxamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MidodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
NaphazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
NorepinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
OrciprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
OxymetazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenmetrazineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylpropanolamineMay enhance the adverse/toxic effect of other Sympathomimetics.
RitodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
SalmeterolMay enhance the adverse/toxic effect of other Sympathomimetics.
TerbutalineMay enhance the adverse/toxic effect of other Sympathomimetics.
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