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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
Dristan inhaler
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Benzedrex 09-19-2014inhalant250 mg/1nasalBF ASCHER AND CO INC2014-09-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
International Brands
NameCompany
BenzedrexNot Available
ObesinNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIILQU92IU8LL
CAS number3595-11-7
WeightAverage: 155.2804
Monoisotopic: 155.167399677
Chemical FormulaC10H21N
InChI KeyInChIKey=JCRIVQIOJSSCQD-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 inhibitorNon-inhibitor0.9671
CYP450 2D6 inhibitorNon-inhibitor0.7367
CYP450 2C19 inhibitorNon-inhibitor0.8882
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Inhalantnasal250 mg/1
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Propylhexedrine.
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Propylhexedrine.
AmitriptylineAmitriptyline may increase the activities of Propylhexedrine.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Propylhexedrine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Propylhexedrine.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Propylhexedrine.
CabergolineCabergoline may increase the hypertensive activities of Propylhexedrine.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Propylhexedrine.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Propylhexedrine.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Propylhexedrine.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Propylhexedrine.
DoxofyllineThe risk or severity of adverse effects can be increased when Propylhexedrine is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Propylhexedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Propylhexedrine.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Propylhexedrine.
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Propylhexedrine.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Propylhexedrine.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Propylhexedrine.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Propylhexedrine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Propylhexedrine.
LinezolidLinezolid may increase the hypertensive activities of Propylhexedrine.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Propylhexedrine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Propylhexedrine.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Propylhexedrine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Propylhexedrine.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Propylhexedrine.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Propylhexedrine.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Propylhexedrine.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Propylhexedrine.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Propylhexedrine.
PhenelzinePhenelzine may increase the hypertensive activities of Propylhexedrine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Propylhexedrine.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Propylhexedrine.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Propylhexedrine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Propylhexedrine.
PrazosinPrazosin may decrease the vasoconstricting activities of Propylhexedrine.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Propylhexedrine.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Propylhexedrine.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Propylhexedrine.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Propylhexedrine.
TranylcypromineTranylcypromine may increase the hypertensive activities of Propylhexedrine.
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