Identification

Name
Oxymetazoline
Accession Number
DB00935  (APRD01158)
Type
Small Molecule
Groups
Approved
Description

A direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251)

Structure
Thumb
Synonyms
  • 2-(4-Tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline
  • 3-[(4,5-dihydro-1H-Imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenol
  • 6-t-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol
  • 6-Tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol
  • Oximetazolinum
  • Oxymetazolina
  • Oxymetazolinum
  • Oxymethazoline
  • Oxymetozoline
Product Ingredients
IngredientUNIICASInChI Key
Oxymetazoline hydrochlorideK89MJ0S5VY2315-02-8BEEDODBODQVSIM-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Clirol Nasal SpraySpray0.5 %NasalComplex Pharma Inc.Not applicableNot applicableCanada
RhofadeCream10 mg/gTopicalAllergan2017-01-18Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
12 Hour NasalSpray.05 g/100mLNasalMeijer Distribution2015-05-06Not applicableUs
12 Hour NasalSpray.05 g/100mLNasalSelect Brands Distributors2000-03-01Not applicableUs
12 Hour NasalSpray.05 g/100mLNasalAltaire Pharmaceuticals Inc.2001-06-01Not applicableUs
12 Hour Original Nasal DecongestantLiquid50 mg/100mLNasalFaria Llc Dba Sheffield Pharmaceutcials2014-05-30Not applicableUs
7 Select NasalSpray.05 g/100mLNasal7 Eleven2014-08-05Not applicableUs
7 Select Original NasalSpray.05 g/mLNasal7 Eleven2016-10-04Not applicableUs
Afrin ColdSpray0.05 mgNasalSchering Plough2002-09-282006-08-01Canada
Afrin No Drip Extra MoisturizingSpray, metered.05 g/100mLNasalFamar Montreal Inc2000-08-312017-05-04Us
Afrin No Drip Extra MoisturizingSpray, metered.05 g/100mLNasalBayer2000-08-31Not applicableUs
Afrin No Drip Original Pump MistSpray, metered.05 g/100mLNasalFamar Montreal Inc1999-08-312017-05-04Us
International/Other Brands
Afrin / Dristan 12-Hour / Duramist Plus / Genasal Nasal Spray Up to 12 Hour Relief / Iliadin / Neo-Synephrine 12 Hour Spray / Nezeril / Nostrilla 12 Hour Nasal Decongestant / OcuClear / Vicks Sinex 12 Hour Nasal Spray / Vicks Sinex 12 Hour Ultra Fine Mist for Sinus Relief
Categories
UNII
8VLN5B44ZY
CAS number
1491-59-4
Weight
Average: 260.3746
Monoisotopic: 260.1888634
Chemical Formula
C16H24N2O
InChI Key
WYWIFABBXFUGLM-UHFFFAOYSA-N
InChI
InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)
IUPAC Name
6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol
SMILES
CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C

Pharmacology

Indication

For treatment of nasal congestion and redness associated with minor irritations of the eye

Structured Indications
Pharmacodynamics

Oxymetazoline a adrenergic alpha-agonists, direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion The sympathomimetic action of oxymetazoline constricts the smaller arterioles of the nasal passages, producing a prolonged (up to 12 hours), gentle and decongesting effect. Oxymetazoline elicits relief of conjunctival hyperemia by causing vasoconstriction of superficial conjunctival blood vessels. The drug's action has been demonstrated in acute allergic conjunctivitis and in chemical (chloride) conjunctivitis.

Mechanism of action

Oxymetazoline is a direct acting sympathomimetic amine, which acts on alpha-adrenergic receptors in the arterioles of the conjunctiva and nasal mucosa. It produces vasoconstriction, resulting in decreased conjunctival congestion in ophthalmic. In nasal it produces constriction, resulting in decreased blood flow and decreased nasal congestion.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Human
AAlpha-2A adrenergic receptor
agonist
Human
UAlpha-2C adrenergic receptor
agonist
Human
UAlpha-2B adrenergic receptor
binder
Human
UAlpha-1B adrenergic receptor
agonist
Human
UAlpha-1D adrenergic receptor
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcebutololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Acebutolol.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Oxymetazoline.Approved, Investigational
AlprenololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Alprenolol.Approved, Withdrawn
AmineptineAmineptine may decrease the antihypertensive activities of Oxymetazoline.Illicit, Withdrawn
AmitriptylineAmitriptyline may decrease the antihypertensive activities of Oxymetazoline.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Oxymetazoline.Approved, Illicit
ArotinololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Arotinolol.Approved
AtenololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Atenolol.Approved
AtomoxetineAtomoxetine may increase the hypertensive activities of Oxymetazoline.Approved
BefunololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Befunolol.Experimental
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Oxymetazoline.Approved, Illicit
Benzylpenicilloyl PolylysineOxymetazoline may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetaxololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Betaxolol.Approved
BevantololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Bevantolol.Approved
BisoprololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Bisoprolol.Approved
BopindololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Bopindolol.Approved
BromocriptineBromocriptine may increase the hypertensive activities of Oxymetazoline.Approved, Investigational
BucindololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Bucindolol.Investigational
BufuralolOxymetazoline may increase the atrioventricular blocking (AV block) activities of Bufuralol.Experimental, Investigational
BunazosinBunazosin may decrease the vasoconstricting activities of Oxymetazoline.Investigational
BupranololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Bupranolol.Approved
CabergolineCabergoline may increase the hypertensive activities of Oxymetazoline.Approved
CarteololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Carteolol.Approved
CarvedilolOxymetazoline may increase the atrioventricular blocking (AV block) activities of Carvedilol.Approved, Investigational
CeliprololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Celiprolol.Approved, Investigational
ChlorphentermineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Chlorphentermine.Illicit, Withdrawn
ClenbuterolThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Clenbuterol.Approved, Vet Approved
ClomipramineClomipramine may decrease the antihypertensive activities of Oxymetazoline.Approved, Vet Approved
CloranololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Cloranolol.Experimental
CyclobenzaprineCyclobenzaprine may decrease the antihypertensive activities of Oxymetazoline.Approved
DesipramineDesipramine may decrease the antihypertensive activities of Oxymetazoline.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Oxymetazoline.Approved
DibenzepinDibenzepin may decrease the antihypertensive activities of Oxymetazoline.Experimental
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Oxymetazoline.Approved
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Oxymetazoline.Approved
DopamineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Dopamine.Approved
DosulepinDosulepin may decrease the antihypertensive activities of Oxymetazoline.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Oxymetazoline.Approved
DoxepinDoxepin may decrease the antihypertensive activities of Oxymetazoline.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Doxofylline.Approved
DronabinolDronabinol may increase the tachycardic activities of Oxymetazoline.Approved, Illicit
DuloxetineDuloxetine may increase the tachycardic activities of Oxymetazoline.Approved
EpanololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Epanolol.Experimental
EphedrineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Ephedrine.Approved
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Oxymetazoline.Approved, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Oxymetazoline.Approved
ErgonovineErgonovine may increase the hypertensive activities of Oxymetazoline.Approved
ErgotamineErgotamine may increase the hypertensive activities of Oxymetazoline.Approved
EsmirtazapineEsmirtazapine may decrease the antihypertensive activities of Oxymetazoline.Investigational
EsmololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Esmolol.Approved
EtilefrineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Etilefrine.Withdrawn
FenoterolThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Fenoterol.Approved
FenozoloneThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Fenozolone.Experimental
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Oxymetazoline.Approved, Investigational
HydroxyamphetamineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Hydroxyamphetamine.Approved
ImipramineImipramine may decrease the antihypertensive activities of Oxymetazoline.Approved
IndenololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Indenolol.Withdrawn
IndoraminIndoramin may decrease the vasoconstricting activities of Oxymetazoline.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Oxymetazoline.Approved
IprindoleIprindole may decrease the antihypertensive activities of Oxymetazoline.Experimental
IsoprenalineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Isoprenaline.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Isoxsuprine.Approved, Withdrawn
LabetalolOxymetazoline may increase the atrioventricular blocking (AV block) activities of Labetalol.Approved
LandiololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Landiolol.Investigational
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Oxymetazoline.Approved
LinezolidLinezolid may increase the hypertensive activities of Oxymetazoline.Approved, Investigational
LofepramineLofepramine may decrease the antihypertensive activities of Oxymetazoline.Experimental
MefenorexThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Mefenorex.Experimental
MephentermineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Mephentermine.Approved
MepindololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Mepindolol.Experimental
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Oxymetazoline.Approved, Investigational
MethamphetamineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Methamphetamine.Approved, Illicit
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Oxymetazoline.Approved
MethylergometrineMethylergometrine may increase the hypertensive activities of Oxymetazoline.Approved
MetoprololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Metoprolol.Approved, Investigational
MianserinThe therapeutic efficacy of Oxymetazoline can be decreased when used in combination with Mianserin.Approved
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Oxymetazoline.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Oxymetazoline.Approved
MirtazapineMirtazapine may decrease the antihypertensive activities of Oxymetazoline.Approved
NabiloneNabilone may increase the tachycardic activities of Oxymetazoline.Approved, Investigational
NadololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Nadolol.Approved
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Oxymetazoline.Approved
NortriptylineNortriptyline may decrease the antihypertensive activities of Oxymetazoline.Approved
NylidrinThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Nylidrin.Approved
OpipramolOpipramol may decrease the antihypertensive activities of Oxymetazoline.Investigational
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Oxymetazoline.Approved
OxprenololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Oxprenolol.Approved
PenbutololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Penbutolol.Approved, Investigational
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Oxymetazoline.Approved, Illicit
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Oxymetazoline.Approved, Illicit
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Oxymetazoline.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Oxymetazoline.Approved, Vet Approved, Withdrawn
PindololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Pindolol.Approved
PractololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Practolol.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Oxymetazoline.Approved
PrenalterolThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Prenalterol.Experimental
ProcaterolThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Procaterol.Approved
PropranololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Propranolol.Approved, Investigational
ProtriptylineProtriptyline may decrease the antihypertensive activities of Oxymetazoline.Approved
PseudoephedrineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Pseudoephedrine.Approved
RacepinephrineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Racepinephrine.Approved
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Oxymetazoline.Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Oxymetazoline.Approved
SotalolOxymetazoline may increase the atrioventricular blocking (AV block) activities of Sotalol.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Oxymetazoline.Approved
SynephrineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Synephrine.Experimental
TalinololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Talinolol.Investigational
TamsulosinTamsulosin may decrease the vasoconstricting activities of Oxymetazoline.Approved, Investigational
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Oxymetazoline.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Oxymetazoline.Approved
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Oxymetazoline.Approved
TertatololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Tertatolol.Experimental
TetryzolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Tetryzoline.Approved
TianeptineTianeptine may decrease the antihypertensive activities of Oxymetazoline.Approved
TimololOxymetazoline may increase the atrioventricular blocking (AV block) activities of Timolol.Approved
TramazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Tramazoline.Investigational
TretoquinolThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Tretoquinol.Experimental
TrimazosinTrimazosin may decrease the vasoconstricting activities of Oxymetazoline.Experimental
TrimipramineTrimipramine may decrease the antihypertensive activities of Oxymetazoline.Approved
TyramineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Tyramine.Investigational, Nutraceutical
UrapidilUrapidil may decrease the vasoconstricting activities of Oxymetazoline.Investigational
VenlafaxineVenlafaxine may increase the tachycardic activities of Oxymetazoline.Approved
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
Human Metabolome Database
HMDB15070
KEGG Compound
C07363
PubChem Compound
4636
PubChem Substance
46505622
ChemSpider
4475
BindingDB
30712
ChEBI
7862
ChEMBL
CHEMBL762
Therapeutic Targets Database
DAP000235
PharmGKB
PA164748840
IUPHAR
124
Guide to Pharmacology
GtP Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Oxymetazoline
ATC Codes
R01AA05 — OxymetazolineR01AB07 — OxymetazolineS01GA04 — Oxymetazoline
AHFS Codes
  • 52:32.00
PDB Entries
Not Available
FDA label
Not Available
MSDS
Download (74.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1CompletedBasic ScienceAnaesthesia therapy1
1CompletedBasic ScienceAcute Rhinitis1
1CompletedTreatmentAllergic Rhinitis (AR)2
1CompletedTreatmentAssess Pharmacokinetics of Ketorolac Tromethamine Intranasal and Assess Effects of a Oxymetazoline Hydrochloride on the PK of Ketorolac Tromethamine / Healthy Volunteers1
1, 2CompletedTreatmentIncontinence, Fecal / Spinal Cord Injuries (SCI)1
2CompletedPreventionConjunctivitis, Seasonal Allergic1
2CompletedTreatmentAllergic Rhinitis (AR)1
2CompletedTreatmentAnaesthesia therapy3
2CompletedTreatmentSeasonal Allergic Rhinitis (SAR)1
2WithdrawnTreatmentAnesthesia, Dental / Intranasal Drug Administration / Nasal Surgical Procedures1
3CompletedTreatmentAnaesthesia therapy3
3CompletedTreatmentErythemas / Rosaceas2
3CompletedTreatmentHerpes Simplex Labialis1
3Not Yet RecruitingTreatmentRhinitis1
3TerminatedTreatmentAnaesthesia therapy1
4CompletedTreatmentAdenoidal Hypertrophy1
4CompletedTreatmentAllergic Rhinitis (AR)1
4CompletedTreatmentNasal Obstruction Present Finding1
4Not Yet RecruitingTreatmentChronic Nasal Congestion / Sleep Apnea Syndrome1
4WithdrawnTreatmentAllergic Rhinitis (AR) / Rhinitis Medicamentosa / Tachyphylaxis1
Not AvailableCompletedTreatmentNasal Obstruction1
Not AvailableEnrolling by InvitationTreatmentAdenoidectomy / Functional Endoscopic Sinus Surgery (FESS) / Turbinate Surgery1
Not AvailableRecruitingBasic ScienceMiddle Ear Disease / Nasal Allergies1
Not AvailableRecruitingTreatmentBlood Pressures / Nasal Bleeding1
Not AvailableTerminatedTreatmentChronic Rhinitis1

Pharmacoeconomics

Manufacturers
  • Schering plough healthcare products inc
  • Johnson and johnson group consumer companies
Packagers
Dosage forms
FormRouteStrength
LiquidNasal50 mg/100mL
SprayNasal.05 g/mL
SprayNasal0.05 mg
Spray, meteredNasal.05 mg/mL
Spray, meteredNasal.05 g/100mL
SprayNasal.05 mg/100mL
SprayNasal.2 mg/.4mL
SprayNasal0.5 %
SprayNasal.0005 g/mL
SolutionNasal0.05 %
SprayNasal.05 g/100mL
SprayNasal.05 mg/100mg
LiquidNasal0.05 %
SprayNasal0.05 %
SolutionNasal.5 mg/mL
SolutionNasal.05 g/100mL
SolutionNasal.05 mg/100mL
Solution / drops; sprayNasal.025 %
SprayNasal5 g/100mL
SprayNasal.05 mg/mL
LiquidTopical.05 g/100mL
SprayNasal.5 mg/mL
Spray, meteredNasal.0005 mL/100mL
Solution / dropsOphthalmic.25 mg
Spray, meteredNasal0.05 %
SprayOral.5 mg/mL
Spray, meteredNasal.2 mg/.4mL
Spray, meteredNasal.5 mg/mL
CreamTopical10 mg/g
SprayNasal7.5 mg/15mL
SprayNasal50 mg/100mL
SprayNasal.512 mg/mL
SprayNasal.0005055 g/mL
SprayNasal.000512 g/mL
SprayNasal.0005095 g/mL
LiquidNasal.05 %
LiquidOphthalmic.25 mg/mL
LiquidOphthalmic.025 %
Solution / dropsOphthalmic0.025 %
SprayNasal.005 g/100mL
Prices
Unit descriptionCostUnit
Oxymetazoline hcl powder84.42USD g
Afrin 0.05% nose spray0.62USD ml
Drixoral cold & allergy tablet sa0.4USD tablet
Afrin no drip sinus pump mist0.38USD ml
Oxymetazoline 0.05% spray0.38USD ml
Anefrin 0.05% nasal spray0.37USD ml
Afrin sinus spray0.33USD ml
Dristan long lasting mist0.32USD ml
Neo-synephrine 12 hour spray0.28USD ml
Visine long lasting eye drops0.27USD ml
12 hour nasal relief spray0.24USD ml
Dristan cold multi-symp tablet0.23USD tablet
Ocuclear eye drops0.23USD ml
CVS Pharmacy nasal spray 0.05%0.22USD ml
No drip 0.05% nasal spray0.13USD ml
Nasal spray 0.05%0.06USD ml
Sinus nasal spray0.06USD ml
Nasal decongestant 0.05% spray0.03USD ml
Pv nasal spray 0.05%0.03USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8580282No2010-04-022030-04-02Us
US6413499No2000-03-202020-03-20Us
US9308191No2010-04-022030-04-02Us
US8883838No2011-12-012031-12-01Us
US7812049No2008-05-022028-05-02Us
US8420688No2004-08-022024-08-02Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)182 °CPhysProp
logP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0515 mg/mLALOGPS
logP3.7ALOGPS
logP3.03ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)10.91ChemAxon
pKa (Strongest Basic)10.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area44.62 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.8 m3·mol-1ChemAxon
Polarizability30.64 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9761
Blood Brain Barrier-0.5388
Caco-2 permeable-0.567
P-glycoprotein substrateSubstrate0.8858
P-glycoprotein inhibitor INon-inhibitor0.9477
P-glycoprotein inhibitor IINon-inhibitor0.6585
Renal organic cation transporterInhibitor0.6039
CYP450 2C9 substrateNon-substrate0.7585
CYP450 2D6 substrateNon-substrate0.5707
CYP450 3A4 substrateNon-substrate0.5394
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.854
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.7951
CarcinogenicityNon-carcinogens0.8923
BiodegradationNot ready biodegradable1.0
Rat acute toxicity4.4155 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8402
hERG inhibition (predictor II)Non-inhibitor0.7432
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.5 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as xylenols. These are aromatic compounds that contain a xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups, and at least one hydroxyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Xylenes
Direct Parent
Xylenols
Alternative Parents
Phenylpropanes / m-Xylenes / Para cresols / Ortho cresols / Imidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds
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Substituents
Xylenol / Phenylpropane / M-xylene / O-cresol / P-cresol / Phenol / Imidolactam / 2-imidazoline / Amidine / Carboxylic acid amidine
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
phenols, carboxamidine, imidazolines (CHEBI:7862)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Yang HT, Endoh M: (+/-)-tamsulosin, an alpha 1A-adrenoceptor antagonist, inhibits the positive inotropic effect but not the accumulation of inositol phosphates in rabbit heart. Eur J Pharmacol. 1996 Oct 3;312(3):281-91. [PubMed:8894610]
  2. Deplanne V, Galzin AM: Functional characterization of alpha-1-adrenoceptor subtypes in the prostatic urethra and trigone of male rabbit. J Pharmacol Exp Ther. 1996 Aug;278(2):527-34. [PubMed:8768700]
  3. Shibata K, Taketani K: [Excitatory effect of noradrenaline on rat airway parasympathetic ganglion neurons]. Fukuoka Igaku Zasshi. 2001 Nov;92(11):377-83. [PubMed:11774707]
  4. Furukawa K, Rosario DJ, Smith DJ, Chapple CR, Uchiyama T, Chess-Williams R: Alpha 1A-adrenoceptor-mediated contractile responses of the human vas deferens. Br J Pharmacol. 1995 Sep;116(1):1605-10. [PubMed:8564226]
  5. Gonzalez-Espinosa C, Romero-Avila MT, Mora-Rodriguez DM, Gonzalez-Espinosa D, Garcia-Sainz JA: Molecular cloning and functional expression of the guinea pig alpha(1a)-adrenoceptor. Eur J Pharmacol. 2001 Aug 31;426(3):147-55. [PubMed:11527538]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. MacKinnon AC, Kilpatrick AT, Kenny BA, Spedding M, Brown CM: [3H]-RS-15385-197, a selective and high affinity radioligand for alpha 2-adrenoceptors: implications for receptor classification. Br J Pharmacol. 1992 Aug;106(4):1011-8. [PubMed:1327384]
  2. Mitrani P, Srinivasan M, Dodds C, Patel MS: Role of the autonomic nervous system in the development of hyperinsulinemia by high-carbohydrate formula feeding to neonatal rats. Am J Physiol Endocrinol Metab. 2007 Apr;292(4):E1069-78. Epub 2006 Dec 12. [PubMed:17164433]
  3. Lepretre N, Mironneau J: Alpha 2-adrenoceptors activate dihydropyridine-sensitive calcium channels via Gi-proteins and protein kinase C in rat portal vein myocytes. Pflugers Arch. 1994 Dec;429(2):253-61. [PubMed:7892112]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name
ADRA2C
Uniprot ID
P18825
Uniprot Name
Alpha-2C adrenergic receptor
Molecular Weight
49521.585 Da
References
  1. Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Epinephrine binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
Molecular Weight
49565.8 Da
References
  1. Uhlen S, Wikberg JE: Delineation of rat kidney alpha 2A- and alpha 2B-adrenoceptors with [3H]RX821002 radioligand binding: computer modelling reveals that guanfacine is an alpha 2A-selective compound. Eur J Pharmacol. 1991 Sep 17;202(2):235-43. [PubMed:1666366]
  2. Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [PubMed:21948594]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735]
  2. Akinaga J, Lima V, Kiguti LR, Hebeler-Barbosa F, Alcantara-Hernandez R, Garcia-Sainz JA, Pupo AS: Differential phosphorylation, desensitization, and internalization of alpha1A-adrenoceptors activated by norepinephrine and oxymetazoline. Mol Pharmacol. 2013 Apr;83(4):870-81. doi: 10.1124/mol.112.082313. Epub 2013 Jan 30. [PubMed:23364786]
  3. Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [PubMed:21948594]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Alpha1-adrenergic receptor activity
Specific Function
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name
ADRA1D
Uniprot ID
P25100
Uniprot Name
Alpha-1D adrenergic receptor
Molecular Weight
60462.205 Da
References
  1. Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735]
  2. Akinaga J, Lima V, Kiguti LR, Hebeler-Barbosa F, Alcantara-Hernandez R, Garcia-Sainz JA, Pupo AS: Differential phosphorylation, desensitization, and internalization of alpha1A-adrenoceptors activated by norepinephrine and oxymetazoline. Mol Pharmacol. 2013 Apr;83(4):870-81. doi: 10.1124/mol.112.082313. Epub 2013 Jan 30. [PubMed:23364786]
  3. Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [PubMed:21948594]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:48