Details of the Drug

General Information of Drug (ID: DM8ZXT6)

Drug Name
Oxymetazoline
Synonyms
Hazol; Iliadin; Nafrine; Navasin; Navisin; Nezeril; Oximetazolina; Oximetazolinum; Oxylazine; Oxymetazolinum; Oxymethazoline; Oxymetozoline; Rhinofrenol; Rhinolitan; Sinerol; Dristan Long Lasting Mentholated Nasal Spray; Dristan Long Lasting Nasal Mist; Drixoral Nasal Solution; Oxymeta zoline; Oxymetazoline hydrochloride crystalline; Afrin Cherry 12 Hour Nasal Spray; Afrin Extra Moisturizing 12 Hour Nasal Spray; Afrin Original 12 Hour Nasal Spray; Afrin Original 12 Hour Nose Drops; Afrin Original 12 Hour Pump Mist; Afrin Sinus 12 Hour Nasal Spray; Duramist Plus Up To 12 Hour Nasal Decongestant Spray; Genasal Nasal Spray Up to 12 Hour Relief; H 990; Nasal Relief 12 Hour Nasal Spray; Nostrilla 12 Hour Nasal Decongestant; Vicks Sinex 12 Hour Nasal Spray; Vicks Sinex 12 Hour Ultra Fine Mist for Sinus Relief; Decongestant (TN); Neo-Synephrine 12 Hour Spray; Operil (TN); Oximetazolina [INN-Spanish]; Oxymetazoline (INN); Oxymetazoline [INN:BAN]; Oxymetazolinum [INN-Latin]; Visine L.R; Visine L.R.; Phenol, 6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethyl-(7CI,8CI); Phenol, 3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethyl-(9CI); 2-(4-tert-Butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline; 3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethyl-6-tert-butyl-phenol; 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; 6-tert-Butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol
Indication
Disease Entry ICD 11 Status REF
Arrhythmia BC9Z Approved [1]
Eye inflammation 9A02 Approved [2]
Fecal incontinence ME07 Approved [1]
Nasal congestion MD11.9 Approved [2]
Therapeutic Class
Nasal Decongestants
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 260.37
Logarithm of the Partition Coefficient (xlogp) 2.9
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 0.895 +/- 0.798 mcgh/L [3]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 60.5 +/- 53.9 ng/L [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 8.3 hours [4]
Metabolism
The drug is metabolized via the human liver enzymes to produce mono-oxygenated and dehydrogenated metabolites [5]
Chemical Identifiers
Formula
C16H24N2O
IUPAC Name
6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol
Canonical SMILES
CC1=CC(=C(C(=C1CC2=NCCN2)C)O)C(C)(C)C
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)
InChIKey
WYWIFABBXFUGLM-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4636
ChEBI ID
CHEBI:7862
CAS Number
1491-59-4
DrugBank ID
DB00935
TTD ID
D09EBS
INTEDE ID
DR1224
ACDINA ID
D01309
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adrenergic receptor Alpha-2 (ADRA2) TTQ8AFT NOUNIPROTAC Agonist [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A1 (UGT1A1)
Main DME 		DEYGVN4 UD11_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Alpha-1A adrenergic receptor (ADRA1A) OTUIWCL5 ADA1A_HUMAN Protein Interaction/Cellular Processes [8]
Alpha-1B adrenergic receptor (ADRA1B) OTSAYAFD ADA1B_HUMAN Protein Interaction/Cellular Processes [9]
Alpha-1D adrenergic receptor (ADRA1D) OTW2CD1O ADA1D_HUMAN Protein Interaction/Cellular Processes [10]
Alpha-2A adrenergic receptor (ADRA2A) OTZFGOTP ADA2A_HUMAN Protein Interaction/Cellular Processes [9]
Alpha-2C adrenergic receptor (ADRA2C) OT5B9RKP ADA2C_HUMAN Protein Interaction/Cellular Processes [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Oxymetazoline (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Methylene blue DMJAPE7 Moderate Decreased metabolism of Oxymetazoline caused by Methylene blue mediated inhibition of non-CYP450 enzyme. Acquired methaemoglobinaemia [3A93] [11]
Levomilnacipran DMV26S8 Moderate Increased risk of rapid heart rate by the combination of Oxymetazoline and Levomilnacipran. Chronic pain [MG30] [12]
Selegiline DM6034S Moderate Decreased metabolism of Oxymetazoline caused by Selegiline mediated inhibition of non-CYP450 enzyme. Depression [6A70-6A7Z] [11]
Isocarboxazid DMAF1NB Moderate Decreased metabolism of Oxymetazoline caused by Isocarboxazid mediated inhibition of non-CYP450 enzyme. Depression [6A70-6A7Z] [11]
Milnacipran DMBFE74 Moderate Additive hypertensive effects by the combination of Oxymetazoline and Milnacipran. Depression [6A70-6A7Z] [12]
Desvenlafaxine DMHD4PE Moderate Increased risk of rapid heart rate by the combination of Oxymetazoline and Desvenlafaxine. Depression [6A70-6A7Z] [12]
Procarbazine DMIK367 Moderate Decreased metabolism of Oxymetazoline caused by Procarbazine mediated inhibition of non-CYP450 enzyme. Hodgkin lymphoma [2B30] [11]
Ozanimod DMT6AM2 Moderate Decreased metabolism of Oxymetazoline caused by Ozanimod mediated inhibition of non-CYP450 enzyme. Multiple sclerosis [8A40] [11]
Sibutramine DMFJTDI Moderate Increased risk of rapid heart rate by the combination of Oxymetazoline and Sibutramine. Obesity [5B80-5B81] [13]
Safinamide DM0YWJC Moderate Decreased metabolism of Oxymetazoline caused by Safinamide mediated inhibition of non-CYP450 enzyme. Parkinsonism [8A00] [11]
Rasagiline DM3WKQ4 Moderate Decreased metabolism of Oxymetazoline caused by Rasagiline mediated inhibition of non-CYP450 enzyme. Parkinsonism [8A00] [11]
Ergonovine DM0VEC1 Major Additive hypertensive effects by the combination of Oxymetazoline and Ergonovine. Postpartum haemorrhage [JA43] [14]
⏷ Show the Full List of 12 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Benzyl alcohol E00010 244 Antimicrobial preservative; Solvent
Butylated hydroxytoluene E00336 31404 Antioxidant
Hydrochloric acid E00015 313 Acidulant
Kyselina citronova E00014 311 Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
methylparaben E00149 7456 Antimicrobial preservative
Potassium chloride E00074 4873 Tonicity agent
Propylparaben sodium E00567 23679044 Antimicrobial preservative
Sodium citrate anhydrous E00102 6224 Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Diisopropyl adipate E00277 23368 Emollient
Oleyl alcohol E00475 5284499 Emollient; Emulsifying agent; Penetration agent; Solubilizing agent
Sodium acetate E00431 517045 Antimicrobial preservative; Buffering agent; Flavoring agent
Calcium chloride E00474 5284359 Antimicrobial preservative; Desiccant
Cetostearyl alcohol E00353 62238 Emollient; Emulsifying agent; Viscosity-controlling agent
Edetate disodium E00186 8759 Complexing agent
Hypromellose E00634 Not Available Coating agent
Medium-chain triglyceride E00640 Not Available Emollient; Lubricant; Surfactant
Polyethylene glycol 300 E00651 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Sodium chloride E00077 5234 Diluent; Tonicity agent
Sodium citrate dihydrate E00369 71474 Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Sodium hydroxide E00234 14798 Alkalizing agent
Stearyl alcohol E00172 8221 Emollient; Emulsifying agent; Stiffening agent; Viscosity-controlling agent
Water E00035 962 Solvent
Ethylene glycol stearate E00312 24762 Emollient; Emulsion stabilizing agent
Lanolin E00375 75778 Emollient; Emulsifying agent; Ointment base
Magnesium chloride E00479 5360315 Viscosity-controlling agent
Phenoxyethanol E00329 31236 Antimicrobial preservative
Hydroxyethyl cellulose E00700 Not Available Coating agent; Suspending agent; Binding agent; Viscosity-controlling agent
⏷ Show the Full List of 27 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Oxymetazoline 1% cream 1% Cream Topical
Oxymetazoline 0.1% solution 0.10% Solution Ophthalmic
Oxymetazoline 0.1mg/spray spray 0.1mg/spray Spray Nasal
Oxymetazoline 6mg/spray spray 6mg/spray Spray Nasal
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Oxymetazoline FDA Label
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 Tobias JD, Cartabuke R, Taghon T: Oxymetazoline (Afrin(R)): maybe there is more that we need to know. Paediatr Anaesth. 2014 Aug;24(8):795-8. doi: 10.1111/pan.12399.
4 FDA Approved Drug Products: UPNEEQ (oxymetazoline hydrochloride ophthalmic solution), 0.1%, for topical ophthalmic use
5 Jaillon P: Clinical pharmacokinetics of prazosin. Clin Pharmacokinet. 1980 Jul-Aug;5(4):365-76. doi: 10.2165/00003088-198005040-00004.
6 Potent alpha(2A)-adrenoceptor-mediated vasoconstriction by brimonidine in porcine ciliary arteries. Invest Ophthalmol Vis Sci. 2001 Aug;42(9):2049-55.
7 Identification and characterization of oxymetazoline glucuronidation in human liver microsomes: evidence for the involvement of UGT1A9. J Pharm Sci. 2011 Feb;100(2):784-93.
8 Cell membrane chromatography competitive binding analysis for characterization of 1A adrenoreceptor binding interactions. Anal Bioanal Chem. 2011 Jul;400(10):3625-33. doi: 10.1007/s00216-011-5026-z. Epub 2011 May 5.
9 Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39.
10 Chromatography studies on bio-affinity of nine ligands of alpha1-adrenoceptor to alpha1D subtypes overexpressed in cell membrane. Sci China C Life Sci. 2004 Aug;47(4):376-81. doi: 10.1360/03yc0109.
11 Cusson JR, Goldenberg E, Larochelle P "Effect of a novel monoamine-oxidase inhibitor, moclobemide on the sensitivity to intravenous tyramine and norepinephrine in humans." J Clin Pharmacol 31 (1991): 462-7. [PMID: 2050833]
12 Product Information. Cymbalta (duloxetine). Lilly, Eli and Company, Indianapolis, IN.
13 Mendelson J, Jones RT, Upton R, Jacob P 3rd "Methamphetamine and ethanol interactions in humans." Clin Pharmacol Ther 57 (1995): 559-68. [PMID: 7768079]
14 Barthel W, Glusa E, Koth W "Interactions of dihydroergotamine with etilefrine in human leg veins in vitro and in situ." Int J Clin Pharmacol Ther Toxicol 25 (1987): 63-9. [PMID: 2881898]