oxymetazoline Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antihistaminics or local vasoconstrictors, antazoline derivatives 2032 1491-59-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • oxymetazoline
  • navasin
  • oxylazine
  • oxymethazoline
  • rhinofrenol
  • rhinolitan
  • oxymetazoline hydrochloride
  • oxymetazoline HCl
Imidazoline derivative with sympathomimetic activity that stimulates alpha-adrenergic receptors in the arterioles of the nasal mucosa to produce vasoconstriction.
  • Molecular weight: 260.38
  • Formula: C16H24N2O
  • CLOGP: 4.61
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 2
  • TPSA: 44.62
  • ALOGS: -3.70
  • ROTB: 3

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.40 mg N

ADMET properties:

PropertyValueReference
BA (Bioavailability) 11 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
May 30, 1986 FDA BAYER HEALTHCARE LLC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anosmia 102.94 20.24 27 2605 3917 46679513
Nasal congestion 37.87 20.24 27 2605 48086 46635344
Cerebral vasoconstriction 36.44 20.24 9 2623 1024 46682406
Ageusia 36.03 20.24 16 2616 11456 46671974
Nasal discomfort 28.83 20.24 10 2622 3728 46679702
Mydriasis 27.72 20.24 13 2619 10540 46672890
Prescription drug used without a prescription 24.47 20.24 7 2625 1395 46682035
Amaurosis 20.58 20.24 5 2627 531 46682899

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anosmia 67.05 20.19 17 1732 2083 29948646
Epistaxis 30.47 20.19 25 1724 52956 29897773

Pharmacologic Action:

SourceCodeDescription
ATC R01AA05 RESPIRATORY SYSTEM
NASAL PREPARATIONS
DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
Sympathomimetics, plain
ATC R01AB07 RESPIRATORY SYSTEM
NASAL PREPARATIONS
DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
Sympathomimetics, combinations excl. corticosteroids
ATC S01GA04 SENSORY ORGANS
OPHTHALMOLOGICALS
DECONGESTANTS AND ANTIALLERGICS
Sympathomimetics used as decongestants
FDA CS M0461078 Imidazolines
FDA PE N0000009908 Vasoconstriction
FDA PE N0000175651 Increased Sympathetic Activity
MeSH PA D018663 Adrenergic Agents
MeSH PA D000322 Adrenergic Agonists
MeSH PA D000316 Adrenergic alpha-Agonists
MeSH PA D002317 Cardiovascular Agents
MeSH PA D014663 Nasal Decongestants
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D019141 Respiratory System Agents
MeSH PA D013566 Sympathomimetics
MeSH PA D014662 Vasoconstrictor Agents
CHEBI has role CHEBI:35524 sympathomimetic
CHEBI has role CHEBI:35569 alpha-adrenergic receptor agonist
CHEBI has role CHEBI:77715 decongestants
FDA EPC N0000192562 Vasoconstrictor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Nasal discharge indication 64531003
Nasal congestion indication 68235000
Red eye indication 75705005
Local anesthesia indication 386761002
Persistent erythema of skin indication 420356000
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Pain in eye contraindication 41652007
Heart disease contraindication 56265001 DOID:114
Arteriosclerotic vascular disease contraindication 72092001
Diabetes mellitus contraindication 73211009 DOID:9351
Eye infection contraindication 128351009
Benign prostatic hyperplasia contraindication 266569009
Angle-closure glaucoma contraindication 392291006 DOID:13550
Visual impairment contraindication 397540003
Disorder of coronary artery contraindication 414024009

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.6 acidic
pKa2 10.99 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
0.1% UPNEEQ RVL PHARMS N212520 July 8, 2020 RX SOLUTION/DROPS OPHTHALMIC July 8, 2023 NEW PRODUCT

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Alpha-2B adrenergic receptor GPCR AGONIST Ki 6.20 IUPHAR SCIENTIFIC LITERATURE
Alpha-1A adrenergic receptor GPCR AGONIST Ki 8.20 IUPHAR SCIENTIFIC LITERATURE
5-hydroxytryptamine receptor 2A GPCR Ki 6.59 PDSP
5-hydroxytryptamine receptor 2C GPCR AGONIST Ki 6.80 IUPHAR
Alpha-1B adrenergic receptor GPCR AGONIST Ki 6.50 IUPHAR
Alpha-1D adrenergic receptor GPCR AGONIST Ki 6.40 IUPHAR
5-hydroxytryptamine receptor 1A GPCR Ki 8.49 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 6.11 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.34 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 6.02 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 6.70 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR AGONIST Ki 9 CHEMBL
Nischarin Membrane receptor Ki 8.21 CHEMBL
5-hydroxytryptamine receptor 1B GPCR Ki 9.52 CHEMBL
5-hydroxytryptamine receptor 1D GPCR Ki 9.40 CHEMBL
Alpha-2A adrenergic receptor GPCR AGONIST Ki 9.54 CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 6.83 PDSP
5-hydroxytryptamine receptor 1E GPCR Ki 6.38 PDSP
Alpha-1B adrenergic receptor GPCR Ki 6.16 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 9.04 DRUG MATRIX
Alpha-2 adrenergic receptor GPCR Ki 7.48 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 8.72 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 8.82 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 7.68 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 7.88 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 6.69 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 8.25 CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 6.48 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 8.19 CHEMBL

External reference:

IDSource
4019463 VUID
N0000147584 NUI
D01022 KEGG_DRUG
2315-02-8 SECONDARY_CAS_RN
4019462 VANDF
4019463 VANDF
C0030071 UMLSCUI
CHEBI:7862 CHEBI
CHEMBL762 ChEMBL_ID
CHEMBL1200791 ChEMBL_ID
D010109 MESH_DESCRIPTOR_UI
DB00935 DRUGBANK_ID
124 IUPHAR_LIGAND_ID
1400 INN_ID
8VLN5B44ZY UNII
4636 PUBCHEM_CID
106101 RXNORM
5218 MMSL
5411 MMSL
5424 MMSL
001810 NDDF
004728 NDDF
29129004 SNOMEDCT_US
387158001 SNOMEDCT_US
9910008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
RHOFADE HUMAN PRESCRIPTION DRUG LABEL 1 0023-5300 CREAM 10 mg TOPICAL NDA 26 sections
good sense nasal HUMAN OTC DRUG LABEL 1 0113-0065 SPRAY 0.05 g NULLSAL OTC monograph final 14 sections
Good Sense Nasal HUMAN OTC DRUG LABEL 1 0113-0304 SPRAY 0.50 mg NULLSAL OTC monograph final 14 sections
good sense nasal HUMAN OTC DRUG LABEL 1 0113-0388 SPRAY 0.05 g NULLSAL OTC monograph final 14 sections
Good Sense Nasal HUMAN OTC DRUG LABEL 1 0113-0817 SPRAY 0.05 g NULLSAL OTC monograph final 14 sections
Nasal HUMAN OTC DRUG LABEL 1 0113-2304 SPRAY 0.05 g NULLSAL OTC monograph final 14 sections
basic care nasal HUMAN OTC DRUG LABEL 1 0113-7388 SPRAY 0.05 g NULLSAL OTC monograph final 13 sections
basic care no drip nasal HUMAN OTC DRUG LABEL 1 0113-7494 SPRAY 0.05 g NULLSAL OTC monograph final 13 sections
Anefrin NasalOriginal HUMAN OTC DRUG LABEL 1 0363-0304 SPRAY 0.05 g NULLSAL OTC monograph final 14 sections
Severe Anefrin HUMAN OTC DRUG LABEL 1 0363-2021 LIQUID 0.05 g NULLSAL OTC monograph final 11 sections
No Drip Nasal Mist HUMAN OTC DRUG LABEL 1 0363-2303 LIQUID 50 mg NULLSAL OTC monograph final 13 sections
Severe Sinus Relief Mist HUMAN OTC DRUG LABEL 1 0363-2305 LIQUID 50 mg NULLSAL OTC monograph final 13 sections
No Drip Nasal Mist HUMAN OTC DRUG LABEL 1 0363-2307 LIQUID 50 mg NULLSAL OTC monograph final 12 sections
Nasal MistWalgreens HUMAN OTC DRUG LABEL 1 0363-7000 LIQUID 0.05 g TOPICAL OTC monograph final 8 sections
Severe Congestion Nasal no dripWalgreens HUMAN OTC DRUG LABEL 1 0363-7001 LIQUID 0.05 g TOPICAL OTC monograph final 9 sections
Maximum Strenth Nasal HUMAN OTC DRUG LABEL 1 0363-7003 LIQUID 0.05 g TOPICAL OTC monograph final 7 sections
Extra Moisturizing No Drip NasalWalgreens HUMAN OTC DRUG LABEL 1 0363-7004 LIQUID 0.05 g TOPICAL OTC monograph final 7 sections
Original No Drip NasalWalgreens HUMAN OTC DRUG LABEL 1 0363-7005 LIQUID 0.05 g TOPICAL OTC monograph final 7 sections
No Drip Anefrin Nasal HUMAN OTC DRUG LABEL 1 0363-7007 LIQUID 0.05 g NULLSAL OTC monograph final 11 sections
Walgreen HUMAN OTC DRUG LABEL 1 0363-7151 SPRAY 0.05 g NULLSAL OTC monograph final 13 sections
DRISTAN 12 HR HUMAN OTC DRUG LABEL 1 0573-1191 SPRAY 0.50 mg NULLSAL OTC monograph final 14 sections
nasal decongestant HUMAN OTC DRUG LABEL 1 0904-6761 SPRAY 0.05 g NULLSAL OTC monograph final 13 sections
Major HUMAN OTC DRUG LABEL 1 0904-7006 SPRAY 0.05 g NULLSAL OTC monograph final 13 sections
7 Select Original Nasal HUMAN OTC DRUG LABEL 1 10202-849 SPRAY 0.05 g NULLSAL OTC monograph final 11 sections
Afrin NoDrip Allergy Sinus Night HUMAN OTC DRUG LABEL 1 11523-0034 SPRAY 0.50 mg NULLSAL OTC monograph final 14 sections
Afrin Allergy Sinus Nasal HUMAN OTC DRUG LABEL 1 11523-0073 SPRAY 0.50 g NULLSAL OTC monograph final 14 sections
AfrinOriginal Pump Mist HUMAN OTC DRUG LABEL 1 11523-1159 SPRAY, METERED 0.05 g NULLSAL OTC monograph final 15 sections
Afrin No Drip NightChamomile HUMAN OTC DRUG LABEL 1 11523-1160 SPRAY, METERED 0.50 mg NULLSAL OTC monograph final 13 sections
Afrin Original Nasal HUMAN OTC DRUG LABEL 1 11523-1168 LIQUID 0.50 mg NULLSAL OTC monograph final 14 sections
Afrin No DripExtra Moisturizing HUMAN OTC DRUG LABEL 1 11523-1783 SPRAY, METERED 0.05 g NULLSAL OTC monograph final 15 sections