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 187.65 63.71 24 58 848 2357155
Ageusia 96.81 63.71 15 67 1983 2356020

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

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
MeSH PA D018663 Adrenergic Agents
MeSH PA D000322 Adrenergic Agonists
MeSH PA D000316 Adrenergic alpha-Agonists
CHEBI has role CHEBI:35569 alpha-adrenergic agonist
CHEBI has role CHEBI:35524 sympathomimetic agent
CHEBI has role CHEBI:77715 nasal decongestant
CHEBI has role CHEBI:50514 vasoconstrictor agent
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
FDA EPC N0000192562 Vasoconstrictor
FDA PE N0000009908 Vasoconstriction
FDA PE N0000175651 Increased Sympathetic Activity
FDA CS M0461078 Imidazolines

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
0.1MG/SPRAY KOVANAZE ST RENATUS N208032 June 29, 2016 RX SPRAY, METERED NASAL 6413499 March 20, 2020 METHOD OF ANESTHETIZING AT LEAST A PORTION OF THE MAXILLARY DENTAL ARCH
1% RHOFADE EPI HLTH N208552 Jan. 18, 2017 RX CREAM TOPICAL 8815929 Jan. 22, 2024 TOPICAL TREATMENT OF PERSISTENT FACIAL ERYTHEMA ASSOCIATED WITH ROSACEA IN ADULTS WITH 1% OXYMETAZOLINE HYDROCHLORIDE CREAM
1% RHOFADE EPI HLTH N208552 Jan. 18, 2017 RX CREAM TOPICAL 8420688 Aug. 2, 2024 TOPICAL TREATMENT OF PERSISTENT FACIAL ERYTHEMA ASSOCIATED WITH ROSACEA IN ADULTS WITH 1% OXYMETAZOLINE HYDROCHLORIDE CREAM
1% RHOFADE EPI HLTH N208552 Jan. 18, 2017 RX CREAM TOPICAL 7812049 May 2, 2028 TOPICAL TREATMENT OF PERSISTENT FACIAL ERYTHEMA ASSOCIATED WITH ROSACEA IN ADULTS WITH 1% OXYMETAZOLINE HYDROCHLORIDE CREAM
0.1MG/SPRAY KOVANAZE ST RENATUS N208032 June 29, 2016 RX SPRAY, METERED NASAL 8580282 April 2, 2030 METHOD OF ANESTHETIZING AT LEAST A PORTION OF THE MAXILLARY DENTAL ARCH
0.1MG/SPRAY KOVANAZE ST RENATUS N208032 June 29, 2016 RX SPRAY, METERED NASAL 9308191 April 2, 2030 METHOD OF ANESTHETIZING AT LEAST A PORTION OF THE MAXILLARY DENTAL ARCH
1% RHOFADE EPI HLTH N208552 Jan. 18, 2017 RX CREAM TOPICAL 10335391 June 11, 2035 ONCE DAILY TOPICAL TREATMENT OF PERSISTENT FACIAL ERYTHEMA ASSOCIATED WITH ROSACEA IN ADULTS WITH 1% OXYMETAZOLINE HYDROCHLORIDE CREAM, WHERE THE PATIENT EXPERIENCES NO REBOUND OR WORSENING OF FACIAL ERYTHEMA POST-TREATMENT
1% RHOFADE EPI HLTH N208552 Jan. 18, 2017 RX CREAM TOPICAL 9974773 June 11, 2035 ONCE DAILY TOPICAL TREATMENT OF PERSISTENT FACIAL ERYTHEMA ASSOCIATED WITH ROSACEA IN ADULTS WITH 1% OXYMETAZOLINE HYDROCHLORIDE CREAM

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
1% RHOFADE EPI HLTH N208552 Jan. 18, 2017 RX CREAM TOPICAL Jan. 18, 2020 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
C0030071 UMLSCUI
D01022 KEGG_DRUG
29129004 SNOMEDCT_US
4019463 VANDF
5411 MMSL
7812 RXNORM
387158001 SNOMEDCT_US
004728 NDDF
8VLN5B44ZY UNII
1400 INN_ID
CHEBI:7862 CHEBI
CHEMBL762 ChEMBL_ID
DB00935 DRUGBANK_ID
CHEMBL1200791 ChEMBL_ID
2315-02-8 SECONDARY_CAS_RN
4636 PUBCHEM_CID
D010109 MESH_DESCRIPTOR_UI
124 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
RHOFADE HUMAN PRESCRIPTION DRUG LABEL 1 0023-5300 CREAM 10 mg TOPICAL NDA 17 sections
good sense nasal HUMAN OTC DRUG LABEL 1 0113-0065 SPRAY 0.05 g NASAL OTC monograph final 9 sections
Good Sense Nasal HUMAN OTC DRUG LABEL 1 0113-0304 SPRAY 0.50 mg NASAL OTC monograph final 9 sections
good sense nasal HUMAN OTC DRUG LABEL 1 0113-0388 SPRAY 0.05 g NASAL OTC monograph final 9 sections
Good Sense Nasal HUMAN OTC DRUG LABEL 1 0113-0817 SPRAY 0.05 g NASAL OTC monograph final 9 sections
Nasal HUMAN OTC DRUG LABEL 1 0113-2304 SPRAY 0.05 g NASAL OTC monograph final 9 sections
basic care nasal HUMAN OTC DRUG LABEL 1 0113-7388 SPRAY 0.05 g NASAL OTC monograph final 14 sections
basic care no drip nasal HUMAN OTC DRUG LABEL 1 0113-7494 SPRAY 0.05 g NASAL OTC monograph final 14 sections
Anefrin Nasal HUMAN OTC DRUG LABEL 1 0363-0304 SPRAY 0.05 g NASAL OTC monograph final 9 sections
Nasal Mist HUMAN OTC DRUG LABEL 1 0363-7000 LIQUID 0.05 g TOPICAL OTC monograph final 5 sections
Severe Congestion Nasal no drip HUMAN OTC DRUG LABEL 1 0363-7001 LIQUID 0.05 g TOPICAL OTC monograph final 5 sections
Maximum Strenth Nasal HUMAN OTC DRUG LABEL 1 0363-7003 LIQUID 0.05 g TOPICAL OTC monograph final 6 sections
Extra Moisturizing No Drip Nasal HUMAN OTC DRUG LABEL 1 0363-7004 LIQUID 0.05 g TOPICAL OTC monograph final 6 sections
Original No Drip Nasal HUMAN OTC DRUG LABEL 1 0363-7005 LIQUID 0.05 g TOPICAL OTC monograph final 6 sections
Walgreen HUMAN OTC DRUG LABEL 1 0363-7151 SPRAY 0.05 g NASAL OTC monograph final 14 sections
DRISTAN 12 HR HUMAN OTC DRUG LABEL 1 0573-1191 SPRAY 0.50 mg NASAL OTC MONOGRAPH FINAL 9 sections
Nasal HUMAN OTC DRUG LABEL 1 0904-5711 SPRAY 5 g NASAL OTC monograph final 10 sections
Major HUMAN OTC DRUG LABEL 1 0904-7006 SPRAY 0.05 g NASAL OTC monograph final 14 sections
7 Select Original Nasal HUMAN OTC DRUG LABEL 1 10202-849 SPRAY 0.05 g NASAL OTC monograph final 11 sections
Afrin HUMAN OTC DRUG LABEL 1 11523-1159 SPRAY, METERED 0.05 g NASAL OTC monograph final 10 sections
Afrin HUMAN OTC DRUG LABEL 1 11523-1167 SPRAY 0.05 g NASAL OTC monograph final 10 sections
Afrin No Drip HUMAN OTC DRUG LABEL 1 11523-1350 SPRAY, METERED 0.05 g NASAL OTC monograph final 10 sections
Afrin No Drip HUMAN OTC DRUG LABEL 1 11523-1783 SPRAY, METERED 0.05 g NASAL OTC monograph final 10 sections
Afrin No Drip HUMAN OTC DRUG LABEL 1 11523-3142 SPRAY, METERED 0.05 g NASAL OTC monograph final 10 sections
Afrin No-Drip HUMAN OTC DRUG LABEL 1 11523-3220 SPRAY, METERED 0.05 mg NASAL OTC monograph final 15 sections
Afrin HUMAN OTC DRUG LABEL 1 11523-7020 SPRAY 0.05 g NASAL OTC monograph final 10 sections
12 Hour Original Nasal Decongestant HUMAN OTC DRUG LABEL 1 11527-140 LIQUID 50 mg NASAL OTC monograph final 13 sections
Up and Up nasal HUMAN OTC DRUG LABEL 1 11673-935 SPRAY 0.05 g NASAL OTC monograph final 14 sections
nasal HUMAN OTC DRUG LABEL 1 11822-0065 SPRAY 0.05 g NASAL OTC monograph final 9 sections
nasal HUMAN OTC DRUG LABEL 1 11822-0304 SPRAY 0.05 g NASAL OTC monograph final 9 sections