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 105.37 19.08 28 2926 4347 53341765
Mydriasis 53.43 19.08 21 2933 11305 53334807
Trigemino-cardiac reflex 49.78 19.08 7 2947 31 53346081
Nasal congestion 38.06 19.08 28 2926 53259 53292853
Prescription drug used without a prescription 36.23 19.08 10 2944 1784 53344328
Cerebral vasoconstriction 35.85 19.08 9 2945 1114 53344998
Ageusia 34.84 19.08 16 2938 12598 53333514
Nasal discomfort 31.71 19.08 11 2943 4175 53341937
Eye irritation 26.36 19.08 15 2939 18434 53327678
Electrocardiogram ST segment depression 23.39 19.08 8 2946 2910 53343202
Amaurosis 20.56 19.08 5 2949 543 53345569

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 64.45 18.74 17 2035 2248 32509226
Brain scan abnormal 28.00 18.74 7 2045 747 32510727
Epistaxis 27.61 18.74 25 2027 55830 32455644
Cerebral artery thrombosis 24.01 18.74 6 2046 639 32510835
Areflexia 22.48 18.74 8 2044 2868 32508606

Pharmacologic Action:

SourceCodeDescription
ATC D11AX27 DERMATOLOGICALS
OTHER DERMATOLOGICAL PREPARATIONS
OTHER DERMATOLOGICAL PREPARATIONS
Other dermatologicals
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
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 PE N0000175651 Increased Sympathetic Activity
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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
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;6MG/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;6MG/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
0.1% UPNEEQ RVL PHARMS N212520 July 8, 2020 RX SOLUTION/DROPS OPHTHALMIC 10912765 Aug. 26, 2031 METHOD OF TREATING BLEPHAROPTOSIS
0.1% UPNEEQ RVL PHARMS N212520 July 8, 2020 RX SOLUTION/DROPS OPHTHALMIC 8357714 Aug. 26, 2031 METHOD OF TREATING BLEPHAROPTOSIS
0.1% UPNEEQ RVL PHARMS N212520 July 8, 2020 RX SOLUTION/DROPS OPHTHALMIC 9867808 Aug. 26, 2031 METHOD OF TREATING BLEPHAROPTOSIS
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 10751325 June 11, 2035 ONCE DAILY TOPICAL TREATMENT OF PERSISTENT FACIAL ERYTHEMA ASSOCIATED WITH ROSACEA IN ADULTS
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
0.1% UPNEEQ RVL PHARMS N212520 July 8, 2020 RX SOLUTION/DROPS OPHTHALMIC 10799481 Dec. 16, 2039 METHOD OF TREATING BLEPHAROPTOSIS
0.1% UPNEEQ RVL PHARMS N212520 July 8, 2020 RX SOLUTION/DROPS OPHTHALMIC 10940138 Dec. 16, 2039 METHOD OF TREATING BLEPHAROPTOSIS

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-1A adrenergic receptor GPCR AGONIST Ki 8.20 IUPHAR SCIENTIFIC LITERATURE
Alpha-2B adrenergic receptor GPCR AGONIST Ki 6.20 IUPHAR SCIENTIFIC LITERATURE
5-hydroxytryptamine receptor 2A GPCR Ki 6.59 PDSP
5-hydroxytryptamine receptor 2B GPCR Ki 6.83 PDSP
5-hydroxytryptamine receptor 2C GPCR AGONIST Ki 6.80 IUPHAR
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
5-hydroxytryptamine receptor 1B GPCR Ki 9.52 CHEMBL
5-hydroxytryptamine receptor 1D GPCR Ki 9.40 CHEMBL
Alpha-2C adrenergic receptor GPCR AGONIST Ki 9 CHEMBL
Cytochrome P450 2D6 Enzyme IC50 6.70 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR AGONIST Ki 6.40 IUPHAR
Alpha-1B adrenergic receptor GPCR AGONIST Ki 6.50 IUPHAR
Alpha-2A adrenergic receptor GPCR AGONIST Ki 9.54 CHEMBL
Nischarin Membrane receptor Ki 8.21 CHEMBL
5-hydroxytryptamine receptor 1E GPCR Ki 6.38 PDSP
5-hydroxytryptamine receptor 1A GPCR Ki 8.49 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 6.16 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 9.04 DRUG MATRIX
Alpha-1A adrenergic receptor GPCR Ki 8.19 CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 6.48 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 8.25 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 7.88 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 7.68 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 8.82 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 6.69 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 8.72 CHEMBL
Alpha-2 adrenergic receptor GPCR Ki 7.48 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
DB00935 DRUGBANK_ID
D010109 MESH_DESCRIPTOR_UI
4636 PUBCHEM_CID
124 IUPHAR_LIGAND_ID
1400 INN_ID
8VLN5B44ZY UNII
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 NASAL OTC monograph final 14 sections
Good Sense Nasal HUMAN OTC DRUG LABEL 1 0113-0304 SPRAY 0.50 mg NASAL OTC monograph final 14 sections
good sense nasal HUMAN OTC DRUG LABEL 1 0113-0388 SPRAY 0.05 g NASAL OTC monograph final 14 sections
Good Sense Nasal HUMAN OTC DRUG LABEL 1 0113-0817 SPRAY 0.05 g NASAL OTC monograph final 14 sections
Nasal HUMAN OTC DRUG LABEL 1 0113-2304 SPRAY 0.05 g NASAL OTC monograph final 14 sections
basic care nasal HUMAN OTC DRUG LABEL 1 0113-7388 SPRAY 0.05 g NASAL OTC monograph final 13 sections
basic care no drip nasal HUMAN OTC DRUG LABEL 1 0113-7494 SPRAY 0.05 g NASAL OTC monograph final 13 sections
Anefrin NasalOriginal HUMAN OTC DRUG LABEL 1 0363-0304 SPRAY 0.05 g NASAL OTC monograph final 14 sections
Severe Anefrin HUMAN OTC DRUG LABEL 1 0363-2021 LIQUID 0.05 g NASAL OTC monograph final 11 sections
No Drip Nasal Mist HUMAN OTC DRUG LABEL 1 0363-2303 LIQUID 50 mg NASAL OTC monograph final 13 sections
Severe Sinus Relief Mist HUMAN OTC DRUG LABEL 1 0363-2305 LIQUID 50 mg NASAL OTC monograph final 13 sections
No Drip Nasal Mist HUMAN OTC DRUG LABEL 1 0363-2307 LIQUID 50 mg NASAL 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 NASAL OTC monograph final 11 sections
Severe Sinus Relief Mist HUMAN OTC DRUG LABEL 1 0363-7009 LIQUID 50 mg NASAL OTC monograph final 15 sections
Walgreen HUMAN OTC DRUG LABEL 1 0363-7151 SPRAY 0.05 g NASAL OTC monograph final 13 sections
DRISTAN 12 HR HUMAN OTC DRUG LABEL 1 0573-1191 SPRAY 0.50 mg NASAL OTC monograph final 14 sections
nasal decongestant HUMAN OTC DRUG LABEL 1 0904-6761 SPRAY 0.05 g NASAL OTC monograph final 13 sections
Major HUMAN OTC DRUG LABEL 1 0904-7006 SPRAY 0.05 g NASAL OTC monograph final 13 sections
7 Select Original Nasal HUMAN OTC DRUG LABEL 1 10202-849 SPRAY 0.05 g NASAL OTC monograph final 11 sections
Zicam Extreme Congestion Relief HUMAN OTC DRUG LABEL 1 10237-464 SPRAY 0.50 mg NASAL OTC monograph final 14 sections
Afrin NoDrip Allergy Sinus Night HUMAN OTC DRUG LABEL 1 11523-0034 SPRAY 0.50 mg NASAL OTC monograph final 14 sections
Afrin Allergy Sinus Nasal HUMAN OTC DRUG LABEL 1 11523-0073 SPRAY 0.50 g NASAL OTC monograph final 14 sections
AfrinOriginal Pump Mist HUMAN OTC DRUG LABEL 1 11523-1159 SPRAY, METERED 0.05 g NASAL OTC monograph final 15 sections
Afrin No Drip NightChamomile HUMAN OTC DRUG LABEL 1 11523-1160 SPRAY, METERED 0.50 mg NASAL OTC monograph final 13 sections