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

Stem definition	Drug id	CAS RN
antihistaminics or local vasoconstrictors, antazoline derivatives	2032	1491-59-4

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
0.40	mg	N

ADMET properties:

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

Approvals:

Date	Agency	Company	Orphan
May 30, 1986	FDA	BAYER HEALTHCARE LLC

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Anosmia	87.99	17.65	27	3570	6833	63478592
Eye irritation	79.85	17.65	34	3563	21937	63463488
Mydriasis	58.82	17.65	23	3574	11933	63473492
Trigemino-cardiac reflex	47.03	17.65	7	3590	48	63485377
Ocular hyperaemia	36.98	17.65	21	3576	25123	63460302
Ageusia	33.19	17.65	16	3581	13712	63471713
Vision blurred	31.41	17.65	32	3565	91892	63393533
Swelling of eyelid	30.43	17.65	10	3587	3146	63482279
Nasal congestion	30.31	17.65	27	3570	65633	63419792
Nasal discomfort	26.41	17.65	10	3587	4750	63480675

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Anosmia	50.91	19.51	16	2147	4008	34950760
Epistaxis	31.10	19.51	27	2136	58224	34896544
Vision blurred	25.94	19.51	22	2141	45941	34908827

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Anosmia	107.67	16.50	34	4811	8810	79730733
Eye irritation	60.24	16.50	28	4817	20653	79718890
Mydriasis	58.04	16.50	26	4819	17617	79721926
Ageusia	37.79	16.50	19	4826	16613	79722930
Trigemino-cardiac reflex	35.44	16.50	7	4838	262	79739281
Epistaxis	34.40	16.50	38	4807	111477	79628066
Vision blurred	32.51	16.50	36	4809	105862	79633681
Hypervolaemia	32.04	16.50	24	4821	42666	79696877
Nasal discomfort	31.36	16.50	12	4833	5471	79734072
Ocular hyperaemia	30.89	16.50	20	4825	28186	79711357

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
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
CHEBI has role	CHEBI:35524	sympathomimetic
CHEBI has role	CHEBI:35569	alpha-adrenergic agonists
CHEBI has role	CHEBI:77715	nasal decongestants
FDA CS	M0461078	Imidazolines
FDA EPC	N0000192562	Vasoconstrictor
FDA PE	N0000009908	Vasoconstriction

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	11.6	acidic
pKa2	10.99	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
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
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
0.1%	UPNEEQ	RVL PHARMS	N212520	July 8, 2020	RX	SOLUTION/DROPS	OPHTHALMIC	11324722	Dec. 16, 2039	METHOD OF TREATING BLEPHAROPTOSIS
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
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

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
0.1%	UPNEEQ	RVL PHARMS	N212520	July 8, 2020	RX	SOLUTION/DROPS	OPHTHALMIC	July 8, 2023	NEW PRODUCT

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN	AGONIST	Ki	8.20	IUPHAR	SCIENTIFIC LITERATURE
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN	AGONIST	Ki	6.20	IUPHAR	SCIENTIFIC LITERATURE
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	6.59	PDSP
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		Ki	6.83	PDSP
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN	AGONIST	Ki	6.80	IUPHAR
5-hydroxytryptamine receptor 6	GPCR	P50406	5HT6R_HUMAN		Ki	6.11	DRUG MATRIX
Muscarinic acetylcholine receptor M4	GPCR	P08173	ACM4_HUMAN		Ki	6.34	DRUG MATRIX
Muscarinic acetylcholine receptor M5	GPCR	P08912	ACM5_HUMAN		Ki	6.02	DRUG MATRIX
5-hydroxytryptamine receptor 1B	GPCR	P28222	5HT1B_HUMAN		Ki	9.52	CHEMBL
5-hydroxytryptamine receptor 1D	GPCR	P28221	5HT1D_HUMAN		Ki	9.40	CHEMBL

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External reference:

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ID	Source
J5C	PDB_CHEM_ID
001810	NDDF
004728	NDDF
106101	RXNORM
124	IUPHAR_LIGAND_ID
1400	INN_ID
2315-02-8	SECONDARY_CAS_RN
29129004	SNOMEDCT_US
387158001	SNOMEDCT_US
4019462	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
7 Select Original Nasal	HUMAN OTC DRUG LABEL	1	10202-849	SPRAY	0.05 g	NASAL	OTC monograph final	11 sections
Anefrin NasalOriginal	HUMAN OTC DRUG LABEL	1	0363-0304	SPRAY	0.05 g	NASAL	OTC monograph final	14 sections
Anefrin NasalOriginal	HUMAN OTC DRUG LABEL	1	0363-0304	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
DRISTAN 12 HR	HUMAN OTC DRUG LABEL	1	0573-1191	SPRAY	0.50 mg	NASAL	OTC monograph final	14 sections
Extra Moisturizing No Drip NasalWalgreens	HUMAN OTC DRUG LABEL	1	0363-7004	LIQUID	0.05 g	TOPICAL	OTC monograph final	7 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

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