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oxymetazoline 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)

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	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 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	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:

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
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)

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

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent 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 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

Bioactivity Summary:

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
Alpha-2C adrenergic receptor	GPCR	P18825	ADA2C_HUMAN	AGONIST	Ki	9	CHEMBL
Cytochrome P450 2D6	Enzyme	P10635	CP2D6_HUMAN		IC50	6.70	DRUG MATRIX
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN	AGONIST	Ki	6.40	IUPHAR
Alpha-1B adrenergic receptor	GPCR	P35368	ADA1B_HUMAN	AGONIST	Ki	6.50	IUPHAR
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN	AGONIST	Ki	9.54	CHEMBL
Nischarin	Membrane receptor	Q9Y2I1	NISCH_HUMAN		Ki	8.21	CHEMBL
5-hydroxytryptamine receptor 1E	GPCR	P28566	5HT1E_HUMAN		Ki	6.38	PDSP
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN		Ki	8.49	DRUG MATRIX
Alpha-1B adrenergic receptor	GPCR		ADA1B_RAT		Ki	6.16	DRUG MATRIX
5-hydroxytryptamine receptor 1B	GPCR		5HT1B_RAT		Ki	9.04	DRUG MATRIX
Alpha-1A adrenergic receptor	GPCR		ADA1A_RAT		Ki	8.19	CHEMBL
Alpha-1D adrenergic receptor	GPCR		ADA1D_RAT		Ki	6.48	CHEMBL
5-hydroxytryptamine receptor 1A	GPCR		5HT1A_RAT		IC50	8.25	CHEMBL
Alpha-1A adrenergic receptor	GPCR		ADA1A_BOVIN		Ki	7.88	CHEMBL
Alpha-2A adrenergic receptor	GPCR		ADA2A_PIG		Ki	7.68	CHEMBL
Alpha-2A adrenergic receptor	GPCR		ADA2A_BOVIN		Ki	8.82	CHEMBL
Alpha-1B adrenergic receptor	GPCR		ADA1B_MESAU		Ki	6.69	CHEMBL
Adrenergic receptor alpha-2	GPCR		ADA2B_RAT ADA2C_RAT ADA2A_RAT		Ki	8.72	CHEMBL
Alpha-2 adrenergic receptor	GPCR		ADA2B_MOUSE ADA2C_MOUSE ADA2A_MOUSE		Ki	7.48	CHEMBL

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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