2-(4-tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline
3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenol
6-t-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol
6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol
Oximetazolinum
Oxymetazolina
Oxymetazoline
Oxymétazoline
Oxymetazolinum
Oxymethazoline
Oxymetozoline

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Oxymetazoline hydrochloride	K89MJ0S5VY	2315-02-8	BEEDODBODQVSIM-UHFFFAOYSA-N

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Rhofade	Cream	1 g/100g	Topical	Aclaris Therapeutics, Inc.	2017-01-18	Not applicable
Rhofade	Cream	10 mg/1g	Topical	Allergan, Inc.	2017-01-18	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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12 Hour Nasal	Spray	0.05 g/100mL	Nasal	Select Brand Distributors	2000-03-01	2020-04-30
12 Hour Nasal	Spray	0.05 g/100mL	Nasal	Healthlife of Usa	2018-01-02	Not applicable
12 Hour Nasal	Spray	0.05 g/100mL	Nasal	Altaire Pharmaceuticals Inc.	2001-06-01	Not applicable
12 Hour Nasal	Spray	.05 g/100mL	Nasal	Meijer Distribution	2015-05-06	Not applicable
12 Hour Original Nasal Decongestant	Liquid	50 mg/100mL	Nasal	Preferred Pharmaceuticals Inc.	2018-01-02	Not applicable
12 Hour Original Nasal Decongestant	Liquid	50 mg/100mL	Nasal	Sheffield Pharmaceuticals LLC	2014-05-30	Not applicable
7 Select Nasal	Spray	0.05 g/100mL	Nasal	7-Eleven	2014-08-05	2019-10-23
7 Select Original Nasal	Spray	0.05 g/1mL	Nasal	7-ELEVEN, INC.	2016-10-04	Not applicable
Aesb - Oxymetazoline Hydrochloride Nasal Solution USP, 0.025%	Solution		Nasal	Bayer	Not applicable	Not applicable
Afrin	Spray	0.05 g/100mL	Topical	Navajo Manufacturing Company Inc.	2017-12-04	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Kovanaze	Oxymetazoline hydrochloride (0.5 mg/1mL) + Tetracaine hydrochloride (30 mg/1mL)	Spray	Nasal	St. Renatus	2016-09-01	Not applicable

International/Other Brands

Dristan 12-Hour / Duramist Plus / Genasal Nasal Spray Up to 12 Hour Relief / Iliadin / Neo-Synephrine 12 Hour Spray / Nezeril / Nostrilla 12 Hour Nasal Decongestant / OcuClear / Vicks Sinex 12 Hour Nasal Spray / Vicks Sinex 12 Hour Ultra Fine Mist for Sinus Relief

Categories

UNII

8VLN5B44ZY

CAS number

1491-59-4

Weight

Average: 260.3746
Monoisotopic: 260.1888634

Chemical Formula

C₁₆H₂₄N₂O

InChI Key

WYWIFABBXFUGLM-UHFFFAOYSA-N

InChI

InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)

IUPAC Name

6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol

SMILES

CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C

Pharmacology

Indication

For treatment of nasal congestion and redness associated with minor irritations of the eye

Associated Conditions

Pharmacodynamics

Oxymetazoline a adrenergic alpha-agonists, direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion The sympathomimetic action of oxymetazoline constricts the smaller arterioles of the nasal passages, producing a prolonged (up to 12 hours), gentle and decongesting effect. Oxymetazoline elicits relief of conjunctival hyperemia by causing vasoconstriction of superficial conjunctival blood vessels. The drug's action has been demonstrated in acute allergic conjunctivitis and in chemical (chloride) conjunctivitis.

Mechanism of action

Oxymetazoline is a direct acting sympathomimetic amine, which acts on alpha-adrenergic receptors in the arterioles of the conjunctiva and nasal mucosa. It produces vasoconstriction, resulting in decreased conjunctival congestion in ophthalmic. In nasal it produces constriction, resulting in decreased blood flow and decreased nasal congestion.

Target	Actions	Organism
AAlpha-1A adrenergic receptor	agonist	Humans
AAlpha-2A adrenergic receptor	agonist partial agonist	Humans
UAlpha-2C adrenergic receptor	agonist	Humans
UAlpha-2B adrenergic receptor	binder	Humans
UAlpha-1B adrenergic receptor	agonist	Humans
UAlpha-1D adrenergic receptor	agonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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1-benzylimidazole	The risk or severity of hypertension can be increased when Oxymetazoline is combined with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acid	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with 3,5-diiodothyropropionic acid.
3,5-Diiodotyrosine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with 3,5-Diiodotyrosine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine	The risk or severity of hypertension can be increased when Oxymetazoline is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of hypertension can be increased when Oxymetazoline is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanine	The risk or severity of adverse effects can be increased when Oxymetazoline is combined with 6-O-benzylguanine.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

No interactions found.

References

General References

Not Available

External Links

Human Metabolome Database: HMDB0015070
KEGG Compound: C07363
PubChem Compound: 4636
PubChem Substance: 46505622
ChemSpider: 4475
BindingDB: 30712
RxNav: 7812
ChEBI: 7862
ChEMBL: CHEMBL762
ZINC: ZINC000000057435
Therapeutic Targets Database: DAP000235
PharmGKB: PA164748840
Guide to Pharmacology: GtP Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Oxymetazoline

ATC Codes

S01GA04 — Oxymetazoline

R01AB07 — Oxymetazoline

R01AA05 — Oxymetazoline

AHFS Codes

52:32.00 — Vasoconstrictors

MSDS

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Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Autonomic Failure / Orthostatic Hypotension	1
1	Completed	Basic Science	Anaesthesia therapy	1
1	Completed	Basic Science	Middle Ear Disease / Nasal Allergies	1
1	Completed	Basic Science	Acute Rhinitis	1
1	Completed	Treatment	Acne Vulgaris	1
1	Completed	Treatment	Allergic Rhinitis (AR)	2
1	Completed	Treatment	Assess Pharmacokinetics of Ketorolac Tromethamine Intranasal and Assess Effects of a Oxymetazoline Hydrochloride on the PK of Ketorolac Tromethamine / Healthy Volunteers	1
1	Not Yet Recruiting	Other	Major Depressive Disorder (MDD)	1
1	Recruiting	Treatment	Fecal Incontinence	1
1, 2	Completed	Treatment	Fecal Incontinence / Spinal Cord Injuries (SCI)	1
2	Completed	Prevention	Conjunctivitis, Seasonal Allergic	1
2	Completed	Supportive Care	Dental Anesthesia Efficacy	1
2	Completed	Supportive Care	Dental Anesthesia Safety	1
2	Completed	Treatment	Allergic Rhinitis (AR)	1
2	Completed	Treatment	Anaesthesia therapy	3
2	Completed	Treatment	Seasonal Allergic Rhinitis (SAR)	1
2	Suspended	Treatment	Apical Periodontitis / Dental Decay	3
2	Withdrawn	Treatment	Anesthesia, Dental / Intranasal Drug Administration / Nasal Surgical Procedures	1
2, 3	Completed	Other	Cognitive Change / Major Depressive Disorder (MDD)	1
2, 3	Completed	Prevention	Healthy Volunteers	2
3	Completed	Treatment	Acne Rosacea	1
3	Completed	Treatment	Acne Rosacea / Erythemas	3
3	Completed	Treatment	Anaesthesia therapy	3
3	Completed	Treatment	Nasal Congestion / Rhinitis	1
3	Completed	Treatment	Psychotic Depression	1
3	Terminated	Treatment	Anaesthesia therapy	1
3	Unknown Status	Supportive Care	Sedation	1
4	Active Not Recruiting	Treatment	Endoscopic Sinus Surgery / Polyps, Nasal	1
4	Completed	Other	Healthy Controls / Major Depressive Disorder (MDD)	1
4	Completed	Prevention	Throat Disorder	1
4	Completed	Treatment	Acne Rosacea	1
4	Completed	Treatment	Adenoidal Hypertrophy	1
4	Completed	Treatment	Allergic Rhinitis (AR)	1
4	Completed	Treatment	Allergic Rhinitis (AR) / Rhinitis Medicamentosa / Tachyphylaxis	1
4	Completed	Treatment	Depression / Suicidal Thoughts	1
4	Completed	Treatment	Nasal Obstruction Present Finding	1
4	Not Yet Recruiting	Diagnostic	Major Depressive Disorder (MDD)	1
4	Not Yet Recruiting	Other	Local Anesthetic Drug Adverse Reaction / Local Infiltration / Pulp Disease, Dental	1
4	Not Yet Recruiting	Treatment	Otitis Media With Effusion	1
4	Recruiting	Treatment	Chronic Nasal Congestion / Sleep Apnea	1
4	Recruiting	Treatment	Rosacea Subtype 1 (Erythematotelangiectatic)	1
4	Withdrawn	Treatment	Allergic Rhinitis (AR) / Rhinitis Medicamentosa / Tachyphylaxis	1
4	Withdrawn	Treatment	Anesthesia, Dental / Endodontic Disease / Inflammations, Endodontic / Local Anesthesia	1
Not Available	Completed	Not Available	Abdominal Surgeries / Liver Dysfunction / Multiorgan Failure / Renal Failure / Respiratory Failure	1
Not Available	Completed	Not Available	Anemia / Iron Deficiency Anemia (IDA)	1
Not Available	Completed	Not Available	High Blood Pressure (Hypertension)	1
Not Available	Completed	Not Available	Nasal Obstruction	1
Not Available	Completed	Not Available	Polycystic Ovary Syndrom / Pregestational Diabetes / Pregnancy	1
Not Available	Completed	Treatment	Adenoidectomy / Functional Endoscopic Sinus Surgery (FESS) / Turbinate Surgery	1
Not Available	Completed	Treatment	Blood Pressures / Epistaxis	1
Not Available	Completed	Treatment	Nasal Obstruction	1
Not Available	Not Yet Recruiting	Diagnostic	Common Mental Disorder	1
Not Available	Recruiting	Not Available	Major Depressive Disorder (MDD)	1
Not Available	Recruiting	Basic Science	OSAS (Obstructive Sleep Apneas Syndrome)	1
Not Available	Recruiting	Other	General Surgery	1
Not Available	Recruiting	Treatment	Rheumatoid Arthritis	1
Not Available	Terminated	Treatment	Chronic Rhinitis	1

Pharmacoeconomics

Manufacturers

Schering plough healthcare products inc
Johnson and johnson group consumer companies

Packagers

Altaire Pharmaceuticals
Bayer Healthcare
Chain Drug
CVS Pharmacy
Palmetto Pharmaceuticals Inc.
Perrigo Co.
Pfizer Inc.
S&P Healthcare
Spectrum Pharmaceuticals
Target Corp.
Walgreen Co.
Wyeth Pharmaceuticals

Dosage forms

Form	Route	Strength
Spray	Topical	0.05 g/100mL
Spray, metered	Nasal	0.05 g/100mL
Spray, metered	Nasal	0.05 mg/1mL
Spray	Nasal	0.05 mg/100mL
Spray	Nasal	0.2 mg/0.4mL
Spray	Nasal	0.05 g/1mL
Solution	Nasal
Spray	Nasal	0.00050 g/1mL
Spray	Nasal
Spray	Nasal	0.05 mg/100mg
Liquid	Nasal	50 mg/100mL
Solution	Nasal	0.05 g/100mL
Spray	Nasal
Solution	Nasal	0.05 mg/100mL
Solution / drops; spray	Nasal
Kit		0.05 g/100mL
Spray	Nasal	5 g/100mL
Solution / drops	Nasal	0.05 g/100mL
Liquid	Topical	0.05 g/100mL
Spray	Nasal	0.05 mg/1mL
Spray, metered	Nasal	0.0005 mL/100mL
Spray, metered	Nasal	0.05 mg/100mL
Spray, metered	Nasal
Spray	Oral	0.5 mg/1mL
Spray, metered	Nasal	0.2 mg/0.4mL
Spray, metered	Nasal	0.5 mg/1mL
Spray	Nasal	0.05 mg/1
Spray	Nasal	50.0 mg/100.0mL
Spray	Nasal	50 mg/100mL
Cream	Topical	1 g/100g
Cream	Topical	10 mg/1g
Spray	Nasal	7.5 mg/15mL
Spray	Nasal	0.5 mg/1mL
Spray	Nasal	0.05 g/100mL
Spray	Nasal	0.512 mg/1mL
Spray	Nasal	0.0005 g/1mL
Liquid	Nasal
Spray	Nasal	0.0005055 g/1mL
Spray	Nasal	0.0005095 g/1mL
Spray	Nasal	0.000512 g/1mL
Liquid	Ophthalmic	0.25 mg/1mL
Liquid	Ophthalmic
Solution / drops	Ophthalmic
Spray	Nasal	.005 g/100mL
Spray	Nasal	.05 g/100mL
Spray	Nasal	.5 mg/1mL

Prices

Unit description	Cost	Unit
Oxymetazoline hcl powder	84.42USD	g
Afrin 0.05% nose spray	0.62USD	ml
Drixoral cold & allergy tablet sa	0.4USD	tablet
Afrin no drip sinus pump mist	0.38USD	ml
Oxymetazoline 0.05% spray	0.38USD	ml
Anefrin 0.05% nasal spray	0.37USD	ml
Afrin sinus spray	0.33USD	ml
Dristan long lasting mist	0.32USD	ml
Neo-synephrine 12 hour spray	0.28USD	ml
Visine long lasting eye drops	0.27USD	ml
12 hour nasal relief spray	0.24USD	ml
Dristan cold multi-symp tablet	0.23USD	tablet
Ocuclear eye drops	0.23USD	ml
CVS Pharmacy nasal spray 0.05%	0.22USD	ml
No drip 0.05% nasal spray	0.13USD	ml
Nasal spray 0.05%	0.06USD	ml
Sinus nasal spray	0.06USD	ml
Nasal decongestant 0.05% spray	0.03USD	ml
Pv nasal spray 0.05%	0.03USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
Unlock Additional Data
US8580282	No	2013-11-12	2030-04-02
US6413499	No	2002-07-02	2020-03-20
US9308191	No	2016-04-12	2030-04-02
US8883838	No	2014-11-11	2031-12-01
US7812049	No	2010-10-12	2028-05-02
US8420688	No	2013-04-16	2024-08-02
US9974773	No	2018-05-22	2035-06-11
US8815929	No	2014-08-26	2024-01-22
US10335391	No	2019-07-02	2035-06-11

Additional Data Available

Filed On

The date on which a patent was filed with the relevant government.

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Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	182 °C	PhysProp
logP	3.4	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0515 mg/mL	ALOGPS
logP	3.7	ALOGPS
logP	3.03	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	10.91	ChemAxon
pKa (Strongest Basic)	10.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	44.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.8 m³·mol^-1	ChemAxon
Polarizability	30.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9761
Blood Brain Barrier	-	0.5388
Caco-2 permeable	-	0.567
P-glycoprotein substrate	Substrate	0.8858
P-glycoprotein inhibitor I	Non-inhibitor	0.9477
P-glycoprotein inhibitor II	Non-inhibitor	0.6585
Renal organic cation transporter	Inhibitor	0.6039
CYP450 2C9 substrate	Non-substrate	0.7585
CYP450 2D6 substrate	Non-substrate	0.5707
CYP450 3A4 substrate	Non-substrate	0.5394
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Inhibitor	0.8931
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.854
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8682
Ames test	Non AMES toxic	0.7951
Carcinogenicity	Non-carcinogens	0.8923
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	4.4155 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8402
hERG inhibition (predictor II)	Non-inhibitor	0.7432

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (10.5 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as xylenols. These are aromatic compounds that contain a xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups, and at least one hydroxyl group.
Kingdom: Organic compounds
Super Class: Benzenoids
Class: Benzene and substituted derivatives
Sub Class: Xylenes
Direct Parent: Xylenols
Alternative Parents: Phenylpropanes / m-Xylenes / Para cresols / Ortho cresols / Imidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds
show 3 more
Substituents: Xylenol / Phenylpropane / M-xylene / O-cresol / P-cresol / Phenol / Imidolactam / 2-imidazoline / Amidine / Carboxylic acid amidine
show 12 more
Molecular Framework: Aromatic heteromonocyclic compounds
External Descriptors: phenols, carboxamidine, imidazolines (CHEBI:7862)

Targets

Details1. Alpha-1A adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name: ADRA1A
Uniprot ID: P35348
Uniprot Name: Alpha-1A adrenergic receptor
Molecular Weight: 51486.005 Da

References

Yang HT, Endoh M: (+/-)-tamsulosin, an alpha 1A-adrenoceptor antagonist, inhibits the positive inotropic effect but not the accumulation of inositol phosphates in rabbit heart. Eur J Pharmacol. 1996 Oct 3;312(3):281-91. [PubMed:8894610]
Deplanne V, Galzin AM: Functional characterization of alpha-1-adrenoceptor subtypes in the prostatic urethra and trigone of male rabbit. J Pharmacol Exp Ther. 1996 Aug;278(2):527-34. [PubMed:8768700]
Shibata K, Taketani K: [Excitatory effect of noradrenaline on rat airway parasympathetic ganglion neurons]. Fukuoka Igaku Zasshi. 2001 Nov;92(11):377-83. [PubMed:11774707]
Furukawa K, Rosario DJ, Smith DJ, Chapple CR, Uchiyama T, Chess-Williams R: Alpha 1A-adrenoceptor-mediated contractile responses of the human vas deferens. Br J Pharmacol. 1995 Sep;116(1):1605-10. [PubMed:8564226]
Gonzalez-Espinosa C, Romero-Avila MT, Mora-Rodriguez DM, Gonzalez-Espinosa D, Garcia-Sainz JA: Molecular cloning and functional expression of the guinea pig alpha(1a)-adrenoceptor. Eur J Pharmacol. 2001 Aug 31;426(3):147-55. [PubMed:11527538]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1.28	N/A	N/A	7908054
Ki (nM)	1.3	N/A	N/A	8935801
Ki (nM)	1.36	N/A	N/A	12954796
Ki (nM)	1.44	N/A	N/A	7908054
Ki (nM)	3.3	N/A	N/A	1353247
Ki (nM)	4.9	N/A	N/A	11408545
Ki (nM)	7.24	N/A	N/A	9605427
Ki (nM)	9.68	N/A	N/A	7996470

Details2. Alpha-2A adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist
Partial agonist

General Function: Thioesterase binding
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name: ADRA2A
Uniprot ID: P08913
Uniprot Name: Alpha-2A adrenergic receptor
Molecular Weight: 48956.275 Da

References

MacKinnon AC, Kilpatrick AT, Kenny BA, Spedding M, Brown CM: [3H]-RS-15385-197, a selective and high affinity radioligand for alpha 2-adrenoceptors: implications for receptor classification. Br J Pharmacol. 1992 Aug;106(4):1011-8. [PubMed:1327384]
Mitrani P, Srinivasan M, Dodds C, Patel MS: Role of the autonomic nervous system in the development of hyperinsulinemia by high-carbohydrate formula feeding to neonatal rats. Am J Physiol Endocrinol Metab. 2007 Apr;292(4):E1069-78. Epub 2006 Dec 12. [PubMed:17164433]
Lepretre N, Mironneau J: Alpha 2-adrenoceptors activate dihydropyridine-sensitive calcium channels via Gi-proteins and protein kinase C in rat portal vein myocytes. Pflugers Arch. 1994 Dec;429(2):253-61. [PubMed:7892112]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	185	N/A	N/A	7996470
Ki (nM)	239.88	N/A	N/A	9605427
Ki (nM)	31	N/A	N/A	1353247

Details3. Alpha-2C adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Protein homodimerization activity
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name: ADRA2C
Uniprot ID: P18825
Uniprot Name: Alpha-2C adrenergic receptor
Molecular Weight: 49521.585 Da

References

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1778.28	N/A	N/A	9605427
Ki (nM)	213	N/A	N/A	2172775
Ki (nM)	2980	N/A	N/A	7996470
Ki (nM)	754	N/A	N/A	1353247

Details4. Alpha-2B adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Epinephrine binding
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name: ADRA2B
Uniprot ID: P18089
Uniprot Name: Alpha-2B adrenergic receptor
Molecular Weight: 49565.8 Da

References

Uhlen S, Wikberg JE: Delineation of rat kidney alpha 2A- and alpha 2B-adrenoceptors with [3H]RX821002 radioligand binding: computer modelling reveals that guanfacine is an alpha 2A-selective compound. Eur J Pharmacol. 1991 Sep 17;202(2):235-43. [PubMed:1666366]
Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [PubMed:21948594]

Details5. Alpha-1B adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name: ADRA1B
Uniprot ID: P35368
Uniprot Name: Alpha-1B adrenergic receptor
Molecular Weight: 56835.375 Da

References

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735]
Akinaga J, Lima V, Kiguti LR, Hebeler-Barbosa F, Alcantara-Hernandez R, Garcia-Sainz JA, Pupo AS: Differential phosphorylation, desensitization, and internalization of alpha1A-adrenoceptors activated by norepinephrine and oxymetazoline. Mol Pharmacol. 2013 Apr;83(4):870-81. doi: 10.1124/mol.112.082313. Epub 2013 Jan 30. [PubMed:23364786]
Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [PubMed:21948594]

Details6. Alpha-1D adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Alpha1-adrenergic receptor activity
Specific Function: This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name: ADRA1D
Uniprot ID: P25100
Uniprot Name: Alpha-1D adrenergic receptor
Molecular Weight: 60462.205 Da

References

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735]
Akinaga J, Lima V, Kiguti LR, Hebeler-Barbosa F, Alcantara-Hernandez R, Garcia-Sainz JA, Pupo AS: Differential phosphorylation, desensitization, and internalization of alpha1A-adrenoceptors activated by norepinephrine and oxymetazoline. Mol Pharmacol. 2013 Apr;83(4):870-81. doi: 10.1124/mol.112.082313. Epub 2013 Jan 30. [PubMed:23364786]
Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [PubMed:21948594]

Drug created on June 13, 2005 07:24 / Updated on May 25, 2020 23:44

Oxymetazoline

Identification

Structure for Oxymetazoline (DB00935)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

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References