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Identification
- Summary
Epinastine is an H1 receptor antagonist used to prevent itching in allergic conjunctivitis.
- Brand Names
- Elestat
- Generic Name
- Epinastine
- DrugBank Accession Number
- DB00751
- Background
Epinastine is used for the prevention of itching associated with allergic conjunctivitis. It has a multi-action effect that inhibits the allergic response in 3 ways: 1. stabilizes mast cells by preventing mast cell degranulation to control the allergic response, 2. prevents histamine binding to both the H1- and H2-receptors to stop itching and provide lasting protection, and 3. prevents the release of proinflammatory chemical mediators from the blood vessel to halt progression of the allergic response.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Epinastine (DB00751)
- Weight
- Average: 249.3104
Monoisotopic: 249.126597495 - Chemical Formula
- C16H15N3
- Synonyms
- (±)-epinastine
- 3-amino-9,13b-dihydro-1H-dibenz(c,f)imidazo(1,5-a)azepine
- Epinastin
- Epinastina
- Epinastine
- épinastine
- Epinastinum
- External IDs
- WAL 801 Cl
Pharmacology
- Indication
For the prevention of itching associated with allergic conjunctivitis.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Allergic conjunctivitis •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Epinastine is an antihistamine and an inhibitor of histamine release from the mast cell for topical administration to the eyes. Epinastine is indicated for the prevention of itching associated with allergic conjunctivitis. Epinastine is a topically active, direct H1-receptor antagonist and an inhibitor of the release of histamine from the mast cell. Epinastine is selective for the histamine H1-receptor and has affinity for the histamine H2 receptor. Epinastine also possesses affinity for the a1-, a2-, and 5-HT2 -receptors. Epinastine does not penetrate the blood/brain barrier and, therefore, is not expected to induce side effects of the central nervous system.
- Mechanism of action
Epinastine has a multiaction effect that inhibits the allergic response in 3 ways: 1. stabilizes mast cells by preventing mast cell degranulation to control the allergic response, 2. prevents histamine binding to both the H1- and H2-receptors to stop itching and provide lasting protection, and 3. prevents the release of proinflammatory chemical mediators from the blood vessel to halt progression of the allergic response.
Target Actions Organism AHistamine H1 receptor antagonistHumans AHistamine H2 receptor antagonistHumans UAlpha-1A adrenergic receptor unknownHumans UAlpha-2A adrenergic receptor unknownHumans U5-hydroxytryptamine receptor 2A antagonistHumans U5-hydroxytryptamine receptor 7 antagonistHumans - Absorption
The absolute bioavailability of epinastine is about 40%.
- Volume of distribution
Not Available
- Protein binding
64%
- Metabolism
Mainly excreted unchanged, less than 10% metabolized.
- Route of elimination
Epinastine is mainly excreted unchanged. The renal elimination is mainly via active tubular secretion.
- Half-life
12 hours
- Clearance
- 56 L/hr [patients with allergic conjunctivitis receiving one drop of ELESTAT® ophthalmic solution in each eye twice daily for seven days]
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Epinastine H1-Antihistamine Action Drug action - 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 Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Epinastine is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Epinastine can be increased when it is combined with Abametapir. Abatacept The metabolism of Epinastine can be increased when combined with Abatacept. Abiraterone The metabolism of Epinastine can be decreased when combined with Abiraterone. Acebutolol The metabolism of Epinastine can be decreased when combined with Acebutolol. - Food Interactions
- No interactions found.
Products
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Ingredient UNII CAS InChI Key Epinastine hydrochloride GFM415S5XL 108929-04-0 VKXSGUIOOQPGAF-UHFFFAOYSA-N - International/Other Brands
- Alegain (Kyorin Rimedio) / Alenapion (Choseido Pharmaceutical) / Alesion (Boehringer Ingelheim) / Alesiotec (Nihon Yakuhin Kogyo) / Alket (Poen) / Allernothin (Morishita Jintan) / Allerstin (Dong Koo) / Alpeed (Daito) / Aplatin (Taiyo Pharmaceutical) / Aresten (Il Sung) / Asmot (Tatsumi Kagaku) / Atergit (Roemmers) / Azusaleon (Shiono Kemikaru) / Elpinan (Towa Yakuhin) / Epinazion (Medisa Shinyaku) / Epioftal (Farmindustria) / Flurinol (Boehringer Ingelheim) / Helvottz (Yoshindo) / Kai lai Zhi (Carelife Pharmaceutical Co Ltd) / Pinasion (Taisho Yakuhin) / Purivist (Allergan) / Relenastine (Lansier) / Relestat (Allergan) / Talerc (Aché) / Timkent (Nisshin Seiyaku) / Yupitel (Iwaki Seiyaku)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Elestat Solution / drops 0.5 mg/1mL Ophthalmic Allergan, Inc. 2004-01-19 Not applicable US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Epinastine Solution / drops 0.5 mg/1mL Ophthalmic Akorn 2017-05-05 Not applicable US Epinastine HCl Solution 0.5 mg/1mL Ophthalmic Av Kare, Inc. 2011-11-15 2015-02-20 US Epinastine HCl Solution 0.5 mg/1mL Ophthalmic Cypress Pharmaceuticals, Inc. 2011-05-02 2013-09-11 US Epinastine Hydrochloride Solution / drops 0.5 mg/1mL Ophthalmic Breckenridge Pharmaceutical, Inc. 2013-11-05 2024-09-30 US Epinastine Hydrochloride Solution 0.5 mg/1mL Ophthalmic Sun Pharmaceutical Industries (Europe) B.V. 2011-11-01 Not applicable US
Categories
- ATC Codes
- S01GX10 — Epinastine
- S01GX — Other antiallergics
- S01G — DECONGESTANTS AND ANTIALLERGICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- Drug Categories
- Acid Reducers
- Antidepressive Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Decongestants and Antiallergics
- Decreased Histamine Release
- Heterocyclic Compounds, Fused-Ring
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Histamine H1 Inhibitors
- Histamine H2 Antagonists
- Neurotransmitter Agents
- Ophthalmics
- Ophthalmologicals
- P-glycoprotein substrates
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Sensory Organs
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzazepines
- Sub Class
- Dibenzazepines
- Direct Parent
- Dibenzazepines
- Alternative Parents
- Azepines / Benzenoids / Imidazolines / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- 2-imidazoline / Aromatic heteropolycyclic compound / Azacycle / Azepine / Benzenoid / Carboximidamide / Dibenzazepine / Guanidine / Hydrocarbon derivative / Organic 1,3-dipolar compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- guanidines, benzazepine (CHEBI:51032)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- Q13WX941EF
- CAS number
- 80012-43-7
- InChI Key
- WHWZLSFABNNENI-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H15N3/c17-16-18-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)19(15)16/h1-8,15H,9-10H2,(H2,17,18)
- IUPAC Name
- 2,4-diazatetracyclo[12.4.0.0^{2,6}.0^{7,12}]octadeca-1(18),3,7,9,11,14,16-heptaen-3-amine
- SMILES
- NC1=NCC2N1C1=CC=CC=C1CC1=CC=CC=C21
References
- Synthesis Reference
Akiharu Isowaki, Tomoko Nakajima, Akira Ohtori, "Percutaneously Absorptive Ophthalmic Preparation Comprising Epinastine." U.S. Patent US20090143359, issued June 04, 2009.
US20090143359- General References
- Walther G, Daniel H, Bechtel WD, Brandt K: New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine. Arzneimittelforschung. 1990 Apr;40(4):440-6. [Article]
- Schilling JC, Adamus WS, Kuthan H: Antihistaminic activity and side effect profile of epinastine and terfenadine in healthy volunteers. Int J Clin Pharmacol Ther Toxicol. 1990 Dec;28(12):493-7. [Article]
- External Links
- Human Metabolome Database
- HMDB0014889
- KEGG Drug
- D01713
- PubChem Compound
- 3241
- PubChem Substance
- 46509056
- ChemSpider
- 3128
- BindingDB
- 50131441
- 39684
- ChEBI
- 51032
- ChEMBL
- CHEMBL1106
- Therapeutic Targets Database
- DAP001074
- PharmGKB
- PA164764489
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Epinastine
- FDA label
- Download (113 KB)
- MSDS
- Download (57 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Allergic Conjunctivitis (AC) 1 somestatus stop reason just information to hide Not Available Completed Not Available Perennial Allergic Rhinitis (PAR) 2 somestatus stop reason just information to hide Not Available Completed Not Available Urticaria 1 somestatus stop reason just information to hide 4 Completed Treatment Allergic Conjunctivitis (AC) 2 somestatus stop reason just information to hide 4 Completed Treatment Allergic Reaction 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Allergan inc
- Packagers
- Allergan Inc.
- Dosage Forms
Form Route Strength Solution Ophthalmic 0.500 mg Solution Intraocular; Ophthalmic 0.5 mg Tablet Oral 20 mg Solution Ophthalmic 0.5 mg/1mL Solution / drops Ophthalmic 0.5 mg/1mL Solution Ophthalmic 0.5 mg Syrup Oral 0.2 g Tablet Oral 10 mg Tablet, extended release Oral Tablet, coated Oral 20 mg Tablet Oral 20.00 mg Tablet Oral 20.000 mg Solution / drops Conjunctival 0.5 mg/ml Liquid Ophthalmic 0.5 mg/1ml Solution 0.5 mg/ml Solution / drops Ophthalmic 0.05 % Solution / drops Ophthalmic 0.5 mg/ml Solution Ophthalmic 0.05 % w/v - Prices
Unit description Cost Unit Elestat 0.05% Solution 5ml Bottle 116.58USD bottle Elestat 0.05% eye drops 22.94USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7429602 No 2008-09-30 2020-11-29 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 205-208 °C Not Available logP 3.51 BIOBYTE (1995) - Predicted Properties
Property Value Source Water Solubility 0.163 mg/mL ALOGPS logP 2.53 ALOGPS logP 3.07 Chemaxon logS -3.2 ALOGPS pKa (Strongest Basic) 8.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 41.62 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 76.9 m3·mol-1 Chemaxon Polarizability 27.33 Å3 Chemaxon Number of Rings 4 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 + 0.9923 Blood Brain Barrier + 0.9787 Caco-2 permeable + 0.5766 P-glycoprotein substrate Substrate 0.5665 P-glycoprotein inhibitor I Non-inhibitor 0.8193 P-glycoprotein inhibitor II Non-inhibitor 0.5736 Renal organic cation transporter Inhibitor 0.7994 CYP450 2C9 substrate Non-substrate 0.8676 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Non-substrate 0.5422 CYP450 1A2 substrate Non-inhibitor 0.5686 CYP450 2C9 inhibitor Non-inhibitor 0.9243 CYP450 2D6 inhibitor Non-inhibitor 0.5228 CYP450 2C19 inhibitor Non-inhibitor 0.8702 CYP450 3A4 inhibitor Non-inhibitor 0.6566 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.726 Ames test AMES toxic 0.5689 Carcinogenicity Non-carcinogens 0.9144 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7509 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9353 hERG inhibition (predictor II) Non-inhibitor 0.8419
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00di-0590000000-b39e6b7f0c2561681ad3 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0090000000-91653437d5b0b0635ca0 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-b52e77f2fd1806d2c197 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0090000000-218336f95f740dc28172 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-3090000000-f89534d25c65cbe24be6 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4l-2590000000-ba87d707561f4d2a7a1b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9430000000-7bb1414fdc204d44f849 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 161.6319906 predictedDarkChem Lite v0.1.0 [M-H]- 152.09908 predictedDeepCCS 1.0 (2019) [M+H]+ 161.9375906 predictedDarkChem Lite v0.1.0 [M+H]+ 154.45709 predictedDeepCCS 1.0 (2019) [M+Na]+ 162.2060906 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.55035 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein-coupled receptor for histamine, a biogenic amine that functions as an immune modulator and a neurotransmitter (PubMed:33828102, PubMed:8280179). Through the H1 receptor, histamine mediates the contraction of smooth muscles and increases capillary permeability due to contraction of terminal venules. Also mediates neurotransmission in the central nervous system and thereby regulates circadian rhythms, emotional and locomotor activities as well as cognitive functions (By similarity)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Tsujii T, Yamamoto E, Ohira T, Saito N, Watanabe S: Effects of sedative and non-sedative H1 antagonists on cognitive tasks: behavioral and near-infrared spectroscopy (NIRS) examinations. Psychopharmacology (Berl). 2007 Sep;194(1):83-91. Epub 2007 May 30. [Article]
- Walther G, Daniel H, Bechtel WD, Brandt K: New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine. Arzneimittelforschung. 1990 Apr;40(4):440-6. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) signaling pathway (By similarity)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HRH2
- Uniprot ID
- P25021
- Uniprot Name
- Histamine H2 receptor
- Molecular Weight
- 40097.65 Da
References
- Bielory L, Ghafoor S: Histamine receptors and the conjunctiva. Curr Opin Allergy Clin Immunol. 2005 Oct;5(5):437-40. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Unknown
- General 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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes
- Specific Function
- alpha1-adrenergic receptor activity
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- Molecular Weight
- 51486.005 Da
References
- Dupont LJ, Meade CJ, Demedts MG, Verleden GM: Epinastine (WAL 801CL) modulates the noncholinergic contraction in guinea-pig airways in vitro by a prejunctional 5-HT1-like receptor. Eur Respir J. 1996 Jul;9(7):1433-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Unknown
- General 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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
- Specific Function
- alpha-1B adrenergic receptor binding
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 50646.17 Da
References
- Dupont LJ, Meade CJ, Demedts MG, Verleden GM: Epinastine (WAL 801CL) modulates the noncholinergic contraction in guinea-pig airways in vitro by a prejunctional 5-HT1-like receptor. Eur Respir J. 1996 Jul;9(7):1433-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:1330647, PubMed:18703043, PubMed:19057895, PubMed:21645528, PubMed:22300836, PubMed:35084960, PubMed:38552625). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:28129538, PubMed:35084960). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:28129538, PubMed:35084960). HTR2A is coupled to G(q)/G(11) G alpha proteins and activates phospholipase C-beta, releasing diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) second messengers that modulate the activity of phosphatidylinositol 3-kinase and promote the release of Ca(2+) ions from intracellular stores, respectively (PubMed:18703043, PubMed:28129538, PubMed:35084960). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:28129538, PubMed:35084960). Affects neural activity, perception, cognition and mood (PubMed:18297054). Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity)
- Specific Function
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Dupont LJ, Pype JL, Meade CJ, DeLeyn P, Deneffe G, Demedts MG, Verleden GM: Epinastine (WAL 801CL) inhibits the electrical field stimulation-induced cholinergic contraction in guinea pig and human airways in vitro. Eur Respir J. 1999 Nov;14(5):1068-75. [Article]
- Dupont LJ, Meade CJ, Demedts MG, Verleden GM: Epinastine (WAL 801CL) modulates the noncholinergic contraction in guinea-pig airways in vitro by a prejunctional 5-HT1-like receptor. Eur Respir J. 1996 Jul;9(7):1433-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone and a mitogen (PubMed:35714614, PubMed:8226867). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:35714614, PubMed:8226867). HTR7 is coupled to G(s) G alpha proteins and mediates activation of adenylate cyclase activity (PubMed:35714614)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HTR7
- Uniprot ID
- P34969
- Uniprot Name
- 5-hydroxytryptamine receptor 7
- Molecular Weight
- 53554.43 Da
References
- Dupont LJ, Pype JL, Meade CJ, DeLeyn P, Deneffe G, Demedts MG, Verleden GM: Epinastine (WAL 801CL) inhibits the electrical field stimulation-induced cholinergic contraction in guinea pig and human airways in vitro. Eur Respir J. 1999 Nov;14(5):1068-75. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Kishimoto W, Hiroi T, Sakai K, Funae Y, Igarashi T: Metabolism of epinastine, a histamine H1 receptor antagonist, in human liver microsomes in comparison with that of terfenadine. Res Commun Mol Pathol Pharmacol. 1997 Dec;98(3):273-92. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Kishimoto W, Hiroi T, Sakai K, Funae Y, Igarashi T: Metabolism of epinastine, a histamine H1 receptor antagonist, in human liver microsomes in comparison with that of terfenadine. Res Commun Mol Pathol Pharmacol. 1997 Dec;98(3):273-92. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Kishimoto W, Hiroi T, Sakai K, Funae Y, Igarashi T: Metabolism of epinastine, a histamine H1 receptor antagonist, in human liver microsomes in comparison with that of terfenadine. Res Commun Mol Pathol Pharmacol. 1997 Dec;98(3):273-92. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- Ishiguro N, Nozawa T, Tsujihata A, Saito A, Kishimoto W, Yokoyama K, Yotsumoto T, Sakai K, Igarashi T, Tamai I: Influx and efflux transport of H1-antagonist epinastine across the blood-brain barrier. Drug Metab Dispos. 2004 May;32(5):519-24. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 21, 2024 12:54