Explore a selection of our essential drug information below, or:
Identification
- Summary
Chlorpheniramine is a histamine-H1 receptor antagonist indicated for the management of symptoms associated with upper respiratory allergies.
- Brand Names
- Aller-chlor, Allerest PE, Children's Nyquil Cold and Cough, Codar Ar, Coricidin Hbp Cold & Flu, Coricidin Hbp Cough and Cold, Dimetapp Long Acting Cough Plus Cold, Robitussin Pediatric Cough & Cold LA, Scot-tussin Sugar Free DM, Sudogest, Tussicaps, Tussionex, Tuxarin, Tuzistra
- Generic Name
- Chlorpheniramine
- DrugBank Accession Number
- DB01114
- Background
A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than promethazine.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Chlorpheniramine (DB01114)
- Weight
- Average: 274.788
Monoisotopic: 274.123676325 - Chemical Formula
- C16H19ClN2
- Synonyms
- 1-(p-chlorophenyl)-1-(2-pyridyl)-3-dimethylaminopropane
- 1-(p-chlorophenyl)-1-(2-pyridyl)-3-N,N-dimethylpropylamine
- 2-[p-chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridine
- 3-(p-chlorophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamine
- Chlorophenylpyridamine
- Chlorphenamin
- Chlorphenamine
- Chlorphenaminum
- Chlorpheniramine
- Chlorpheniramine polistirex
- Chlorpheniraminum
- Clorfenamina
- Clorfeniramina
- γ-(4-chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine
- γ-(4-chlorophenyl)-γ-(2-pyridyl)propyldimethylamine
Pharmacology
- Indication
For the treatment of rhinitis, urticaria, allergy, common cold, asthma and hay fever.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Allergic contact dermatitis Combination Product in combination with: Triamcinolone (DB00620) ••• ••• ••••••• Used in combination to treat Allergic reactions Combination Product in combination with: Calcium levulinate (DB13800) •••••••••••• •••••••••• •••••••• Symptomatic treatment of Allergic rhinitis ••• ••• Used in combination for symptomatic treatment of Allergic rhinitis (ar) Combination Product in combination with: Acetaminophen (DB00316), Phenylephrine (DB00388) ••• ••• •••••••• •••••• Used in combination for symptomatic treatment of Allergic rhinitis (ar) Combination Product in combination with: Tramazoline (DB13064) ••• ••• ••••• - Associated Therapies
- 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
In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Chlorpheniramine, is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) of the alkylamine class. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.
- Mechanism of action
Chlorpheniramine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
Target Actions Organism AHistamine H1 receptor antagonistHumans USodium-dependent serotonin transporter inhibitorHumans USodium-dependent noradrenaline transporter inhibitorHumans USodium-dependent dopamine transporter inhibitorHumans - Absorption
Well absorbed in the gastrointestinal tract.
- Volume of distribution
Not Available
- Protein binding
72%
- Metabolism
Primarily hepatic via Cytochrome P450 (CYP450) enzymes.
- Route of elimination
Not Available
- Half-life
21-27 hours
- Clearance
Not Available
- 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
Oral LD50 (rat): 306 mg/kg; Oral LD50 (mice): 130 mg/kg; Oral LD50 (guinea pig): 198 mg/kg [Registry of Toxic Effects of Chemical Substances. Ed. D. Sweet, US Dept. of Health & Human Services: Cincinatti, 2010.] Also a mild reproductive toxin to women of childbearing age.
- Pathways
Pathway Category Chlorphenamine 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 Chlorpheniramine is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Chlorpheniramine can be increased when it is combined with Abametapir. Abatacept The metabolism of Chlorpheniramine can be increased when combined with Abatacept. Abiraterone The metabolism of Chlorpheniramine can be decreased when combined with Abiraterone. Acalabrutinib The metabolism of Chlorpheniramine can be decreased when combined with Acalabrutinib. - Food Interactions
- Avoid alcohol.
- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Chlorpheniramine gluconate 79YPK3BAIT 25387-68-2 OCMSTKFGYJZBIY-IFWQJVLJSA-N Chlorpheniramine hydrochloride 5S6VUP419V 56343-98-7 NOXNCSQBTYNMHD-UHFFFAOYSA-N Chlorpheniramine maleate V1Q0O9OJ9Z 113-92-8 DBAKFASWICGISY-BTJKTKAUSA-N Chlorpheniramine tannate 72JT935YTT 1405-56-7 KOOFUFFGNZKXFG-HBNMXAOGSA-N - Product Images
- International/Other Brands
- Chlo-Amine / Chlor-Trimeton (Schering-Plough) / Haynon / Piriton (GlaxoSmithKline)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Chlorpheniramine Maleate Injection USP Liquid 10 mg / mL Intramuscular; Intravenous; Subcutaneous Omega Laboratories Ltd Not applicable Not applicable Canada 
Chlortripolon Inj 10mg/ml Liquid 10 mg / mL Intramuscular; Intravenous; Subcutaneous Schering Plough 1953-12-31 1999-08-04 Canada Truemed Group LLC Tablet 4 mg/1 Oral Truemed Group LLC 2022-09-17 Not applicable US 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 4 Hour Allergy Relief Tablet 4 mg/1 Oral Better Living Brands, LLC 1992-12-19 2022-07-22 US Aller-chlor Tablet 4 mg/1 Oral RUGBY LABORATORIES 1992-12-19 Not applicable US Aller-chlor Syrup 2 mg/5mL Oral RUGBY LABORATORIES 2014-03-20 2020-09-30 US Aller-chlor Tablet 4 mg/1 Oral A-S Medication Solutions 1992-12-19 Not applicable US Aller-chlor Tablet 4 mg/1 Oral Lake Erie Medical DBA Quality Care Products LLC 1992-12-19 2017-06-01 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 999 Cold Remedy Chlorpheniramine maleate (2 mg/6000mg) + Acetaminophen (100 mg/6000mg) Capsule Oral China Resources Sanjiu Medical & Pharmaceutical Co., Ltd. 2003-07-03 Not applicable US 999 Cold Remedy Granular Chlorpheniramine maleate (4 mg/90g) + Acetaminophen (200 mg/90g) Granule Oral China Resources Sanjiu Medical & Pharmaceutical Co., Ltd. 2003-07-03 Not applicable US 999 Cold Remedy Granular Chlorpheniramine maleate (4 mg/90g) + Acetaminophen (200 mg/90g) Capsule Oral China Resources Sanjiu Medical & Pharmaceutical Co Ltd 2003-07-03 2013-09-21 US 999 GANMAOLING Cold Chlorpheniramine maleate (2 mg/1) + Acetaminophen (100 mg/1) + Caffeine (2 mg/1) Capsule Oral Kingsway 2012-07-30 Not applicable US A-FERİN 1 MG +160 MG/5 ML PEDİYATRİK ŞURUP, 100 ML Chlorpheniramine maleate (1 mg/5mL) + Acetaminophen (160 mg/5mL) Syrup Oral HÜSNÜ ARSAN İLAÇLARI A.Ş. 1999-06-07 Not applicable Turkey 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Allergy DN II Chlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) Kit Oral Breckenridge Pharmaceutical, Inc. 2008-11-01 2010-03-31 US Allergy DN II Chlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) Kit Oral Breckenridge Pharmaceutical, Inc. 2008-11-01 2010-03-31 US Allergy DN PE Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Phenylephrine hydrochloride (40 mg/1) + Phenylephrine hydrochloride (10 mg/1) Kit Oral Breckenridge Pharmaceutical, Inc. 2008-11-01 2010-03-31 US AlleRx Dose Pack Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Phenylephrine hydrochloride (10 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Kit Oral Cornerstone Therapeutics Inc. 2008-02-01 2012-10-31 US AlleRx Dose Pack DF Chlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) Kit Oral Cornerstone Therapeutics Inc. 2006-08-01 2012-10-31 US
Categories
- ATC Codes
- R06AB54 — Chlorphenamine, combinations
- R06AB — Substituted alkylamines
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- Drug Categories
- Anti-Allergic Agents
- Antidepressive Agents
- Antihistamines for Systemic Use
- Antipruritics
- Central Nervous System Depressants
- Combined Inhibitors of Serotonin/Norepinephrine Reuptake
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Moderate Risk QTc-Prolonging Agents
- Neurotransmitter Agents
- OCT1 inhibitors
- OCT2 Inhibitors
- Propylamine Derivatives
- Pyridines
- QTc Prolonging Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin Modulators
- Substituted Alkylamines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pheniramines. These are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Pheniramines
- Direct Parent
- Pheniramines
- Alternative Parents
- Chlorobenzenes / Aralkylamines / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Chlorobenzene / Halobenzene / Heteroaromatic compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- tertiary amino compound, pyridines, monochlorobenzenes (CHEBI:52010)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 3U6IO1965U
- CAS number
- 132-22-9
- InChI Key
- SOYKEARSMXGVTM-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3
- IUPAC Name
- [3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
- SMILES
- CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1
References
- Synthesis Reference
Anil M. Salpekar, John Johnson, "Acetaminophen compositions containing low doses of chlorpheniramine maleate, method for preparing same and tablets formed therefrom." U.S. Patent US4631284, issued April, 1975.
US4631284- General References
- External Links
- Human Metabolome Database
- HMDB0001944
- KEGG Drug
- D07398
- KEGG Compound
- C06905
- PubChem Compound
- 2725
- PubChem Substance
- 46508253
- ChemSpider
- 2624
- BindingDB
- 35938
- 2400
- ChEBI
- 52010
- ChEMBL
- CHEMBL505
- Therapeutic Targets Database
- DAP000336
- PharmGKB
- PA448960
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Chlorphenamine
- MSDS
- Download (72.8 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 Basic Science Pain 1 somestatus stop reason just information to hide Not Available Completed Other Acetaminophen Toxicity 1 somestatus stop reason just information to hide Not Available Completed Prevention Poisoning 1 somestatus stop reason just information to hide Not Available Completed Treatment Agitated; State, Acute Reaction to Stress 1 somestatus stop reason just information to hide Not Available Completed Treatment Condyloma Anal / Fissure in Ano / Haemorrhoids / Rectal Fistulas 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Amend
- Anip Acquisition Co.
- A-S Medication Solutions LLC
- Breckenridge Pharmaceuticals
- C.O. Truxton Inc.
- Cardinal Health
- Consolidated Midland Corp.
- Contract Pharm
- Cypress Pharmaceutical Inc.
- Deltex Pharmaceuticals Inc.
- Direct Dispensing Inc.
- Dispensing Solutions
- Edwards Pharmaceuticals
- Hi Tech Pharmacal Co. Inc.
- Iopharm Laboratories Inc.
- Ivax Pharmaceuticals
- Kowa Pharmaceuticals America Inc.
- Kraft Pharmaceutical Co. Inc.
- Larken Laboratories Inc.
- Liberty Pharmaceuticals
- Magna Pharmaceuticals
- Major Pharmaceuticals
- Mallinckrodt Inc.
- McNeil Laboratories
- Meda AB
- Misemer Pharmaceuticals Inc.
- Mismer Pharmace
- Nucare Pharmaceuticals Inc.
- PD-Rx Pharmaceuticals Inc.
- Pecos Pharmaceutical Inc.
- Perrigo Co.
- Physicians Total Care Inc.
- Prepackage Specialists
- Provident Pharmaceuticals LLC
- Qualitest
- Rico Pharmacal
- River's Edge Pharmaceuticals
- Rugby Laboratories
- S&P Healthcare
- Schering-Plough Inc.
- Time-Cap Labs
- Tya Pharmaceuticals
- Watson Pharmaceuticals
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Capsule Oral 4 mg Capsule Oral Solution Oral Tablet Oral 500.000 mg Tablet Oral 4.000 mg Capsule, liquid filled Not applicable Granule, effervescent Oral Powder, for solution Oral Syrup Oral 2 mg/5mL Capsule, gelatin coated Oral Tablet, coated Oral Tablet 4 mg Tablet Oral 500.00 mg Liquid; tablet Intramuscular; Oral; Subcutaneous Tablet, sugar coated Oral 1 mg Liquid; tablet Oral; Parenteral Tablet Oral 3.000 mg Suspension Oral Syrup Oral 4 mg/5ml Syrup Oral 2 mg/5mL Solution Oral 500.000 mg Tablet Oral 5.000 mg Granule, for solution Oral Liquid Topical Syrup Oral 1 mg/5ml Tablet, extended release Oral 12 mg/1 Tablet, extended release Oral 12 mg Kit; tablet; tablet, extended release Oral Tablet Oral 12 mg / tab Syrup Oral 2.5 MG/5ML Tablet Oral 2 mg Solution / drops Oral Tablet Oral 4000 MG Powder Not applicable 1 kg/1kg Tablet Oral Tablet Oral 4 mg/1 Tablet, film coated, extended release Oral 12 mg/1 Injection Intramuscular; Intravenous; Subcutaneous Elixir Oral 4 mg/5ml Liquid Intramuscular; Intravenous; Subcutaneous 10 mg / mL Syrup Oral 2.5 mg / 5 mL Suspension Syrup Oral 0.04 g Syrup Oral 50 mg Spray, metered Nasal 4 mg/1mL Solution Parenteral 10.000 mg Tablet Oral 12.0000 mg Syrup Oral 0.05 g Tablet, coated Oral 8 mg Tablet, coated Oral 12 mg Solution Parenteral 10 mg Aerosol, spray Oral 5 mg/1mL Solution Oral 2.500 g Syrup Oral 40 mg Kit; tablet, film coated Oral Kit; tablet, coated Oral Kit; tablet Oral Capsule, coated pellets Oral Tablet Oral 4.00 mg Capsule, gelatin coated; kit; tablet Oral Syrup Oral 90 mg/5mL Syrup Oral 62.5 mg/5mL Tablet, sugar coated Oral Solution / drops Nasal Syrup Oral 0.050 g Lozenge Oral 2 mg/1 Kit; powder, for solution Oral Capsule; kit Oral Kit; liquid Oral Tablet Oral 300 mg Tablet Oral 15 mg Syrup Oral 0.0500 g Syrup Oral 72 mg/5mL Tablet, film coated Oral Liquid Oral 2 mg/1mL Liquid Oral 2 mg/5mL Tablet, coated Oral 4 mg/1 Tablet, effervescent Oral Tablet 2 mg Granule Oral 650.00 mg Kit; powder Oral Capsule Oral 4 mg Tablet; tablet, film coated Oral Spray Nasal 3 mg/ml Syrup Oral 0.500 g Syrup Oral 160 mg/5mL Solution Oral 55.000 mg Granule Oral Capsule Oral 1.25 mg/1 Tablet Oral 4 mg / tab Suspension 0.5 mg/60mL Capsule, delayed release pellets Oral Syrup Oral 15 mg Syrup Oral 1 mg Tablet 5 mg Solution Intramuscular 200.000 mg Capsule Oral Tablet, film coated Oral 4 mg/1 Syrup Oral 135 mg/5mL Syrup Oral 40 mg/5mL Tablet Oral 375.000 mg Tablet, multilayer Oral Syrup Oral 16.7 mg/5mL Tablet 150 mg Tablet 1 mg Tablet Oral 4.000 mg Tablet, film coated Oral 2 mg Powder Oral Tablet Oral Syrup Oral 125 mg/5ml Liquid Oral 2.5 mg/5ml Injection Intramuscular; Intravenous; Subcutaneous 10 mg/ml Solution Oral 0.1000 g Tablet Oral 15.000 mg Tablet Oral 300.000 mg Tablet 15 mg Syrup Oral 50.000 mg Syrup Oral Liquid Oral Tablet, multilayer, extended release Oral Spray Nasal Capsule, coated Oral Kit; tablet; tablet, film coated Oral Tablet Oral 12.5 mg Tablet, chewable Oral Tablet Oral 162.00 mg Tablet, delayed release Oral Syrup Oral 0.5 mg/5mL Elixir Oral Kit; syrup Oral Tablet 12.5 mg Injection, solution Syrup Oral Tablet, coated Oral Tablet, extended release Oral Capsule, extended release Oral Suspension, extended release Oral Suspension Oral 1000 mg/1 Kit Oral Solution / drops Ophthalmic Capsule, liquid filled Oral Capsule Oral 250.000 mg Elixir 4 MG/5ML Tablet, coated Oral 4 mg Solution Parenteral 10 mg/1ml Tablet, sugar coated Oral 4 mg Tablet, film coated Oral 4 mg Solution Tablet Oral 4 mg Tablet Oral 2 mg Solution Nasal Syrup Tablet Elixir Capsule - Prices
Unit description Cost Unit Ahist 12 mg tablet 1.1USD tablet Myci chlor-tan 8 mg caplet 0.75USD caplet Chlorpheniramine powder 0.67USD g Chlor-trimeton allergy 0.31USD each Chlor-trimeton 8 mg repetab 0.24USD tablet Aller-chlor 4 mg tablet 0.06USD tablet Pediacare allergy solution 0.05USD ml Allergy 4 mg tablet 0.04USD tablet Chlorpheniramine 4 mg tablet 0.02USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7863287 No 2011-01-04 2027-02-28 US US8062667 No 2011-11-22 2029-03-29 US US8790700 No 2014-07-29 2027-03-15 US US9066942 No 2015-06-30 2032-01-03 US US6383471 No 2002-05-07 2019-04-06 US US6248363 No 2001-06-19 2019-11-23 US US9107921 No 2015-08-18 2032-01-03 US US10238640 No 2019-03-26 2024-05-25 US
Properties
- State
- Liquid
- Experimental Properties
Property Value Source boiling point (°C) 142 °C Not Available water solubility 5500 mg/L (at 37 °C) BEILSTEIN logP 3.38 HANSCH,C ET AL. (1995) pKa 9.13 (at 25 °C) PERRIN,DD (1965) - Predicted Properties
Property Value Source Water Solubility 0.0519 mg/mL ALOGPS logP 3.74 ALOGPS logP 3.58 Chemaxon logS -3.7 ALOGPS pKa (Strongest Basic) 9.47 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 16.13 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 80.85 m3·mol-1 Chemaxon Polarizability 30.82 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9754 Blood Brain Barrier + 0.962 Caco-2 permeable + 0.8749 P-glycoprotein substrate Substrate 0.6136 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.9376 Renal organic cation transporter Inhibitor 0.7916 CYP450 2C9 substrate Non-substrate 0.8026 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.6472 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9096 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9023 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7501 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9183 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 3.3361 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8702 hERG inhibition (predictor II) Inhibitor 0.7145
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 169.3019979 predictedDarkChem Lite v0.1.0 [M-H]- 158.42586 predictedDeepCCS 1.0 (2019) [M+H]+ 170.0916979 predictedDarkChem Lite v0.1.0 [M+H]+ 160.78386 predictedDeepCCS 1.0 (2019) [M+Na]+ 170.0162979 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.877 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.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Tagawa M, Kano M, Okamura N, Higuchi M, Matsuda M, Mizuki Y, Arai H, Iwata R, Fujii T, Komemushi S, Ido T, Itoh M, Sasaki H, Watanabe T, Yanai K: Neuroimaging of histamine H1-receptor occupancy in human brain by positron emission tomography (PET): a comparative study of ebastine, a second-generation antihistamine, and (+)-chlorpheniramine, a classical antihistamine. Br J Clin Pharmacol. 2001 Nov;52(5):501-9. [Article]
- Salata JJ, Jurkiewicz NK, Wallace AA, Stupienski RF 3rd, Guinosso PJ Jr, Lynch JJ Jr: Cardiac electrophysiological actions of the histamine H1-receptor antagonists astemizole and terfenadine compared with chlorpheniramine and pyrilamine. Circ Res. 1995 Jan;76(1):110-9. [Article]
- Hasenohrl RU, Kuhlen A, Frisch C, Galosi R, Brandao ML, Huston JP: Comparison of intra-accumbens injection of histamine with histamine H1-receptor antagonist chlorpheniramine in effects on reinforcement and memory parameters. Behav Brain Res. 2001 Oct 15;124(2):203-11. [Article]
- Yasuda SU, Wellstein A, Likhari P, Barbey JT, Woosley RL: Chlorpheniramine plasma concentration and histamine H1-receptor occupancy. Clin Pharmacol Ther. 1995 Aug;58(2):210-20. [Article]
- Nicholson AN, Pascoe PA, Turner C, Ganellin CR, Greengrass PM, Casy AF, Mercer AD: Sedation and histamine H1-receptor antagonism: studies in man with the enantiomers of chlorpheniramine and dimethindene. Br J Pharmacol. 1991 Sep;104(1):270-6. [Article]
- Casy AF, Drake AF, Ganellin CR, Mercer AD, Upton C: Stereochemical studies of chiral H-1 antagonists of histamine: the resolution, chiral analysis, and biological evaluation of four antipodal pairs. Chirality. 1992;4(6):356-66. doi: 10.1002/chir.530040606. [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
- Unknown
- Actions
- Inhibitor
- General Function
- Serotonin transporter that cotransports serotonin with one Na(+) ion in exchange for one K(+) ion and possibly one proton in an overall electroneutral transport cycle. Transports serotonin across the plasma membrane from the extracellular compartment to the cytosol thus limiting serotonin intercellular signaling (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Essential for serotonin homeostasis in the central nervous system. In the developing somatosensory cortex, acts in glutamatergic neurons to control serotonin uptake and its trophic functions accounting for proper spatial organization of cortical neurons and elaboration of sensory circuits. In the mature cortex, acts primarily in brainstem raphe neurons to mediate serotonin uptake from the synaptic cleft back into the pre-synaptic terminal thus terminating serotonin signaling at the synapse (By similarity). Modulates mucosal serotonin levels in the gastrointestinal tract through uptake and clearance of serotonin in enterocytes. Required for enteric neurogenesis and gastrointestinal reflexes (By similarity). Regulates blood serotonin levels by ensuring rapid high affinity uptake of serotonin from plasma to platelets, where it is further stored in dense granules via vesicular monoamine transporters and then released upon stimulation (PubMed:17506858, PubMed:18317590). Mechanistically, the transport cycle starts with an outward-open conformation having Na1(+) and Cl(-) sites occupied. The binding of a second extracellular Na2(+) ion and serotonin substrate leads to structural changes to outward-occluded to inward-occluded to inward-open, where the Na2(+) ion and serotonin are released into the cytosol. Binding of intracellular K(+) ion induces conformational transitions to inward-occluded to outward-open and completes the cycle by releasing K(+) possibly together with a proton bound to Asp-98 into the extracellular compartment. Na1(+) and Cl(-) ions remain bound throughout the transport cycle (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Additionally, displays serotonin-induced channel-like conductance for monovalent cations, mainly Na(+) ions. The channel activity is uncoupled from the transport cycle and may contribute to the membrane resting potential or excitability (By similarity)
- Specific Function
- actin filament binding
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (PubMed:2008212, PubMed:8125921). Can also mediate sodium- and chloride-dependent transport of dopamine (PubMed:11093780, PubMed:8125921)
- Specific Function
- actin binding
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates sodium- and chloride-dependent transport of dopamine (PubMed:10375632, PubMed:11093780, PubMed:1406597, PubMed:15505207, PubMed:19478460, PubMed:8302271). Also mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (By similarity). Regulator of light-dependent retinal hyaloid vessel regression, downstream of OPN5 signaling (By similarity)
- Specific Function
- amine binding
- Gene Name
- SLC6A3
- Uniprot ID
- Q01959
- Uniprot Name
- Sodium-dependent dopamine transporter
- Molecular Weight
- 68494.255 Da
References
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
Enzymes
- 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
- Flockhart Table of Drug Interactions [Link]
- 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
- Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. [Article]
- Yasuda SU, Wellstein A, Likhari P, Barbey JT, Woosley RL: Chlorpheniramine plasma concentration and histamine H1-receptor occupancy. Clin Pharmacol Ther. 1995 Aug;58(2):210-20. [Article]
- Yasuda SU, Zannikos P, Young AE, Fried KM, Wainer IW, Woosley RL: The roles of CYP2D6 and stereoselectivity in the clinical pharmacokinetics of chlorpheniramine. Br J Clin Pharmacol. 2002 May;53(5):519-25. [Article]
- He N, Zhang WQ, Shockley D, Edeki T: Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes. Eur J Clin Pharmacol. 2002 Feb;57(12):847-51. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). 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:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion 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 all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins during embryogenesis (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). 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:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone, DHEA), a precursor in the biosynthesis of androgen and estrogen steroid hormones (PubMed:17178770, PubMed:9555064). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1), particularly D-ring hydroxylated estrone at the C16-alpha position (PubMed:12865317, PubMed:14559847). Mainly hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in atRA clearance during fetal development (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics including anticonvulsants (PubMed:9555064)
- Specific Function
- all-trans retinoic acid 18-hydroxylase activity
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57469.95 Da
References
- Flockhart Table of Drug Interactions [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:9260930, PubMed:9687576). Functions as a Na(+)-independent, bidirectional uniporter (PubMed:21128598, PubMed:9687576). Cation cellular uptake or release is driven by the electrochemical potential, i.e. membrane potential and concentration gradient (PubMed:15212162, PubMed:9260930, PubMed:9687576). However, may also engage electroneutral cation exchange when saturating concentrations of cation substrates are reached (By similarity). Predominantly expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (PubMed:15783073). Implicated in monoamine neurotransmitters uptake such as histamine, dopamine, adrenaline/epinephrine, noradrenaline/norepinephrine, serotonin and tyramine, thereby supporting a physiological role in the central nervous system by regulating interstitial concentrations of neurotransmitters (PubMed:16581093, PubMed:17460754, PubMed:9687576). Also capable of transporting dopaminergic neuromodulators cyclo(his-pro), salsolinol and N-methyl-salsolinol, thereby involved in the maintenance of dopaminergic cell integrity in the central nervous system (PubMed:17460754). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Also transports guanidine and endogenous monoamines such as vitamin B1/thiamine, creatinine and N-1-methylnicotinamide (NMN) (PubMed:12089365, PubMed:15212162, PubMed:17072098, PubMed:24961373, PubMed:9260930). Mediates the uptake and efflux of quaternary ammonium compound choline (PubMed:9260930). Mediates the bidirectional transport of polyamine agmatine and the uptake of polyamines putrescine and spermidine (PubMed:12538837, PubMed:21128598). Able to transport non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). Also involved in the uptake of xenobiotic 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:12395288, PubMed:16394027). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- acetylcholine transmembrane transporter activity
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:11388889, PubMed:11408531, PubMed:12439218, PubMed:12719534, PubMed:15389554, PubMed:16263091, PubMed:16272756, PubMed:16581093, PubMed:19536068, PubMed:21128598, PubMed:23680637, PubMed:24961373, PubMed:34040533, PubMed:9187257, PubMed:9260930, PubMed:9655880). Functions as a pH- and Na(+)-independent, bidirectional transporter (By similarity). Cation cellular uptake or release is driven by the electrochemical potential (i.e. membrane potential and concentration gradient) and substrate selectivity (By similarity). Hydrophobicity is a major requirement for recognition in polyvalent substrates and inhibitors (By similarity). Primarily expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (By similarity). Most likely functions as an uptake carrier in enterocytes contributing to the intestinal elimination of organic cations from the systemic circulation (PubMed:16263091). Transports endogenous monoamines such as N-1-methylnicotinamide (NMN), guanidine, histamine, neurotransmitters dopamine, serotonin and adrenaline (PubMed:12439218, PubMed:24961373, PubMed:35469921, PubMed:9260930). Also transports natural polyamines such as spermidine, agmatine and putrescine at low affinity, but relatively high turnover (PubMed:21128598). Involved in the hepatic uptake of vitamin B1/thiamine, hence regulating hepatic lipid and energy metabolism (PubMed:24961373). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Transports dopaminergic neuromodulators cyclo(his-pro) and salsolinol with lower efficency (PubMed:17460754). Also capable of transporting non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). May contribute to the transport of cationic compounds in testes across the blood-testis-barrier (Probable). Also involved in the uptake of xenobiotics tributylmethylammonium (TBuMA), quinidine, N-methyl-quinine (NMQ), N-methyl-quinidine (NMQD) N-(4,4-azo-n-pentyl)-quinuclidine (APQ), azidoprocainamide methoiodide (AMP), N-(4,4-azo-n-pentyl)-21-deoxyajmalinium (APDA) and 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:11408531, PubMed:15389554, PubMed:35469921, PubMed:9260930)
- Specific Function
- (R)-carnitine transmembrane transporter activity
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 07, 2024 17:56