Carbinoxamine
Identification
- Name
- Carbinoxamine
- Accession Number
- DB00748
- Description
Carbinoxamine is a first generation antihistamine that competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. The product label for carbinoxamine as an over the counter cough and cold medicine is being modified to state "do not use" in children under 4 years of age in order to prevent and reduce misuse, as many unapproved carbinoxamine-containing preparations contained inappropriate labeling, which promoted unapproved uses (including management of congestion, cough, the common cold, and the use in children under 2 years of age), which can potentially cause serious health risks.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Carbinoxamine (DB00748)
- Weight
- Average: 290.788
Monoisotopic: 290.118590947 - Chemical Formula
- C16H19ClN2O
- Synonyms
- (±)-carbinoxamine
- {2-[(4-Chloro-phenyl)-pyridin-2-yl-methoxy]-ethyl}-dimethyl-amine
- 2-(p-chloro-α-(2-(dimethylamino)ethoxy)benzyl)pyridine
- Carbinoxamin
- Carbinoxamina
- Carbinoxamine
- Carbinoxamine base
- Carbinoxaminum
- Paracarbinoxamine
Pharmacology
- Indication
For symptomatic relief of seasonal and perennial allergic rhinitis and vasomotor rhinitis, as well as allergic conjunctivitis caused by foods and inhaled allergens. Also for the relief of allergic reactions to blood or plasma, and the symptomatic management of mild, uncomplicated allergic skin manifestations of urticaria and angioedema.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Carbinoxamine is a first generation antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, carbinoxamine competes with free histamine for binding at HA-receptor sites. Carbinoxamine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of carbinoxamine.
- Mechanism of action
Carbinoxamine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. Carbinoxamine's anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
Target Actions Organism AHistamine H1 receptor antagonistHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
10 to 20 hours
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Carbinoxamine 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 Unlock Additional DataAcebutolol The risk or severity of QTc prolongation can be increased when Carbinoxamine is combined with Acebutolol. Acetazolamide The risk or severity of adverse effects can be increased when Carbinoxamine is combined with Acetazolamide. Acetophenazine The risk or severity of adverse effects can be increased when Carbinoxamine is combined with Acetophenazine. Aclidinium Carbinoxamine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Carbinoxamine. Adenosine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Carbinoxamine. Agomelatine The risk or severity of adverse effects can be increased when Carbinoxamine is combined with Agomelatine. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Carbinoxamine. Alfentanil The risk or severity of adverse effects can be increased when Carbinoxamine is combined with Alfentanil. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Carbinoxamine. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Avoid alcohol. Ingesting alcohol may increase drowsiness caused by carbinoxamine.
- Take on an empty stomach.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Carbinoxamine maleate 02O55696WH 3505-38-2 GVNWHCVWDRNXAZ-BTJKTKAUSA-N - International/Other Brands
- Allergefon (SERP) / Clistin / Histin (Kenyaku) / Karbinal / Rotoxamine / Satinmin (Shou Chan)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataKarbinal ER Suspension, extended release 4 mg/5mL Oral Avadel Pharmaceuticals (Usa), Inc. 2014-01-03 2018-02-16 US 
Karbinal ER Suspension, extended release 4 mg/5mL Oral Aytu Therapeutics, LLC 2014-01-03 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataArbinoxa Solution 0.8 mg/1mL Oral Hawthorn Pharmaceuticals, Inc. 2011-04-01 2016-11-18 US Arbinoxa Tablet 4 mg/1 Oral Hawthorn Pharmaceuticals, Inc. 2010-08-23 2017-10-01 US Carbinoxamine Maleate Solution 4 mg/5mL Oral Physicians Total Care, Inc. 2004-03-10 2011-06-30 US Carbinoxamine Maleate Tablet 6 mg/1 Oral Foxland Pharmaceuticals, Inc. 2017-12-18 Not applicable US Carbinoxamine Maleate Tablet 4 mg/1 Oral Biocomp Pharma, Inc. 2011-05-27 Not applicable US Carbinoxamine Maleate Tablet 4 mg/1 Oral Mikart, LLC 2003-03-19 Not applicable US Carbinoxamine Maleate Syrup 4 mg/5mL Oral Creekwood Pharmaceuticals, Inc. 2010-10-27 2012-10-27 US Carbinoxamine Maleate Tablet 6 mg/1 Oral Mikart, LLC 2016-05-31 Not applicable US Carbinoxamine Maleate Syrup 4 mg/5mL Oral Breckenridge Pharmaceutical, Inc. 2012-12-10 Not applicable US Carbinoxamine Maleate Tablet 4 mg/1 Oral River’s Edge Pharmaceuticals, LLC 2011-12-01 2011-12-01 US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Carbinoxamine/Pseudoephedrine/DM Carbinoxamine maleate (1 mg/1mL) + Dextromethorphan hydrobromide monohydrate (4 mg/1mL) + Pseudoephedrine hydrochloride (15 mg/1mL) Liquid Oral Physicians Total Care, Inc. 2003-01-15 2007-08-08 US Coldec DS Carbinoxamine maleate (2 mg/5mL) + Pseudoephedrine hydrochloride (25 mg/5mL) Syrup Oral Breckenridge Pharmaceutical, Inc. 2003-05-01 2004-03-31 US Rondamine DM Carbinoxamine maleate (1 mg/1mL) + Dextromethorphan hydrobromide monohydrate (4 mg/1mL) + Pseudoephedrine hydrochloride (15 mg/1mL) Liquid Oral Major 2002-02-05 2008-05-30 US
Categories
- ATC Codes
- R06AA08 — Carbinoxamine
- Drug Categories
- Aminoalkyl Ethers
- Antihistamines for Systemic Use
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Moderate Risk QTc-Prolonging Agents
- Neurotransmitter Agents
- Photosensitizing Agents
- QTc Prolonging Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzylethers
- Direct Parent
- Benzylethers
- Alternative Parents
- Chlorobenzenes / Pyridines and derivatives / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- Amine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzylether / Chlorobenzene / Dialkyl ether / Ether / Halobenzene
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- tertiary amino compound, pyridines, monochlorobenzenes (CHEBI:3398)
Chemical Identifiers
- UNII
- 982A7M02H5
- CAS number
- 486-16-8
- InChI Key
- OJFSXZCBGQGRNV-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H19ClN2O/c1-19(2)11-12-20-16(15-5-3-4-10-18-15)13-6-8-14(17)9-7-13/h3-10,16H,11-12H2,1-2H3
- IUPAC Name
- {2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylamine
- SMILES
- CN(C)CCOC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1
References
- Synthesis Reference
Tilford. C.H. and Shelton, R.S.; U.S. Patent 2,606,195;August 5,1952; assigned to The Wm.S. Merrell Company. Swain, A.P.; U.S. Patent 2800,485; July 23,1957; assigned to McNeil Laboratories, Inc.
- General References
- BEALE HD, RAWLING FF, FIGLEY KD: Clistin maleate; a clinical appraisal of a new antihistaminic. J Allergy. 1954 Nov;25(6):521-4. [PubMed:13211145]
- External Links
- Human Metabolome Database
- HMDB0014886
- KEGG Compound
- C06871
- PubChem Compound
- 2564
- PubChem Substance
- 46506787
- ChemSpider
- 2466
- BindingDB
- 81464
- 20220
- ChEBI
- 3398
- ChEMBL
- CHEMBL864
- Therapeutic Targets Database
- DAP001069
- PharmGKB
- PA164746898
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Carbinoxamine
- MSDS
- Download (74.6 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Mcneil pharmaceutical co div mcneilab inc
- Boca pharmacal inc
- Cypress pharmaceutical inc
- Mikart inc
- Invagen pharmaceuticals inc
- Ortho mcneil pharmaceutical inc
- Packagers
- Boca Pharmacal
- Breckenridge Pharmaceuticals
- Great Southern Laboratories
- Mikart Inc.
- Pamlab LLC
- Pan American
- Physicians Total Care Inc.
- Scientific Laboratories Inc.
- Sovereign Pharmaceuticals Ltd.
- Teamm Pharmaceuticals Inc.
- Tri Med Laboratories Inc.
- Zerxis Pharmaceuticals
- Zyber Pharmaceuticals
- Dosage Forms
Form Route Strength Solution Oral 0.8 mg/1mL Tablet Oral 60 mg Tablet Oral 4 MG Solution Oral 4 mg/5mL Syrup Oral 4 mg/5mL Tablet Oral 4 mg/1 Tablet Oral 6 mg/1 Syrup Oral Suspension, extended release Oral 4 mg/5mL Suspension Oral 16.7 mg/5ml Capsule Oral 20 mg Suspension Oral 20 mg Liquid Oral - Prices
Unit description Cost Unit Palgic 4 mg tablet 0.87USD tablet Carbinoxamine maleate 4 mg tablet 0.65USD 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 Unlock Additional DataUS8062667 No 2011-11-22 2029-03-29 US US9522191 No 2016-12-20 2027-06-15 US Additional Data Available- Filed OnFiled OnAvailable for Purchase
The date on which a patent was filed with the relevant government.
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Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) < 25 °C PhysProp boiling point (°C) 160 °C at 1.00E-01 mm Hg PhysProp logP 2.6 Not Available - Predicted Properties
Property Value Source Water Solubility 0.228 mg/mL ALOGPS logP 3.03 ALOGPS logP 3.27 ChemAxon logS -3.1 ALOGPS pKa (Strongest Basic) 8.87 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 25.36 Å2 ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 82.13 m3·mol-1 ChemAxon Polarizability 31.7 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 + 0.9787 Blood Brain Barrier + 0.955 Caco-2 permeable + 0.7503 P-glycoprotein substrate Substrate 0.6804 P-glycoprotein inhibitor I Non-inhibitor 0.5997 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Inhibitor 0.7956 CYP450 2C9 substrate Non-substrate 0.8203 CYP450 2D6 substrate Substrate 0.5558 CYP450 3A4 substrate Substrate 0.6473 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8452 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8403 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5557 Ames test Non AMES toxic 0.8751 Carcinogenicity Non-carcinogens 0.9182 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.9003 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7085 hERG inhibition (predictor II) Inhibitor 0.6835
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - EI-B GC-MS splash10-0ab9-9000000000-a413c068c7a879eb2068 Mass Spectrum (Electron Ionization) MS splash10-0ab9-9200000000-c3abf61d5cdaa81de77d 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 MS/MS Spectrum - , positive LC-MS/MS splash10-0uxr-0490000000-9ece1371a4992f21aa52
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific 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 catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Oishi R, Shishido S, Yamori M, Saeki K: Comparison of the effects of eleven histamine H1-receptor antagonists on monoamine turnover in the mouse brain. Naunyn Schmiedebergs Arch Pharmacol. 1994 Feb;349(2):140-4. [PubMed:7513381]
- Ramadan AA, Mandil H: Spectrophotometric determination of carbinoxamine maleate in pharmaceutical formulations by ternary complex formation with Cu(II) and eosin. Anal Biochem. 2006 Jun 1;353(1):133-7. Epub 2006 Mar 9. [PubMed:16574052]
- Darby WJ: Nutrition, food needs and technologic priorities: the World Food Conference. Nutr Rev. 1975 Aug;33(8):225-34. [PubMed:1143714]
- Yang J, Dudley GB: [1,2]-Anionic rearrangement of 2-benzyloxypyridine and related pyridyl ethers. J Org Chem. 2009 Oct 16;74(20):7998-8000. doi: 10.1021/jo901707x. [PubMed:19761204]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Drug created on June 13, 2005 07:24 / Updated on November 02, 2020 20:52