Identification
- Summary
Carbinoxamine is a first generation antihistamine used to treat allergic rhinitis, vasomotor rhinitis, allergic conjunctivitis, allergic reactions, and mild allergic reactions.
- Brand Names
- Karbinal, Ryvent
- Generic Name
- Carbinoxamine
- DrugBank Accession Number
- DB00748
- Background
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.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- 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 Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Carbinoxamine is combined with 1,2-Benzodiazepine. 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. 
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- Avoid alcohol. Ingesting alcohol may increase drowsiness caused by carbinoxamine.
- Take on an empty stomach.
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 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 Karbinal ER Suspension, extended release 4 mg/5mL Oral Aytu Therapeutics, LLC 2014-01-03 Not applicable US 
Karbinal ER Suspension, extended release 4 mg/5mL Oral Avadel Pharmaceuticals (Usa), Inc. 2014-01-03 2018-02-16 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Arbinoxa 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 Tablet 4 mg/1 Oral Par Pharmaceutical, Inc. 2008-05-30 2020-12-04 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 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 River’s Edge Pharmaceuticals, LLC 2011-12-01 2011-12-01 US Carbinoxamine Maleate Tablet 4 mg/1 Oral Mikart, LLC 2003-03-19 Not applicable 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 - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BECAME TABLET Carbinoxamine maleate (4 mg) + Pseudoephedrine hydrochloride (60 mg) Tablet Oral YUNG SHIN PHARMACEUTICAL (SINGAPORE) PTE LTD 1994-12-15 Not applicable Singapore RHINOPRONT UZUN ETKILI 100 GR SUSPANSIYON Carbinoxamine (1.3 mg/5ml) + Phenylpropanolamine (16.7 mg/5ml) Suspension Oral ABDİ İBRAHİM İLAÇ PAZARLAMA A.Ş. 2020-08-14 Not applicable Turkey 
RHINOPRONT UZUN ETKILI KAPSUL, 10 ADET Carbinoxamine (4 mg) + Phenylephrine (20 mg) Capsule Oral ABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey RHINOTUSSAL UZUN ETKILI 100 GR SUSPANSIYON Carbinoxamine (4 mg) + Phenylpropanolamine (20 mg) Suspension Oral ABDİ İBRAHİM İLAÇ PAZARLAMA A.Ş. 2020-08-14 Not applicable Turkey RHINOTUSSAL UZUN ETKILI KAPSUL, 10 ADET Carbinoxamine (4 mg) + Phenylephrine (20 mg) Capsule Oral ABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey - 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
- 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)
- Affected organisms
- Humans and other mammals
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. [Article]
- 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 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 Capsule Oral Liquid Oral Tablet Oral 4 mg - 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 US8062667 No 2011-11-22 2029-03-29 US US9522191 No 2016-12-20 2027-06-15 US
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
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- 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. [Article]
- 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. [Article]
- Darby WJ: Nutrition, food needs and technologic priorities: the World Food Conference. Nutr Rev. 1975 Aug;33(8):225-34. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [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]
Carriers
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- BinderRegulator
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Components:
References
- Martinez-Gomez MA, Carril-Aviles MM, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ: Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. J Chromatogr A. 2007 Apr 20;1147(2):261-9. doi: 10.1016/j.chroma.2007.02.054. Epub 2007 Feb 22. [Article]
Drug created at June 13, 2005 13:24 / Updated at January 02, 2022 11:57