Carbinoxamine

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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
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
Medicalerrors
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Toxicity

Not Available

Pathways
PathwayCategory
Carbinoxamine H1-Antihistamine ActionDrug 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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Carbinoxamine is combined with 1,2-Benzodiazepine.
AcebutololThe risk or severity of QTc prolongation can be increased when Carbinoxamine is combined with Acebutolol.
AcetazolamideThe risk or severity of adverse effects can be increased when Carbinoxamine is combined with Acetazolamide.
AcetophenazineThe risk or severity of adverse effects can be increased when Carbinoxamine is combined with Acetophenazine.
AclidiniumCarbinoxamine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Carbinoxamine.
AdenosineThe risk or severity of QTc prolongation can be increased when Adenosine is combined with Carbinoxamine.
AgomelatineThe risk or severity of adverse effects can be increased when Carbinoxamine is combined with Agomelatine.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Carbinoxamine.
AlfentanilThe risk or severity of adverse effects can be increased when Carbinoxamine is combined with Alfentanil.
Interactions
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Food Interactions
  • Avoid alcohol. Ingesting alcohol may increase drowsiness caused by carbinoxamine.
  • Take on an empty stomach.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Carbinoxamine maleate02O55696WH3505-38-2GVNWHCVWDRNXAZ-BTJKTKAUSA-N
International/Other Brands
Allergefon (SERP) / Clistin / Histin (Kenyaku) / Karbinal / Rotoxamine / Satinmin (Shou Chan)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Karbinal ERSuspension, extended release4 mg/5mLOralAytu Therapeutics, LLC2014-01-03Not applicableUS flag
Karbinal ERSuspension, extended release4 mg/5mLOralAvadel Pharmaceuticals (Usa), Inc.2014-01-032018-02-16US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ArbinoxaTablet4 mg/1OralHawthorn Pharmaceuticals, Inc.2010-08-232017-10-01US flag
ArbinoxaSolution0.8 mg/1mLOralHawthorn Pharmaceuticals, Inc.2011-04-012016-11-18US flag
Carbinoxamine MaleateTablet4 mg/1OralBreckenridge Pharmaceutical, Inc.2012-12-10Not applicableUS flag
Carbinoxamine MaleateSyrup4 mg/5mLOralMikart, LLC2003-04-25Not applicableUS flag
Carbinoxamine MaleateSyrup4 mg/5mLOralCreekwood Pharmaceuticals, Inc.2010-10-272012-10-27US flag
Carbinoxamine MaleateTablet4 mg/1OralPar Pharmaceutical, Inc.2008-05-302020-12-04US flag
Carbinoxamine MaleateTablet4 mg/1OralRiver’s Edge Pharmaceuticals, LLC2011-12-012011-12-01US flag
Carbinoxamine MaleateTablet6 mg/1OralFoxland Pharmaceuticals, Inc.2017-12-18Not applicableUS flag
Carbinoxamine MaleateTablet4 mg/1OralBiocomp Pharma, Inc.2011-05-27Not applicableUS flag
Carbinoxamine MaleateTablet4 mg/1OralMikart, LLC2003-03-19Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
RHINOPRONT UZUN ETKILI 100 GR SUSPANSIYONCarbinoxamine (1.3 mg/5ml) + Phenylpropanolamine (16.7 mg/5ml)SuspensionOralABDİ İBRAHİM İLAÇ PAZARLAMA A.Ş.2020-08-14Not applicableTurkey flag
RHINOPRONT UZUN ETKILI KAPSUL, 10 ADETCarbinoxamine (4 mg) + Phenylephrine (20 mg)CapsuleOralABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
RHINOTUSSAL UZUN ETKILI 100 GR SUSPANSIYONCarbinoxamine (4 mg) + Phenylpropanolamine (20 mg)SuspensionOralABDİ İBRAHİM İLAÇ PAZARLAMA A.Ş.2020-08-14Not applicableTurkey flag
RHINOTUSSAL UZUN ETKILI KAPSUL, 10 ADETCarbinoxamine (4 mg) + Phenylephrine (20 mg)CapsuleOralABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Carbinoxamine/Pseudoephedrine/DMCarbinoxamine maleate (1 mg/1mL) + Dextromethorphan hydrobromide monohydrate (4 mg/1mL) + Pseudoephedrine hydrochloride (15 mg/1mL)LiquidOralPhysicians Total Care, Inc.2003-01-152007-08-08US flag
Coldec DSCarbinoxamine maleate (2 mg/5mL) + Pseudoephedrine hydrochloride (25 mg/5mL)SyrupOralBreckenridge Pharmaceutical, Inc.2003-05-012004-03-31US flag
Rondamine DMCarbinoxamine maleate (1 mg/1mL) + Dextromethorphan hydrobromide monohydrate (4 mg/1mL) + Pseudoephedrine hydrochloride (15 mg/1mL)LiquidOralMajor2002-02-052008-05-30US flag

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
  1. 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]
Human Metabolome Database
HMDB0014886
KEGG Compound
C06871
PubChem Compound
2564
PubChem Substance
46506787
ChemSpider
2466
BindingDB
81464
RxNav
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

Clinical Trials
PhaseStatusPurposeConditionsCount

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
FormRouteStrength
SolutionOral0.8 mg/1mL
TabletOral
TabletOral
SolutionOral4 mg/5mL
SyrupOral4 mg/5mL
TabletOral4 mg/1
TabletOral6 mg/1
SyrupOral
Suspension, extended releaseOral4 mg/5mL
SuspensionOral
CapsuleOral
LiquidOral
TabletOral4 mg
Prices
Unit descriptionCostUnit
Palgic 4 mg tablet0.87USD tablet
Carbinoxamine maleate 4 mg tablet0.65USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8062667No2011-11-222029-03-29US flag
US9522191No2016-12-202027-06-15US flag

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
boiling point (°C)160 °C at 1.00E-01 mm HgPhysProp
logP2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.228 mg/mLALOGPS
logP3.03ALOGPS
logP3.27ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.36 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity82.13 m3·mol-1ChemAxon
Polarizability31.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9787
Blood Brain Barrier+0.955
Caco-2 permeable+0.7503
P-glycoprotein substrateSubstrate0.6804
P-glycoprotein inhibitor INon-inhibitor0.5997
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterInhibitor0.7956
CYP450 2C9 substrateNon-substrate0.8203
CYP450 2D6 substrateSubstrate0.5558
CYP450 3A4 substrateSubstrate0.6473
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8452
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8403
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5557
Ames testNon AMES toxic0.8751
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.9003 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7085
hERG inhibition (predictor II)Inhibitor0.6835
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0ab9-9000000000-a413c068c7a879eb2068
Mass Spectrum (Electron Ionization)MSsplash10-0ab9-9200000000-c3abf61d5cdaa81de77d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0uxr-0490000000-9ece1371a4992f21aa52

Targets

Drugtargets
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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
  1. 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]
  2. 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]
  3. Darby WJ: Nutrition, food needs and technologic priorities: the World Food Conference. Nutr Rev. 1975 Aug;33(8):225-34. [PubMed:1143714]
  4. 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]
  5. 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 13:24 / Updated on May 06, 2021 01:40