CARBINOXAMINE, 4,4'-DIPHENYLDISULFONATE

First approved in 1953

Details

Stereochemistry	RACEMIC
Molecular Formula	2C16H19ClN2O.C12H10O6S2
Molecular Weight	895.91
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of CARBINOXAMINE, 4,4'-DIPHENYLDISULFONATE

Structure Search

SMILES

CN(C)CCOC(C1=CC=C(Cl)C=C1)C2=NC=CC=C2.CN(C)CCOC(C3=CC=C(Cl)C=C3)C4=NC=CC=C4.OS(=O)(=O)C5=CC=C(C=C5)C6=CC=C(C=C6)S(O)(=O)=O

InChI

InChIKey=GNLQXOUGUFGRRD-UHFFFAOYSA-N

InChI=1S/2C16H19ClN2O.C12H10O6S2/c2*1-19(2)11-12-20-16(15-5-3-4-10-18-15)13-6-8-14(17)9-7-13;13-19(14,15)11-5-1-9(2-6-11)10-3-7-12(8-4-10)20(16,17)18/h2*3-10,16H,11-12H2,1-2H3;1-8H,(H,13,14,15)(H,16,17,18)

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/pro/carbinoxamine.html

Carbinoxamine is a histamine-H1 receptor blocking agent. It is an antihistamine with anticholinergic (drying) and sedative properties. Carbinoxamine appears to compete with histamine (type H1) for receptor sites on effector cells in the gastrointestinal tract, blood vessels and respiratory tract. Carbinoxamine is effective for the symptomatic treatment of seasonal and perennial allergic rhinitis; vasomotor rhinitis; allergic conjunctivitis due to inhalant allergens and foods; mild, uncomplicated allergic skin manifestations of urticaria and angioedema; dermatographism; as therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Most common adverse reactions are: sedation, sleepiness, dizziness, disturbed coordination, epigastric distress, and thickening of bronchial secretions. Avoid concomitant use of alcohol and CNS depressants (hypnotics sedatives, tranquilizers, etc.) due to additive adverse effects.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf	Antagonist 2778		2.3 nM [Ki]
Cytochrome P450 2D6 61 Target ID: CHEMBL289 Sources: DOI: 10.14896/jssxmeeting.21.0.296.1	Inhibitor 8297		25.0 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Seasonal allergic rhinitis 64 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf	Palliative	Approved 8429	CARBINOXAMINE MALEATE Approved Use Carbinoxamine maleate is effective for the symptomatic treatment of: Seasonal and perennial allergic rhinitis. Vasomotor rhinitis. Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Amelioration of the severity of allergic reactions to blood or plasma. Launch Date 1.04803199E12
Perennial allergic rhinitis 47 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf	Palliative	Approved 8429	CARBINOXAMINE MALEATE Approved Use Carbinoxamine maleate is effective for the symptomatic treatment of: Seasonal and perennial allergic rhinitis. Vasomotor rhinitis. Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Amelioration of the severity of allergic reactions to blood or plasma. Launch Date 1.04803199E12
Vasomotor rhinitis 21 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf	Palliative	Approved 8429	CARBINOXAMINE MALEATE Approved Use Carbinoxamine maleate is effective for the symptomatic treatment of: Seasonal and perennial allergic rhinitis. Vasomotor rhinitis. Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Amelioration of the severity of allergic reactions to blood or plasma. Launch Date 1.04803199E12
Allergic conjunctivitis 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf	Palliative	Approved 8429	CARBINOXAMINE MALEATE Approved Use Carbinoxamine maleate is effective for the symptomatic treatment of: Seasonal and perennial allergic rhinitis. Vasomotor rhinitis. Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Amelioration of the severity of allergic reactions to blood or plasma. Launch Date 1.04803199E12
Urticaria 39 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf	Palliative	Approved 8429	CARBINOXAMINE MALEATE Approved Use Carbinoxamine maleate is effective for the symptomatic treatment of: Seasonal and perennial allergic rhinitis. Vasomotor rhinitis. Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Amelioration of the severity of allergic reactions to blood or plasma. Launch Date 1.04803199E12
Angioedema 20 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf	Palliative	Approved 8429	CARBINOXAMINE MALEATE Approved Use Carbinoxamine maleate is effective for the symptomatic treatment of: Seasonal and perennial allergic rhinitis. Vasomotor rhinitis. Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Amelioration of the severity of allergic reactions to blood or plasma. Launch Date 1.04803199E12
Anaphylaxis 46 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf	Palliative	Approved 8429	CARBINOXAMINE MALEATE Approved Use Carbinoxamine maleate is effective for the symptomatic treatment of: Seasonal and perennial allergic rhinitis. Vasomotor rhinitis. Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Amelioration of the severity of allergic reactions to blood or plasma. Launch Date 1.04803199E12

C_max

Value	Dose	Co-administered	Analyte	Population
16.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1363194	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: PHENYLPROPANOLAMINE	PHENYLPROPANOLAMINE	CARBINOXAMINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
13.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7488301	4 mg 2 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered: PHENYLEPHRINE	PHENYLEPHRINE	CARBINOXAMINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7488301	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: PHENYLEPHRINE	PHENYLEPHRINE	CARBINOXAMINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
14.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1363194	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: PHENYLPROPANOLAMINE	PHENYLPROPANOLAMINE	CARBINOXAMINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
22 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7488301	4 mg 2 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered: PHENYLEPHRINE	PHENYLEPHRINE	CARBINOXAMINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
30 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7488301	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: PHENYLEPHRINE	PHENYLEPHRINE	CARBINOXAMINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
31% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17339039	unknown, unknown		CARBINOXAMINE MALEATE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1O6TT5
ABI Chem	AC1Q71EO
Aurora Fine Chemicals LLC	K01.232.366	http://online.aurorafinechemicals.com/info?ID=K01.232.366
BioSynth	J-019843	https://www.biosynth.com/en/products/all-products/products/J-019843.html
Chemspace	CSSB00000743508	https://chem-space.com/CSSB00000743508
Combi-Blocks	QZ-9568	http://www.combi-blocks.com/cgi-bin/find.cgi?QZ-9568
Enamine	EN300-51917	https://www.enaminestore.com/catalog/EN300-51917
Hairui	HR125120	http://www.hairuichem.com/en/product/3505-38-2.html
PubChem	6506779	https://pubchem.ncbi.nlm.nih.gov/compound/6506779

PubMed

Title	Date	PubMed
The need for rational therapeutics in the use of cough and cold medicine in infants.	1992 Apr	1557278
Simultaneous determination of ingredients in a cold medicine by cyclodextrin-modified microemulsion electrokinetic chromatography.	2005 Mar 9	15740912
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.	2007 Apr 20	17339039
Possible role of pseudoephedrine and other over-the-counter cold medications in the deaths of very young children.	2007 Mar	17316256
Discovery of novel and cardioselective diltiazem-like calcium channel blockers via virtual screening.	2008 Sep 25	18754582
LC for analysis of two sustained-release mixtures containing cough cold suppressant drugs.	2010 Jul	20822669
4-(4-Chloro-phen-yl)-4-hy-droxy-piperidinium maleate maleic acid solvate.	2010 Jul 14	21588324
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

Tablets: 1 or 2 tablets (4 to 8 mg) 3 to 4 times daily Oral Solution: 1 or 2 teaspoonfuls (4 to 8 mg) 3 to 4 times daily.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

CARBINOXAMINE, 4,4'-DIPHENYLDISULFONATE

Common Name

English

PYRIDINE, 2-(P-CHLORO-.ALPHA.-(2-(DIMETHYLAMINO)ETHOXY)BENZYL)-, 4,4'-BIPHENYLDISULFONATE (2:1)

Common Name

English

4,4'-BIPHENYLDISULFONIC ACID, COMPD. WITH 2-(P-CHLORO-.ALPHA.-(2-(DIMETHYLAMINO)ETHOXY)BENZYL)PYRIDINE

Common Name

English

CARBINOXAMINE DIPHENYLDISULFONATE ANHYDROUS

Common Name

English

Carbinoxamine diphenyl disulfonate [WHO-DD]

Common Name

English

4,4'-BIPHENYLDISULFONIC ACID, COMPD. WITH 2-(P-CHLORO-.ALPHA.-(2-(DIMETHYLAMINO)ETHOXY)BENZYL)PYRIDINE (1:2)

Common Name

English

(1,1'-BIPHENYL)-4,4'-DISULFONIC ACID, COMPD. WITH 2-((4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY)-N,N-DIMETHYLETHANAMINE (1:2)

Common Name

English

(±)-CARBINOXAMINE, 4,4'-DIPHENYLDISULFONATE

Common Name

English

Code System Code Type Description

CAS

5144-38-7