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 2003
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 2003
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 2003
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 2003
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 2003
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 2003
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 2003

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
Clistin maleate; a clinical appraisal of a new antihistaminic.	1954 Nov	13211145
[Serous otitis media. Comparative study of carbinoxamine- pseudoephedrine vs astemizole-pseudoephedrine].	1997 May-Jun	9377115
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
Cold-syrup induced movement disorder.	2001 Jun	11437145
Quantitation of antihistamines in pharmaceutical preparations by liquid chromatography with a micellar mobile phase of sodium dodecyl sulfate and pentanol.	2001 Nov-Dec	11767132
Mechanism of the condensation of homocysteine thiolactone with aldehydes.	2006 Oct 25	16952131
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
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