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Details

Stereochemistry RACEMIC
Molecular Formula C16H19ClN2O.C4H4O4
Molecular Weight 406.86
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CARBINOXAMINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CN(C)CCOC(C1=CC=C(Cl)C=C1)C2=CC=CC=N2

InChI

InChIKey=GVNWHCVWDRNXAZ-BTJKTKAUSA-N
InChI=1S/C16H19ClN2O.C4H4O4/c1-19(2)11-12-20-16(15-5-3-4-10-18-15)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-10,16H,11-12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Description
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

1953
193
Targets

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
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
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
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
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
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
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Clistin maleate; a clinical appraisal of a new antihistaminic.
1954 Nov
[Antimycobacterial antihistaminics].
1989 Aug
The need for rational therapeutics in the use of cough and cold medicine in infants.
1992 Apr
[Serous otitis media. Comparative study of carbinoxamine- pseudoephedrine vs astemizole-pseudoephedrine].
1997 May-Jun
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.
2001 Apr
Simultaneous determination of ingredients in a cold medicine by cyclodextrin-modified microemulsion electrokinetic chromatography.
2005 Mar 9
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.
2005 Oct
Spectrophotometric determination of carbinoxamine maleate in pharmaceutical formulations by ternary complex formation with Cu(II) and eosin.
2006 Jun 1
Mechanism of the condensation of homocysteine thiolactone with aldehydes.
2006 Oct 25
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.
2007 Apr 20
Possible role of pseudoephedrine and other over-the-counter cold medications in the deaths of very young children.
2007 Mar
Discovery of novel and cardioselective diltiazem-like calcium channel blockers via virtual screening.
2008 Sep 25
[1,2]-Anionic rearrangement of 2-benzyloxypyridine and related pyridyl ethers.
2009 Oct 16
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
LC for analysis of two sustained-release mixtures containing cough cold suppressant drugs.
2010 Jul
4-(4-Chloro-phen-yl)-4-hy-droxy-piperidinium maleate maleic acid solvate.
2010 Jul 14
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

JP2008526895A
32
JP2013237711A
14
US2606195
6

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 MALEATE
JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
2-(P-CHLORO-.ALPHA.-(2-(DIMETHYLAMINO)ETHOXY)BENZYL)PYRIDINE MALEATE (1:1)
Common Name English
CARBINOXAMINE MALEATE [VANDF]
Common Name English
ETHANAMINE, 2-((4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY)-N,N-DIMETHYL-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
CLISTIN
Brand Name English
CARBINOXAMINE MALEATE [USP MONOGRAPH]
Common Name English
CARBINOXAMINE MALEATE [MI]
Common Name English
NSC-62362
Code English
CARBINOXAMINE MALEATE [ORANGE BOOK]
Common Name English
CARBINOXAMINE MALEATE [USP-RS]
Common Name English
CARBINOXAMINE MALEATE [JAN]
Common Name English
Carbinoxamine maleate [WHO-DD]
Common Name English
CARBINOXAMINE MALEATE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
Code System Code Type Description
DRUG BANK
DBSALT000963
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
PUBCHEM
5282409
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
NCI_THESAURUS
C47432
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
EVMPD
SUB01044MIG
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID0047828
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
DAILYMED
02O55696WH
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
MERCK INDEX
m3070
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY Merck Index
NSC
62362
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
MESH
C004649
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
CAS
3505-38-2
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
FDA UNII
02O55696WH
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
RS_ITEM_NUM
1096000
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
ECHA (EC/EINECS)
222-498-0
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
RXCUI
91066
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY RxNorm
SMS_ID
100000092119
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
ChEMBL
CHEMBL864
Created by admin on Fri Dec 15 15:03:43 UTC 2023 , Edited by admin on Fri Dec 15 15:03:43 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of CARBINOXAMINE
NIH
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