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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19ClN2O.C4H4O4
Molecular Weight 406.8607
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CARBINOXAMINE MALEATE, (S)-

SMILES

CN(C)CCO[C@@]([H])(c1ccc(cc1)Cl)c2ccccn2.C(\[H])(=C(\[H])/C(=O)O)/C(=O)O

InChI

InChIKey=GVNWHCVWDRNXAZ-ZSJYYTRTSA-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-/t16-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C16H19ClN2O
Molecular Weight 290.7884
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0723
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00748 | https://www.google.com/patents/DE2436664A1 | https://www.ncbi.nlm.nih.gov/pubmed/4400865 | https://www.ncbi.nlm.nih.gov/pubmed/4149638 | https://www.ncbi.nlm.nih.gov/pubmed/16460947 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf

Rotoxamine ((S)-carbinoxamine) is maleic acid salt of the levorotatory isomer of Carbinoxamine (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 an 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. Rotoxamine is used to treat runny or stuffy nose, sneezing, itching, watery eyes, hives, skin rash, itching, and other symptoms of allergies and the common cold.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
KARBINAL

Approved Use

INDICATIONS AND USAGE. Karbinal ER (carbinoxamine maleate) Extended-release Oral Suspension is an H1 receptor antagonist indicated 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

1.36442885E12
Primary
KARBINAL

Approved Use

INDICATIONS AND USAGE. Karbinal ER (carbinoxamine maleate) Extended-release Oral Suspension is an H1 receptor antagonist indicated 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

1.36442885E12
Primary
KARBINAL

Approved Use

INDICATIONS AND USAGE. Karbinal ER (carbinoxamine maleate) Extended-release Oral Suspension is an H1 receptor antagonist indicated 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

1.36442885E12
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
Cold-syrup induced movement disorder.
2001 Jun
Quantitation of antihistamines in pharmaceutical preparations by liquid chromatography with a micellar mobile phase of sodium dodecyl sulfate and pentanol.
2001 Nov-Dec
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
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
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

Sample Use Guides

Tablet (carbinoxamine maleate 4 mg): 1 tablet orally daily as needed; may increase dosage as needed up to a maximum of 24 mg/day in divided doses every 6 to 8 hours
Route of Administration: Oral
In Vitro Use Guide
Male Holtzman rats weighing 150-220 g were used to Hepatic microsomal fractions preparation. Incubation mixtures contained 0.1-0.5 mkmol of Rotoxamine (l- Carbinoxamine): 15 mkmol of magnesium chloride: 50 mkmol of phosphate buffer (pH 7.4): 3 mkmol of neutralized semicarbazide: and an NADPH-generating system consisting of 16 mkmoI of DL-isocitrate, 1.6 mkmol of NADP, 1 enzyme unit of isocitrate dehydrogenase, and 2-3 mg of microsomal protein per ml in a total volume of 3.0 ml. Incubations were carried out in air at 37}C for 10 min.
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:24:07 UTC 2021
Edited
by admin
on Sat Jun 26 12:24:07 UTC 2021
Record UNII
33U3685HDG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBINOXAMINE MALEATE, (S)-
Common Name English
ETHANAMINE, 2-((S)-(4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY)-N,N-DIMETHYL-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
CAS
1078131-59-5
Created by admin on Sat Jun 26 12:24:07 UTC 2021 , Edited by admin on Sat Jun 26 12:24:07 UTC 2021
PRIMARY
FDA UNII
33U3685HDG
Created by admin on Sat Jun 26 12:24:07 UTC 2021 , Edited by admin on Sat Jun 26 12:24:07 UTC 2021
PRIMARY
PUBCHEM
23723101
Created by admin on Sat Jun 26 12:24:07 UTC 2021 , Edited by admin on Sat Jun 26 12:24:07 UTC 2021
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER