U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19ClN2O
Molecular Weight 290.7884
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROTOXAMINE

SMILES

CN(C)CCO[C@@]([H])(c1ccc(cc1)Cl)c2ccccn2

InChI

InChIKey=OJFSXZCBGQGRNV-INIZCTEOSA-N
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/t16-/m0/s1

HIDE SMILES / InChI

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
[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
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

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.
Name Type Language
ROTOXAMINE
INN   USAN  
USAN   INN  
Official Name English
ROTOXAMINE [USAN]
Common Name English
CARBINOXAMINE, (S)-
Common Name English
ROTOXAMINE [INN]
Common Name English
MCN-R-73-Z
Code English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 06:39:24 UTC 2021 , Edited by admin on Sat Jun 26 06:39:24 UTC 2021
Code System Code Type Description
INN
1036
Created by admin on Sat Jun 26 06:39:24 UTC 2021 , Edited by admin on Sat Jun 26 06:39:24 UTC 2021
PRIMARY
EPA CompTox
5560-77-0
Created by admin on Sat Jun 26 06:39:24 UTC 2021 , Edited by admin on Sat Jun 26 06:39:24 UTC 2021
PRIMARY
PUBCHEM
170336
Created by admin on Sat Jun 26 06:39:24 UTC 2021 , Edited by admin on Sat Jun 26 06:39:24 UTC 2021
PRIMARY
ChEMBL
CHEMBL1552819
Created by admin on Sat Jun 26 06:39:24 UTC 2021 , Edited by admin on Sat Jun 26 06:39:24 UTC 2021
PRIMARY
EVMPD
SUB10392MIG
Created by admin on Sat Jun 26 06:39:24 UTC 2021 , Edited by admin on Sat Jun 26 06:39:24 UTC 2021
PRIMARY
FDA UNII
VED9E376NC
Created by admin on Sat Jun 26 06:39:24 UTC 2021 , Edited by admin on Sat Jun 26 06:39:24 UTC 2021
PRIMARY
CAS
5560-77-0
Created by admin on Sat Jun 26 06:39:24 UTC 2021 , Edited by admin on Sat Jun 26 06:39:24 UTC 2021
PRIMARY
NCI_THESAURUS
C73054
Created by admin on Sat Jun 26 06:39:24 UTC 2021 , Edited by admin on Sat Jun 26 06:39:24 UTC 2021
PRIMARY