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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19ClN2O.C4H6O6
Molecular Weight 440.875
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROTOXAMINE TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CN(C)CCO[C@@H](C1=CC=C(Cl)C=C1)C2=CC=CC=N2

InChI

InChIKey=YNDXBZSTECRKLI-RAUFAAFNSA-N
InChI=1S/C16H19ClN2O.C4H6O6/c1-19(2)11-12-20-16(15-5-3-4-10-18-15)13-6-8-14(17)9-7-13;5-1(3(7)8)2(6)4(9)10/h3-10,16H,11-12H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t16-;1-,2-/m01/s1

HIDE SMILES / InChI

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C16H19ClN2O
Molecular Weight 290.788
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Simultaneous determination of ingredients in a cold medicine by cyclodextrin-modified microemulsion electrokinetic chromatography.
2005 Mar 9
[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
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 Fri Dec 15 16:24:40 UTC 2023
Edited
by admin
on Fri Dec 15 16:24:40 UTC 2023
Record UNII
90897H496X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROTOXAMINE TARTRATE
Common Name English
CARBINOXAMINE L-FORM D-TARTRATE [MI]
Common Name English
CARBINOXAMINE L-FORM D-TARTRATE
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 16:24:40 UTC 2023 , Edited by admin on Fri Dec 15 16:24:40 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL1552819
Created by admin on Fri Dec 15 16:24:40 UTC 2023 , Edited by admin on Fri Dec 15 16:24:40 UTC 2023
PRIMARY
PUBCHEM
118984414
Created by admin on Fri Dec 15 16:24:40 UTC 2023 , Edited by admin on Fri Dec 15 16:24:40 UTC 2023
PRIMARY
CAS
49746-00-1
Created by admin on Fri Dec 15 16:24:40 UTC 2023 , Edited by admin on Fri Dec 15 16:24:40 UTC 2023
PRIMARY
MERCK INDEX
m3070
Created by admin on Fri Dec 15 16:24:40 UTC 2023 , Edited by admin on Fri Dec 15 16:24:40 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C76678
Created by admin on Fri Dec 15 16:24:40 UTC 2023 , Edited by admin on Fri Dec 15 16:24:40 UTC 2023
PRIMARY
FDA UNII
90897H496X
Created by admin on Fri Dec 15 16:24:40 UTC 2023 , Edited by admin on Fri Dec 15 16:24:40 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY