Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H19ClN2O.C4H4O4 |
| Molecular Weight | 406.86 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.CN(C)CCO[C@@H](C1=CC=C(Cl)C=C1)C2=CC=CC=N2
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
| 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 |
| Molecular Formula | C4H4O4 |
| Molecular Weight | 116.0722 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
DescriptionCurator'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
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.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL231 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | KARBINAL Approved UseINDICATIONS 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 Date2013 |
|||
| Primary | KARBINAL Approved UseINDICATIONS 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 Date2013 |
|||
| Primary | KARBINAL Approved UseINDICATIONS 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 Date2013 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| 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 |
|
| [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 |
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
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
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admin
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Edited
Sat Dec 16 01:29:25 GMT 2023
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Sat Dec 16 01:29:25 GMT 2023
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| Record UNII |
33U3685HDG
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| Record Status |
Validated (UNII)
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| Record Version |
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RACEMATE -> ENANTIOMER |
