ROTOXAMINE

First approved in 1960

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H19ClN2O
Molecular Weight	290.788
Optical Activity	( - )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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
Sources: https://www.drugs.com/dosage/carbinoxamine.html
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16460947	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Allergic rhinitis 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf	Primary	Approved 8429	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 2013
Vasomotor rhinitis 21 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf	Primary	Approved 8429	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 2013
Angioedema 20 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022556s000lbl.pdf	Primary	Approved 8429	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 2013

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00I7EJ
AAA Chemistry	AR-1L7907
ABI Chem	AC1L55F0
ABI Chem	AC1Q3N5C
AK Scientific	6631AB
AK Scientific	V1556
Alinda	ALBB-023749
Alinda	IBS-L0035350
ApexBio Technology	B6147
AstaTech	C74801
BLD Pharm	BD119988
BOC Sciences	3505-38-2
BOC Sciences	486-16-8
BlocksMatrix Scientific	155633
Bosche Scientific	C3546
Chem Scene	CS-8018
ChemDiv	BB57-4994
Combi-Blocks	QJ-8449
Combi-Blocks	QZ-9568
Compound Cloud	170336
Compound Cloud	2564
Compound Cloud	5282409
Compound Cloud	BCC0065117
Enamine	EN300-51917
Enamine	EN300-749621
Enamine	EN300-755282
Hairui	HR125120
Hairui	HR134137
Hangzhou APIChem Technology	AC-5507
Hangzhou APIChem Technology	AC-5508
Hangzhou Yuhao Chemical Technology	RT10082
HongKong Chemhere	SCA38747
Lab Network	LN01343752
MedChem Express	HY-B1589A
MolPort	MolPort-001-537-638
MolPort	MolPort-003-666-137
Molnova	M14197
MuseChem	R007681
NCI Plated 2007	62362
Norris Pharm	NSZB-A067348
Princeton BioMolecular Research	OSSL_298528
Ryan Scientific	Piroctone_olamine
Scientific Exchange	M-323564
Scientific Exchange	Q-034829
Sigma Aldrich	1096000
Sigma Aldrich	1096000\|USP
Sigma Aldrich	C8278
Sigma Aldrich	C8278\|SIAL
THE BioTek	bt-403974	https://www.thebiotek.com/product/others/bt-403974
TargetMol	T2222
Tetrahedron	TS35346
Tetrahedron	TS39374
TimTec	SBB067454
TimTec	ST45026379
Toronto Research Chemicals	B692195
Toronto Research Chemicals	C175920
Toronto Research Chemicals	T892600
ZINC	ZINC000000000122	http://zinc15.docking.org/substances/ZINC000000000122
eMolecules	18597487
eMolecules	1985937
eMolecules	207083389
eMolecules	45772631
eMolecules	48848072
eNovation Chemicals	D756535
mcule	MCULE-2463311442
mcule	MCULE-8298496189
mcule	MCULE-9375103807

PubMed

Title	Date	PubMed
Clistin maleate; a clinical appraisal of a new antihistaminic.	1954 Nov	13211145
[Antimycobacterial antihistaminics].	1989 Aug	2513793
The need for rational therapeutics in the use of cough and cold medicine in infants.	1992 Apr	1557278
[Serous otitis media. Comparative study of carbinoxamine- pseudoephedrine vs astemizole-pseudoephedrine].	1997 May-Jun	9377115
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
Cold-syrup induced movement disorder.	2001 Jun	11437145
Quantitation of antihistamines in pharmaceutical preparations by liquid chromatography with a micellar mobile phase of sodium dodecyl sulfate and pentanol.	2001 Nov-Dec	11767132
Discovery of novel and cardioselective diltiazem-like calcium channel blockers via virtual screening.	2008 Sep 25	18754582
[1,2]-Anionic rearrangement of 2-benzyloxypyridine and related pyridyl ethers.	2009 Oct 16	19761204
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
LC for analysis of two sustained-release mixtures containing cough cold suppressant drugs.	2010 Jul	20822669
4-(4-Chloro-phen-yl)-4-hy-droxy-piperidinium maleate maleic acid solvate.	2010 Jul 14	21588324
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

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

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