Basic information
- CAS
3505-38-2- Standard SMILES
CN(C)CCOC(c1ccc(Cl)cc1)c1ccccn1.O=C(O)/C=C\C(=O)O- InChIKey
GVNWHCVWDRNXAZ-BTJKTKAUSA-N- Molecular formula
- C20H23ClN2O5
- Average molar mass
- 406.9 g/mol
- Monoisotopic mass
- 406.1295495
Overview
Carbinoxamine maleate is the maleic acid salt of carbinoxamine. An ethanolamine-type antihistamine, used for treating hay fever, as well as mild cases of Parkinson's disease. It has a role as a H1-receptor antagonist, an antiparkinson drug, a muscarinic antagonist and an anti-allergic agent. It contains a carbinoxamine.
Names & identifiers
- Preferred name
- Carbinoxamine Maleate
- IUPAC
- (Z)-but-2-enedioic acid;2-[(4-chlorophenyl)-pyridin-2-ylmethoxy]-N,N-dimethylethanamine
- English name
- Carbinoxamine maleate salt
- Molecular formula
- C20H23ClN2O5
- Molecular weight
- 406.86
Names & synonyms
CARBINOXAMINE MALEATE3505-38-2p-Carbinoxamine maleateParacarbinoxamine maleateKarbinal ERNSC-62362DTXSID0047828NSC6236202O55696WH2-(p-Chloro-alpha-(2-(dimethylamino)ethoxy)benzyl)pyridine maleateDTXCID5027805CHEBI:31353
Show more names
clistinciberonlergefinhislosineAllergefonMaleate clistinmaleateclistinemaleateallergefonmaleate
2-(p-Chloro-alpha-(2-(dimethylamino)ethoxy)benzyl)pyridine bimaleateEthanamine, 2-((4-chlorophenyl)-2-pyridinylmethoxy)-N,N-dimethyl-, (Z)-2-butenedioate (1:1)Ethanamine, 2-((4-chlorophenyl)-2-pyridinylmethoxy)-N,N-dimethyl-,(2Z)-2-butenedioate(1:1)Ethanamine, 2-[(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethyl-, (Z)-2-butenedioate (1:1)DavenolKarbinalRyVentRefChem:54715
Database identifiers
- CAS
3505-38-2- PubChem CID
- 5282409
- DTXSID
DTXSID0047828
Properties
Computed structural properties
- Topological polar surface area
- 100 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 8
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 386
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihistamines
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section167.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 116 · 116-1180C
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Water Solubility
- Completely soluble in water
- solubility
- Chloroform: Slightly Soluble; Methanol: Slightly Soluble
- form
- Solid
- color
- White to Almost white
- Merck
- 14 · 14,1799
- Major Application
- pharmaceutical small molecule
- 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-
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (97.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 85 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - Ethanamine, 2-[(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethyl-, (Z)-2-butenedioate (1:1): Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (97.6%)
Toxicology
Toxicity Summary
Carbinoxamine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. Carbinoxamine's anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Carbinoxamine maleate
vNo-DILI-concern
Chemistry & industry
Pharmacology
Metabolism/MetabolitesHalf Life: 10 to 20 hours
FDA Pharmacological Classification
CARBINOXAMINE MALEATE
Histamine H1 Receptor Antagonists [MoA]; Histamine-1 Receptor Antagonist [EPC]
MeSH Pharmacological Classification
Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.
Uses & manufacturing
Uses
For symptomatic relief of seasonal and perennial allergic rhinitis and vasomotor rhinitis, as well as allergic conjunctivitis caused by foods and inhaled allergens. Also for the relief of allergic reactions to blood or plasma, and the symptomatic management of mild, uncomplicated allergic skin manifestations of urticaria and angioedema.
General Manufacturing InformationEthanamine, 2-[(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethyl-, (2Z)-2-butenedioate (1:1): ACTIVE
Applications
DescriptionCarbinoxamine is a competitive histamine H1 receptor antagonist (Ki = 2.3 nM) and first generation antihistamine. It also competes with [3H]diltiazem, an L-type calcium channel blocker, for binding to the benzothiazepine site on rat cardiomyocytes (Ki = 1.08 nM). Carbinoxamine decreases negative inotropic activity in isolated guinea pig left atria by 76% (EC50 = 250 nM) and negative chronotropic activity in guinea pig spontaneously beating isolated right atria (EC50s = 250 and 480 nM, respectively) by 48% compared with control. Formulations containing carbinoxamine have been used in the treatment of allergic rhinitis.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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