Grundinformationen
- CAS
486-16-8- Standard-SMILES
CN(C)CCOC(c1ccc(Cl)cc1)c1ccccn1- InChIKey
OJFSXZCBGQGRNV-UHFFFAOYSA-N- Summenformel
- C16H19ClN2O
- Durchschnittliche Molmasse
- 290,79 g/mol
- Monoisotopische Masse
- 290,1185909
Überblick
Carbinoxamine is an organochlorine compound that is 2-(4-chlorobenzyl)pyridine in which one of the benzylic hydrogens is substituted by 2-(dimethylamino)ethoxy group. It is an ethanolamine-type antihistamine, used as its maleate salt 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 is a member of pyridines, a tertiary amino compound and a member of monochlorobenzenes.
Namen und Bezeichner
- Bevorzugter Name
- Carbinoxamine
- IUPAC
- 2-[(4-chlorophenyl)-pyridin-2-ylmethoxy]-N,N-dimethylethanamine
- Lokaler Name
- Carbinoxamin
- Englischer Name
- carbinoxamine
- Summenformel
- C16H19ClN2O
- Molmasse
- 290.78786
Namen und Synonyme
carbinoxamine486-16-8ParacarbinoxamineAllergefonCarbinoxaminaCarbinoxaminum(+-)-CarbinoxamineCarbinoxamine basePalgic2-(p-Chloro-alpha-(2-(dimethylamino)ethoxy)benzyl)pyridine982A7M02H5Ethanamine, 2-((4-chlorophenyl)-2-pyridinylmethoxy)-N,N-dimethyl-
Weitere Namen anzeigen
C06871carbinoxamine USP/EP/BPCarbinoxamine (base and/or unspecified salts)2-[p-Chloro-α-(2-dimethylaminoethoxy)benzyl]pyridine2-[p-chloro-a-(2-dimethylaminoethoxy)benzyl]pyridine2-[p-Chloro-α-[2-(dimethylamino)ethoxy]benzyl]pyridine
Ethanamine, 2-[(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethyl-CHEBI:3398DTXSID4022737N,N-Dimethyl-2-(p-chloro-alpha-(2-pyridyl)benzyloxy)ethylamineArbinoxa{2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylamine{2-[(4-Chloro-phenyl)-pyridin-2-yl-methoxy]-ethyl}-dimethyl-amine(2-((4-chlorophenyl)(pyridin-2-yl)methoxy)ethyl)dimethylamine
Datenbank-Bezeichner
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,9
- Polarare Oberfläche (TPSA)
- 25,4 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 20
- Formalladung
- 0
- Komplexität
- 267
Experimentelle und physikochemische Eigenschaften
LogP2.6
Solubility2.28e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihistamines
Pharmaceuticals
Melting Point
< 25 °C
< 25 °C
Physical DescriptionSolid
Collision Cross Section169.28 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Siedepunkt
- 0.1 · bp0.1 158-162°
- pka
- 8.1 · pKa 8.1 (Uncertain)
- NIST chemische Informationen
- Carbinoxamine base(486-16-8)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
HepatotoxicityLike many first generation antihistamines, carbinoxamine has not been linked to liver test abnormalities or to clinically apparent liver injury. The reason for its hepatic safety may relate to low daily dose and limited duration of use.
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
Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)
carbinoxamine
Clistin®
Antihistamines
Not Applicable
no-DILI-concern
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemie und Industrie
Pharmakologische Informationen
ATC Code
R - Respiratory system
QR - Respiratory system
Pharmacodynamics
Carbinoxamine is 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 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. Rather than preventing the release of histamine, as do cromolyn and nedocromil, carbinoxamine competes with free histamine for binding at HA-receptor sites. Carbinoxamine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of carbinoxamine.
Mechanism of Action
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.
Biological Half-Life10 to 20 hours
Metabolism/MetabolitesHalf Life: 10 to 20 hours
FDA Pharmacological Classification
982A7M02H5
CARBINOXAMINE
Mechanisms of Action [MoA] - Histamine H1 Receptor Antagonists
Established Pharmacologic Class [EPC] - Histamine-1 Receptor Antagonist
Carbinoxamine is a Histamine-1 Receptor Antagonist. The mechanism of action of carbinoxamine is as a Histamine H1 Receptor Antagonist.
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