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Dexmedetomidine

HCID 5311068
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Grundinformationen

CAS
113775-47-6
Standard-SMILES
Cc1cccc([C@H](C)c2cnc[nH]2)c1C
InChIKey
CUHVIMMYOGQXCV-NSHDSACASA-N
Summenformel
C13H16N2
Durchschnittliche Molmasse
200,28 g/mol
Monoisotopische Masse
200,13134851

Überblick

Dexmedetomidine is a medetomidine. It has a role as an analgesic, a non-narcotic analgesic, an alpha-adrenergic agonist and a sedative. It is an enantiomer of a levomedetomidine.

Namen und Bezeichner

Bevorzugter Name
Dexmedetomidine
IUPAC
5-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole
Englischer Name
Dexmedetomidine
Summenformel
C13H16N2
Molmasse
200.28

Namen und Synonyme

DEXMEDETOMIDINE113775-47-6DexmedetomidinaDexmedetomidinumMPV 1440MPV-1440Medetomidine, (s)-(+)-4-((S)-alpha,2,3-Trimethylbenzyl)imidazole4-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole67VB76HONOCHEBI:4466DTXSID10873388
Weitere Namen anzeigen
(S)-5-(1-(2,3-diMethylphenyl)ethyl)-1H-iMidazoled-Medetomidine(S)-Medetomidine(+)-MedetomidineDexmedetomidine D6Dexmedetomidine 98%Medetomidine (S)-IsomerMedetomidine Impurity 56
4-((1S)-1-(2,3-dimethylphenyl)ethyl)-1H-imidazole4-((1S)-1-(2,3-dimethylphenyl)ethyl)-3H-imidazole4-[(1S)-1-(2,3-dimethylphenyl)ethyl]-3H-imidazole1H-Imidazole, 4-(1-(2,3-dimethylphenyl)ethyl)-, (R)-MPV1440RefChem:919964Hydrochloride, DexmedetomidineDTXCID00820907

Datenbank-Bezeichner

CAS
113775-47-6
PubChem CID
5311068
DTXSID
DTXSID10873388
ChEMBL
CHEMBL778

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
3,1
Polarare Oberfläche (TPSA)
28,7 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
2
Schwere Atome
15
Formalladung
0
Komplexität
205

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

DEA NFLIS-Drug Category -> Analgesics

Pharmaceuticals -> Listed in ZINC15

LogP · 2 Einträge

2.8

2.79

Solubility · 2 Einträge

Freely soluble in water

1.74e-01 g/L

Human Drugs · 2 Einträge

Breast Feeding; Lactation; Milk, Human; Hypnotics and Sedatives; Anesthetics, Intravenous; Adrenergic alpha-2 Receptor Agonists; Analgesics

EMA approved medicines: Human medicine

Animal Drugs · 5 Einträge

EMA approved medicines: Veterinary medicine

EMA approved medicines: Veterinary medicine

EMA approved medicines: Veterinary medicine

EMA approved medicines: Veterinary medicine

Active Ingredients (Dexmedetomidine) -> FDA Greenbook

Physical DescriptionSolid
Dissociation Constants7.1

Sicherheit und Regulatorisches

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GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H317 (66.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P260, P261, P264, P270, P272, P280, P302+P352, P308+P316, P318, P319, P321, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Sens. 1 (66.7%)

Toxikologische Informationen

Adverse Effects · 1 Eintrag

The most common adverse effects of dexmedetomidine are hypotension, bradycardia, and hypertension. Hypertension can result from the stimulation of alpha subtypes of receptors in vascular smooth muscles. Hypertension usually does not require treatment and can be avoided by the slow administration or omission of the loading dose. Hypotension and bradycardia are the results of the stimulation of presynaptic alpha receptors, which leads to a decreased release of norepinephrine; this is in addition to the decrease in the central sympathetic outflow. These are concerns regardless of the route of administration.

Toxicity SummaryAt present, there is no chemical reversal or antidote for dexmedetomidine. Supportive care and close monitoring are the staples of treatment for overdose.
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

N - Nervous system

QN - Nervous system

Protein Binding94%
Pharmacodynamics · 1 Eintrag

Dexmedetomidine activates 2-adrenoceptors, and causes the decrease of sympathetic tone, with attenuation of the neuroendocrine and hemodynamic responses to anesthesia and surgery; it reduces anesthetic and opioid requirements; and causes sedation and analgesia.

Mechanism of Action · 1 Eintrag

Dexmedetomidine is a specific and selective alpha-2 adrenoceptor agonist. By binding to the presynaptic alpha-2 adrenoceptors, it inhibits the release if norepinephrine, therefore, terminate the propagation of pain signals. Activation of the postsynaptic alpha-2 adrenoceptors inhibits the sympathetic activity decreases blood pressure and heart rate.

Biological Half-Life2 hours
Metabolism/Metabolites · 2 Einträge

Hepatic

Dexmedetomidine has known human metabolites that include (2S,3S,4S,5R)-6-[5-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazol-3-ium-3-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid and (2S,3S,4S,5R)-6-[5-[(1S)-1-(2,3-dimethylphenyl)ethyl]imidazol-1-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid.

FDA Pharmacological Classification · 6 Einträge

67VB76HONO

DEXMEDETOMIDINE

Mechanisms of Action [MoA] - Adrenergic alpha2-Agonists

Established Pharmacologic Class [EPC] - Central alpha-2 Adrenergic Agonist

Physiologic Effects [PE] - General Anesthesia

Dexmedetomidine is a Central alpha-2 Adrenergic Agonist. The mechanism of action of dexmedetomidine is as an Adrenergic alpha2-Agonist. The physiologic effect of dexmedetomidine is by means of General Anesthesia.

MeSH Pharmacological Classification · 3 Einträge

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
ChEBI
CHEBI:4466
UNII
67VB76HONO
EC Number
601-281-8
Nikkaji
J263.999H

Physikochemische Eigenschaften

Schmelzpunkt
146 · 146-149°C
Siedepunkt
381.9 · 381.9±11.0 °C(Predicted)
Dichte
1.053 · 1.053±0.06 g/cm3 (20 ºC 760 Torr)
storage temp.
Sealed in dry,Room Temperature
Löslichkeit
10 mM · Soluble in DMSO > 10 mM
Aggregatzustand
Powder
pka
13.89 · 13.89±0.10(Predicted)
Farbe
White to off-white
InChI
InChI=1S/C13H16N2/c1-9-5-4-6-12(10(9)2)11(3)13-7-14-8-15-13/h4-8,11H,1-3H3,(H,14,15)/t11-/m0/s1
InChIKey
CUHVIMMYOGQXCV-NSHDSACASA-N
SMILES
C1NC([C@H](C2=CC=CC(C)=C2C)C)=CN=1
Alarmwort
Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H317

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.

A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS.

Compounds that bind to and activate ADRENERGIC ALPHA-2 RECEPTORS.

Absorption, Distribution and Excretion · 3 Einträge

A mass balance study demonstrated that after nine days an average of 95% of the radioactivity, following intravenous administration of radiolabeled dexmedetomidine, was recovered in the urine and 4% in the feces. Fractionation of the radioactivity excreted in urine demonstrated that products of N-glucuronidation accounted for approximately 34% of the cumulative urinary excretion. The majority of metabolites are excreted in the urine.

118 L

39 L/h [Healthy volunteers receiving IV infusion (0.2-0.7 mcg/kg/hr)]

Cellular LocationsMembrane

Verwendung und Herstellung

Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Anwendungen · 1 Eintrag

VerwendenDexmedetomidine is a sedative drug that has many benefits when given to children under anesthesia, such as improved pain relief and reduced agitation following their surgery. The FDA-approved indications for dexmedetomidine are sedation of intubated and mechanically ventilated patients in the intensive care unit (ICU) and peri-procedural (or peri-operative) sedation of non-intubated patients.

Ergänzende Hinweise

DefinitionChEBI: Dexmedetomidine is a medetomidine. It has a role as an alpha-adrenergic agonist, a non-narcotic analgesic, an analgesic and a sedative. It is an enantiomer of a levomedetomidine.