N-ethyl-3-hydroxy-N,N-dimethylanilinium

• ChemBase ID: 883
• Molecular Formular: C10H16NO+
• Molecular Mass: 166.24014
• Monoisotopic Mass: 166.12318914
• SMILES: Oc1cc([N+](CC)(C)C)ccc1
• Canonical SMILES: CC[N+](c1cccc(c1)O)(C)C
• InChI: InChI=1S/C10H15NO/c1-4-11(2,3)9-6-5-7-10(12)8-9/h5-8H,4H2,1-3H3/p+1
• InChIKey: VWLHWLSRQJQWRG-UHFFFAOYSA-O

NAMES AND DATABASE IDS

Names

• IUPAC name: N-ethyl-3-hydroxy-N,N-dimethylanilinium
• IUPAC Traditional name: edrophonium
• Brand Name: Antirex; Enlon; Enlon Plus; Reversol; Tensilon; Tensilon chloride
• Synonyms: EDR; Edrophone Chloride; Edrophonium Chloride; Edrophonium Ion; Edrophonum; Edrophonium

Database IDs

• CAS Number: 116-38-1
• PubChem SID: 46507530; 160964346
• PubChem CID: 3202

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.5937195
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -1.8696398
• LogD (pH = 7.4): -0.9596521
• Log P: -1.9138073
• Molar Refractivity: 62.4088 cm^3
• Polarizability: 19.740566 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.55
• LOG S: -3.62
• Solubility (Water): 4.86e-02 g/l

PROPERTIES

Physical Property

• Solubility: Appreciable as liquid hydrochloride salt
• Hydrophobicity(logP): -2.95

DETAILS

DrugBank - DB01010

• Drug Groups: approved
• Description: A rapid-onset, short-acting cholinesterase inhibitor used in cardiac arrhythmias and in the diagnosis of myasthenia gravis. It has also been used as an antidote to curare principles. [PubChem]
• Indication: For the differential diagnosis of myasthenia gravis and as an adjunct in the evaluation of treatment requirements in this disease. It may also be used for evaluating emergency treatment in myasthenic crises.
• Pharmacology: Edrophonium is a short and rapid-acting anticholinesterase drug. Its effect is manifest within 30 to 60 seconds after injection and lasts an average of 10 minutes. Edrophonium's pharmacologic action is due primarily to the inhibition or inactivation of acetylcholinesterase at sites of cholinergic transmission. Nicotinic acetylcholine (nAChR)receptors are found throughout the body, especially on muscle. Stimulation of these receptors causes to muscle contraction. In myasthenia gravis the body's immune system destroys many of the nicotinic acetylcholine receptors, so that the muscle becomes less responsive to nervous stimulation. Edrophonium chloride increases the amount of acetylcholine at the nerve endings. Increased levels of acetylcholine allow the remaining receptors to function more efficiently.
• Toxicity: With drugs of this type, muscarine-like symptoms (nausea, vomiting, diarrhea, sweating, increased bronchial and salivary secretions and bradycardia) often appear with overdosage (cholinergic crisis).
• Affected Organisms: Humans and other mammals
• Absorption: Rapidly absorbed.
• Half Life: Distribution half-life is 7 to 12 minutes. Elimination half-life is 33 to 110 minutes.
• Elimination: Edrophonium is primarily renally excreted with 67% of the dose appearing in the urine.; Hepatic metabolism and biliary excretion have also been demonstrated in animals
• Distribution: * 1.6±0.4 L/kg [Adults]; * 2.2±1.5 L/kg [Children (0.08-10 yrs)]; * 1.8±1.2 L/kg [Elderly (65-75 yrs)]
• Clearance: * 6.8 +/- 2. mL/kg/min [Adults]; * 6.4 +/- 3.9 mL/kg/min [Children (0.08-10 yrs)]; * 2.9 +/- 1.9 mL/kg/min [Elderly (65-75 yrs)]
• External Links: Wikipedia; RxList; Drugs.com