Etidocaine

Last updated
Etidocaine
Etidocaine.svg
Clinical data
Trade names Duranest
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a603026
Pregnancy
category
  • AU:B1
Routes of
administration
Parenteral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability n/a
Metabolism Hepatic
Elimination half-life 2.5 hours
Excretion Renal
Identifiers
  • N-(2,6-dimethylphenyl)-
    2-(ethyl(propyl)amino)butanamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.048.296 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H28N2O
Molar mass 276.424 g·mol−1
3D model (JSmol)
  • O=C(Nc1c(C)cccc1C)C(CC)N(CC)CCC
  • InChI=1S/C17H28N2O/c1-6-12-19(8-3)15(7-2)17(20)18-16-13(4)10-9-11-14(16)5/h9-11,15H,6-8,12H2,1-5H3,(H,18,20) Yes check.svgY
  • Key:VTUSIVBDOCDNHS-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Etidocaine, marketed under the trade name Duranest, is an amide-type local anesthetic given by injection during surgical procedures and labor and delivery. Etidocaine has a long duration of activity, and the main disadvantage of using during dentistry is increased bleeding during surgery. [1]

Contents

Synthesis

Patent: 2-bromobutyryl chloride synthesis: Etidocaine synthesis.svg
Patent: 2-bromobutyryl chloride synthesis:

The amide reaction between 2,6-xylidine (1) and 2-bromobutyryl chloride [22118-12-3] (2) gives 2-Bromo-N-(2,6-Dimethylphenyl)Butanamide [53984-81-9] (3). Alkylation with N-Ethylpropylamine [20193-20-8] (4) gives Etidocaine (5).

Related Research Articles

Anesthesia is a state of controlled, temporary loss of sensation or awareness that is induced for medical or veterinary purposes. It may include some or all of analgesia, paralysis, amnesia, and unconsciousness. An individual under the effects of anesthetic drugs is referred to as being anesthetized.

<span class="mw-page-title-main">Local anesthetic</span> Medications to reversibly block pain

A local anesthetic (LA) is a medication that causes absence of pain sensation. In the context of surgery, a local anesthetic creates an absence of pain in a specific location of the body without a loss of consciousness, as opposed to a general anesthetic. When it is used on specific nerve pathways, paralysis also can be achieved.

<span class="mw-page-title-main">Procaine</span> Local anesthetic drug

Procaine is a local anesthetic drug of the amino ester group. It is most commonly used in dental procedures to numb the area around a tooth and is also used to reduce the pain of intramuscular injection of penicillin. Owing to the ubiquity of the trade name Novocain or Novocaine, in some regions, procaine is referred to generically as novocaine. It acts mainly as a sodium channel blocker. Today it is used therapeutically in some countries due to its sympatholytic, anti-inflammatory, perfusion-enhancing, and mood-enhancing effects.

<span class="mw-page-title-main">Lidocaine</span> Local anesthetic

Lidocaine, also known as lignocaine and sold under the brand name Xylocaine among others, is a local anesthetic of the amino amide type. It is also used to treat ventricular tachycardia. When used for local anaesthesia or in nerve blocks, lidocaine typically begins working within several minutes and lasts for half an hour to three hours. Lidocaine mixtures may also be applied directly to the skin or mucous membranes to numb the area. It is often used mixed with a small amount of adrenaline (epinephrine) to prolong its local effects and to decrease bleeding.

<span class="mw-page-title-main">Anesthetic</span> Drug that causes anesthesia

An anesthetic or anaesthetic is a drug used to induce anesthesia ⁠— ⁠in other words, to result in a temporary loss of sensation or awareness. They may be divided into two broad classes: general anesthetics, which result in a reversible loss of consciousness, and local anesthetics, which cause a reversible loss of sensation for a limited region of the body without necessarily affecting consciousness.

ATC code N01Anesthetics is a therapeutic subgroup of the Anatomical Therapeutic Chemical Classification System, a system of alphanumeric codes developed by the World Health Organization (WHO) for the classification of drugs and other medical products. Subgroup N01 is part of the anatomical group N Nervous system.

<span class="mw-page-title-main">Bupivacaine</span> Pair of enantiomers

Bupivacaine, marketed under the brand name Marcaine among others, is a medication used to decrease feeling in a specific area. In nerve blocks, it is injected around a nerve that supplies the area, or into the spinal canal's epidural space. It is available mixed with a small amount of epinephrine to increase the duration of its action. It typically begins working within 15 minutes and lasts for 2 to 8 hours.

<span class="mw-page-title-main">Oxybuprocaine</span>

Oxybuprocaine (INN), also known as benoxinate or BNX, is an ester-type local anesthetic, which is used especially in ophthalmology and otolaryngology. Oxybuprocaine is sold by Novartis under the brand names Novesine or Novesin.

Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

<span class="mw-page-title-main">Articaine</span> Chemical compound

Articaine is a dental amide-type local anesthetic. It is the most widely used local anesthetic in a number of European countries and is available in many countries. It is the only local anaesthetic to contain a thiophene ring, meaning it can be described as 'thiophenic'; this conveys lipid solubility.

<span class="mw-page-title-main">Prilocaine</span> Local anesthetic of the amino amide type

Prilocaine is a local anesthetic of the amino amide type first prepared by Claes Tegner and Nils Löfgren. In its injectable form, it is often used in dentistry. It is also often combined with lidocaine as a topical preparation for dermal anesthesia, for treatment of conditions like paresthesia. As it has low cardiac toxicity, it is commonly used for intravenous regional anaesthesia (IVRA).

<span class="mw-page-title-main">Levobupivacaine</span> Chemical compound

Levobupivacaine (rINN) is a local anaesthetic drug belonging to the amino amide group. It is the S-enantiomer of bupivacaine.

<span class="mw-page-title-main">Cinchocaine</span> Chemical compound

Cinchocaine (INN/BAN) or dibucaine (USAN) is an amide local anesthetic. Among the most potent and toxic of the long-acting local anesthetics, current use of cinchocaine is generally restricted to spinal and topical anesthesia. It is sold under the brand names Cincain, Nupercainal, Nupercaine and Sovcaine.

Dental anesthesia is the application of anesthesia to dentistry. It includes local anesthetics, sedation, and general anesthesia.

<span class="mw-page-title-main">Trimecaine</span> Chemical compound

Trimecaine (systematic name (2,4,6-trimethylphenylcarbamoylmethyl)diethylammonium chloride, chemical formula C15H25ClN2O) is an organic compound used as a local anesthetic and cardial antiarrhythmic. It is white crystalline powder readily soluble in water and ethanol. It is an active ingredient in products available under trademarks Mesdicain, Mesocain, Mesokain and others.

<span class="mw-page-title-main">Butanilicaine</span> Chemical compound

Butanilicaine is a local anesthetic. It is also known by the name Hostacaine.

<span class="mw-page-title-main">Intravenous regional anesthesia</span>

Intravenous regional anesthesia (IVRA) or Bier's block anesthesia is an anesthetic technique on the body's extremities where a local anesthetic is injected intravenously and isolated from circulation in a target area. The technique usually involves exsanguination of the target region, which forces blood out of the extremity, followed by the application of pneumatic tourniquets to safely stop blood flow. The anesthetic agent is intravenously introduced into the limb and allowed to diffuse into the surrounding tissue while tourniquets retain the agent within the desired area.

<span class="mw-page-title-main">Isobucaine</span>

Isobucaine is a local anesthetic.

<span class="mw-page-title-main">Pyrrocaine</span> Chemical compound

Pyrrocaine is a local anesthetic drug. The cogency of pyrrocaine is equivalent to lidocaine in blocking the motor nerve and sensory. Pyrrocaine was proven to be somewhat harmless compared to lidocaine. No signs of methemoglobinemia was found while observing. It was considered unsafe for acute porphyria treatment. No evidence is found that it is profitly used now.

References

  1. Sisk AL (1992). "Long-acting local anesthetics in dentistry". Anesthesia Progress. 39 (3): 53–60. PMC   2148750 . PMID   1308373.
  2. DE2162744 idem H Adams, G Kronberg, B Takman, U.S. Patent 3,812,147 (1974 to Astra Pharma Prod).
  3. Org. Synth. 1950, 30, 62. DOI: 10.15227/orgsyn.030.0062