enflurane

Trade name: ethrane

Small moleculeapproved

Approved

Aug 28, 1972

Enflurane (2-chloro-1,1,2,-trifluoroethyl-difluoromethyl ether) is a halogenated ether structural isomer of isoflurane. Developed by Ross Terrell in 1963, it was first used clinically in 1966. It was increasingly used for inhalational anesthesia during the 1970s and 1980s but is no longer in common use. Clinically, enflurane produces a dose-related depression of myocardial contractility with an associated decrease in myocardial oxygen consumption. Between 2% and 5% of the inhaled dose is oxidized in the liver, producing fluoride ions and difluoromethoxy-difluoroacetic acid. This is significantly higher than the metabolism of its structural isomer isoflurane. The exact mechanism of the action of general anesthetics has not been delineated. Enflurane acts as a positive allosteric modulator of the GABAA, glycine, and 5-HT3 receptors, and as a negative allosteric modulator of the AMPA, kainate, and NMDA receptors, as well as of nicotinic acetylcholine receptors. — NCATS

Clinical trial activity

1 trials · 1 clinical orgs · 4 marketing orgs

Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Earliest trial started Dec 1, 2008 (NCT00815269)

Timeline

1970s

  1. Aug 28, 1972

    Baxter — Earliest FDA Approval

  2. Aug 28, 1972

    Baxter — NDA Organization

  3. Aug 28, 1972

    Baxalta — NDA Secondary Org

1980s

  1. Jul 27, 1987

    Abbott — Marketing Organization

1990s

  1. Jul 29, 1994

    Piramal — Marketing Organization

Indications

Mechanism of action

Approval history

  • approvedAug 28, 1972

Chemistry & pharmacology

Loading structure…

SMILES

FC(F)OC(F)(F)C(F)Cl
Mol. weight
184.492 g/mol
Lipinski Ro5
Pass
Rule of 3
Yes
Chirality
Racemic Mixture
Inorganic
No
Polymer
No
Delivery
Topical
Availability
Discontinued

Oral

No

Parenteral

No

Topical

Yes

Sources

Also known as

  • 2-chloro-1,1,2-trifluoroethyl difluoromethyl ether
  • 2-chloro-1,1,2-trifluoroethyl difluoromethyl ether
  • alyrane
  • alyrane
  • anesthetic compound no. 347
  • anesthetic compound no. 347
  • efrane
  • efrane
  • efrane
  • enflurane
  • enflurane
  • enflurane
  • enflurane
  • enflurane
  • enflurane
  • enflurane
  • enflurane
  • enflurane
  • enflurane
  • (+/-)-enflurane
  • enflurano
  • enflurano
  • enfluranum
  • enfluranum
  • ethrane
  • ethrane
  • ethrane
  • ethrane
  • methylflurether
  • methylflurether
  • methylflurether

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT00815269N/ADec 1, 2008Nanjing Medical University
Showing 1 of 1 trials
Page 1 / 1

Organizations

Research & Development (1)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Nanjing Medical UniversityAcademic/Hospital1112008
1 organizations
Page 1 / 1

Marketing (4)

OrganizationOrg typeRelationshipDate
AbbottFor profitMKTGJul 27, 1987
BaxaltaFor profitNDA2Aug 28, 1972
BaxterFor profitNDAAug 28, 1972
PiramalFor profitMKTGJul 29, 1994