Ethoheptazine

Last updated
Ethoheptazine
Ethoheptazine2DACS.svg
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Clinical data
Trade names Zactane, Equagesic
Other namesZactane
Routes of
administration 		Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • Ethyl 1-methyl-4-phenylazepane-4-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.917 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H23NO2
Molar mass 261.365 g·mol−1
3D model (JSmol)
  • O=C(OCC)C2(c1ccccc1)CCN(C)CCC2
  • InChI=1S/C16H23NO2/c1-3-19-15(18)16(14-8-5-4-6-9-14)10-7-12-17(2)13-11-16/h4-6,8-9H,3,7,10-13H2,1-2H3 Yes check.svgY
  • Key:WGJHHMKQBWSQIY-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Ethoheptazine [1] (trade name Zactane) is an opioid analgesic from the phenazepane family. It was invented in the 1950s [2] and is a ring expanded analogue of pethidine. [3]

Ethoheptazine produces similar effects to other opioids, including analgesia, sedation, dizziness, and nausea. [4] It was sold by itself as Zactane, and is still available as a combination product with acetylsalicylic acid and meprobamate as Equagesic, which is used for the treatment of conditions where both pain and anxiety are present. [5] It was also investigated for use as an antitussive. [6]

It is no longer prescribed, as it is no longer FDA approved, and not available for United States' Pharmacy Processing. Revocation of FDA Approved Medications Status stems from a combination of efficacy vs. toxicity, and the more-varied and historically safer benzodiazepines class. Only reversal of the FDA's decision, allows removing the drug from the CSD. Ethoheptazine is not listed as a controlled substance under the Controlled Substances Act, 1970 in the United States. [7] The controlled status (Schedule IV) of Equagesic was due to the meprobamate content. [8] [7] Regulation elsewhere varies.

References

  1. ↑ ES 310184,"Procedure for the preparation of a new derivative of pirazolidine-hexametilenimina with therapeutic properties."
  2. ↑ Batterman RC, Golbey M, Grossman AJ, Leifer P (October 1957). "Analgesic effectiveness of orally administered ethoheptazine in man". The American Journal of the Medical Sciences. 234 (4): 413–9. doi:10.1097/00000441-195710000-00004. PMID   13469802. S2CID   32299049.
  3. ↑ Diamond J, Bruce WF, Tyson FT (January 1964). "Synthesis and Properties of the Analgesic DL-α-1,3-dimethyl-4-phenyl-4-propionoxyazacycloheptane (Proheptazine)". Journal of Medicinal Chemistry. 7: 57–60. doi:10.1021/jm00331a013. PMID   14186026.
  4. ↑ Cinelli P, Zucchini M (March 1962). "[Current pharmaco-therapeutic possibilities in the treatment of pain. Experiments with ethoeptazine]". Minerva Medica (in Italian). 53: 637–42. PMID   13879557.
  5. ↑ Scheiner JJ, Richards DJ (September 1974). "Treatment of musculoskeletal pain and associated anxiety with an ethoheptazine-aspirin-meprobamate combination (equagesic): a controlled study". Current Therapeutic Research, Clinical and Experimental. 16 (9): 928–36. PMID   4214668.
  6. ↑ Overton DA, Batta SK (November 1979). "Investigation of narcotics and antitussives using drug discrimination techniques". The Journal of Pharmacology and Experimental Therapeutics. 211 (2): 401–8. doi:10.1016/S0022-3565(25)31847-1. PMC   8331839 . PMID   41087.
  7. 1 2 "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice. Archived from the original on 2016-03-02. Retrieved 2016-02-27.
  8. ↑ PDR 1978, pp 1618
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