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Ethoheptazine

From Wikipedia, the free encyclopedia
Opioid analgesic drug
Pharmaceutical compound
Ethoheptazine
Clinical data
Trade namesZactane, Equagesic
Other namesZactane
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • Ethyl 1-methyl-4-phenylazepane-4-carboxylate
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.000.917Edit this at Wikidata
Chemical and physical data
FormulaC16H23NO2
Molar mass261.365 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 checkY
  • Key:WGJHHMKQBWSQIY-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ethoheptazine[1] (trade nameZactane) is anopioidanalgesic from the phenazepane family. It was invented in the 1950s[2] and is a ring expanded analogue ofpethidine.[3]

Ethoheptazine produces similar effects to other opioids, includinganalgesia,sedation,dizziness, andnausea.[4] It was sold by itself as Zactane, and is still available as a combination product withacetylsalicylic acid andmeprobamate asEquagesic, 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 themeprobamate content.[8][7] Regulation elsewhere varies.

References

[edit]
  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 possiblities 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. ^ab"Conversion Factors for Controlled Substances".Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice. Archived fromthe original on 2016-03-02. Retrieved2016-02-27.
  8. ^PDR 1978, pp 1618
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