ethoheptazine

{{Short description|Opioid analgesic drug}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 461096586

| IUPAC_name = Ethyl 1-methyl-4-phenylazepane-4-carboxylate

| image = Ethoheptazine2DACS.svg

| image_class = skin-invert-image

| image2 = Ethoheptazine-3D-balls.png

| image_class2 = bg-transparent

| width = 200

| tradename = Zactane, Equagesic

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US = Schedule IV

| legal_US_comment = (Some preparations)

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 77-15-6

| ATC_prefix = none

| ATC_suffix =

| PubChem = 6469

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 170797

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB08988

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 6225

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3A4G3A848U

| C=16 | H=23 | N=1 | O=2

| smiles = O=C(OCC)C2(c1ccccc1)CCN(C)CCC2

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WGJHHMKQBWSQIY-UHFFFAOYSA-N

| synonyms = Zactane

}}

Ethoheptazine{{cite patent | country = ES | number = 310184 | title = Procedure for the preparation of a new derivative of pirazolidine-hexametilenimina with therapeutic properties. }} (trade name Zactane) is an opioid analgesic from the phenazepane family. It was invented in the 1950s{{cite journal | vauthors = Batterman RC, Golbey M, Grossman AJ, Leifer P | title = Analgesic effectiveness of orally administered ethoheptazine in man | journal = The American Journal of the Medical Sciences | volume = 234 | issue = 4 | pages = 413–9 | date = October 1957 | pmid = 13469802 | doi = 10.1097/00000441-195710000-00004 | s2cid = 32299049 }} and is a ring expanded analogue of pethidine.{{cite journal | vauthors = Diamond J, Bruce WF, Tyson FT | title = Synthesis and Properties of the Analgesic DL-α-1,3-dimethyl-4-phenyl-4-propionoxyazacycloheptane (Proheptazine). | journal = Journal of Medicinal Chemistry | volume = 7 | pages = 57–60 | date = January 1964 | pmid = 14186026 | doi = 10.1021/jm00331a013 }}

Ethoheptazine produces similar effects to other opioids, including analgesia, sedation, dizziness, and nausea.{{cite journal | vauthors = Cinelli P, Zucchini M | title = [Current pharmaco-therapeutic possiblities in the treatment of pain. Experiments with ethoeptazine] | language = it | journal = Minerva Medica | volume = 53 | pages = 637–42 | date = March 1962 | pmid = 13879557 }} 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.{{cite journal | vauthors = Scheiner JJ, Richards DJ | title = Treatment of musculoskeletal pain and associated anxiety with an ethoheptazine-aspirin-meprobamate combination (equagesic): a controlled study | journal = Current Therapeutic Research, Clinical and Experimental | volume = 16 | issue = 9 | pages = 928–36 | date = September 1974 | pmid = 4214668 }} It was also investigated for use as an antitussive.{{cite journal | vauthors = Overton DA, Batta SK | title = Investigation of narcotics and antitussives using drug discrimination techniques | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 211 | issue = 2 | pages = 401–8 | date = November 1979 | doi = 10.1016/S0022-3565(25)31847-1 | pmid = 41087 | pmc = 8331839 }}

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. The controlled status (Schedule IV) of Equagesic was due to the meprobamate content.PDR 1978, pp 1618{{cite web | title = Conversion Factors for Controlled Substances | url = http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html | work = Diversion Control Division | publisher = Drug Enforcement Agency, U.S. Department of Justice | access-date = 2016-02-27 | archive-date = 2016-03-02 | archive-url = https://web.archive.org/web/20160302162948/http://deadiversion.usdoj.gov/quotas/conv_factor/index.html | url-status = dead }} Regulation elsewhere varies.