エトヘプタジン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2017/09/11 09:04:11」(JST)
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Ethoheptazine
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Clinical data |
Trade names |
Equagesic |
Synonyms |
Zactane |
Routes of
administration |
Oral |
ATC code |
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Legal status |
Legal status |
- US: Schedule IV (Some preparations)
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Identifiers |
IUPAC name
- Ethyl 1-methyl-4-phenylazepane-4-carboxylate
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CAS Number |
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PubChem CID |
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DrugBank |
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ChemSpider |
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UNII |
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ChEMBL |
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ECHA InfoCard |
100.000.917 |
Chemical and physical data |
Formula |
C16H23NO2 |
Molar mass |
261.36 g/mol |
3D model (JSmol) |
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SMILES
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O=C(OCC)C2(c1ccccc1)CCN(C)CCC2
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InChI
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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 Y
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Key:WGJHHMKQBWSQIY-UHFFFAOYSA-N Y
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NY (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 related to other drugs such as proheptazine and 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]
Its no longer sold in the United States however it may be sold again if the law is changed to remove 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][9] Regulation elsewhere varies. The Canadian Controlled Drugs & Substances act specifically excludes the phenazepine opioids, including proheptazine, from control.[10]
References
- ^ ES Patent 310184
- ^ Batterman RC, Golbey M, Grossman AJ, Leifer P. Analgesic effectiveness of orally administered ethoheptazine in man. American Journal of the Medical Sciences. 1957 Oct;234(4):413-9.
- ^ Diamond J, Bruce WF, Tyson FT. Synthesis and Properties of the Analgesic DL-α-1,3-dimethyl-4-phenyl-4-propionoxyazacycloheptane (Proheptazine). Journal of Medicinal Chemistry. 1964 Jan;7:57-60.
- ^ Cinelli P, Zucchini M. Current pharmaco-therapeutic possibilities in the treatment of pain. Experiments with ethoeptazine. (Italian). Minerva Medica. 1962 Mar 3;53:637-42.
- ^ Scheiner JJ, Richards DJ. Treatment of musculoskeletal pain and associated anxiety with an ethoheptazine-aspirin-meprobamate combination (equagesic): a controlled study. Current Therapeutic Research, Clinical and Experimental. 1974 Sep;16(9):928-36.
- ^ J Pharmacol Exp Ther November 1979 211:401-408
- ^ http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html
- ^ PDR 1978, pp 1618
- ^ http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html
- ^ http://laws-lois.justice.gc.ca/eng/acts/C-38.8/
Analgesics (N02A, N02B)
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Opioids |
Opiates/opium |
- Codeine# (+paracetamol, +aspirin)
- Morphine# (+naltrexone)
- Opium
- Laudanum
- Paregoric
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Semisynthetic |
- Acetyldihydrocodeine
- Benzylmorphine
- Buprenorphine (+naloxone)
- Desomorphine
- Diamorphine (heroin)
- Dihydrocodeine (+paracetamol)
- Dihydromorphine
- Ethylmorphine
- Hydrocodone (+paracetamol, +ibuprofen, +aspirin)
- Hydromorphinol
- Hydromorphone
- Nicocodeine
- Nicodicodeine
- Nicomorphine
- Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone)
- Oxymorphone
- Thebacon
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Synthetic |
- Alfentanil
- Alphaprodine
- Anileridine
- Butorphanol
- Carfentanil
- Dextromoramide
- Dextropropoxyphene
- Dezocine
- Fentanyl (+fluanisone)
- Ketobemidone
- Levorphanol
- Lofentanil
- Meptazinol
- Methadone
- Nalbuphine
- NFEPP
- Pentazocine
- Pethidine (meperidine)
- Phenadoxone
- Phenazocine
- Piminodine
- Piritramide
- Propiram
- Remifentanil
- Sufentanil
- Tapentadol
- Tilidine
- Tramadol
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|
Paracetamol-type |
- Acetanilide‡
- Bucetin‡
- Butacetin‡
- Paracetamol (acetaminophen)#
- Parapropamol‡
- Phenacetin‡
- Propacetamol‡
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NSAIDs |
Propionates |
- Fenoprofen
- Flurbiprofen
- Ibuprofen#
- Ketoprofen
- Naproxen
- Oxaprozin
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Oxicams |
|
Acetates |
- Diclofenac
- Indometacin
- Ketorolac
- Nabumetone
- Sulindac
- Tolmetin
|
COX-2 inhibitors |
- Celecoxib
- Etoricoxib
- Lumiracoxib
- Parecoxib
- Rofecoxib ‡
- Valdecoxib ‡
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Fenamates |
- Meclofenamic acid
- Mefenamic acid
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Salicylates |
- Aspirin (acetylsalicylic acid)# (+paracetamol/caffeine)
- Benorylate
- Diflunisal
- Ethenzamide
- Magnesium salicylate
- Salicin
- Salicylamide
- Salsalate
- Wintergreen (methyl salicylate)
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Pyrazolones |
- Aminophenazone‡
- Ampyrone
- Metamizole (dipyrone)
- Nifenazone
- Phenazone
- Propyphenazone (+paracetamol/caffeine)
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Others |
|
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Cannabinoids |
- Cannabidiol
- Cannabis
- Nabilone
- Nabiximols
- Tetrahydrocannabinol (dronabinol)
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Ion channel
modulators |
Calcium blockers |
- Gabapentin
- Gabapentin enacarbil
- Pregabalin
- Ziconotide
|
Sodium blockers |
- Carbamazepine
- Lacosamide
- Local anesthetics (e.g., cocaine, lidocaine)
- Mexiletine
- Nefopam
- Tricyclic antidepressants (e.g., amitriptyline#)
- Nav1.7/1.8-selective: DSP-2230§
- Funapide§
- PF-05089771§
- Raxatrigine§
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Potassium openers |
|
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Myorelaxants |
- Carisoprodol
- Chlorzoxazone
- Cyclobenzaprine
- Mephenoxalone
- Methocarbamol
- Orphenadrine
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Others |
- Analgesic adjuvant
- Analgecine
- Camphor
- Capsaicin
- Clonidine
- Ketamine
- Menthol
- Methoxyflurane
- Nefopam
- Proglumide
- Tricyclic antidepressants (e.g., amitriptyline#)
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Opioid receptor modulators
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MOR |
|
DOR |
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KOR |
- Agonists: 3CS-nalmefene
- 6'-GNTI
- 8-CAC
- 18-MC
- 14-Methoxymetopon
- β-Chlornaltrexamine
- β-Funaltrexamine
- Adrenorphin (metorphamide)
- Akuuamicine
- Alazocine (SKF-10047)
- Allomatrine
- Apadoline
- Asimadoline
- BAM-12P
- BAM-18P
- BAM-22P
- Big dynorphin
- Bremazocine
- BRL-52537
- Butorphan
- Butorphanol
- BW-373U86
- Cebranopadol
- Ciprefadol
- CR665
- Cyclazocine
- Cyclorphan
- Cyprenorphine
- Desmetramadol (desmethyltramadol)
- Diamorphine (heroin)
- Diacetylnalorphine
- Difelikefalin
- Dihydroetorphine
- Dihydromorphine
- Diprenorphine
- Dynorphin A
- Dynorphin B (rimorphin)
- Eluxadoline
- Enadoline
- Eptazocine
- Erinacine E
- Ethylketazocine
- Etorphine
- Fedotozine
- Fentanyl
- Gemazocine
- GR-89696
- GR-103545
- Hemorphin-4
- Herkinorin
- HS665
- Hydromorphone
- HZ-2
- Ibogaine
- ICI-199,441
- ICI-204,448
- Ketamine
- Ketazocine
- Laudanosine
- Leumorphin (dynorphin B-29)
- Levallorphan
- Levomethorphan
- Levorphanol
- Lexanopadol
- Lofentanil
- LPK-26
- Lufuradom
- Matrine
- MB-1C-OH
- Menthol
- Metazocine
- Metkefamide
- Mianserin
- Mirtazapine
- Morphine
- Moxazocine
- MR-2034
- N-MPPP
- Nalbuphine
- Nalbuphine sebacate
- NalBzOH
- Nalfurafine
- Nalmefene
- Nalodeine (N-allylnorcodeine)
- Nalorphine
- Naltriben
- Niravoline
- Norbuprenorphine
- Norbuprenorphine-3-glucuronide
- Noribogaine
- Norketamine
- Oripavine
- Oxilorphan
- Oxycodone
- Pentazocine
- Pethidine (meperidine)
- Phenazocine
- Proxorphan
- Racemethorphan
- Racemorphan
- RB-64
- Salvinorin A (salvia)
- Salvinorin B ethoxymethyl ether
- Salvinorin B methoxymethyl ether
- Samidorphan
- Spiradoline (U-62,066)
- TH-030418
- Thienorphine
- Tifluadom
- Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline)
- U-50,488
- U-54,494A
- U-69,593
- Xorphanol
- Antagonists: 4′-Hydroxyflavanone
- 4',7-Dihydroxyflavone
- 5'-GNTI
- 6'-GNTI
- 6β-Naltrexol
- 6β-Naltrexol-d4
- β-Chlornaltrexamine
- Buprenorphine/samidorphan
- Amentoflavone
- ANTI
- Apigenin
- Arodyne
- AT-076
- Axelopran
- AZ-MTAB
- Binaltorphimine
- BU09059
- Buprenorphine
- Catechin
- Catechin gallate
- CERC-501 (LY-2456302)
- Clocinnamox
- Cyclofoxy
- Dezocine
- DIPPA
- EGC
- ECG
- Epicatechin
- Hyperoside
- JDTic
- LY-255582
- LY-2196044
- LY-2444296
- LY-2459989
- LY-2795050
- MeJDTic
- Methylnaltrexone
- ML190
- ML350
- MR-2266
- N-Fluoropropyl-JDTic
- Naloxone
- Naltrexone
- Naltrindole
- Naringenin
- Norbinaltorphimine
- Noribogaine
- Pawhuskin A
- PF-4455242
- RB-64
- Quadazocine
- Taxifolin
- UPHIT
- Zyklophin
- Unknown/unsorted: Akuammicine
- Akuammine
- Coronaridine
- Cyproterone acetate
- Dihydroakuuamine
- Ibogamine
- Tabernanthine
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NOP |
- Agonists: (Arg14,Lys15)Nociceptin
- ((pF)Phe4)Nociceptin(1-13)NH2
- (Phe1Ψ(CH2-NH)Gly2)Nociceptin(1-13)NH2
- Ac-RYYRWK-NH2
- Ac-RYYRIK-NH2
- BU08070
- Buprenorphine
- Cebranopadol
- Dihydroetorphine
- Etorphine
- JNJ-19385899
- Levomethorphan
- Levorphanol
- Levorphanol
- Lexanopadol
- MCOPPB
- MT-7716
- NNC 63-0532
- Nociceptin (orphanin FQ)
- Nociceptin (1-11)
- Nociceptin (1-13)NH2
- Norbuprenorphine
- Racemethorphan
- Racemorphan
- Ro64-6198
- Ro65-6570
- SCH-221510
- SCH-486757
- SR-8993
- SR-16435
- TH-030418
- Antagonists: (Nphe1)Nociceptin(1-13)NH2
- AT-076
- BAN-ORL-24
- J-113397
- JTC-801
- LY-2940094
- NalBzOH
- Nociceptin (1-7)
- Nocistatin
- SB-612111
- SR-16430
- Thienorphine
- Trap-101
- UFP-101
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Unsorted |
- β-Casomorphins
- Amidorphin
- BAM-20P
- Cytochrophin-4
- Deprolorphin
- Gliadorphin (gluteomorphin)
- Gluten exorphins
- Hemorphins
- Kava constituents
- MEAGL
- MEAP
- NEM
- Neoendorphins
- Nepetalactone (catnip)
- Peptide B
- Peptide E
- Peptide F
- Peptide I
- Rubiscolins
- Soymorphins
|
Others |
- Enkephalinase inhibitors: Amastatin
- BL-2401
- Candoxatril
- D -Phenylalanine
- Dexecadotril (retorphan)
- Ecadotril (sinorphan)
- Kelatorphan
- Racecadotril (acetorphan)
- RB-101
- RB-120
- RB-3007
- Opiorphan
- Selank
- Semax
- Spinorphin
- Thiorphan
- Tynorphin
- Ubenimex (bestatin)
- Propeptides: β-Lipotropin (proendorphin)
- Prodynorphin
- Proenkephalin
- Pronociceptin
- Proopiomelanocortin (POMC)
- Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
|
See also: Receptor/signaling modulators • Signaling peptide/protein receptor modulators
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English Journal
- Mefenamic acid, chlormezanone-paracetamol, ethoheptazine-aspirin-meprobamate: a comparative study in acute low back pain.
- Sweetman BJ, Baig A, Parsons DL.
- The British journal of clinical practice.Br J Clin Pract.1987 Feb;41(2):619-24.
- PMID 2960369
- Fixed drug eruption masquerading as herpes simplex labialis.
- Boyle J, Moul B.
- British medical journal (Clinical research ed.).Br Med J (Clin Res Ed).1984 Sep 29;289(6448):802.
- PMID 6236869
- Determination of ethoheptazine in human post mortem material.
- Drost RH, Boelens M, Maes RA, Sunshine I.
- Journal of chromatography.J Chromatogr.1983 Oct 14;277:352-5.
- PMID 6643621
Related Pictures
★リンクテーブル★
[★]
- 英
- ethoheptazine
- 同
- エチルヘプタジン ethyl heptazine