エチルケトシクラゾシン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/10/28 18:10:38」(JST)
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Ethylketazocine
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Systematic (IUPAC) name |
(1S,9R)-10-(cyclopropylmethyl)-1-ethyl-4-hydroxy-13-methyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-8-one
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Identifiers |
CAS Registry Number |
36292-66-7 |
ATC code |
None |
PubChem |
CID: 644273 |
ChemSpider |
559289 |
Chemical data |
Formula |
C19H25NO2 |
Molecular mass |
299.407 |
SMILES
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O=C2c1c(cc(O)cc1)[C@@]3(C([C@H]2N(CC3)CC4CC4)C)CC
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InChI
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InChI=1S/C19H25NO2/c1-3-19-8-9-20(11-13-4-5-13)17(12(19)2)18(22)15-7-6-14(21)10-16(15)19/h6-7,10,12-13,17,21H,3-5,8-9,11H2,1-2H3/t12?,17-,19+/m1/s1
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Key:SEJUQQOPVAUETF-MKFRLIFGSA-N
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Ethylketazocine (WIN-35,197-2), also known as ethylketocyclazocine (EKC), is an opioid drug of the benzomorphan family which has been used extensively in scientific research in the last few decades as a tool to aid in the study of the κ-opioid receptor.[1] However, due to its relatively poor selectivity for the κ-opioid receptor over the μ- and δ-opioid receptors (of which it has approximately 80% and 20% of the affinity for, respectively, in comparison), as well as its relatively poor intrinsic activity at all sites (i.e., acts as a partial agonist with mixed agonist and antagonist properties), it has been mostly replaced in recent times by newer and more potent and selective compounds like U-50,488 and ICI-199,441.[1][2][3]
See also
References
- ^ a b William O. Foye; Thomas L. Lemke (24 September 2007). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 657. ISBN 978-0-7817-6879-5. Retrieved 22 April 2012.
- ^ Edythe D. London (1993). Imaging Drug Action in the Brain. CRC Press. p. 130. ISBN 978-0-8493-8843-9. Retrieved 22 April 2012.
- ^ Enno Freye (3 April 2008). Opioids in Medicine: A Comprehensive Review on the Mode of Action and the Use of Analgesics in Different Clinical Pain States. Springer. p. 103. ISBN 978-1-4020-5946-9. Retrieved 22 April 2012.
Opioidergics
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|
Receptor
(ligands) |
MOR |
|
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DOR |
|
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KOR |
- Agonists: 6'-GNTI
- 8-CAC
- 18-MC
- 14-Methoxymetopon
- β-Chlornaltrexamine
- β-Funaltrexamine
- Adrenorphin (metorphamide)
- Akuuamicine
- Alazocine
- Allomatrine
- Asimadoline
- BAM-12P
- BAM-18P
- BAM-22P
- Big dynorphin
- Bremazocine
- BRL-52537
- Butorphanol
- BW-373U86
- Cebranopadol
- Ciprefadol
- CR665
- Cyclazocine
- Cyclorphan
- Cyprenorphine
- Diamorphine (heroin)
- Diacetylnalorphine
- Difelikefalin
- Dihydroetorphine
- Dihydromorphine
- 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
- Levorphanol
- Lexanopadol
- Lofentanil
- LPK-26
- Lufuradom
- Matrine
- MB-1C-OH
- Menthol
- Metazocine
- Metkefamide
- Mianserin
- Mirtazapine
- Morphine
- Moxazocine
- N-MPPP
- Nalbuphine
- NalBzOH
- Nalfurafine
- Nalmefene
- Nalorphine
- Naltriben
- Norbuprenorphine
- Norbuprenorphine-3-glucuronide
- Norketamine
- O-Desmethyltramadol
- Oripavine
- Oxilorphan
- Oxycodone
- Pentazocine
- Pethidine (meperidine)
- Phenazocine
- Proxorphan
- RB-64
- Salvinorin A (salvia)
- Salvinorin B ethoxymethyl ether
- Salvinorin B methoxymethyl ether
- SKF-10047
- 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
- 6β-Naltrexol
- 6β-Naltrexol-d4
- β-Chlornaltrexamine
- ALKS-5461
- Amentoflavone
- ANTI
- Apigenin
- Arodyne
- AT-076
- Axelopran
- Binaltorphimine
- BU09059
- Buprenorphine
- Catechin
- Catechin gallate
- CERC-501 (LY-2456302)
- Clocinnamox
- Dezocine
- DIPPA
- Diprenorphine
- EGC
- ECG
- Epicatechin
- Hyperoside
- JDTic
- LY-255582
- LY-2196044
- LY-2459989
- LY-2795050
- Methylnaltrexone
- ML190
- ML350
- MR-2266
- Naloxone
- Naltrexone
- Naltrindole
- Naringenin
- Norbinaltorphimine
- Noribogaine
- Pawhuskin A
- PF-4455242
- 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
- Lexanopadol
- MCOPPB
- MT-7716
- NNC 63-0532
- Nociceptin (orphanin FQ)
- Nociceptin (1-11)
- Nociceptin (1-13)NH2
- Norbuprenorphine
- 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 /
unknown |
- β-Casomorphins
- Amidorphin
- BAM-20P
- Cytochrophin-4
- Deprolorphin
- Gliadorphin (gluteomorphin)
- Gluten exorphins
- Hemorphins
- Kava constituents
- MEAGL
- MEAP
- NEM
- Neoendorphins
- Peptide B
- Peptide E
- Peptide F
- Peptide I
- Rubiscolins
- Soymorphins
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Enzyme
(inhibitors) |
Enkephalinase |
- 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)
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Others |
- Propeptides: β-Lipotropin (proendorphin)
- Prodynorphin
- Proenkephalin
- Pronociceptin
- Proopiomelanocortin (POMC)
- Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
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See also: Neuropeptidergics • Peptidergics
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English Journal
- Predicted structures for kappa opioid G-protein coupled receptor bound to selective agonists.
- Li Q1,2, Kim SK1, Goddard WA 3rd1, Chen G2, Tan H2.
- Journal of chemical information and modeling.J Chem Inf Model.2015 Mar 23;55(3):614-27. doi: 10.1021/ci500523z. Epub 2015 Feb 17.
- Human kappa opioid receptor (κ-OR), a G protein-coupled receptor (GPCR), has been identified as a drug target for treatment of such human disorders as pain perception, neuroendocrine physiology, affective behavior, and cognition. In order to find more selective and active agonists, one would like t
- PMID 25642595
- Selectively promiscuous opioid ligands: discovery of high affinity/low efficacy opioid ligands with substantial nociceptin opioid peptide receptor affinity.
- Kumar V1, Ridzwan IE, Grivas K, Lewis JW, Clark MJ, Meurice C, Jimenez-Gomez C, Pogozheva I, Mosberg H, Traynor JR, Husbands SM.
- Journal of medicinal chemistry.J Med Chem.2014 May 22;57(10):4049-57. doi: 10.1021/jm401964y. Epub 2014 May 9.
- Emerging clinical and preclinical evidence suggests that a compound displaying high affinity for μ, κ, and δ opioid (MOP, KOP, and DOP) receptors and antagonist activity at each, coupled with moderate affinity and efficacy at nociceptin opioid peptide (NOP) receptors will have utility as a relaps
- PMID 24761755
- Latent inhibition in an insect: the role of aminergic signaling.
- Fernández VM1, Giurfa M, Devaud JM, Farina WM.
- Learning & memory (Cold Spring Harbor, N.Y.).Learn Mem.2012 Nov 16;19(12):593-7. doi: 10.1101/lm.028167.112.
- Latent inhibition (LI) is a decrement in learning performance that results from the nonreinforced pre-exposure of the to-be-conditioned stimulus, in both vertebrates and invertebrates. In vertebrates, LI development involves dopamine and serotonin; in invertebrates there is yet no information. We st
- PMID 23161448
Japanese Journal
- 中枢性鎮痛薬Eptazocineのマウス,ラットにおける虚血性脳障害に対する保護効果
- 田村 智昭,谷口 登志悦,宮本 鉄雄,青城 優,脇 功巳
- 日本薬理学雑誌 97(2), 65-74, 1991
- マウス,ラットを用いた各種虚血性脳障害モデルにおいて,中枢性鎮痛薬eptazocineの脳保護効果について検討した.1)マウス断頭負荷試験,頭部打撲負荷致死試験(20g,30cm)においてeptazocine(3,10mg/kg)は開口運動持続時間,生存時間を各々用量依存的に延長した.2)ラット両側総頸動脈結紮(BLCO)負荷試験においてBLCO処置直後にeptazocine(3,10mg/kg) …
- NAID 130000758950
- Enkephalin誘導体EK-399のラットにおける弁別刺激効果
- 西田 信之,安原 吉高,千葉 祐広
- 日本薬理学雑誌 97(6), 361-369, 1991
- … ー・オペラントボヅクスを用い,給水制限したラットに訓練薬または生理食塩液を皮下投与後,水を報酬として2つのレバーのうち正しいレバーを選択させる訓練を行った.訓練薬としてEK-399,morphine,ethylketocyclazocine(EKC)及びN-allylnormetazocine(NANM)を用いた.いずれの訓練薬においても,平均38-53セッション後にラットは安定した高い正選択率を示すようになった.90%以上の正選択率を示したラットを用い,naloxone拮抗試験 …
- NAID 130000758920
Related Links
- ChemicalBook あなたのためにETHYLKETOCYCLAZOCINE, (-)-[9-3H]-の化学的 性質を提供して、融点、価格、蒸気圧、沸点、毒性、比重、沸点、密度、分子式、分子量 、物理的な性質、毒性 税関のコードなどの情報、同時にあなたは ...
- The receptor binding of the kappa agonist [3H]ethylketocyclazocine to brain homogenates in vitro and ketocyclazocine (kappa) analgesia in vivo has been investigated and compared to morphine, a mu agonist. Saturation analysis of ...
★リンクテーブル★
[★]
- 英
- opioid
- 同
- 類麻薬
- 関
- オピオイド受容体
作用
縮瞳
- モルフィンと多くのμ,κアゴニストは瞳孔の縮小を引き起こす。これは瞳孔を支配する副交感神経の興奮による。μアゴニストを中毒量投与すると縮瞳し、pinpoints pupupilsはpathognomonicである。(GOO.559)
オピオイドとオピオイド類似物質の作用
- GOO.552
+アゴニスト ーアンタゴニスト P partial agonist
各鎮痛薬のオピオイド受容体への作用
- μ受容体 κ受容体
- レミフェンタニル +++ ー
- フェンタニル +++ -
- モルヒネ +++ +
- ペチジン ++ +
- トラマドール + -
- ペンタゾシン ー ++
- ブプレノルフィン P ー
- ナロキソン ー -