U-47700: Difference between revisions
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[[Category:Designer drugs]] |
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==See also== |
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[[AH-7921]] |
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[[U-47700]] |
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[[U-77891]] |
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{{analgesic-stub}} |
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Revision as of 17:35, 25 January 2016
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| Routes of administration | oral, parenteral |
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| Formula | C16H22Cl2N2O |
| Molar mass | 329.27 g·mol−1 |
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U-47700[1] is an opioid analgesic drug developed by a team at Upjohn in the 1970s.[2] U-47700 was derived from an earlier opioid AH-7921. U-47700 is selective for the µ-opioid receptor, having around 7.5 x the potency of morphine in animal models.[3][4]
U-47700 is the result of a great deal of work elucidating the quantitative structure–activity relationship of the scaffold. The team looked for the key moieties which gave the greatest activity.[5] Upjohn posted over a dozen patents on related compounds, each optimizing one moiety[6][7][8][9][10][11][12] until they discovered that U-47700 was the most active.[13]
U-47700 became the lead compound of selective kappa-opioid receptor ligands such as U-50488 (containing a single methylene spacer difference) and U-69,593, which share very similar structures.[14] Its structure led to other chemists experimenting with it to see if rigid analogues would retain activity.[15] Although not used medically, the selective kappa ligands are used in research.[16]
U-47700 has never been studied in humans, but would be expected to produce effects similar to those of other potent opioid agonists, including strong analgesia, sedation, euphoria, constipation, itching and respiratory depression which could be harmful or fatal.[original research?] Tolerance and dependence would be expected to develop.[original research?] Since affinity to kappa receptors has not been measured, it may also induce dysphoria and other unwanted side-effects but its 3D-QSAR makes this most unlikely.[17] Its structure is somewhat similar to U-50488, a pure kappa agonist.
Legal Status
U-47700 will become illegal in Sweden on 26 January 2016.[18]
See also
References
- ^ U-47700 at DistilBio
- ^ Jacob Szmuszkovicz (4 July 1978). "Patent US4098904 - Analgesic n-(2-aminocycloaliphatic)benzamides".
- ^ B. Vernon Cheney, Jacob Szmuszkovicz, Robert A. Lahti, Dominic A. Zichi (December 1985). "Factors affecting binding of trans-N-[2-(methylamino)cyclohexyl]benzamides at the primary morphine receptor". Journal of Medicinal Chemistry. 28 (12): 1853–1864. doi:10.1021/jm00150a017. PMID 2999404.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ N. J. Harper, G. B. A. Veitch, D. G. Wibberley (November 1974). "1-(3,4-Dichlorobenzamidomethyl)cyclohexyldimethylamine and related compounds as potential analgesics". Journal of Medicinal Chemistry. 17 (11): 1188–1193. doi:10.1021/jm00257a012. PMID 4416926.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Erik T. Michalson, Jacob Szmuszkovicz (1989). "Medicinal agents incorporating the 1,2-diamine functionality". Progress in Drug Research. 33: 135–149. doi:10.1007/978-3-0348-9146-2_6. PMID 2687936.
- ^ Darrell D Mullins (28 June 1966). "Patent US US3258489 - N-(1-aminocyclohexylmethyl)anilines and n-(1-nitrocyclohexylmethyl)an-ilines".
- ^ Norman James Harper, George Bryan Austin Veitch (17 August 1976). "Patent US3975443 - 1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine".
- ^ Jacob Szmuszkovicz Kalamazoo (3 March 1970). "Patent US3499033 - Ethers of alpha-phenyl-2-aminocycloalkanemethanols".
- ^ Jacob Szmuszkovicz (5 May 1970). "Patent US3510492 - 2-anilino and 2-anilinomethyl cycloalkylamines".
- ^ Ronald H Rynbrandt, Louis L Skaletzky (7 March 1972). "Patent US3647804 - Cycloalkanecarboxamides".
- ^ W. Roll (23 July 1974). "Patent US3825595 - N-cyclopentyl-n-2-hydroxyalkyl-ring-substituted benzamides".
- ^ Norman James Harper, George Bryan Austin Veitch (20 September 1977). "Patent US4049663 - Ethylene diamine derivatives".
- ^ Alan F. Casy, Robert T. Parfitt (1986). Opioid Analgesics, Chemistry and Receptors. Springer US. p. 395. ISBN 978-1-4899-0587-1.
- ^ G. Loew, J. Lawson, L. Toll, G. Frenking, IP. Berzetei-Gurske, W. Polgar (1988). "Structure activity studies of two classes of beta-amino-amides: the search for kappa-selective opioids" (PDF). NIDA Research Monograph. 90: 144–151.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Shikai Zhao, Michael J. Totleben, Stephen A. Mizsak, Jeremiah P. Freeman, Jacob Szmuszkovicz (2000). "Phenanthridone Analogs of the Opiate Agonist U-47,700 in the trans-1,2-Diaminocyclohexane Benzamide Series". Heterocycles. 52 (1): 325–332. doi:10.3987/COM-99-S27.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Jacob Szmuszkovicz (1999). U-50,488 and the к receptor: A personalized account covering the period 1973 to 1990. Birkhäuser Basel. pp. 167–195. doi:10.1007/978-3-0348-8730-4_4. ISBN 978-3-0348-8730-4.
- ^ Marta Filizola, Hugo O. Villar, Gilda H. Loew (April 2001). "Differentiation of δ, μ, and κ opioid receptor agonists based on pharmacophore development and computed physicochemical properties". Journal of Computer-Aided Molecular Design. 15 (4): 297–307. doi:10.1023/A:1011187320095. PMID 11349813.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.
See also
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