Chemistry:U-77891
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| Routes of administration | By mouth, parenteral |
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| Formula | C18H24Br2N2O |
| Molar mass | 444.211 g·mol−1 |
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U-77891 is an opioid analgesic drug that was first synthesized in 1983 by the Upjohn company.[1] It was originally synthesized to prove that the removal of a single methylene spacer of the benzamide would alter a κ-opioid receptor agonist such as U-50488 into an μ-opioid receptor agonist, as well as producing a semi-rigid derivative of U-47700. This would help elucidate the relative positions of the hydrogen-bond acceptors and substituted aromatic system to find the compound with the lowest Ki value in a series of benzamide opioids dating back to the 1970s.[2] The original work found a mixture of agonists and antagonists.[3]
U-77891 acts as an agonist of the μ-opioid, δ-opioid and κ-opioid receptors with Ki values of 2, 105 and 2300 nM, respectively.[2] The compound has ED50 values of 0.02 mg/kg and 0.21 mg/kg in mouse phenylquinone writhing and tail-flick assays.[2] One reason for the high potency is the LogP of 4.57,[4] allowing it to accumulate in fatty tissue such as the brain.
See also
References
- ↑ Jacob Szmuszkovicz, John M. McCall, Lester J. Kaplan, Moses W. McMillan (18 May 1983). "US Patent 4598088 - 2-pyrrolyl-cycloalkyl-amide analgesics". The Upjohn Company. https://www.google.com/patents/US4598088.
- ↑ 2.0 2.1 2.2 "Synthesis, opioid receptor binding profile, and antinociceptive activity of 1-azaspiro[4.5]decan-10-yl amides". Journal of Medicinal Chemistry 32 (6): 1259–65. June 1989. doi:10.1021/jm00126a019. PMID 2542556.
- ↑ Moses W. McMillan, Jacob Szmuszkovicz (9 April 1981). "US Patent 4466977 - N-[2-Amino(oxy- or thia- group-substituted-cycloaliphatic)benzeneacetamides and -benzamide analgesics"]. The Upjohn Company. https://www.google.com/patents/US4466977.
- ↑ "Properties Viewer". chemicalize.org. http://www.chemicalize.org/structure/#!mol=3%2C4-dibromo-N-methyl-N-%5B%285S%2C6R%29-1-methyl-1-azaspiro%5B4.5%5Ddecan-6-yl%5Dbenzamide&source=fp.
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