U-77891 is an
opioid
Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioid us ...
analgesic drug that was first synthesized in 1983 by the
Upjohn
The Upjohn Company was a pharmaceutical manufacturing firm founded in 1886 in Hastings, Michigan, by Dr. William E. Upjohn who was an 1875 graduate of the University of Michigan medical school. The company was originally formed to make ''friabl ...
company. It was originally synthesized to prove that the removal of a single methylene
spacer of the
benzamide
Benzamide is a organic compound with the chemical formula of C6H5C(O)NH2. It is the simplest amide derivative of benzoic acid
Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benz ...
would alter a
κ-opioid receptor agonist such as
U-50488
U-50488 is a drug which acts as a highly selective κ-opioid agonist, but without any μ-opioid antagonist effects. It has analgesic, diuretic and antitussive effects, and reverses the memory impairment produced by anticholinergic
Anticholi ...
into an
μ-opioid receptor agonist, as well as producing a semi-rigid derivative of
U-47700
U-47700, also known as U4, pink heroin, pinky, and pink, is an opioid analgesic drug developed by a team at Upjohn in the 1970s which has around 7.5 times the potency of morphine in animal models.
U-47700 is a structural isomer of the earlier o ...
. 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.
The original work found a mixture of agonists and antagonists.
U-77891 acts as an agonist of the μ-opioid,
δ-opioid and κ-opioid receptors with K
i values of 2, 105 and 2300 nM, respectively.
The compound has
ED50 values of 0.02 mg/kg and 0.21 mg/kg in mouse phenylquinone writhing and
tail-flick assays.
One reason for the high potency is the
LogP of 4.57,
allowing it to accumulate in fatty tissue such as the brain.
See also
*
AH-7921
AH-7921 is an opioid analgesic drug selective for the μ-opioid receptor, having around 90% the potency of morphine when administered orally. It was discovered in the 1970s by a team at Allen and Hanburys located in the United Kingdom. The drug ...
*
U-47700
U-47700, also known as U4, pink heroin, pinky, and pink, is an opioid analgesic drug developed by a team at Upjohn in the 1970s which has around 7.5 times the potency of morphine in animal models.
U-47700 is a structural isomer of the earlier o ...
*
U-50488
U-50488 is a drug which acts as a highly selective κ-opioid agonist, but without any μ-opioid antagonist effects. It has analgesic, diuretic and antitussive effects, and reverses the memory impairment produced by anticholinergic
Anticholi ...
*
U-69,593
U-69,593 is a drug which acts as a potent and selective κ1-opioid receptor agonist. In animal studies it has been shown to produce antinociception, anti-inflammation, anxiolysis (at low doses), respiratory depression, and diuresis, while ...
References
Benzamides
Bromoarenes
Synthetic opioids
Mu-opioid receptor agonists
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