Chemistry:AP-237
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| Formula | C17H24N2O |
| Molar mass | 272.392 g·mol−1 |
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AP-237 (also known as Bucinnazine and 1-butyryl-4-cinnamylpiperazine) is an opioid analgesic drug that was widely used in China to treat pain in cancer patients as of 1986.[1] It is one of the most potent compound among a series of analgesic acyl piperazines compounds first synthesized and reported in Japan in the 1970s.[2][3][4] AP-237 has analgesic potency comparable to that of morphine but with a relatively higher therapeutic index. The drug were initially claimed to be a non-narcotic analgesic. However, subsequent studies have shown AP-237 and similar acyl piperazines to be potent and selective agonists of μ-opioid receptor (MOR) with relatively low affinity for the δ-opioid receptor and the κ-opioid receptor.[5] In accordance with these studies, results from the intravenous self-administration experiments in rats showed that AP-237 has a marked reinforcing effect with tolerance and dependence quickly developing.[1] In addition, the morphine antagonist naloxone reverses the effect of AP-237 and precipitates withdrawal symptoms in AP-237 treated rats further indicating a mechanism of analgesia mediated via selective agonist activity at μ-opioid receptors.
References
- ↑ 1.0 1.1 Qing T, Zhi-Ji C, and Wei-Ping W. Experimental Study on the Dependence-Producing Properties of Qiang Tong Ding (AP-237). Chin. J. Clin. Pharmacol. 1986 -02, http://en.cnki.com.cn/Article_en/CJFDTotal-GLYZ198602003.htm
- ↑ Nishimura N, Kiuchi M, Kanetake Y, Takahashi T. Clinical exaluation of a new analgesic agent Ap-237. Masui. 1970 Jun;19(6):653-6. Japanese. No abstract available. PMID 4916908
- ↑ Carrano RA, Kimura KK, McCurdy DH. Analgesic and tolerance studies with AP-237, a new analgesic. Arch Int Pharmacodyn Ther. 1975 Jan;213(1):41-57. PMID 1156018
- ↑ Carrano RA, Kimura KK, Landes RC, McCurdy DH. General pharmacology of a new analgesic-AP-237. Arch Int Pharmacodyn Ther. 1975 Jan;213(1):28-40. PMID 1156016
- ↑ Barlocco, D; Cignarella, G; Greco, G; Novellino, E (1993). "Computer-aided structure-affinity relationships in a set of piperazine and 3,8-diazabicyclo3.2.1octane derivatives binding to the mu-opioid receptor". Journal of Computer-Aided Molecular Design. 7 (5): 557–71. doi:10.1007/bf00124362. PMID 8294946
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