Nalbuphine

Chemical Name N-cyclobutylmethyl-14-hydroxydihydronormorphinone Common Name — 

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The quest for compounds that combined the analgesic properties of morphine, were nonaddictive, and lacked the side effects of nalorphine, led to the development of the dmgs shown in Table 3. These compounds have both agonist and antagonist activities. Nalbuphine (14) (23) and buprenorphine... 

Naltrexone completely blocks the effects of IV opiates, as well as drugp with agonist-antagonist actions (butorphanol, nalbuphine, and pentazocine). The mechanism of action appears to be the same as that for naloxone... 

CifiHpNO, 33522-95-1) see Nalbuphine Naloxone 2 -hydroxy-4 -(2,5-dihydro-5-oxo-3-furyl)acetophenone (C12H10O4 3447-63-0) see Benfurodil hemisuccinate 0-(4-hydroxy-3,5-diiodophenyl)-3,S-diiodo-a-methyl-tyrosine... 

Acylation of 14 with cyclobutylcarbonyl chloride followed by the same series of transformations as above leads to intermediate 22. Reduction of the carbonyl group in that molecule with sodium borohydride gives the analgesic agonist/antagonist nalbuphine (23). 7... 

Nalbuphine (Nubain, various) Semisynthetic N/A Intranasal IM 1 (one spray) 10 <15/5... 

The narcotic agonist/antagonist nalbuphine (8.88) is poorly bioavailable in humans (ca. 10%), mostly due to extensive first-pass metabolism. Two prodrugs were examined, namely the acetylsalicylate (8.89) and the anthran-ilate (8.90) [125]. The hydrolysis of these compounds in rat plasma was fast (tU2 values of some minutes and 1 - 2 h, respectively), while it was slow in dog plasma (lW2 ca. 3 h and 15 h, respectively) and in human plasma (t1/2 ca. 7-10 h and 50-60 h, respectively). Hydrolysis in dog tissue homogenates was also markedly slower than in rat. The dog was, thus, considered to be a fair animal model, and it is of interest that, in this species, the oral bioavailability of 8.88, 8.89, and 8.90 were ca. 6, 20, and 50%, respectively. 

B. J. Aungst, M. J. Myers, E. Shefter, E. G. Shami, Prodrugs for Improved Oral Nalbuphine Bioavailabihty Inter-Species Differences in the Disposition of Nalbuphine and Its Acetylsalicylate and Anthranilate Esters , Int. J. Pharm. 1987, 38, 199 - 209. 

Nalbuphine (Nubain) Narcotic Analgesic I nj 10, 20 mg/mL 10mglM/SC/IVq3-6h prn... 

The drugs naltrexone and nalbuphine are semi-synthetic analogues of the analgesic morphine. Morphine is a good painkiller, but has some unpleasant side effects, the most serious of which is the likelihood of becoming addicted. 

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