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Stinchcomb, Audra L.; Dua, Rajesh K.; Paliwal, Anupam; Woodard, Ronald W.; Flynn, Gordon L.

doi:10.1023/a:1016299824162

Cited by 20 publications

(6 citation statements)

References 12 publications

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“…Buprenorphine propionate and buprenorphine decanoate (internal standard; Fig. 1) were synthesized by using the method reported previously [4]. In brief, the buprenorphine base was reacted with propionyl chloride or decanoyl chloride (Fluka, Buchs, Switzerland) in the presence of dimethylaminopyridine.…”

Section: Chemicals and Reagentsmentioning

confidence: 99%

“…The usual recommended doses are 200-600 g by IV or IM injection every 6-8 h, 30-45 g intrathecally or 100-300 g epidurally every 6-12 h, or 400 g sublingually every 6-8 h [1][2][3]. Recently, an ester of buprenorphine, buprenorphine propionate, was synthesized and studied [4][5][6]. The ester was found to be more lipophilic than buprenorphine [4].…”

Section: Introductionmentioning

confidence: 99%

“…Recently, an ester of buprenorphine, buprenorphine propionate, was synthesized and studied [4][5][6]. The ester was found to be more lipophilic than buprenorphine [4]. Previous study also found that buprenorphine propionate when prepared as a depot had a long-lasting analgesic effect, which was 7.5-fold longer than the traditional dosage form of buprenorphine in saline preparation, following IM injection in rats [6].…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, the depot formulation of buprenorphine propionate is worth further evaluation. In this formulation, buprenorphine propionate was synthesized through a prodrug design with esterification [4,5,[8][9][10]. Buprenorphine propionate was suspected to be a prodrug of buprenorphine in in vivo study.…”

Section: Introductionmentioning

confidence: 99%

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Simultaneous determination of buprenorphine and its prodrug, buprenorphine propionate, by high-performance liquid chromatography with fluorescence detection: application to pharmacokinetic studies in rabbits☆This

Liu

Kuei

et al. 2005

Journal of Chromatography B

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Section: Chemicals and Reagentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Simultaneous determination of buprenorphine and its prodrug, buprenorphine propionate, by high-performance liquid chromatography with fluorescence detection: application to pharmacokinetic studies in rabbits☆This

Liu

Kuei

et al. 2005

Journal of Chromatography B

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“…N-Cyclopropylmethyl Nororipavine(10). To a slurry of sodium tert-butoxide (0.67 g; 7.04 mmol) in freshly distilled DMSO (4.7 mL) was added tert-dodecanethiol (1.42 g; 7.04 mmol, distilled) in one portion.…”

mentioning

confidence: 99%

Synthesis of Buprenorphine from Oripavine via N-Demethylation of Oripavine Quaternary Salts

et al. 2011

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Buprenorphine was synthesized from oripavine by a sequence involving the conversion of oripavine into its cyclopropylmethyl quaternary salt, N-demethylation with thiolate to N-cyclopropylmethyl nororipavine, and conversion of this material to the title compound by previously available methods. The new synthesis avoids toxic reagents used previously, is shorter, and proceeds in comparable yields. Experimental and spectral data are provided for all new compounds.

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The novel depot of buprenorphine propionate has a long‐acting effect on physical dependence on morphine

Liu

Lin

Shieh

et al. 2006

Drug Development Research

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Buprenorphine is a promising drug for the treatment of physical dependence on opioids. The aim of the present study was to evaluate the efficacy and duration of action of a novel depot form of a buprenorphine prodrug, buprenorphine propionate, on physical dependence on morphine. Following intramuscular injection in morphine-dependent mice, the efficacy and duration of action of buprenorphine propionate in sesame oil were evaluated. Two other dosage forms of buprenorphine were used as controls. Intramuscular injection of buprenorphine HCl (0.1 mmol/kg in saline) attenuated the severity of morphine dependence (Po0.05) with a 9-h duration of action. However, a further increase in dose up to 60-fold could not further increase its duration of action. On the other hand, buprenorphine base and propionate when prepared in sesame oil produced longer durations of action than did buprenorphine HCl in saline under an equimolar basis of 6 mmol/kg (Po0.05, for each comparison). Among dosage forms, buprenorphine propionate in sesame oil produced the longest duration of action, 11.3-fold longer than that of buprenorphine HCl in saline and 2-fold longer than buprenorphine base in oil. In conclusion, the novel depot of buprenorphine propionate produced a dose-related long-acting effect on physical dependence on morphine in mice. Drug Dev.

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Untitled

Cited by 20 publications

References 12 publications

Simultaneous determination of buprenorphine and its prodrug, buprenorphine propionate, by high-performance liquid chromatography with fluorescence detection: application to pharmacokinetic studies in rabbits☆This

Simultaneous determination of buprenorphine and its prodrug, buprenorphine propionate, by high-performance liquid chromatography with fluorescence detection: application to pharmacokinetic studies in rabbits☆This

Synthesis of Buprenorphine from Oripavine via N-Demethylation of Oripavine Quaternary Salts

The novel depot of buprenorphine propionate has a long‐acting effect on physical dependence on morphine

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