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Literature DB >> 2560821

Naloxone-6 alpha-spirohydantoin: a long-acting opiate antagonist.

Abstract

We have synthesized a novel derivative of naloxone, naloxyl-6 alpha-spirohydantoin. The compound was rigorously purified and its stereochemical structure characterized. In tests in vivo in mice, it was less toxic than the parent compound and it showed weak anticonvulsive activity. It exerted antagonist effects comparable to those of naloxone but its effects were longer lasting, persisting for a week.

Entities: Chemical Species

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Year: 1989 PMID： 2560821 DOI： 10.1007/BF00965514

Source DB: PubMed Journal: Neurochem Res ISSN： 0364-3190 Impact factor: 3.996

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References

21 in total

1. Stereospecific synthesis of the 6beta-hydroxy metabolites of naltrexone and naloxone.

Authors: N Chatterjie; C E Inturrisi
Journal: J Med Chem Date: 1975-05 Impact factor: 7.446

2. Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties.

Authors: P S Portoghese; D L Larson; J B Jiang; T P Caruso; A E Takemori
Journal: J Med Chem Date: 1979-02 Impact factor: 7.446

Naloxone-6 alpha-spirohydantoin: a long-acting opiate antagonist.

1. Stereospecific synthesis of the 6beta-hydroxy metabolites of naltrexone and naloxone.

2. Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties.

3. Naloxone-6-spirohydantoin: a new non-toxic compound with anticonvulsive properties.

4. Isolation and stereochemical identification of a metabolite of naltrexone from human urine.

5. Irreversible opiate agonists and antagonists: V. Hydrazone and acylhydrazone derivatives of naltrexone.

6. A nonmetabolized analogue of phenytoin.

7. Study of the syn and anti isomerism of the long-lasting opiate antagonist naloxazone and related compounds.

8. Irreversible opiate agonists and antagonists: the 14-hydroxydihydromorphinone azines.

9. Long-acting opiate agonists and antagonists: 14-hydroxydihydromorphinone hydrazones.

10. Anticonvulsant properties of spirohydantoins derived from optical isomers of camphor.