Chemistry:Naltrindole
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| Routes of administration | IV |
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| Formula | C26H26N2O3 |
| Molar mass | 414.505 g·mol−1 |
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Naltrindole is a highly potent, highly selective delta opioid receptor antagonist used in biomedical research. In May 2012 a paper was published in Nature with the structure of naltrindole in complex with the mouse δ-opioid G-protein coupled receptor, solved by X-ray crystallography.[1]
Drug design
Since peptide compounds are unable to cross the blood–brain barrier, researchers developed naltrindole to be a non-peptide antagonist analog of the delta-preferring endogenous opiate enkephalin. Enkephalin contains an aromatic phenyl group on its Phe4 residue, which was hypothesized to be the "address" sequence responsible for the opiate's delta opioid receptor affinity.[2] Thus, attachment of a phenyl-containing indole molecule to the C-ring of naltrexone's morphinan base successfully produced a drug with the high receptor affinity of naltrexone, but which binds almost exclusively to the delta opioid receptor.[3]
References
- ↑ "Structure of the δ-opioid receptor bound to naltrindole". Nature 485 (7398): 400–4. May 2012. doi:10.1038/nature11111. PMID 22596164. Bibcode: 2012Natur.485..400G.
- ↑ "Peptides as receptor selectivity modulators of opiate pharmacophores". Journal of Medicinal Chemistry 29 (7): 1222–5. July 1986. doi:10.1021/jm00157a018. PMID 2879914.
- ↑ "Naltrindole, a highly selective and potent non-peptide delta opioid receptor antagonist". European Journal of Pharmacology 146 (1): 185–6. January 1988. doi:10.1016/0014-2999(88)90502-X. PMID 2832195.
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