Naltrindole
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Naltrindole
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| Systematic (IUPAC) name | |
| 17-Cyclopropylmethyl-6,7-dehydro-4,5-epoxy -3,14-dihydroxy-6,7,2',3'-indolomorphinan | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Routes | IV |
| Identifiers | |
| CAS number | 111555-53-4 |
| ATC code | None |
| PubChem | CID 5497186 |
| IUPHAR ligand | 1641 |
| ChemSpider | 4593753  |
| ChEMBL | CHEMBL567175 |
| Chemical data | |
| Formula | C26H26N2O3 |
| Mol. mass | 414.496 g/mol |
| SMILES | eMolecules & PubChem |
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Naltrindole is a highly potent, highly selective delta opioid receptor antagonist used in biomedical research. On 17th may 2012 a paper was published in Nature with the structure of Naltrindole in complex with the 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
- ^ S. Granier, A. Manglik, A. C. Kruse, T. S. Kobilka, F. S. Thian, W. I. Weis & B. K. Kobilka. "Structure of the δ-opioid receptor bound to naltrindole." nature. Nature 485, 400–404 (17 May 2012). doi:10.1038/nature11111 PMID 22596164
- ^ Lipkowski AW, Tam SW, Portoghese PS. "Peptides as receptor selectivity modulators of opiate pharmacophores." Journal of Medicinal Chemistry. 1986 Jul;29(7):1222-5. PMID 2879914
- ^ Portoghese PS, Sultana M, Takemori AE. "Naltrindole, a highly selective and potent non-peptide delta opioid receptor antagonist." European Journal of Pharmacology. 1988 Jan 27;146(1):185-6. doi:10.1016/0014-2999(88)90502-X PMID 2832195
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