Naltrindole

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Naltrindole
File:Naltrindole.png
Systematic (IUPAC) name
17-Cyclopropylmethyl-6,7-dehydro-4,5-epoxy -3,14-dihydroxy-6,7,2',3'-indolomorphinan
Clinical data
Routes of
administration
IV
Identifiers
CAS Number 111555-53-4
ATC code none
PubChem CID 5497186
IUPHAR/BPS 1641
Chemical data
Formula C26H26N2O3
Molar mass 414.496 g/mol[[Script error: No such module "String".]]
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Naltrindole is a highly potent, highly selective delta opioid receptor antagonist used in biomedical research.

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[1]. 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[2].

References

  1. 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
  2. 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. PMID 2832195