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Naltrindole



Naltrindole
Systematic (IUPAC) name
17-Cyclopropylmethyl-6,7-dehydro-4,5-epoxy -3,14-dihydroxy-6,7,2',3'-indolomorphinan
Identifiers
CAS number 111555-53-4
ATC code  ?
PubChem 5497186
Chemical data
Formula C26H26N2O3 
Mol. mass 414.496 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes IV

Naltrindole is a highly potent, highly selective delta opioid receptor antagonist used in biomedical research.

Additional recommended knowledge

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
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Naltrindole". A list of authors is available in Wikipedia.
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