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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H26N2O3
Molecular Weight 414.4962
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NALTRINDOLE

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]15CCN(CC6CC6)[C@H](C4)[C@]5(O)CC7=C2NC8=C7C=CC=C8

InChI

InChIKey=WIYUZYBFCWCCQJ-IFKAHUTRSA-N
InChI=1S/C26H26N2O3/c29-19-8-7-15-11-20-26(30)12-17-16-3-1-2-4-18(16)27-22(17)24-25(26,21(15)23(19)31-24)9-10-28(20)13-14-5-6-14/h1-4,7-8,14,20,24,27,29-30H,5-6,9-13H2/t20-,24+,25+,26-/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H26N2O3
Molecular Weight 414.4962
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Naltrindole is a highly potent, highly selective delta opioid receptor antagonist. It is predominantly used as a molecular probe in biomedical studies exploring the manipulation of delta opioid receptors. Naltrindole was shown to inhibit cancer cell growth in vitro; potentially through a nonopioid receptor-dependant mechanism.

CNS Activity

Curator's Comment: the referenced study was conducted on rats

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P32300
Gene ID: 18386.0
Gene Symbol: Oprd1
Target Organism: Mus musculus (Mouse)
37.0 pM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Naltrindole, a highly selective and potent non-peptide delta opioid receptor antagonist.
1988 Jan 27
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
1990 Jun
Characterization of [3H]naltrindole binding to delta opioid receptors in rat brain.
1992
Cloning and functional comparison of kappa and delta opioid receptors from mouse brain.
1993 Jul 15
Molecular cloning and expression of a rat kappa opioid receptor.
1993 Nov 1
Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors.
1994 Feb
Effects of selective opioid receptor antagonists on morphine-induced changes in striatal and limbic dopamine metabolism.
1995 Sep
Naltrexone, naltrindole, and CTOP block cocaine-induced sensitization to seizures and death.
1997
Involvement of opioid mu 1 receptors in morphine-induced conditioned place preference in rats.
1997 Sep
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.
1998 Mar
Mu- and delta-opioid receptor antagonists reduce levodopa-induced dyskinesia in the MPTP-lesioned primate model of Parkinson's disease.
2001 Sep
Effect of systemic FR140423, a new analgesic compound, in a rat model of postoperative pain: contribution of delta-opioid receptors.
2003 Oct 16
Involvement of the opioid system in the effects induced by nicotine on anxiety-like behaviour in mice.
2005 Sep
Cannabidiol is an allosteric modulator at mu- and delta-opioid receptors.
2006 Feb
Mechanistic investigation of N,N-diethyl-4-(phenyl-piperidin-4-ylidenemethyl)-benzamide-induced insulin depletion in the rat and RINm5F cells.
2008 Sep
Characteristics and comparative severity of respiratory response to toxic doses of fentanyl, methadone, morphine, and buprenorphine in rats.
2009 Dec 15
Modulation of MDMA-induced behavioral and transcriptional effects by the delta opioid antagonist naltrindole in mice.
2009 Jul
Role of mu- and delta-opioid receptors in the nucleus accumbens in cocaine-seeking behavior.
2009 Jul
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: the referenced study was conducted on rats
Naltrindole (0.5 and 1 mg/kg) antagonized swim-stress-induced antinociception in adult and 25-day old rats; but in 20-day old rats, naltrindole (1 mg/kg) had no effect.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Curator's Comment: referenced study was conducted on boar
Stock solutions of Naltrindole were thawed and diluted in Beltsville-Thawing Solution to 200 micro-M. Three 1:10 serial dilutions were made in Beltsville-Thawing Solution. Subsequently, 200 micro-L of standardized Boar Sperm was added to 200 micro-L of Naltrindole solution. The final concentration of Naltrindole was 100, 10, and 1 micro-M. The Naltrindole-Sperm mixtures were incubated at 38 deg-C with shaking, and 25 micro-L aliquots were sampled at 5, 10, 15, 30, and 60 minutes. each aliquot was analyzed for membrane and mitochondrial integrity, including signs of early destabilization, as well as sperm kinematics. Naltrindole did not affect sperm motility at any concentration. However, the highest concentration of naltrindole (100 micro-M) caused a significant decrease in sperm viability after 60 minutes.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:53:12 GMT 2023
Edited
by admin
on Sat Dec 16 09:53:12 GMT 2023
Record UNII
G167Z38QA4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NALTRINDOLE
Common Name English
4,8-METHANOBENZOFURO(2,3-A)PYRIDO(4,3-B)CARBAZOLE-1,8A(9H)-DIOL, 7-(CYCLOPROPYLMETHYL)-5,6,7,8,14,14B-HEXAHYDRO-, (4BS,8R,8AS,14BR)-
Systematic Name English
NTI
Common Name English
Code System Code Type Description
CAS
111555-53-4
Created by admin on Sat Dec 16 09:53:12 GMT 2023 , Edited by admin on Sat Dec 16 09:53:12 GMT 2023
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WIKIPEDIA
Naltrindole
Created by admin on Sat Dec 16 09:53:12 GMT 2023 , Edited by admin on Sat Dec 16 09:53:12 GMT 2023
PRIMARY
FDA UNII
G167Z38QA4
Created by admin on Sat Dec 16 09:53:12 GMT 2023 , Edited by admin on Sat Dec 16 09:53:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID60912216
Created by admin on Sat Dec 16 09:53:12 GMT 2023 , Edited by admin on Sat Dec 16 09:53:12 GMT 2023
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PUBCHEM
5497186
Created by admin on Sat Dec 16 09:53:12 GMT 2023 , Edited by admin on Sat Dec 16 09:53:12 GMT 2023
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