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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
37.0 pM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
G167Z38QA4
Record Status Validated (UNII)
Record Version