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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO
Molecular Weight 257.3706
Optical Activity ( + )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALAZOCINE, (+)-

SMILES

C[C@@H]1[C@@H]2CC3=C(C=C(O)C=C3)[C@@]1(C)CCN2CC=C

InChI

InChIKey=LGQCVMYAEFTEFN-DQYPLSBCSA-N
InChI=1S/C17H23NO/c1-4-8-18-9-7-17(3)12(2)16(18)10-13-5-6-14(19)11-15(13)17/h4-6,11-12,16,19H,1,7-10H2,2-3H3/t12-,16+,17+/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H23NO
Molecular Weight 257.3706
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

(+)-SKF-10,047 is a sigma-opioid receptor agonist. (+)-SKF-10,047 is distinct from its (-)-enantiomer in binding pattern and associated behavioural effects. (+)-SKF-10,047 stress-induced motor suppression, while its (-)-optical isomer was inactive. Besides activation of sigma-1 receptor, (+)-SKF-10,047 is inhibitor of Na(V)1.2 and Na(V)1.4 channels.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
18.0 nM [Ki]
140.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
To evaluate effect of (+)-SKF-10,047 on conditioned fear stress, the drug was administered subcutaneously at 20 min before motility was measured in the test trial. (+)-SKF-10,047 (3 and 6 mg/kg) dose-dependently attenuated the conditioned fear stress.
Route of Administration: Other
In Vitro Use Guide
Inhibition of sigma opioid receptor from guinea brains was studied using radioligand binding assay, with 3H-SKF10047 used as a radioligand. (+)-SKF-10,047 displaces [3H]-(+)*SKF10047 with Ki of 18 nM
Substance Class Chemical
Record UNII
YR49MN7Q8G
Record Status Validated (UNII)
Record Version