U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H25NS
Molecular Weight 263.441
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GACYCLIDINE

SMILES

C[C@H]1CCCC[C@]1(N2CCCCC2)C3=CC=CS3

InChI

InChIKey=DKFAAPPUYWQKKF-GOEBONIOSA-N
InChI=1S/C16H25NS/c1-14-8-3-4-10-16(14,15-9-7-13-18-15)17-11-5-2-6-12-17/h7,9,13-14H,2-6,8,10-12H2,1H3/t14-,16+/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H25NS
Molecular Weight 263.441
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Gacyclidine (GK11) is a derivative of phencyclidine with neuroprotective properties. Tritiated gacyclidine and its enantiomers bind to NMDA receptors with binding parameters similar to those of other non‐competitive NMDA receptor antagonists. Beneficial effects of gacyclidine include reduction of lesion size and improvement of functional parameters after injury. In traumatic brain injury models, gacyclidine also improves behavioral parameters and neuronal survival. In an animal model of Amyotrophic lateral sclerosis (ALS), functional alteration of locomotor activity was evident and improved the survival of mice, suggesting that chronic administration of gacyclidine beginning at early symptomatic stage may be beneficial for patients with ALS. Gacyclidine has also been associated with altered mental status and end organ damage in patients.

Approval Year

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:02:38 GMT 2023
Edited
by admin
on Fri Dec 15 16:02:38 GMT 2023
Record UNII
9290ND070R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GACYCLIDINE
INN   WHO-DD  
INN  
Official Name English
OTO-313
Common Name English
PIPERIDINE, 1-((1R,2S)-2-METHYL-1-(2-THIENYL)CYCLOHEXYL)-, REL-
Common Name English
1-(CIS-2-METHYL-1-(2-THIENYL)CYCLOHEXYL)PIPERIDINE
Common Name English
gacyclidine [INN]
Common Name English
NST-001
Code English
Gacyclidine [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1509
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
Code System Code Type Description
WIKIPEDIA
GACYCLIDINE
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
SMS_ID
100000078130
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
FDA UNII
9290ND070R
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
DRUG BANK
DB13096
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
INN
7575
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
MESH
C070707
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
PUBCHEM
176265
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID30218313
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL1742478
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
EVMPD
SUB13938MIG
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
NCI_THESAURUS
C76779
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
CAS
68134-81-6
Created by admin on Fri Dec 15 16:02:38 GMT 2023 , Edited by admin on Fri Dec 15 16:02:38 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY