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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25NO3.ClH
Molecular Weight 375.889
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ORG-25935 HYDROCHLORIDE

SMILES

Cl.COC1=CC=C2[C@H]([C@@H](CN(C)CC(O)=O)CCC2=C1)C3=CC=CC=C3

InChI

InChIKey=SDTLOODMXMDJFX-JKSHRDEXSA-N
InChI=1S/C21H25NO3.ClH/c1-22(14-20(23)24)13-17-9-8-16-12-18(25-2)10-11-19(16)21(17)15-6-4-3-5-7-15;/h3-7,10-12,17,21H,8-9,13-14H2,1-2H3,(H,23,24);1H/t17-,21+;/m1./s1

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C21H25NO3
Molecular Weight 339.4281
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24525661 | https://www.ncbi.nlm.nih.gov/pubmed/22394471

Org 25935 (SCH 900435) is a synthetic drug developed by Organon International, which acts as a selective inhibitor of the glycine transporter GlyT-1. In human trial for prevention of relapse in alcohol-dependent patients in Org 25935 demonstrated no benefit over placebo in preventing alcohol relapse. Org 25935 was tested as an adjunctive treatment to atypical antipsychotics in predominant persistent negative symptoms of schizophrenia, where it did not differ significantly from placebo in reducing negative symptoms or improving cognitive functioning. Clinical trials against panic disorder did not show any benefit compared to placebo.

CNS Activity

Originator

Organon
34
Curator's Comment: Aquired by Shering-Plough, and then by Merck

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Sodium- and chloride-dependent glycine transporter 1
5
Target ID: P48067
Gene ID: 6536.0
Gene Symbol: SLC6A9
Target Organism: Homo sapiens (Human)
Inhibitor
8297
Inhibitor
8297
 5.96 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
159 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17098748
8 mg 2 times / day multiple, oral
dose: 8 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ORG-25935 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
165 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17098748
12 mg 2 times / day multiple, oral
dose: 12 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ORG-25935 plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
243 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17098748
16 mg 2 times / day multiple, oral
dose: 16 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ORG-25935 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
72 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17098748
4 mg 2 times / day multiple, oral
dose: 4 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ORG-25935 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
16 mg 2 times / day multiple, oral (max)
Highest studied dose
Dose: 16 mg, 2 times / day
Route: oral
Route: multiple
Dose: 16 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/24525661
Page: p.194
unhealthy, 38.8± 11.0
n = 73
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 38.8± 11.0
Sex: M+F
Population Size: 73
Sources:
https://pubmed.ncbi.nlm.nih.gov/24525661
Page: p.194
Sources:
https://pubmed.ncbi.nlm.nih.gov/24525661
Page: p.194
Sourcing

Sourcing

Vendor/AggregatorIDURL
Axon MedChem
1563
https://www.axonmedchem.com/product/1563
MolPort
MolPort-042-665-714
https://www.molport.com/shop/molecule-link/MolPort-042-665-714
MuseChem
I008026
https://www.musechem.com/product/I008026.html
eMolecules
275059136
https://orderbb.emolecules.com/search/#?query=275059136
eMolecules
36367158
https://orderbb.emolecules.com/search/#?query=36367158
PubMed

PubMed

TitleDatePubMed
Evaluation of the glycine transporter inhibitor Org 25935 as augmentation to cognitive-behavioral therapy for panic disorder: a multicenter, randomized, double-blind, placebo-controlled trial.
2012 May
The selective glycine uptake inhibitor org 25935 as an adjunctive treatment to atypical antipsychotics in predominant persistent negative symptoms of schizophrenia: results from the GIANT trial.
2014 Apr
Efficacy and safety of the glycine transporter-1 inhibitor org 25935 for the prevention of relapse in alcohol-dependent patients: a randomized, double-blind, placebo-controlled trial.
2014 Sep
Patents

Patents

US6410592
2

Sample Use Guides

In Vivo Use Guide
In clinical trial against schizophrenia Org 25935 was tested at 4 to 8 mg twice daily and 12 to 16 mg twice daily.
Route of Administration: Oral
In Vitro Use Guide
Compound inhibition of GlyT-1 activity was determined with a scintillation proximity assay (SPA) using radiolabeled glycine ([14C]-glycine) and Cytostar-T plates. ORG 25935 inhibited GlyT-1 with IC50 of 5.96 nM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:39:54 GMT 2023
Edited
by admin
on Fri Dec 15 15:39:54 GMT 2023
Record UNII
H6MSM69SSM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ORG-25935 HYDROCHLORIDE
Common Name English
GLYCINE, N-METHYL-N-(((1R,2S)-1,2,3,4-TETRAHYDRO-6-METHOXY-1-PHENYL-2-NAPHTHALENYL)METHYL)-, HYDROCHLORIDE
Systematic Name English
ORG 25935 HYDROCHLORIDE
Code English
2-(((1R,2S)-6-METHOXY-1-PHENYL-1,2,3,4-TETRAHYDRONAPHTHALEN-2-YL)METHYL-METHYLAMINO)ACETIC ACID, HYDROCHLORIDE
Systematic Name English
Code System Code Type Description
CAS
1146978-08-6
Created by admin on Fri Dec 15 15:39:54 GMT 2023 , Edited by admin on Fri Dec 15 15:39:54 GMT 2023
PRIMARY
PUBCHEM
11740218
Created by admin on Fri Dec 15 15:39:54 GMT 2023 , Edited by admin on Fri Dec 15 15:39:54 GMT 2023
PRIMARY
DRUG BANK
DBSALT002157
Created by admin on Fri Dec 15 15:39:54 GMT 2023 , Edited by admin on Fri Dec 15 15:39:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID701029795
Created by admin on Fri Dec 15 15:39:54 GMT 2023 , Edited by admin on Fri Dec 15 15:39:54 GMT 2023
PRIMARY
CAS
949588-40-3
Created by admin on Fri Dec 15 15:39:54 GMT 2023 , Edited by admin on Fri Dec 15 15:39:54 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
FDA UNII
H6MSM69SSM
Created by admin on Fri Dec 15 15:39:54 GMT 2023 , Edited by admin on Fri Dec 15 15:39:54 GMT 2023
PRIMARY
Related Record Type Details
Structure of ORG-25935
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ORG-25935
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