Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H22ClN.C4H6O6 |
| Molecular Weight | 401.882 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O.CC(C)C[C@H](N)C1(CCC1)C2=CC=C(Cl)C=C2
InChI
InChIKey=ZGVBAFVARMNSSD-APBURCQWSA-N
InChI=1S/C15H22ClN.C4H6O6/c1-11(2)10-14(17)15(8-3-9-15)12-4-6-13(16)7-5-12;5-1(3(7)8)2(6)4(9)10/h4-7,11,14H,3,8-10,17H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t14-;1-,2-/m01/s1
| Molecular Formula | C4H6O6 |
| Molecular Weight | 150.0868 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C15H22ClN |
| Molecular Weight | 251.795 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/10844103Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12423077 | https://www.ncbi.nlm.nih.gov/pubmed/20195828
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12423077 | https://www.ncbi.nlm.nih.gov/pubmed/20195828
(-)-DDMS (S-Didesmethylsibutramine, (S)-DDMS) is one of sibutramine active metabolites. Sibutramine is widely used in the treatment of obesity. Sibutramine acts by inhibiting the reuptake of serotonin and noradrenaline in synapses, thereby enhancing both satiety and energy expenditure. In preclinical models (S)-Didesmethylsibutramine affected locomotor behavior and the Porsolt test but appeared to be completely inactive on food intake. (S)-enantiomers of didesmethylsibutramine may, to some extent, contribute to sibutramine’s side effect profile.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103 |
62.0 nM [IC50] | ||
Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103 |
4300.0 nM [IC50] | ||
Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103 |
12.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103
Rats were treated with (-)-DDMS at doses 2.5–10 mg/kg, i.p.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10844103
Synaptosomes (isolated from male Wistar rat hypothalamus, whole brain, or corpus striatum) and monoamines were prepared in Krebs’ buffer, which was oxygenated and then incubated in a deep well plates. Uptake was performed by incubating the synaptosomes in the presence and absence of each of the test compounds ((-)-DDMS or (+)-DDMS). Uptake was then stopped by filtration through a unifilter 96-well plate, which was washed with Krebs buffer in order to eliminate the free radiolabeled monoamine. Radioactivity taken up by synaptosomes was retained on the filter and then measured with a microplate scintillation counter.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:20:53 GMT 2025
by
admin
on
Mon Mar 31 18:20:53 GMT 2025
|
| Record UNII |
ZE3XB0U62Q
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
101042998
Created by
admin on Mon Mar 31 18:20:53 GMT 2025 , Edited by admin on Mon Mar 31 18:20:53 GMT 2025
|
PRIMARY | |||
|
ZE3XB0U62Q
Created by
admin on Mon Mar 31 18:20:53 GMT 2025 , Edited by admin on Mon Mar 31 18:20:53 GMT 2025
|
PRIMARY | |||
|
259729-95-8
Created by
admin on Mon Mar 31 18:20:53 GMT 2025 , Edited by admin on Mon Mar 31 18:20:53 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |