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

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
Structure of DIDESMETHYLSIBUTRAMINE D-TARTRATE, (R)-

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-FYEOGULHSA-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-/m10/s1

HIDE SMILES / InChI

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

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

Description
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 (R-Didesmethylsibutramine , (R)-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 (R)-enantiomer of Didesmethylsibutramine was clearly more potent than the (S)-enantiomers and (R)-didesmethylsibutramine shows some activity in all tests. (S)-didesmethylsibutramine affected locomotor behavior and the Porsolt test but appeared to be completely inactive on food intake. R-Didesmethylsibutramine is more potent than sibutramine in depressing food intake and decreasing body weight, suggest that these enantioselective metabolites might be safer and more effective than sibutramine as potential therapies for obesity.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
13.0 nM [IC50]
140.0 nM [IC50]
8.9 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Enantioselective behavioral effects of sibutramine metabolites.
2000 May 26
Patents

Patents

Sample Use Guides

Rats were treated with (+)-DDMS at doses 2.5–10 mg/kg, i.p.
Route of Administration: Intraperitoneal
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 Fri Dec 15 17:37:17 GMT 2023
Edited
by admin
on Fri Dec 15 17:37:17 GMT 2023
Record UNII
HQ81B20FW4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIDESMETHYLSIBUTRAMINE D-TARTRATE, (R)-
Common Name English
(R)-DIDESMETHYL SIBUTRAMINE D-TARTRATE
Common Name English
CYCLOBUTANEMETHANAMINE, 1-(4-CHLOROPHENYL)-.ALPHA.-(2-METHYLPROPYL)-, (.ALPHA.R)-, (2S,3S)-2,3-DIHYDROXYBUTANEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID50725170
Created by admin on Fri Dec 15 17:37:17 GMT 2023 , Edited by admin on Fri Dec 15 17:37:17 GMT 2023
PRIMARY
CAS
259729-93-6
Created by admin on Fri Dec 15 17:37:17 GMT 2023 , Edited by admin on Fri Dec 15 17:37:17 GMT 2023
PRIMARY
FDA UNII
HQ81B20FW4
Created by admin on Fri Dec 15 17:37:17 GMT 2023 , Edited by admin on Fri Dec 15 17:37:17 GMT 2023
PRIMARY
PUBCHEM
11246629
Created by admin on Fri Dec 15 17:37:17 GMT 2023 , Edited by admin on Fri Dec 15 17:37:17 GMT 2023
PRIMARY