Sibutramine Hydrochloride
Basic information
- CAS
84485-00-7- Standard SMILES
CC(C)CC(N(C)C)C1(c2ccc(Cl)cc2)CCC1.Cl- InChIKey
UWAOJIWUVCMBAZ-UHFFFAOYSA-N- Molecular formula
- C17H27Cl2N
- Average molar mass
- 316.3 g/mol
- Monoisotopic mass
- 315.1520553
Overview
Sibutramine Hydrochloride is the hydrochloride salt form of sibutramine, a phenethylamine derivative with appetite depressant property. Sibutramine hydrochloride metabolites M1 and M2 competitively inhibit the reuptake of norepinephrine, serotonin, and to a lesser degree dopamine by pre-synaptic nerve terminals, thereby promoting a sense of satiety, leading to a decrease in calorie intake, and possibly an increase in resting metabolic rate. This agent does not exhibit anticholinergic or antihistaminic effects.
Names & identifiers
- Preferred name
- Sibutramine Hydrochloride
- IUPAC
- 1-[1-(4-chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine;hydrochloride
Names & synonyms
Sibutramine hydrochlorideSIBUTRAMINE HCl84485-00-7BTS 54524DTXSID4045927Sibutramine hydrochloride anhydrous9GG866ZP1ENSC-758928DTXCID2025927Sibutramine hydrochloride civCyclobutanemethanamine, 1-(4-chlorophenyl)-N,N-dimethyl-alpha-(2-methylpropyl)-, hydrochlorideRefChem:56625
Show more names
BTS-54524OGM0YHD1WFYeducC17H27Cl2N1-[1-(4-chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine hydrochlorideSibutramine (hydrochloride)(S)-(-)-Sibutramine hcl(R)-(+)-SIBUTRAMINE HCL
Database identifiers
- CAS
84485-00-7- PubChem CID
- 64764
- DTXSID
DTXSID4045927- ChEMBL
CHEMBL1200765、CHEMBL3989830- UNII
- 9GG866ZP1E
Properties
Computed structural properties
- Topological polar surface area
- 3.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 5
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 275
Experimental & physicochemical properties
Solubility<0.7 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section168 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Sibutramine hydrochloride
vLess-DILI-concern
4
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems.
Agents that are used to suppress appetite.
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Related reactions
24 records
Compound notes
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