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Last update 08 May 2025

(R)-Desmethylsibutramine

Last update 08 May 2025

Overview

R&D Status

Clinical Result

Translational Medicine

Overview

Basic Info

Drug Type

Small molecule drug

Synonyms

(+)-Desmethylsibutramine, (+)-Didesmethylsibutramine, R-DDMS

+ [3]

Target

DAT x adrenergic receptor

Action

antagonists

Mechanism

Dopamine reuptake inhibitors, adrenergic receptor antagonists(Adrenergic receptors antagonists)

Therapeutic Areas

Urogenital DiseasesOther Diseases

Active Indication-

Inactive Indication

Attention Deficit Disorder With HyperactivityDepressive DisorderDepressive Disorder, Major+ [2]

Originator Organization

Sumitomo Pharma America, Inc.

Active Organization-

Inactive Organization

Sumitomo Pharma America, Inc.

License Organization-

Drug Highest PhaseDiscontinuedPhase 2

First Approval Date-

Regulation-

Structure/Sequence

Molecular FormulaC16H24ClN

InChIKeyPLXKZKLXYHLWHR-OAHLLOKOSA-N

CAS Registry229639-54-7

Clinical Trials associated with (R)-Desmethylsibutramine

CTRI/2008/091/000265

/ CompletedPhase 3

A comparative clinical trial of R-Sibutramine versus racemate Sibutramine in the management of obesity

Start Date16 Jul 2009

Sponsor / Collaborator

Emcure Pharmaceuticals Ltd.

100 Clinical Results associated with (R)-Desmethylsibutramine

100 Translational Medicine associated with (R)-Desmethylsibutramine

100 Patents (Medical) associated with (R)-Desmethylsibutramine

Literatures (Medical) associated with (R)-Desmethylsibutramine

01 Jan 2021·Journal of Chromatography BQ3 · MEDICINE

Metabolic analysis of the illegal analogues of anti-obesity drugs using LC-Q-TOF-MS/MS

Q3 · MEDICINE

Article

Author: Choe, Sanggil ; Lee, Sooyeun ; Pyo, Jaesung ; Jeong, Daseul ; Kim, Kang Min

With an increase in the obese population, the indiscriminate demand for anti-obesity drugs for rapid weight loss or maintenance has grown. As a result, illegal substances that could induce unexpected negative health effects or fatal side effects are being produced and mixed into consumer products. In the present study, the metabolites of five major illegal anti-obesity drugs are analyzed for the first time. Our data can be utilized to identify related compounds and predict their toxicological effects. Didesmethylsibutramine, desmethylsibutramine, homosibutramine, chlorosibutramine, and benzylsibutramine were metabolized in in vitro and in vivo models, and the metabolites were identified using liquid chromatography quadrupole-time of flight mass spectrometry (LC-Q-TOF-MS) and tandem mass spectrometry (LC-Q-TOF-MS/MS). The in vivo metabolite analysis was carried out using urine and feces samples from rats, and the in vitro metabolite analysis was performed by incubating the analogues with human liver microsomes. We found that each sibutramine analogue was metabolized into several constituents: 2 (M1-2), 5 (M1-5), 11 (M1-11), 7 (N1-7), and 5 (O1-5). In conclusion, our metabolic study could be used for toxicological detection of illegal obesity treatments and metabolite identification in forensic cases.

17 Dec 2014·Journal of Toxicology and Environmental Health, Part AQ3 · MEDICINE

EnantioselectiveN-Demethylation and Hydroxylation of Sibutramine in Human Liver Microsomes and Recombinant Cytochrome P-450 Isoforms

Q3 · MEDICINE

Article

Author: Min-Jung Kim ; Jae-Gook Shin ; Dong-Hyun Kim ; Dhananjay D. Shinde ; Ji-Woo Lee ; Eun-Sook Jeong ; Yang-Weon Kim

The enantioselective metabolism of sibutramine was examined using human liver microsomes (HLM) and recombinant cytochrome P-450 (CYP) isoforms. This drug is metabolized to N-mono-desmethyl- (M1) and N,N-di-desmethylsibutramine (M2), and subsequent hydroxylation results in hydroxyl M1 (HM1) and hydroxyl M2 (HM2). No significant difference was noted in formation of M1from sibutramine between R- and S-sibutramine in HLM. However, S-enantiomers of M1 and M2 were preferentially metabolized to M2, HM1, and HM2compared to R-enantiomers in HLM, and intrinsic clearance (Clint) ratios of S-enantiomers/R-enantiomers were 1.97, 4.83, and 9.94 for M2, HM1, and HM2, respectively. CYP3A4 and CYP3A5 were only involved in the formation of M1, whereas CYP2B6 and CYP2C19 were responsible for all metabolic reactions of sibutramine. CYP2C19 and CYP3A5 displayed catalytic preference for S-sibutramine to S-M1, whereas CYP2B6 and CYP3A4 showed little or no stereoselectivity in metabolism of sibutramine to M1. In the case of M2 formation, CYP2B6 metabolized S-M1 more rapidly than R-M1 with a Clint ratio of 2.14. However, CYP2C19 catalyzed less S-M1 than R-M1 and the Clint ratio of S-M1 to R-M1 was 0.65. The most significant enantioselectivity was observed in formation of HM1 from M1, and HM2 from M2. CYP2B6 and CYP2C19 exhibited preferential catalysis of formation of hydroxyl metabolites from S-enantiomers rather than R-enantiomers. These results indicate that S-sibutramine was more rapidly metabolized by CYP isoforms than R-sibutramine, and that enantioselective metabolism needs to be considered in drug interactions involving sibutramine and co-administered drugs.

04 May 2014·Food Additives & Contaminants: Part AQ3 · AGRICULTURAL & FORESTRY SCIENCE

Monitoring of 29 weight loss compounds in foods and dietary supplements by LC-MS/MS

Q3 · AGRICULTURAL & FORESTRY SCIENCE

Article

Author: Hyung Joo Kim ; Ji Hyun Lee ; Woo Seong Kim ; Hyoung Joon Park ; Sooyeul Cho ; So-Hyun Cho

Because of the rapid growth in dietary supplement availability and public concern for weight control, the investigation of foods and various dietary supplements illegally adulterated with weight loss compounds has become increasingly important. A total of 29 weight loss compounds, including sennoside, sibutramine, ephedrine and their analogues, found to be adulterated in foods and dietary supplements were simultaneously examined by LC-MS/MS. The 188 samples were collected between 2009 and 2012 in South Korea, and method validation was performed to determine the adulterants to the weight loss compounds. LODs, LOQs and linearity ranged from 0.03 to 7.5 ng ml⁻¹, from 0.08 to 30.00 ng ml⁻¹, and from 0.990 to 0.999, respectively. The results showed that nine weight loss compounds, namely bisacodyl, desmethylsibutramine, didesmethylsibutramine, ephedrine, fluoxetine, pseudoephedrine, sennoside A, sennoside B and sibutramine, were detected in 62 of all collected samples and were found in order of frequency as follows: sibutramine, 25.7%; sennoside A, 22.9%; sennoside B, 20.0%; fluoxetine, 8.6%; desmethylsibutramine, 7.1%; bisacodyl, ephedrine, and pseudoephedrine, 4.3%; and didesmethylsibutramine, 2.9%. Sibutramine, which was the most frequently found adulterant, ranged in levels from 0.03 to 132.40 mg g⁻¹ (2010), from 0.88 to 76.2 mg g⁻¹ (2011), and from 0.07 to 0.24 mg g⁻¹ (2012). Although the concentrations of most compounds ranged widely, some compounds such as bisacodyl and fluoxetine were found at high concentrations in several samples.

100 Deals associated with (R)-Desmethylsibutramine

R&D Status

10 top R&D records.

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Indication	Highest Phase	Country/Location	Organization	Date
Attention Deficit Disorder With Hyperactivity	Phase 2	United States	-	-
Depressive Disorder	Phase 2	-	Sumitomo Pharma America, Inc.	-
Depressive Disorder, Major	Phase 2	United States	-	-
Erectile Dysfunction	Phase 2	United States	-	-
Urinary Incontinence, Stress	Phase 2	United States	-	-

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(R)-Desmethylsibutramine

Overview

Basic Info

Structure/Sequence

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R&D Status

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Translational Medicine

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Clinical Trial

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