SIBUTRAMINE MESYLATE HEMIHYDRATE

Details

Stereochemistry	MIXED
Molecular Formula	2C17H26ClN.2CH4O3S.H2O
Molecular Weight	769.923
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of SIBUTRAMINE MESYLATE HEMIHYDRATE

Structure Search

SMILES

O.CS(O)(=O)=O.CS(O)(=O)=O.CC(C)CC(N(C)C)C1(CCC1)C2=CC=C(Cl)C=C2.CC(C)CC(N(C)C)C3(CCC3)C4=CC=C(Cl)C=C4

InChI

InChIKey=DITYBRVAUNNHNJ-UHFFFAOYSA-N

InChI=1S/2C17H26ClN.2CH4O3S.H2O/c2*1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8-15(18)9-7-14;2*1-5(2,3)4;/h2*6-9,13,16H,5,10-12H2,1-4H3;2*1H3,(H,2,3,4);1H2

HIDE SMILES / InChI

Molecular Formula	C17H26ClN
Molecular Weight	279.848
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm228830.htm

Subitramine is a potent inhibitor of monoamines (serotonin, dopamine, noradrenaline) reuptake that was approved by FDA for the treatmen of obesity. Sibutramine is metabolized to metabolites M1 and M2 which are more active toward the monoamine transporters.The drug was withdrawn from the market because of clinical trial data indicating an increased risk of heart attack and stroke. It was sold under a variety of brand names including Reductil, Meridia and Sibutrex.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Sodium-dependent serotonin transporter 41 Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	Inhibitor 8504	298.0 nM [Ki]
Sodium-dependent dopamine transporter 43 Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	Inhibitor 8504	943.0 nM [Ki]
Sodium-dependent noradrenaline transporter 39 Target ID: P23975 Gene ID: 6530.0 Gene Symbol: SLC6A2 Target Organism: Homo sapiens (Human) Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	Inhibitor 8504	5451.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 206 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	Primary		Withdrawn	MERIDIA Approved Use MERIDIA is indicated for the management of obesity, including weight loss and maintenance of weight loss, and should be used in conjunction with a reduced calorie diet. Launch Date 1997

C_max

Value	Dose	Analyte	Population
7.12 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15823773/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.09 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15823773/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DIDESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4368.5 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29403750/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	SIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
4067.7 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29403750/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
6579.8 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29403750/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DIDESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
4 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DESMETHYLSIBUTRAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
6.4 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DIDESMETHYLSIBUTRAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
133.03 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15823773/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
205.86 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15823773/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DIDESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
23296.9 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29403750/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	SIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
100736.1 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29403750/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
194500.9 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29403750/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DIDESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
25.5 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DESMETHYLSIBUTRAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
92.1 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DIDESMETHYLSIBUTRAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
22.31 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15823773/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
23.07 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15823773/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DIDESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29403750/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	SIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
25.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29403750/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
23.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29403750/	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DIDESMETHYLSIBUTRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
17.2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DIDESMETHYLSIBUTRAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
6% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		DESMETHYLSIBUTRAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
6% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		DIDESMETHYLSIBUTRAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	Disc. AE: Hypertension, Tachycardia... AEs leading to discontinuation/dose reduction: Hypertension (0.4%) Tachycardia (0.4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf
15 mg 1 times / day multiple, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23444896/	unhealthy, mean 32 years Health Status: unhealthy Age Group: mean 32 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23444896/	Disc. AE: Palpitations... Other AEs: Palpitations... AEs leading to discontinuation/dose reduction: Palpitations (1 patient) Other AEs: Palpitations (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/23444896/
20 mg 1 times / day multiple, oral Studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23444896/	unhealthy, mean 32 years Health Status: unhealthy Age Group: mean 32 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23444896/	Other AEs: Palpitations, Paresthesia... Other AEs: Palpitations (1 patient) Paresthesia (1 patient) Anxiety (1 patient) Insomnia (1 patient) Fatigue (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/23444896/
20 mg 1 times / day multiple, oral Studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	unhealthy, mean 42.9 years Health Status: unhealthy Age Group: mean 42.9 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	Disc. AE: Hypertension, Tachycardia... Other AEs: Dry mouth, Anorexia... AEs leading to discontinuation/dose reduction: Hypertension (<1.4%) Tachycardia (<3%) Other AEs: Dry mouth (32.2%) Anorexia (32.2%) Insomnia (10.3%) Increased appetite (11.6%) Nausea (8.2%) Dyspepsia (5.5%) Nervousness (12.3%) Asthenia (8.9%) Dizziness (12.3%) Constipation (12.3%) Rash (4.1%) Palpitation (4.1%) Vasodilation (4.8%) Dyspnea (1.4%) Taste perversion (4.1%) Hypertension (1.4%) Sweating (4.1%) Tachycardia (6.8%) Ecchymosis (1.4%) Paresthesia (3.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	unhealthy, mean 43.3 years Health Status: unhealthy Age Group: mean 43.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	Disc. AE: Hypertension, Tachycardia... Other AEs: Dry mouth, Anorexia... AEs leading to discontinuation/dose reduction: Hypertension (<2%) Tachycardia (<3%) Other AEs: Dry mouth (16.7%) Anorexia (18.7%) Insomnia (9.4%) Increased appetite (16.7%) Nausea (3.4%) Dyspepsia (4.4%) Nervousness (6.4%) Asthenia (7.9%) Dizziness (7.9%) Constipation (10.8%) Rash (4.9%) Palpitation (4.9%) Vasodilation (2%) Dyspnea (1.5%) Taste perversion (2%) Hypertension (4.9%) Sweating (1%) Tachycardia (4.4%) Ecchymosis (0.5%) Paresthesia (3.9%) Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/
30 mg 1 times / day multiple, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	unhealthy, mean 43.4 years Health Status: unhealthy Age Group: mean 43.4 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	Disc. AE: Hypertension, Tachycardia... Other AEs: Dry mouth, Anorexia... AEs leading to discontinuation/dose reduction: Hypertension (2%) Tachycardia (3%) Other AEs: Dry mouth (31.8%) Anorexia (31.8%) Insomnia (24.5%) Increased appetite (21.2%) Nausea (12.6%) Dyspepsia (12.6%) Nervousness (11.3%) Asthenia (10.6%) Dizziness (7.9%) Constipation (7.9%) Rash (7.3%) Palpitation (6%) Vasodilation (5.3%) Dyspnea (4.6%) Taste perversion (4.6%) Hypertension (3.3%) Sweating (2.6%) Tachycardia (2.6%) Ecchymosis (2%) Paresthesia (1.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/
5 mg 1 times / day multiple, oral Minumum effective dose Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	unhealthy, mean 43.4 years Health Status: unhealthy Age Group: mean 43.4 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	Disc. AE: Hypertension, Tachycardia... Other AEs: Dry mouth, Anorexia... AEs leading to discontinuation/dose reduction: Hypertension (<1.2%) Tachycardia (<1.8%) Other AEs: Dry mouth (11.8%) Anorexia (18.9%) Insomnia (8.3%) Increased appetite (16.6%) Nausea (4.1%) Dyspepsia (4.1%) Nervousness (5.3%) Asthenia (7.1%) Dizziness (8.9%) Constipation (13%) Rash (4.1%) Vasodilation (2.4%) Dyspnea (0.6%) Taste perversion (1.2%) Hypertension (1.2%) Sweating (1.2%) Tachycardia (1.8%) Ecchymosis (1.2%) Paresthesia (2.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/
15 mg 1 times / day multiple, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	unhealthy, mean 44.2 years Health Status: unhealthy Age Group: mean 44.2 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	Disc. AE: Hypertension, Tachycardia... Other AEs: Dry mouth, Anorexia... AEs leading to discontinuation/dose reduction: Hypertension (<2%) Tachycardia (<3%) Other AEs: Dry mouth (25.5%) Anorexia (21.4%) Insomnia (10.2%) Increased appetite (14.3%) Nausea (5.1%) Dyspepsia (8.2%) Nervousness (7.7%) Asthenia (6.1%) Dizziness (8.2%) Constipation (11.7%) Rash (7.1%) Palpitation (2.6%) Vasodilation (2%) Dyspnea (1%) Taste perversion (2.6%) Hypertension (5.1%) Sweating (2.6%) Tachycardia (7.7%) Ecchymosis (3.1%) Paresthesia (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/
1 mg 1 times / day multiple, oral Minumum effective dose Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	unhealthy, mean 44.5 years Health Status: unhealthy Age Group: mean 44.5 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	Disc. AE: Hypertension, Tachycardia... Other AEs: Dry mouth, Anorexia... AEs leading to discontinuation/dose reduction: Hypertension (<2%) Tachycardia (<0.7%) Other AEs: Dry mouth (6%) Anorexia (20.1%) Insomnia (12.1%) Increased appetite (11.4%) Nausea (3.4%) Dyspepsia (4%) Nervousness (4.7%) Asthenia (2.7%) Dizziness (4.7%) Constipation (6.7%) Rash (5.4%) Palpitations (2%) Vasodilation (1.3%) Dyspnea (1.3%) Taste perversion (0.7%) Hypertension (2%) Tachycardia (0.7%) Paresthesia (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 CYP3A 227 OCT2 779	CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C19 1119 CYP2E1 729 CYP3A5 446

Drug as perpetrator

Target	Modality	Activity
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 0.829 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 15.6 uM]
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19002438/	yes [IC50 29 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP2A6 911	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP3A 317	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	yes
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	yes
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf#page=3 Page: 3.0	yes	yes (co-administration study) Comment: Ketoconazole: resulted in moderate increases in AUC and Cmax of 58% and 36% for M1 and of 20% and 19% for M2, respectively; Erythromycin: resulted in small increases in the AUC (less than 14%) for M1 and M2. A small reduction in Cmax for M1 (11%) and a slight increase in Cmax for M2 (10%) were observed. Other tested drugs that are substrates and/or inhibitors of CYP 450 isozymes were tested. Cimetidine: resulted insmall increases in combined (M1 and M2) plasma Cmax (3.4%) and AUC (7.3%); Simvastatin: no significant effect on plasma Cmax and AUC of M2 or M1 and M2 combined. The Cmax (16%) and AUC (12%) of M1 were slightly decreased. Simvastatin slightly decreased sibutramine Cmax (14%) and AUC (21%); Omeprazole: slightly increased plasma Cmax and AUC of M1 and M2 combined (approximately 15%). M2 Cmax and AUC were not significantly affected whereas M1 Cmax (30%) and AUC (40%) were modestly increased. Plasma Cmax (57%) and AUC (67%) of unchanged sibutramine were moderately increased; Olanzapine: Olanzapine had no significant effect on plasma Cmax and AUC of M2 and M1 and M2 combined, or the AUC of M1; Lorazepam: Lorazepam had no significant effect on the pharmacokinetics of sibutramine metabolites M1 and M2. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf#page=3 Page: 3.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/18781376/

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1706	http://www.3bsc.com/index/pro_info.php?id=56247
AA Blocks	AA00JOBX	https://www.aablocks.com/goods/Goods/detail?id=AA00JOBX
Aaron Chemicals	AR00JP3P	http://www.aaronchem.com/84485-00-7
abcr GmbH	AB376861	http://www.abcr.de/shop/en/AB376861
AbMole Bioscience	M5958	http://www.abmole.com/products/sibutramine-hcl.html
Achemtek	0104-018656	http://www.achemtek.com/84485-00-7
Alsachim	1918	http://www.alsachim.com/product-C2844-glo.bal-view.html
Aurora Fine Chemicals LLC	A13.140.569	http://online.aurorafinechemicals.com/info?ID=A13.140.569
BioChemPartner	BCP04098	http://www.biochempartner.com/84485-00-7-BCP04098
BioCrick	BCC5252	http://www.biocrick.com/Sibutramine-hydrochloride-BCC5252.html
Boerchem	BC209342	http://www.boerchem.com/?product_35511.html
Chem Scene	CS-2856	http://www.chemscene.com/84485-00-7.html
ChemMol	30104779	http://www.chemmol.com/chemmol/30104779.html
ChemMol	44008671	http://www.chemmol.com/chemmol/44008671.html
ChemMol	49422609	http://www.chemmol.com/chemmol/49422609.html
ChemMol	97900788	http://www.chemmol.com/chemmol/97900788.html
ChemShuttle	159801	http://www.chemshuttle.com/catalogsearch/result/?q=84485-00-7&cat=
Clearsynth	CS-O-02273	https://www.clearsynth.com/en/CSO02273.html
Clearsynth	CS-O-02319	https://www.clearsynth.com/en/CSO02319.html
Clearsynth	CS-T-84979	https://www.clearsynth.com/en/CST84979.html
eNovation Chemicals	D320135	http://www.enovationchem.com/productDetails.asp?productID=D320135
Lab Network	LN00643799	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00643799
LGC Standards	DRE-C16944000	https://www.lgcstandards.com/US/en/p/DRE-C16944000
MedChem Express	HY-14469	https://www.medchemexpress.com/Sibutramine-hydrochloride.html
OChem	7531	http://www.ocheminc.com/index.php?act=psearch&pid=494S599
Smolecule	S543171	http://www.smolecule.com/products/s543171
Synblock Inc	AB07665	http://www.synblock.com/product/84485-00-7.html
THE BioTek	bt-283286	https://www.thebiotek.com/product/inhibitors/bt-283286
Tocris	2290	https://www.tocris.com/products/sibutramine-hydrochloride_2290
Yuhao Chemical	LT1280	http://www.chemyuhao.com/84485-00-7.html

PubMed

Title	Date	PubMed
Bridging Functional and Structural Cardiotoxicity Assays Using Human Embryonic Stem Cell-Derived Cardiomyocytes for a More Comprehensive Risk Assessment.	2015-11	26259608
Effects of oral anorexiant sibutramine on the expression of cytochromes P450s in human hepatocytes and cancer cell lines.	2013-12	24038852
Potent inhibition of cytochrome P450 2B6 by sibutramine in human liver microsomes.	2013-09-05	23777987
[Long-term effects of weight-reducing drugs in hypertensive patients--a survey of a Cochrane review].	2011-02-21	21333255
Elevation of QT dispersion after obesity drug sibutramine.	2010-11	20671571
Diabesity: therapeutic options.	2010-06	20518802
[32-year-old patient with acute myocardial infarction possibly induced by the appetite suppressant sibutramine].	2010-05	20446231
The role of adiponectin in the pathogenesis and treatment of non-alcoholic fatty liver disease.	2010-05	20415685
Oleanolic acid, a natural triterpenoid improves blood glucose tolerance in normal mice and ameliorates visceral obesity in mice fed a high-fat diet.	2010-04-15	20188082
Pharmacotherapy for obesity.	2009-12	20002075
Multiple effects of sibutramine on ejaculation and on vas deferens and seminal vesicle contractility.	2009-09-15	19482040
Sibutramine versus continuous positive airway pressure in obese obstructive sleep apnoea patients.	2009-09	19357147
Long-term effects of weight-reducing drugs in hypertensive patients.	2009-07-08	19588440
The use of sibutramine in the management of obesity and related disorders: an update.	2009	19475780
Sibutramine-induced acute myocardial infarction in a young lady.	2008-11	18788006
Sibutramine: current status as an anti-obesity drug and its future perspectives.	2008-08	18671470
[Pharmacological therapy of obesity].	2008-04	18773755
The endocannabinoid system as a target for obesity treatment.	2008	19046740
Myocardial infarction induced by appetite suppressants in Malaysia.	2007-11-01	17978302
Open channel block of A-type, kv4.3, and delayed rectifier K+ channels, Kv1.3 and Kv3.1, by sibutramine.	2007-05	17312186
Optimal treatment of obesity-related hypertension: the Hypertension-Obesity-Sibutramine (HOS) study.	2007-04-17	17404163
Use of sibutramine in obese mexican adolescents: a 6-month, randomized, double-blind, placebo-controlled, parallel-group trial.	2006-05	16861099
[Pharmacotherapy of obesity].	2004-10-07	15532736
Long-term pharmacotherapy for overweight and obesity: a systematic review and meta-analysis of randomized controlled trials.	2003-12	12975638
The effects of sibutramine and orlistat on the ultrasonographic findings, insulin resistance and liver enzyme levels in obese patients with non-alcoholic steatohepatitis.	2003-09	14502318
Effects of sibutramine on ventricular dimensions and heart valves in obese patients during weight reduction.	2002-09	12228789
Organic hypomania secondary to sibutramine-citalopram interaction.	2002-02	11874219
Efficacy and safety of sibutramine for weight loss in obese patients with hypertension well controlled by beta-adrenergic blocking agents: a placebo-controlled, double-blind, randomised trial.	2002-01	11840225
Sibutramine in overweight/obese hypertensive patients.	2001-12	11916102
An assessment of the safety and efficacy of sibutramine, an anti-obesity drug with a novel mechanism of action.	2000-10	12119986
[Obesity: principles of drug therapy].	2000-08	11026090
Sibutramine: a serotonin-norepinephrine reuptake-inhibitor for the treatment of obesity.	1999-09	10492502
Sibutramine: a novel anti-obesity drug. A review of the pharmacological evidence to differentiate it from d-amphetamine and d-fenfluramine.	1998-08	9758240
Sibutramine: a review of the pharmacology of a novel anti-obesity agent.	1997-03	9130038
Dexfenfluramine. An updated review of its therapeutic use in the management of obesity.	1996-11	9118819

Patents

Sample Use Guides

In Vivo Use Guide

The recommended starting dose is 10 mg administered once daily with or without food.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Wed Apr 02 21:09:38 GMT 2025` Edited by `admin` on `Wed Apr 02 21:09:38 GMT 2025`
Record UNII	F3BM7G49ET
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SIBUTRAMINE MESILATE HEMIHYDRATE

Preferred Name

English

SIBUTRAMINE MESYLATE HEMIHYDRATE

Common Name

English

Cyclobutanemethanamine, 1-(4-chlorophenyl)-N,N-dimethyl-?-(2-methylpropyl)-, methanesulfonate, hydrate (2:2:1)

Systematic Name

English

Sibutramine methanesulfonate hemihydrate

Common Name

English

Code System Code Type Description

CAS

676598-09-7

Created by admin on Wed Apr 02 21:09:38 GMT 2025 , Edited by admin on Wed Apr 02 21:09:38 GMT 2025

PRIMARY

FDA UNII

F3BM7G49ET

Created by admin on Wed Apr 02 21:09:38 GMT 2025 , Edited by admin on Wed Apr 02 21:09:38 GMT 2025

PRIMARY

Related Record Type Details


					NTF6Z4MEY2

SIBUTRAMINE MESYLATE

ANHYDROUS->SOLVATE

Amount:


					WV5EC51866

SIBUTRAMINE

PARENT -> SALT/SOLVATE

Amount:

Related Record Type Details


					WV5EC51866

SIBUTRAMINE

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdfCurator's Comment: description was created based on several sources, including http://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm228830.htm

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Overview

OverviewOther

Drug as perpetrator​

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Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm228830.htm

C_max

T_1/2

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Drug as perpetrator