SIBUTRAMINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H26ClN
Molecular Weight	279.848
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CC(N(C)C)C1(CCC1)C2=CC=C(Cl)C=C2

InChI

InChIKey=UNAANXDKBXWMLN-UHFFFAOYSA-N

InChI=1S/C17H26ClN/c1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8-15(18)9-7-14/h6-9,13,16H,5,10-12H2,1-4H3

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	( + / - )

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is metabolized to metabolites M1 and M2 which are more active toward the monoamine transporters.The drug was withdrawn from the market because of clinical trial data indicating an increased risk of heart attack and stroke.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Obesity 206 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	Primary		Withdrawn	MERIDIA Approved Use MERIDIA is indicated for the management of obesity, including weight loss and maintenance of weight loss, and should be used in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
Sibutramine: a review of the pharmacology of a novel anti-obesity agent.	1997 Mar	9130038
Sibutramine: a novel anti-obesity drug. A review of the pharmacological evidence to differentiate it from d-amphetamine and d-fenfluramine.	1998 Aug	9758240
Sibutramine: a serotonin-norepinephrine reuptake-inhibitor for the treatment of obesity.	1999 Sep	10492502
[Obesity: principles of drug therapy].	2000 Aug	11026090
Sibutramine in overweight/obese hypertensive patients.	2001 Dec	11916102
Organic hypomania secondary to sibutramine-citalopram interaction.	2002 Feb	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 Jan	11840225
Optimal treatment of obesity-related hypertension: the Hypertension-Obesity-Sibutramine (HOS) study.	2007 Apr 17	17404163
[Pharmacological therapy of obesity].	2008 Apr	18773755
Pharmacotherapy for obesity.	2009 Dec	20002075
Long-term effects of weight-reducing drugs in hypertensive patients.	2009 Jul 8	19588440
Multiple effects of sibutramine on ejaculation and on vas deferens and seminal vesicle contractility.	2009 Sep 15	19482040
Oleanolic acid, a natural triterpenoid improves blood glucose tolerance in normal mice and ameliorates visceral obesity in mice fed a high-fat diet.	2010 Apr 15	20188082
Diabesity: therapeutic options.	2010 Jun	20518802
[32-year-old patient with acute myocardial infarction possibly induced by the appetite suppressant sibutramine].	2010 May	20446231
The role of adiponectin in the pathogenesis and treatment of non-alcoholic fatty liver disease.	2010 May	20415685
Elevation of QT dispersion after obesity drug sibutramine.	2010 Nov	20671571
Potent inhibition of cytochrome P450 2B6 by sibutramine in human liver microsomes.	2013 Sep 5	23777987

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 09:30:15 GMT 2025` Edited by `admin` on `Wed Apr 02 09:30:15 GMT 2025`
Record UNII	WV5EC51866
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUTRAMIN

Preferred Name

English

SIBUTRAMINE

Official Name

English

SIBUTRAMINE [MI]

Common Name

English

(±)-SIBUTRAMINE

Common Name

English

(±)-1-(P-CHLOROPHENYL)-.ALPHA.-ISOBUTYL-N,N-DIMETHYLCYCLOBUTANEMETHYLAMINE

Common Name

English

RACEMIC SIBUTRAMINE

Common Name

English

sibutramine [INN]

Common Name

English

Sibutramine [WHO-DD]

Common Name

English

CYCLOBUTANEMETHANAMINE, 1-(4-CHLOROPHENYL)-N,N-DIMETHYL-.ALPHA.-(2-METHYLPROPYL)-

Systematic Name

English

1-(4-CHLOROPHENYL)-N,N-DIMETHYL-.ALPHA.-(2-METHYLPROPYL)CYCLOBUTANEMETHANAMINE

Systematic Name

English

MEDARIA

Brand Name

English

CF-ALLI

Brand Name

English

SIBUTRAMINE [VANDF]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175372