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is metabolized to metabolites M1 and M2 which are more active toward the monoamine transporters.The drug was withdrawn from the market because of clinical trial data indicating an increased risk of heart attack and stroke.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 40 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 8228	298.0 nM [Ki]
Sodium-dependent dopamine transporter 42 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 8228	943.0 nM [Ki]
Sodium-dependent noradrenaline transporter 38 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 8228	5451.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 204 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf	Primary		Withdrawn	MERIDIA Approved Use MERIDIA is indicated for the management of obesity, including weight loss and maintenance of weight loss, and should be used in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 8.801568E11

C_max

Value	Dose	Analyte	Population
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
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
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
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
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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
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
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
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
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

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
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
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
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
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
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

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 (max) 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 Page: 14	unhealthy, adult n = 2068 Health Status: unhealthy Condition: obesity Age Group: adult Sex: unknown Population Size: 2068 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020632s034s035lbl.pdf Page: 14	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 Page: 14
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 n = 7 Health Status: unhealthy Condition: vasovagal syncope Age Group: mean 32 years Sex: M+F Population Size: 7 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 n = 7 Health Status: unhealthy Condition: vasovagal syncope Age Group: mean 32 years Sex: M+F Population Size: 7 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 n = 146 Health Status: unhealthy Condition: obesity Age Group: mean 42.9 years Sex: M+F Population Size: 146 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 n = 203 Health Status: unhealthy Condition: obesity Age Group: mean 43.3 years Sex: M+F Population Size: 203 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 n = 151 Health Status: unhealthy Condition: obesity Age Group: mean 43.4 years Sex: M+F Population Size: 151 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 n = 169 Health Status: unhealthy Condition: obesity Age Group: mean 43.4 years Sex: M+F Population Size: 169 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 n = 196 Health Status: unhealthy Condition: obesity Age Group: mean 44.2 years Sex: M+F Population Size: 196 Sources: https://pubmed.ncbi.nlm.nih.gov/10102256/	Disc. AE: Hypertension, Tachycardia... Other AEs: Dizziness, Dry mouth... AEs leading to discontinuation/dose reduction: Hypertension (<2%) Tachycardia (<3%) Other AEs: Dizziness (8.2%) 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%) 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 n = 149 Health Status: unhealthy Condition: obesity Age Group: mean 44.5 years Sex: M+F Population Size: 149 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 1709	inhibitor 1752 substrate 1010	inhibitor 1837 substrate 1193	inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2A6 704 CYP2B6 799 CYP2C8 901 CYP2C19 1463 CYP2E1 876 CYP3A 211 OCT2 638	CYP1A2 1032 CYP2A6 523 CYP2B6 660 CYP2C8 688 CYP2C19 985 CYP2E1 648 CYP3A5 391

Drug as perpetrator

Target	Modality	Activity
CYP2B6 985	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 0.829 uM]
CYP2D6 1875	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 15.6 uM]
OCT2 639	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/19002438/	yes [IC50 29 uM]
CYP1A2 1673	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP2A6 736	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP2C19 1537	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP2C8 955	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP2C9 1803	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP2E1 964	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]
CYP3A 295	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23777987/ Page: 5.0	yes [IC50 >50 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1032	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2A6 523	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2C8 688	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2C9 1010	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2D6 1193	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2E1 648	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	no
CYP2B6 660	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	yes
CYP2C19 985	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	yes
CYP3A5 391	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/18474675/ Page: 5.0	yes
CYP3A4 1709	substrate 3326 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 1632	inhibitor 1613 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
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
LGC Standards	DRE-C16944000	https://www.lgcstandards.com/US/en/p/DRE-C16944000
Lab Network	LN00643799	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00643799
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
abcr GmbH	AB376861	http://www.abcr.de/shop/en/AB376861
eNovation Chemicals	D320135	http://www.enovationchem.com/productDetails.asp?productID=D320135

PubMed

Title	Date	PubMed
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
Effects of sibutramine on ventricular dimensions and heart valves in obese patients during weight reduction.	2002 Sep	12228789
Long-term pharmacotherapy for overweight and obesity: a systematic review and meta-analysis of randomized controlled trials.	2003 Dec	12975638
[Pharmacotherapy of obesity].	2004 Oct 7	15532736
Optimal treatment of obesity-related hypertension: the Hypertension-Obesity-Sibutramine (HOS) study.	2007 Apr 17	17404163
Myocardial infarction induced by appetite suppressants in Malaysia.	2007 Nov 1	17978302
Sibutramine versus continuous positive airway pressure in obese obstructive sleep apnoea patients.	2009 Sep	19357147
Diabesity: therapeutic options.	2010 Jun	20518802
Elevation of QT dispersion after obesity drug sibutramine.	2010 Nov	20671571
[Long-term effects of weight-reducing drugs in hypertensive patients--a survey of a Cochrane review].	2011 Feb 21	21333255
Effects of oral anorexiant sibutramine on the expression of cytochromes P450s in human hepatocytes and cancer cell lines.	2013 Dec	24038852

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 `Thu Jul 06 23:06:04 UTC 2023` Edited by `admin` on `Thu Jul 06 23:06:04 UTC 2023`
Record UNII	WV5EC51866
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

BUTRAMIN

Brand 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