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Compound Detail

CHEMBL1419

SIBUTRAMINE
💊 Approved Drug
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💊 Approved Drug
CC(C)CC(N(C)C)C1(c2ccc(Cl)cc2)CCC1

Basic Information

ChEMBL ID CHEMBL1419
Name SIBUTRAMINE
Phase Approved
Structure Type MOL
InChI Key UNAANXDKBXWMLN-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Butramin Cf-alli Medaria Racemic sibutramine Reductil Sibutramina Sibutramine
7
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
7
Known Names
1
Indications

Molecular Properties

279.9
MW (Da)
4.74
ALogP
1
HBA
0
HBD
3.2
PSA (Ų)
0.75
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Withdrawn
Chirality Racemic

Routes of Administration

Oral

Flags

Withdrawn Natural Product
USAN Year 1990

Extended Properties

Molecular Formula C17H26ClN
MW 279.86
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness 0.03

Indications

Obesity

ATC Classification

A08AA10
sibutramine
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS

Drug Warnings

Withdrawn
neurotoxicity
Increased risk of heart attack and stroke
Country: India; European Union; Hong Kong; United States; New Zealand; Canada; Indonesia; Egypt; Guatemala; Australia   Year: 2010
Withdrawn
cardiotoxicity
Higher rate of cardiovascular events in obese and overweight patients using sibutramine than in patients managing their weight through exercise and diet alone
Country: India; European Union; Hong Kong; United States; New Zealand; Canada; Indonesia; Egypt; Guatemala; Australia   Year: 2010
Withdrawn
cardiotoxicity
Increased risk of heart attack and stroke
Country: India; European Union; Hong Kong; United States; New Zealand; Canada; Indonesia; Egypt; Guatemala; Australia   Year: 2010
Withdrawn
cardiotoxicity
Increase of risk of cardivascular events in patients with history of cardiovascular disease; Based on data from the SCOUT trial (which showed a higher rate of cardiovascular events in obese and overwe...
Country: India; European Union; Hong Kong; United States; New Zealand; Canada; Indonesia; Egypt; Guatemala; Australia   Year: 2010
Withdrawn
cardiotoxicity
Increased risk of heart attack and stroke
Country: India; European Union; Hong Kong; United States; New Zealand; Canada; Indonesia; Egypt; Guatemala; Australia   Year: 2010

Activity Summary

IC50 6 meas. best 6.2
Ki 6 meas. best 6.3
EC50 2 meas. best 5.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL238
Ki 6.3 6.3 502.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 6.2 6.2 632.0 1
Unchecked
CHEMBL612545
Ki 6.14 5.86 719.0 2
Unchecked
CHEMBL612545
IC50 6.09 5.83 809.0 2
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 5.96 5.96 1091.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 5.96 5.96 1108.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 5.68 5.68 2085.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 5.62 5.62 2390.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.25 5.25 5665.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.25 5.25 5619.0 1
Trypanosoma cruzi
CHEMBL368
EC50 5.1 5.1 8000.0 1
ADMET
CHEMBL612558
EC50 5.0 5.0 10000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter Ki = 502.0 nM 6.3 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -
Sodium-dependent dopamine transporter IC50 = 632.0 nM 6.2 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -
Unchecked Ki = 719.0 nM 6.14 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Unchecked IC50 = 809.0 nM 6.09 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Alpha-2B adrenergic receptor Ki = 1091.0 nM 5.96 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Sodium-dependent serotonin transporter Ki = 1108.0 nM 5.96 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Sodium-dependent serotonin transporter IC50 = 2085.0 nM 5.68 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Alpha-2B adrenergic receptor IC50 = 2390.0 nM 5.62 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Unchecked Ki = 2647.0 nM 5.58 DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand... -
Unchecked IC50 = 2722.0 nM 5.57 DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand... -
Sodium-dependent noradrenaline transporter IC50 = 5665.0 nM 5.25 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Sodium-dependent noradrenaline transporter Ki = 5619.0 nM 5.25 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Trypanosoma cruzi EC50 = 8000.0 nM 5.1 Antitrypanosomal activity against Trypanosoma cruzi amastigotes infected in BESM... 20547819
ADMET EC50 = 10000.0 nM 5.0 Cytotoxicity against BESM cells after 88 hrs by HTS assay 20547819

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 270
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20392645 10.1016/j.bmc.2010.03.055 Rattus norvegicus 5
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2
22309223 10.1021/jm201596h Rattus norvegicus 2
37468498 10.1038/s41467-023-40064-9 Alpha-2C adrenergic receptor 2
19773162 10.1016/j.bmcl.2009.09.003 Rattus norvegicus 2
26736071 10.1021/acs.jmedchem.5b01704 Rattus norvegicus 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine