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Compound Detail

CHEMBL127516

BUTAMBEN
💊 Approved Drug
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💊 Approved Drug
CCCCOC(=O)c1ccc(N)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL127516
Name BUTAMBEN
Phase Approved
Structure Type MOL
InChI Key IUWVALYLNVXWKX-UHFFFAOYSA-N

Known Names

ABBOTT-34842 FREE BASE Butamben Butesin Butyl aminobenzoate Butyl p-aminobenzoate Butyl paba NSC-128464 P-aminobenzoic acid butyl ester
1
Targets
5
Activities
1
Assay Types
0
PK Parameters
20
Publications
8
Known Names
2
Mechanisms

Molecular Properties

193.2
MW (Da)
2.23
ALogP
3
HBA
1
HBD
52.3
PSA (Ų)
0.45
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product
USAN Year 1975

Extended Properties

Molecular Formula C11H15NO2
MW 193.25
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness -0.25

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Transient receptor potential cation channel subfamily V member 4 inhibitor INHIBITOR Transient receptor potential cation channel subfamily V member 4 ✓ ✓
Transient receptor potential cation channel subfamily A member 1 inhibitor INHIBITOR Transient receptor potential cation channel subfamily A member 1 ✓ ✓

Drug Warnings

Withdrawn
neurotoxicity
associated with severe adverse reactions, such as severe tissue slough and transverse myelitis
Country: United States   Year: 1964
Withdrawn
dermatological toxicity
associated with severe adverse reactions, such as severe tissue slough and transverse myelitis
Country: United States   Year: 1964

Activity Summary

IC50 5 meas. best 6.86

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.86 5.92 136.8 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 136.8 nM 6.86 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Unchecked IC50 = 586.0 nM 6.23 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 4564.5 nM 5.34 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 5607.5 nM 5.25 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 290
22041064 10.1016/j.bmcl.2011.10.020 Bone morphogenetic protein 2 7
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
37468498 10.1038/s41467-023-40064-9 Androgen receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
2579237 10.1021/jm00381a019 Sodium channel alpha subunits; brain (Types I, II, III) 2
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
22961681 10.1124/dmd.112.047068 Bile salt export pump 1

Data from ChEMBL 36 via Core Engine