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Compound Detail

CHEMBL146095

GLAFENINE
💊 Approved Drug
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💊 Approved Drug
O=C(OCC(O)CO)c1ccccc1Nc1ccnc2cc(Cl)ccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL146095
Name GLAFENINE
Phase Approved
Structure Type MOL
InChI Key GWOFUCIGLDBNKM-UHFFFAOYSA-N

Known Names

Glafenin Glafenina Glafenine NSC-757808 R 1707 R-1707
2
Targets
2
Activities
1
Assay Types
0
PK Parameters
20
Publications
6
Known Names
2
Indications
1
Mechanisms

Molecular Properties

372.8
MW (Da)
3.14
ALogP
6
HBA
3
HBD
91.7
PSA (Ų)
0.58
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Racemic

Flags

Withdrawn Natural Product
USAN Stem -fenine

Extended Properties

Molecular Formula C19H17ClN2O4
MW 372.81
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -0.52

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclooxygenase inhibitor INHIBITOR Cyclooxygenase ✓ ✓

Indications

Fever Pain

ATC Classification

N02BG03
glafenine
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Drug Warnings

Withdrawn
immune system toxicity
associated with severe allergic responses, including anaphylactoid reactions
Country: Worldwide   Year: 1984
Withdrawn
immune system toxicity
associated with severe allergic responses, including anaphylactoid reactions
Country: Worldwide   Year: 1984
Withdrawn
immune system toxicity
associated with severe allergic responses, including anaphylactoid reactions
Country: Worldwide   Year: 1984
Withdrawn
immune system toxicity
associated with severe allergic responses, including anaphylactoid reactions; reports of anaphylactic shock
Country: Worldwide   Year: 1984

Activity Summary

IC50 2 meas. best 4.65

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bile salt export pump
CHEMBL6020
 IC50 4.65 4.65 22300.0 1
Bile salt export pump
CHEMBL2073674
 IC50 4.49 4.49 32200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bile salt export pump IC50 = 22300.0 nM 4.65 Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells ass... 21965623
Bile salt export pump IC50 = 32200.0 nM 4.49 Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of S... 21965623

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 4
458805 10.1021/jm00191a017 Mus musculus 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 4
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 4
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 3
8386248 10.1021/jm00056a010 Mus musculus 3
37468498 10.1038/s41467-023-40064-9 Adenosine receptor A3 2
22931300 10.1021/tx300075j Liver microsomes 2

Data from ChEMBL 36 via Core Engine