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Compound Detail

CHEMBL76222

REBIMASTAT
🧪 Phase II
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🧪 Phase II
CNC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](S)CCN1C(=O)N(C)C(C)(C)C1=O)C(C)(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL76222
Name REBIMASTAT
Phase Phase II
Structure Type MOL
InChI Key GTXSRFUZSLTDFX-HRCADAONSA-N

Known Names

BMS 275291-01 BMS-275291 BMS-275291-01 D-2163 D2163 Rebimastat
6
Targets
12
Activities
1
Assay Types
0
PK Parameters
12
Publications
6
Known Names
4
Indications
6
Mechanisms

Molecular Properties

499.7
MW (Da)
1.16
ALogP
6
HBA
4
HBD
127.9
PSA (Ų)
0.26
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -stat
USAN Year 2003

Extended Properties

Molecular Formula C23H41N5O5S
MW 499.68
Aromatic Rings 0
Heavy Atoms 34
NP-Likeness 0.02

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Matrix metalloproteinase 9 inhibitor INHIBITOR Matrix metalloproteinase-9 ✓ ✓
Matrix metalloproteinase 14 inhibitor INHIBITOR Matrix metalloproteinase-14 ✓ ✓
Matrix metalloproteinase 8 inhibitor INHIBITOR Neutrophil collagenase ✓ ✓
Matrix metalloproteinase 13 inhibitor INHIBITOR Collagenase 3 ✓ ✓
Matrix metalloproteinase-1 inhibitor INHIBITOR Interstitial collagenase ✓ ✓
Matrix metalloproteinase-2 inhibitor INHIBITOR 72 kDa type IV collagenase ✓ ✓

Indications

Breast Neoplasms Lung Neoplasms Prostatic Neoplasms Sarcoma

Activity Summary

IC50 12 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Interstitial collagenase
CHEMBL332
 IC50 8.05 7.825 9.0 2
Matrilysin
CHEMBL4073
 IC50 7.64 7.64 23.0 1
Matrix metalloproteinase-9
CHEMBL321
 IC50 7.6 7.59 25.0 3
72 kDa type IV collagenase
CHEMBL333
 IC50 7.41 7.3967 39.0 3
Matrix metalloproteinase-14
CHEMBL3869
 IC50 7.4 7.4 40.0 1
Stromelysin-1
CHEMBL283
 IC50 6.8 6.8 157.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Interstitial collagenase IC50 = 9.0 nM 8.05 Inhibition of MMP-1 (unknown origin) 34157437
Matrilysin IC50 = 23.0 nM 7.64 Inhibition of MMP-7 (unknown origin) 34157437
Interstitial collagenase IC50 = 25.0 nM 7.6 In vitro selective inhibition against matrix metalloprotease-1 (MMP-1) using a f... 11754593
Matrix metalloproteinase-9 IC50 = 25.0 nM 7.6 In vitro selective inhibition against Matrix metalloprotease-9 (MMP-9) using flu... 11754593
Matrix metalloproteinase-9 IC50 = 25.0 nM 7.6 Inhibition of MMP-9 (unknown origin) 32224379
Matrix metalloproteinase-9 IC50 = 27.0 nM 7.57 Inhibition of MMP-9 (unknown origin) 34157437
72 kDa type IV collagenase IC50 = 39.0 nM 7.41 Inhibition of MMP-2 (unknown origin) 34157437
Matrix metalloproteinase-14 IC50 = 40.0 nM 7.4 Inhibition of MMP-14 (unknown origin) 34157437
72 kDa type IV collagenase IC50 = 41.0 nM 7.39 In vitro selective inhibition against matrix metalloprotease-2 (MMP-2) using flu... 11754593
72 kDa type IV collagenase IC50 = 41.0 nM 7.39 Inhibition of MMP-2 (unknown origin) 32224379
Stromelysin-1 IC50 = 157.0 nM 6.8 Inhibition of Matrix metalloprotease-3 (MMP-3) in fluorimetric assay 11754593
Stromelysin-1 IC50 = 157.0 nM 6.8 Inhibition of MMP-3 (unknown origin) 34157437

Literature References

PubMed DOI Target Context # Activities
11754593 10.1021/jm0103920 Interstitial collagenase 1
11754593 10.1021/jm0103920 72 kDa type IV collagenase 1
11754593 10.1021/jm0103920 Stromelysin-1 1
11754593 10.1021/jm0103920 Matrix metalloproteinase-9 1
34157437 10.1016/j.ejmech.2021.113623 Interstitial collagenase 1
34157437 10.1016/j.ejmech.2021.113623 72 kDa type IV collagenase 1
34157437 10.1016/j.ejmech.2021.113623 Stromelysin-1 1
34157437 10.1016/j.ejmech.2021.113623 Matrix metalloproteinase-9 1
34157437 10.1016/j.ejmech.2021.113623 Matrix metalloproteinase-14 1
34157437 10.1016/j.ejmech.2021.113623 Matrilysin 1
32224379 10.1016/j.ejmech.2020.112260 Matrix metalloproteinase-9 1
32224379 10.1016/j.ejmech.2020.112260 72 kDa type IV collagenase 1

Data from ChEMBL 36 via Core Engine