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Compound Detail

CHEMBL75094

PRINOMASTAT
🧪 Phase III
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🧪 Phase III
CC1(C)SCCN(S(=O)(=O)c2ccc(Oc3ccncc3)cc2)[C@H]1C(=O)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL75094
Name PRINOMASTAT
Phase Phase III
Structure Type MOL
InChI Key YKPYIPVDTNNYCN-INIZCTEOSA-N

Known Names

AG-3340 AG3340 KB-R-9896 Prinomastat
10
Targets
55
Activities
2
Assay Types
3
PK Parameters
20
Publications
4
Known Names
3
Indications

Molecular Properties

423.5
MW (Da)
2.26
ALogP
7
HBA
2
HBD
108.8
PSA (Ų)
0.56
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -stat
USAN Year 1999

Extended Properties

Molecular Formula C18H21N3O5S2
MW 423.52
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.86

Indications

Lung Neoplasms Prostatic Neoplasms, Castration-Resistant Central Nervous System Neoplasms

Activity Summary

IC50 36 meas. best 10.32
Ki 19 meas. best 10.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Collagenase 3
CHEMBL280
 Ki 10.52 10.4533 0.0 3
Stromelysin-1
CHEMBL283
 Ki 10.52 9.8867 0.0 3
Matrix metalloproteinase-9
CHEMBL321
 Ki 10.52 10.055 0.0 2
72 kDa type IV collagenase
CHEMBL333
 Ki 10.52 10.23 0.0 6
Matrix metalloproteinase-9
CHEMBL321
 IC50 10.32 9.558 0.0 5
72 kDa type IV collagenase
CHEMBL333
 IC50 10.32 9.5383 0.0 6
Collagenase 3
CHEMBL280
 IC50 9.7 9.16 0.2 4
Stromelysin-1
CHEMBL283
 IC50 9.64 8.866 0.2 5
Matrix metalloproteinase-14
CHEMBL3869
 IC50 9.52 9.52 0.3 1
Neutrophil collagenase
CHEMBL4588
 IC50 9.27 9.27 0.5 1
Interstitial collagenase
CHEMBL332
 IC50 8.31 7.8571 4.9 7
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 8.26 6.9 5.5 3
Interstitial collagenase
CHEMBL332
 Ki 8.09 8.0875 8.2 4
Matrilysin
CHEMBL4073
 IC50 7.27 7.15 54.0 3
Matrilysin
CHEMBL4073
 Ki 7.27 7.27 54.0 1
THP-1
CHEMBL614245
 IC50 5.07 5.07 8600.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 4864.0 nM Rattus norvegicus
T1/2 1.6 hr Rattus norvegicus
T1/2 1.6 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
72 kDa type IV collagenase Ki = 0.03 nM 10.52 Inhibition of MMP-2 (unknown origin) 34157437
Stromelysin-1 Ki = 0.03 nM 10.52 Inhibition of MMP-3 (unknown origin) 34157437
Matrix metalloproteinase-9 Ki = 0.03 nM 10.52 Inhibition of MMP-9 (unknown origin) 34157437
Collagenase 3 Ki = 0.03 nM 10.52 Inhibition of MMP-13 (unknown origin) 34157437
Collagenase 3 Ki = 0.038 nM 10.42 Inhibition of collagenase (Matrix metalloprotease-13) 10579818
Collagenase 3 Ki = 0.038 nM 10.42 Inhibition of matrix metalloprotease-13 (MMP-13). 10669559
Matrix metalloproteinase-9 IC50 = 0.048 nM 10.32 In vitro selective inhibition against Matrix metalloprotease-9 (MMP-9) using flu... 11754593
72 kDa type IV collagenase IC50 = 0.048 nM 10.32 In vitro selective inhibition against matrix metalloprotease-2 (MMP-2) using flu... 11754593
72 kDa type IV collagenase Ki = 0.05 nM 10.3 Inhibition of Matrix metalloprotease-2 14711305
72 kDa type IV collagenase Ki = 0.05 nM 10.3 Inhibition of human MMP-2 assessed as inhibition constant using MCA-Pro-Leu-Gly-... 32224379
72 kDa type IV collagenase Ki = 0.08 nM 10.1 Inhibition of human matrix metalloprotease-2 12217351
72 kDa type IV collagenase Ki = 0.083 nM 10.08 Inhibition of gelatinase-A (Matrix metalloprotease-2) 10579818
72 kDa type IV collagenase Ki = 0.083 nM 10.08 Inhibition of matrix metalloprotease-2 (MMP-2). 10669559
72 kDa type IV collagenase IC50 = 0.09 nM 10.05 Inhibition of human matrix metalloprotease-2 15713379
Collagenase 3 IC50 = 0.2 nM 9.7 Inhibition of Matrix metalloprotease-13 (MMP-13) in fluorimetric assay 11754593
Matrix metalloproteinase-9 IC50 = 0.2 nM 9.7 Inhibitory activity against matrix metalloprotease-9 (MMP9) 12930146
Matrix metalloproteinase-9 IC50 = 0.2 nM 9.7 Inhibition of Matrix metalloprotease-9 11212095
Stromelysin-1 IC50 = 0.23 nM 9.64 Inhibition of human matrix metalloprotease-3 15713379
Matrix metalloproteinase-9 IC50 = 0.26 nM 9.59 Inhibition of human matrix metalloprotease-9 15713379
Matrix metalloproteinase-9 Ki = 0.26 nM 9.59 Inhibition of human MMP-9 assessed as inhibition constant using MCA-Pro-Leu-Gly-... 32224379

Literature References

PubMed DOI Target Context # Activities
15713379 10.1016/j.bmcl.2005.01.024 Unchecked 4
14711305 10.1021/jm0308491 Unchecked 3
11549451 10.1016/s0960-894x(01)00487-5 Rattus norvegicus 3
10579818 10.1021/jm990330y Interstitial collagenase 2
10579818 10.1021/jm990330y 72 kDa type IV collagenase 2
31415980 10.1016/j.ejmech.2019.111563 A549 2
10579851 10.1021/jm990377j Disintegrin and metalloproteinase domain-containing protein 17 2
10579818 10.1021/jm990330y Stromelysin-1 2
10579818 10.1021/jm990330y Matrilysin 2
10579818 10.1021/jm990330y Collagenase 3 2
23287054 10.1016/j.ejmech.2012.10.016 Lewis lung carcinoma cell line 2
11133099 10.1016/s0960-894x(00)00584-9 72 kDa type IV collagenase 1
12217351 10.1016/s0960-894x(02)00564-4 72 kDa type IV collagenase 1
11133099 10.1016/s0960-894x(00)00584-9 Interstitial collagenase 1
11133099 10.1016/s0960-894x(00)00584-9 Collagenase 3 1
32224379 10.1016/j.ejmech.2020.112260 72 kDa type IV collagenase 1
11212095 10.1016/s0960-894x(00)00646-6 Stromelysin-1 1
11212095 10.1016/s0960-894x(00)00646-6 Interstitial collagenase 1
12930146 10.1021/jm0307638 Collagenase 3 1
12930146 10.1021/jm0307638 Stromelysin-1 1

Data from ChEMBL 36 via Core Engine