| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H21N3O5S2 |
| Molecular Weight | 423.506 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)SCCN([C@H]1C(=O)NO)S(=O)(=O)C2=CC=C(OC3=CC=NC=C3)C=C2
InChI
InChIKey=YKPYIPVDTNNYCN-INIZCTEOSA-N
InChI=1S/C18H21N3O5S2/c1-18(2)16(17(22)20-23)21(11-12-27-18)28(24,25)15-5-3-13(4-6-15)26-14-7-9-19-10-8-14/h3-10,16,23H,11-12H2,1-2H3,(H,20,22)/t16-/m0/s1
| Molecular Formula | C18H21N3O5S2 |
| Molecular Weight | 423.506 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Prinomastat is a synthetic hydroxamic acid derivative with potential antineoplastic activity. Prinomastat inhibits matrix metalloproteinases (MMPs) (specifically, MMP-2, 9, 13, and 14), thereby inducing extracellular matrix degradation, and inhibiting angiogenesis, tumor growth and invasion, and metastasis. As a lipophilic agent, prinomastat crosses the blood-brain barrier. Pfizer conducted multicenter, randomized, double-bind, placebo-controlled trials to evaluate the safety and efficacy of prinomastat in combination with standard chemotherapy in patients with advanced hormone refractory prostate cancer and non-small cell lung cancer. However, this study has been terminated for the reason that Prinomastat did not improve the outcome of chemotherapy in non-small cell Lung cancer patients.
CNS Activity
Originator
Approval Year
Cmax
AUC
T1/2
Sourcing
PubMed
Patents
Sample Use Guides
15 mg twice daily orally continuously, in combination with gemcitabine 1,250 mg/m2 days 1 and 8 plus cisplatin 75 mg/m2 day 1, every 21 days for up to six cycles.
Route of Administration:
Oral
Prinomastat did not significantly inhibit glioma cell growth at concentrations of 100
nM to 100 uM using BrdUrd staining, [3
H]thymidine labeling, or
the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide
assay; significant inhibition of proliferation occurred only
at concentrations of 1 mM
