Prinomastat

Prinomastat (code name AG-3340) is a matrix metalloproteinase (MMP) inhibitor with specific selectivity for MMPs 2, 3, 9, 13, and 14. Investigations have been carried out to determine whether the inhibition of these MMPs is able to block tumour metastasis by preventing MMP degradation of the extracellular matrix proteins and angiogenesis. Prinomastat underwent a Phase III trial to investigate its effectiveness against non-small cell lung cancer (NSCLC), in combination with gemcitabine chemotherapy. However, it was discovered that Prinomastat did not improve the outcome of chemotherapy in advanced non-small-cell lung cancer.^[1][2]

Prinomastat

Clinical data
ATC code	None
Pharmacokinetic data
Elimination half-life	1–5 hours[1]
Identifiers
IUPAC name (3S)-N-Hydroxy-2,2-dimethyl-4-(4-pyridin-4-yloxyphenyl)sulfonylthiomorpholine-3-carboxamide
CAS Number	192329-42-3
PubChem CID	466151
IUPHAR/BPS	6505
ChemSpider	409762
UNII	10T6626FRK
ChEMBL	ChEMBL75094
CompTox Dashboard (EPA)	DTXSID3043946
Chemical and physical data
Formula	C18H21N3O5S2
Molar mass	423.50 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1([C@@H](N(CCS1)S(=O)(=O)C2=CC=C(C=C2)OC3=CC=NC=C3)C(=O)NO)C
InChI 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 Key:YKPYIPVDTNNYCN-INIZCTEOSA-N