Prinomastat

Prinomastat
Clinical data
ATC code	None;
Pharmacokinetic data
Elimination half-life	1–5 hours
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	423.5 g/mol 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;

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]

References

^ ^a ^b Bissett D, O'Byrne KJ, von Pawel J, Gatzemeier U, Price A, Nicolson M, Mercier R, Mazabel E, Penning C, Zhang MH, Collier MA, Shepherd FA (February 2005). "Phase III study of matrix metalloproteinase inhibitor prinomastat in non-small-cell lung cancer" (PDF). Journal of Clinical Oncology. 23 (4): 842–9. doi:10.1200/JCO.2005.03.170. PMID 15681529.
^ Hande, KR; Collier, M; Paradiso, L; Stuart-Smith, J; Dixon, M; Clendeninn, N; Yeun, G; Alberti, D; Binger, K; Wilding, G (February 2004). "Phase I and pharmacokinetic study of prinomastat, a matrix metalloprotease inhibitor" (PDF). Clinical Cancer Research. 10 (3): 909–15. doi:10.1158/1078-0432.CCR-0981-3. PMID 14871966.