Prinomastat

Chemical compound
  • None
Pharmacokinetic dataElimination half-life1–5 hours[1]Identifiers
  • (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 Edit this at Wikidata
Chemical and physical dataFormulaC18H21N3O5S2Molar mass423.50 g·mol−13D model (JSmol)
  • Interactive image
  • 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

  1. ^ a b Bissett D, O'Byrne KJ, von Pawel J, Gatzemeier U, Price A, Nicolson M, et al. (February 2005). "Phase III study of matrix metalloproteinase inhibitor prinomastat in non-small-cell lung cancer". Journal of Clinical Oncology. 23 (4): 842–849. doi:10.1200/JCO.2005.03.170. PMID 15681529.
  2. ^ Hande KR, Collier M, Paradiso L, Stuart-Smith J, Dixon M, Clendeninn N, et al. (February 2004). "Phase I and pharmacokinetic study of prinomastat, a matrix metalloprotease inhibitor". Clinical Cancer Research. 10 (3): 909–915. doi:10.1158/1078-0432.CCR-0981-3. PMID 14871966.