Prinomastat

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Prinomastat
Clinical data
ATC code
  • None
Pharmacokinetic data
Elimination half-life1–5 hours[1]
Identifiers
  • (3S)-N-Hydroxy-2,2-dimethyl-4-(4-pyridin-4-yloxyphenyl)sulfonylthiomorpholine-3-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H21N3O5S2
Molar mass423.50 g·mol−1
3D model (JSmol)
  • CC1([C@@H](N(CCS1)S(=O)(=O)C2=CC=C(C=C2)OC3=CC=NC=C3)C(=O)NO)C
  • 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.
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