CHEBI:138885 - prinomastat

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ChEBI Name prinomastat
Definition A hydroxamic acid that is (3S)-N-hydroxy-2,2-dimethylthiomorpholine-3-carboxamide in which the hydrogen attached to the thiomorpholine nitrogen has been replaced by a [4-(pyridin-4-yloxy)phenyl]sulfonyl group. It is a selective inhibitor with of matrix metalloproteinases (MMPs) 2, 3, 9, 13, and 14.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H21N3O5S2
Net Charge 0
Average Mass 423.509
Monoisotopic Mass 423.09226
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
SMILES S(=O)(=O)(N1[C@H](C(SCC1)(C)C)C(=O)NO)C2=CC=C(OC3=CC=NC=C3)C=C2
Roles Classification
Biological Role(s): matrix metalloproteinase inhibitor

EC (gelatinase B) inhibitor
An EC 3.4.24.* (metalloendopeptidase) inhibitor that interferes with the action of gelatinase B (EC
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing prinomastat (CHEBI:138885) has role antineoplastic agent (CHEBI:35610)
prinomastat (CHEBI:138885) has role EC (gelatinase B) inhibitor (CHEBI:79088)
prinomastat (CHEBI:138885) has role matrix metalloproteinase inhibitor (CHEBI:50664)
prinomastat (CHEBI:138885) is a aromatic ether (CHEBI:35618)
prinomastat (CHEBI:138885) is a hydroxamic acid (CHEBI:24650)
prinomastat (CHEBI:138885) is a pyridines (CHEBI:26421)
prinomastat (CHEBI:138885) is a sulfonamide (CHEBI:35358)
prinomastat (CHEBI:138885) is a thiomorpholines (CHEBI:36393)
prinomastat (CHEBI:138885) is conjugate base of prinomastat(1+) (CHEBI:138886)
Incoming prinomastat(1+) (CHEBI:138886) is conjugate acid of prinomastat (CHEBI:138885)
INNs Sources
prinomastat WHO MedNet
prinomastat WHO MedNet
prinomastat WHO MedNet
prinomastatum WHO MedNet
Synonyms Sources
(S)-2,2-dimethyl-4-{[p-(4-pyridyloxy)phenyl]sulfonyl}-3-thiomorpholinecarbohydroxamic acid ChemIDplus
AG 3340 ChemIDplus
AG-3340 ChemIDplus
AG3340 ChemIDplus
Manual Xrefs Databases
DB05100 DrugBank
PN0 PDBeChem
Prinomastat Wikipedia
US5753653 Patent
WO9720824 Patent
View more database links
Registry Number Type Source
192329-42-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10980656 PubMed citation Europe PMC
11114600 PubMed citation Europe PMC
11436949 PubMed citation Europe PMC
11726397 PubMed citation Europe PMC
12187478 PubMed citation Europe PMC
12187492 PubMed citation Europe PMC
14871966 PubMed citation Europe PMC
15279727 PubMed citation Europe PMC
15492635 PubMed citation Europe PMC
15681529 PubMed citation Europe PMC
16103944 PubMed citation Europe PMC
16502351 PubMed citation Europe PMC
22308038 PubMed citation Europe PMC
23403478 PubMed citation Europe PMC
Last Modified
27 October 2017