Details of the Drug

General Information of Drug (ID: DM9HOKG)

Drug Name

Prinomastat

Synonyms

AG-3354; AG-3362; Prinomastat (USAN/INN); (3S)-N-hydroxy-2,2-dimethyl-4-(4-pyridin-4-yloxyphenyl)sulfonylthiomorpholine-3-carboxamide

Indication

Disease Entry	ICD 11	Status	REF
Lung cancer	2C25.0	Approved	[1]
Brain cancer	2A00	Discontinued in Phase 3	[1]
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Therapeutic Class

Anticancer Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

423.5

Logarithm of the Partition Coefficient (xlogp)

1.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Half-life: The concentration or amount of drug in body reduced by one-half in 2 - 5 hours [2]

Chemical Identifiers

Formula: C18H21N3O5S2
IUPAC Name: (3S)-N-hydroxy-2,2-dimethyl-4-(4-pyridin-4-yloxyphenyl)sulfonylthiomorpholine-3-carboxamide
Canonical 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
InChIKey: YKPYIPVDTNNYCN-INIZCTEOSA-N

Cross-matching ID

Repurposed Drugs (RPD)

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Matrix metalloproteinase-1 (MMP-1)	TTMX39J	MMP1_HUMAN	Inhibitor	[3]
Matrix metalloproteinase-2 (MMP-2)	TTLM12X	MMP2_HUMAN	Inhibitor	[3]
Matrix metalloproteinase-7 (MMP-7)	TTMTWOS	MMP7_HUMAN	Inhibitor	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[4]
Collagenase 3 (MMP13)	OTY8BZIE	MMP13_HUMAN	Gene/Protein Processing	[4]
Neutrophil collagenase (MMP8)	OTZXH19L	MMP8_HUMAN	Gene/Protein Processing	[4]
Stromelysin-1 (MMP3)	OTGBI74Z	MMP3_HUMAN	Gene/Protein Processing	[4]

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Molecular Interaction Atlas (MIA)

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6505).
2	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3	AG-3340 (Agouron Pharmaceuticals Inc). IDrugs. 2000 Mar;3(3):336-45.
4	Synthesis and in vitro evaluation of targeted tetracycline derivatives: effects on inhibition of matrix metalloproteinases. Bioorg Med Chem. 2007 Mar 15;15(6):2368-74. doi: 10.1016/j.bmc.2007.01.026. Epub 2007 Jan 19.