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Prinomastat

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Overview

Structure
DrugBank ID
DB05100
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
1
Phase 3
2
Phase 4
0
Mechanism of Action

Identification

Generic Name
Prinomastat
DrugBank Accession Number
DB05100
Background

Prinomastat is a synthetic hydroxamic acid derivative with potential antineoplastic activity. Prinomastat inhibits matrix metalloproteinases (MMPs) (specifically, MMP-2, 9, 13, and 14), thereby inducing extracellular matrix degradation, and inhibiting angiogenesis, tumor growth and invasion, and metastasis. As a lipophilic agent, prinomastat crosses the blood-brain barrier.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 423.506
Monoisotopic: 423.092262177
Chemical Formula
C18H21N3O5S2
Synonyms
  • Prinomastat
  • Prinomastatum
External IDs
  • AG-3340
  • AG3340
  • KB-R 9896
  • KB-R-9896
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Pharmacology

Indication

Investigated for use/treatment in brain cancer, lung cancer, and prostate cancer.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
A72 kDa type IV collagenase
inhibitor
Humans
AInterstitial collagenase
inhibitor
Humans
AMatrilysin
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

2-5 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Prinomastat

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Ethers
Direct Parent
Diarylethers
Alternative Parents
Alpha amino acids and derivatives / Benzenesulfonamides / Benzenesulfonyl compounds / Phenoxy compounds / Phenol ethers / Thiomorpholines / Pyridines and derivatives / Organosulfonamides / Sulfonyls / Heteroaromatic compounds
show 8 more
Substituents
1,4-thiazinane / Alpha-amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Carbonyl group / Carboxylic acid derivative / Dialkylthioether
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
10T6626FRK
CAS number
192329-42-3
InChI Key
YKPYIPVDTNNYCN-INIZCTEOSA-N
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
IUPAC Name
(3S)-N-hydroxy-2,2-dimethyl-4-[4-(pyridin-4-yloxy)benzenesulfonyl]thiomorpholine-3-carboxamide
SMILES
CC1(C)SCCN([C@H]1C(=O)NO)S(=O)(=O)C1=CC=C(OC2=CC=NC=C2)C=C1

References

General References
  1. Shalinsky DR, Brekken J, Zou H, McDermott CD, Forsyth P, Edwards D, Margosiak S, Bender S, Truitt G, Wood A, Varki NM, Appelt K: Broad antitumor and antiangiogenic activities of AG3340, a potent and selective MMP inhibitor undergoing advanced oncology clinical trials. Ann N Y Acad Sci. 1999 Jun 30;878:236-70. [Article]
  2. Deryugina EI, Ratnikov BI, Strongin AY: Prinomastat, a hydroxamate inhibitor of matrix metalloproteinases, has a complex effect on migration of breast carcinoma cells. Int J Cancer. 2003 May 1;104(5):533-41. [Article]
  3. Scatena R: Prinomastat, a hydroxamate-based matrix metalloproteinase inhibitor. A novel pharmacological approach for tissue remodelling-related diseases. Expert Opin Investig Drugs. 2000 Sep;9(9):2159-65. [Article]
KEGG Drug
D03797
PubChem Compound
466151
PubChem Substance
175426943
ChemSpider
409762
BindingDB
50082556
ChEBI
138885
ChEMBL
CHEMBL75094
ZINC
ZINC000000580328
PDBe Ligand
PN0
Wikipedia
Prinomastat
PDB Entries
3qm4 / 3tda / 6csd

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data
3CompletedTreatmentLung Cancer1somestatusstop reasonjust information to hide
3CompletedTreatmentProstate Cancer1somestatusstop reasonjust information to hide
2CompletedTreatmentBrain and Central Nervous System Tumors1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0986 mg/mLALOGPS
logP1.88ALOGPS
logP1.2Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.7Chemaxon
pKa (Strongest Basic)5.94Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area108.83 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity105.87 m3·mol-1Chemaxon
Polarizability41.19 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9508
Blood Brain Barrier-0.5364
Caco-2 permeable-0.6419
P-glycoprotein substrateNon-substrate0.7148
P-glycoprotein inhibitor INon-inhibitor0.6303
P-glycoprotein inhibitor IINon-inhibitor0.6027
Renal organic cation transporterNon-inhibitor0.8762
CYP450 2C9 substrateNon-substrate0.717
CYP450 2D6 substrateNon-substrate0.8124
CYP450 3A4 substrateNon-substrate0.5304
CYP450 1A2 substrateNon-inhibitor0.734
CYP450 2C9 inhibitorNon-inhibitor0.6707
CYP450 2D6 inhibitorNon-inhibitor0.8338
CYP450 2C19 inhibitorNon-inhibitor0.5746
CYP450 3A4 inhibitorNon-inhibitor0.8131
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6747
Ames testNon AMES toxic0.616
CarcinogenicityNon-carcinogens0.5532
BiodegradationNot ready biodegradable0.9971
Rat acute toxicity2.4167 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8634
hERG inhibition (predictor II)Non-inhibitor0.6423
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0000900000-298f1e2cb67438b9c4df
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0101900000-95672bdac1ee3895d843
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-008c-4139100000-f30981d8ffe4086fb5d6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0412900000-169295fe9ae2bd51994a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0934000000-cc5edb8b706d214f8c27
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05pn-2629000000-15d1a97d74121e20def3
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-209.6395601
predicted
DarkChem Lite v0.1.0
[M-H]-184.42932
predicted
DeepCCS 1.0 (2019)
[M+H]+209.9554601
predicted
DarkChem Lite v0.1.0
[M+H]+186.78731
predicted
DeepCCS 1.0 (2019)
[M+Na]+209.3885601
predicted
DarkChem Lite v0.1.0
[M+Na]+193.78812
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. 72 kDa type IV collagenase
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Ubiquitinous metalloproteinase that is involved in diverse functions such as remodeling of the vasculature, angiogenesis, tissue repair, tumor invasion, inflammation, and atherosclerotic plaque rupture. As well as degrading extracellular matrix proteins, can also act on several nonmatrix proteins such as big endothelial 1 and beta-type CGRP promoting vasoconstriction. Also cleaves KISS at a Gly-|-Leu bond. Appears to have a role in myocardial cell death pathways. Contributes to myocardial oxidative stress by regulating the activity of GSK3beta. Cleaves GSK3beta in vitro. Involved in the formation of the fibrovascular tissues in association with MMP14
Specific Function
endopeptidase activity
Gene Name
MMP2
Uniprot ID
P08253
Uniprot Name
72 kDa type IV collagenase
Molecular Weight
73881.695 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Details2. Interstitial collagenase
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X (PubMed:1645757, PubMed:2153297, PubMed:2557822). In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity (PubMed:16807369)
Specific Function
endopeptidase activity
Gene Name
MMP1
Uniprot ID
P03956
Uniprot Name
Interstitial collagenase
Molecular Weight
54006.61 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Details3. Matrilysin
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Degrades casein, gelatins of types I, III, IV, and V, and fibronectin. Activates procollagenase
Specific Function
endopeptidase activity
Gene Name
MMP7
Uniprot ID
P09237
Uniprot Name
Matrilysin
Molecular Weight
29676.62 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at October 21, 2007 22:23 / Updated at August 26, 2024 19:23