General Information of Drug (ID: DM9HOKG)

Drug Name
Prinomastat Drug Info
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]
Therapeutic Class
Anticancer Agents
Cross-matching ID
PubChem CID
466151
ChEBI ID
CHEBI:138885
CAS Number
CAS 192329-42-3
TTD Drug ID
DM9HOKG

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Clinical Trial Drug(s)
Patented Agent(s)
Discontinued Drug(s)
Investigative Drug(s)
Approved Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Marimastat DM6V34C Pancreatic cancer 2C10 Phase 3 [4]
CIPEMASTAT DM803GL Rheumatoid arthritis FA20 Phase 3 [5]
Apratastat DM8W4N9 Rheumatoid arthritis FA20 Phase 2 [6]
PMID29130358-Compound-Figure18(14a) DMHIBTZ N. A. N. A. Patented [7]
PMID29130358-Compound-Figure10(2a) DMFWXPS N. A. N. A. Patented [7]
BMS 275291 DMKSFPE Kaposi sarcoma 2B57 Discontinued in Phase 3 [8]
GM6001 DM7V9CT Corneal ulcer 9A76 Discontinued in Phase 2 [9]
RS-130830 DMOTANY Hepatitis C virus infection 1E51.1 Discontinued in Phase 2 [10]
XL784 DMICR39 Diabetic nephropathy GB61.Z Discontinued in Phase 2 [11]
SC-44463 DMBPNKT N. A. N. A. Terminated [12]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Epigallocatechin gallate DMCGWBJ Hepatic fibrosis DB93.0 Phase 3 [13]
Marimastat DM6V34C Pancreatic cancer 2C10 Phase 3 [4]
Neovastat DMXTYWJ Non-small-cell lung cancer 2C25.Y Phase 1 [14]
Metastat DMTQ4PN Acne vulgaris ED80 Phase 1 [15]
PMID29130358-Compound-Figure18(14a) DMHIBTZ N. A. N. A. Patented [7]
PMID29130358-Compound-Figure10(2a) DMFWXPS N. A. N. A. Patented [7]
PMID29130358-Compound-Figure16(9b) DMPAQLZ N. A. N. A. Patented [7]
PMID29130358-Compound-SB-3CT DMC64XQ N. A. N. A. Patented [7]
PMID29130358-Compound-Figure16(9a) DMKX5R8 N. A. N. A. Patented [7]
PMID29130358-Compound-Figure18(14) DM7WXJ9 N. A. N. A. Patented [7]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Marimastat DM6V34C Pancreatic cancer 2C10 Phase 3 [4]
BMS 275291 DMKSFPE Kaposi sarcoma 2B57 Discontinued in Phase 3 [8]
SC-44463 DMBPNKT N. A. N. A. Terminated [12]
BB-3644 DM7YRFE Solid tumour/cancer 2A00-2F9Z Terminated [16]
MMI270 DM38N2K Discovery agent N.A. Investigative [17]
IK-862 DMJA4UE Discovery agent N.A. Investigative [18]
SR-973 DMU48OD Discovery agent N.A. Investigative [19]
SL422 DM3I2US Discovery agent N.A. Investigative [20]
3-Benzenesulfonyl-heptanoic acid hydroxyamide DM7XDCF Discovery agent N.A. Investigative [21]
3-Cyclohexanesulfonyl-heptanoic acid hydroxyamide DMJSOTE Discovery agent N.A. Investigative [21]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [22]
Selenium DM25CGV N. A. N. A. Approved [23]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [24]
Quercetin DM3NC4M Obesity 5B81 Approved [25]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [26]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [27]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [28]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [29]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [30]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [31]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Stromelysin-1 (MMP3)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [32]
Fluvastatin DM4MDJY Arteriosclerosis BD40 Approved [32]
Pravastatin DM6A0X7 Adult acute monocytic leukemia Approved [32]
Atorvastatin DMF28YC Acute coronary syndrome BA41 Approved [32]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [33]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [34]
Ciprofloxacin XR DM2NLS9 Acute gonococcal cervicitis Approved [35]
Methotrexate DM2TEOL Anterior urethra cancer Approved [36]
Quercetin DM3NC4M Obesity 5B81 Approved [37]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [38]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Neutrophil collagenase (MMP8)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [39]
Doxycycline DM7ICNU Acne vulgaris ED80 Approved [3]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [40]
Tetracycline DMZA017 Acne vulgaris ED80 Approved [3]
Edetic acid DM10D85 Hypercalcaemia 5B91.0 Investigative [41]
Formaldehyde DM7Q6M0 Discovery agent N.A. Investigative [42]
⏷ Show the Full List of 6 Drug(s)
Drug(s) Affected By Collagenase 3 (MMP13)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ofloxacin DM0VQN3 Acute gonococcal cervicitis Approved [43]
Clindamycin DM15HL8 Acne vulgaris ED80 Approved [44]
Ciprofloxacin XR DM2NLS9 Acute gonococcal cervicitis Approved [43]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [45]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [46]
Glucosamine DM4ZLFD Osteoarthritis FA00-FA05 Approved [47]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [48]
Doxycycline DM7ICNU Acne vulgaris ED80 Approved [44]
Acocantherin DM7JT24 Atrial fibrillation BC81.3 Approved [49]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [50]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

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

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

References

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4 Metalloelastase (MMP-12) induced inflammatory response in mice airways: effects of dexamethasone, rolipram and marimastat. Eur J Pharmacol. 2007 Mar 15;559(1):75-81.
5 Matrix metalloproteinase inhibition lowers mortality and brain injury in experimental pneumococcal meningitis. Infect Immun. 2014 Apr;82(4):1710-8.
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8 Phase 1/2 trial of BMS-275291 in patients with human immunodeficiency virus-related Kaposi sarcoma: a multicenter trial of the AIDS Malignancy Consortium. Cancer. 2008 Mar 1;112(5):1083-8.
9 Introduction of the 4-(4-bromophenyl)benzenesulfonyl group to hydrazide analogs of Ilomastat leads to potent gelatinase B (MMP-9) inhibitors with i... Bioorg Med Chem. 2008 Sep 15;16(18):8745-59.
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12 A potent, selective inhibitor of matrix metalloproteinase-3 for the topical treatment of chronic dermal ulcers. J Med Chem. 2003 Jul 31;46(16):3514-25.
13 Regioselective synthesis of methylated epigallocatechin gallate via nitrobenzenesulfonyl (Ns) protecting group. Bioorg Med Chem Lett. 2009 Aug 1;19(15):4171-4.
14 Neovastat, a naturally occurring multifunctional antiangiogenic drug, in phase III clinical trials. Semin Oncol. 2001 Dec;28(6):620-5.
15 Strategies for MMP inhibition in cancer: innovations for the post-trial era. Nat Rev Cancer. 2002 Sep;2(9):657-72.
16 Tumour microenvironment - opinion: validating matrix metalloproteinases as drug targets and anti-targets for cancer therapy. Nat Rev Cancer. 2006 Mar;6(3):227-39.
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19 Synthesis and evaluation of succinoyl-caprolactam gamma-secretase inhibitors. Bioorg Med Chem Lett. 2006 May 1;16(9):2357-63.
20 Design, synthesis, and structure-activity relationships of macrocyclic hydroxamic acids that inhibit tumor necrosis factor alpha release in vitro and in vivo. J Med Chem. 2001 Aug 2;44(16):2636-60.
21 Hydroxamic acid derivatives as potent peptide deformylase inhibitors and antibacterial agents. J Med Chem. 2000 Jun 15;43(12):2324-31.
22 Oxidative Stress-Protective and Anti-Melanogenic Effects of Loliolide and Ethanol Extract from Fresh Water Green Algae, Prasiola japonica. Int J Mol Sci. 2018 Sep 18;19(9):2825. doi: 10.3390/ijms19092825.
23 Inhibition of invasion and induction of apoptosis by selenium in human malignant brain tumour cells in vitro. Int J Oncol. 2007 May;30(5):1263-71.
24 Impaired migration of trophoblast cells caused by simvastatin is associated with decreased membrane IGF-I receptor, MMP2 activity and HSP27 expression. Hum Reprod. 2007 Apr;22(4):1161-7. doi: 10.1093/humrep/del464. Epub 2006 Dec 11.
25 Quercetin Suppresses the Migration and Invasion in Human Colon Cancer Caco-2 Cells Through Regulating Toll-like Receptor 4/Nuclear Factor-kappa B Pathway. Pharmacogn Mag. 2016 May;12(Suppl 2):S237-44. doi: 10.4103/0973-1296.182154. Epub 2016 May 11.
26 Troglitazone but not conjugated linoleic acid reduces gene expression and activity of matrix-metalloproteinases-2 and -9 in PMA-differentiated THP-1 macrophages. J Nutr Biochem. 2008 Sep;19(9):594-603. doi: 10.1016/j.jnutbio.2007.08.003. Epub 2007 Dec 21.
27 Multifaceted suppression of aggressive behavior of thyroid carcinoma by all-trans retinoic acid induced re-differentiation. Mol Cell Endocrinol. 2012 Jan 2;348(1):260-9. doi: 10.1016/j.mce.2011.09.002. Epub 2011 Sep 6.
28 Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action. Dermatoendocrinol. 2009 May;1(3):177-87.
29 Arsenic trioxide (As2O3) inhibits invasion of HT1080 human fibrosarcoma cells: role of nuclear factor-kappaB and reactive oxygen species. J Cell Biochem. 2005 Aug 1;95(5):955-69. doi: 10.1002/jcb.20452.
30 Aspirin inhibits MMP-2 and MMP-9 expressions and activities through upregulation of PPARalpha/gamma and TIMP gene expressions in ox-LDL-stimulated macrophages derived from human monocytes. Pharmacology. 2009;83(1):18-25. doi: 10.1159/000166183. Epub 2008 Oct 30.
31 Repetitive nonlethal oxidant injury to retinal pigment epithelium decreased extracellular matrix turnover in vitro and induced sub-RPE deposits in vivo. Invest Ophthalmol Vis Sci. 2006 Sep;47(9):4098-112. doi: 10.1167/iovs.05-1230.
32 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
33 Cannabidiol Modulates the Immunophenotype and Inhibits the Activation of the Inflammasome in Human Gingival Mesenchymal Stem Cells. Front Physiol. 2016 Nov 24;7:559. doi: 10.3389/fphys.2016.00559. eCollection 2016.
34 Unique signatures of stress-induced senescent human astrocytes. Exp Neurol. 2020 Dec;334:113466. doi: 10.1016/j.expneurol.2020.113466. Epub 2020 Sep 17.
35 Ciprofloxacin enhances the stimulation of matrix metalloproteinase 3 expression by interleukin-1beta in human tendon-derived cells. A potential mechanism of fluoroquinolone-induced tendinopathy. Arthritis Rheum. 2002 Nov;46(11):3034-40. doi: 10.1002/art.10617.
36 Reduction of synovial sublining layer inflammation and proinflammatory cytokine expression in psoriatic arthritis treated with methotrexate. Arthritis Rheum. 2004 Oct;50(10):3286-95. doi: 10.1002/art.20518.
37 Quercetin inhibits IL-1-induced proliferation and production of MMPs, COX-2, and PGE2 by rheumatoid synovial fibroblast. Inflammation. 2012 Aug;35(4):1585-94. doi: 10.1007/s10753-012-9473-2.
38 Rofecoxib regulates the expression of genes related to the matrix metalloproteinase pathway in humans: implication for the adverse effects of cyclooxygenase-2 inhibitors. Clin Pharmacol Ther. 2006 Apr;79(4):303-15. doi: 10.1016/j.clpt.2005.12.306.
39 Transcriptional and Metabolic Dissection of ATRA-Induced Granulocytic Differentiation in NB4 Acute Promyelocytic Leukemia Cells. Cells. 2020 Nov 5;9(11):2423. doi: 10.3390/cells9112423.
40 Identification of vitamin D3 target genes in human breast cancer tissue. J Steroid Biochem Mol Biol. 2016 Nov;164:90-97.
41 Treatment with human metalloproteinase-8 gene delivery ameliorates experimental rat liver cirrhosis. Gastroenterology. 2004 Apr;126(4):1122-33; discussion 949. doi: 10.1053/j.gastro.2003.12.045.
42 Characterization of formaldehyde's genotoxic mode of action by gene expression analysis in TK6 cells. Arch Toxicol. 2013 Nov;87(11):1999-2012.
43 Contrasting effects of fluoroquinolone antibiotics on the expression of the collagenases, matrix metalloproteinases (MMP)-1 and -13, in human tendon-derived cells. Rheumatology (Oxford). 2005 Dec;44(12):1514-7. doi: 10.1093/rheumatology/kei087. Epub 2005 Sep 7.
44 Chloramphenicol causes mitochondrial stress, decreases ATP biosynthesis, induces matrix metalloproteinase-13 expression, and solid-tumor cell invasion. Toxicol Sci. 2010 Jul;116(1):140-50. doi: 10.1093/toxsci/kfq085. Epub 2010 Mar 25.
45 Simvastatin inactivates beta1-integrin and extracellular signal-related kinase signaling and inhibits cell proliferation in head and neck squamous cell carcinoma cells. Cancer Sci. 2007 Jun;98(6):890-9.
46 Matrix metalloproteinases of epithelial origin in facial sebum of patients with acne and their regulation by isotretinoin. J Invest Dermatol. 2005 Oct;125(4):673-84. doi: 10.1111/j.0022-202X.2005.23848.x.
47 Glucosamine promotes chondrogenic phenotype in both chondrocytes and mesenchymal stem cells and inhibits MMP-13 expression and matrix degradation. Osteoarthritis Cartilage. 2007 Jun;15(6):646-55. doi: 10.1016/j.joca.2007.01.014. Epub 2007 Mar 6.
48 Identification of transcriptome signatures and biomarkers specific for potential developmental toxicants inhibiting human neural crest cell migration. Arch Toxicol. 2016 Jan;90(1):159-80.
49 Ouabain impairs cell migration, and invasion and alters gene expression of human osteosarcoma U-2 OS cells. Environ Toxicol. 2017 Nov;32(11):2400-2413. doi: 10.1002/tox.22453. Epub 2017 Aug 10.
50 Expression profiling in squamous carcinoma cells reveals pleiotropic effects of vitamin D3 analog EB1089 signaling on cell proliferation, differentiation, and immune system regulation. Mol Endocrinol. 2002 Jun;16(6):1243-56.