Details of the Drug

General Information of Drug (ID: DMJK5CT)

Drug Name
STX-140
Synonyms
(9beta,13alpha,14beta,17alpha)-2-Methoxyestra-1,3,5(10)-Triene-3,17-Diyl Disulfamate; STX140; CHEMBL218382; 2-MeOE2bisMATE; 2-methoxyestradiol-3,17-O,O-bis-sulfamate; STX 140; 2-MeOEbisMATE; 2gd8; 2-methoxyestradiol 3,17-O,O-bis-sulfamate; 2-MbM; 2-methoxyestradiol-3,17-O,O-bis(sulfamate); SCHEMBL446846; BDBM50200936; DB08416; (9beta,17beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diyl disulfamate; Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, disulfamate, (17beta)-; 401600-86-0; Angiomates; Estrone sulphatase inhibitors, Ipsen; STX-213; STX-641; Steroid sulfatase inhibitors, Sterix Ltd; 2-MeOE2-bis MATE; 2-MeSEMATE; 2-ethyl-estradiol bis-sulfamate; 2-methoxyestradiol, Sterix; 2-methoxyestradiol-bis-sulfamate; 2-methoxyestradiol-bis-sulfamate, Sterix
Indication
Disease Entry ICD 11 Status REF
Osteoporosis FB83.0 Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 460.6
Logarithm of the Partition Coefficient (xlogp) 2.6
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 9
Chemical Identifiers
Formula
C19H28N2O7S2
IUPAC Name
[(8R,9S,13S,14S,17S)-2-methoxy-13-methyl-3-sulfamoyloxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] sulfamate
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OS(=O)(=O)N)CCC4=CC(=C(C=C34)OC)OS(=O)(=O)N
InChI
InChI=1S/C19H28N2O7S2/c1-19-8-7-12-13(15(19)5-6-18(19)28-30(21,24)25)4-3-11-9-17(27-29(20,22)23)16(26-2)10-14(11)12/h9-10,12-13,15,18H,3-8H2,1-2H3,(H2,20,22,23)(H2,21,24,25)/t12-,13+,15-,18-,19-/m0/s1
InChIKey
AQSNIXKAKUZPSI-SSTWWWIQSA-N
Cross-matching ID
PubChem CID
9804302
ChEBI ID
CHEMBL218382
CAS Number
401600-86-0
UNII
S57SQE6LE5
DrugBank ID
DB08416
TTD ID
D07ZNI
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Carbonic anhydrase II (CA-II) TTANPDJ CAH2_HUMAN Inhibitor [2]
Steryl-sulfatase (STS) TTHM0R1 STS_HUMAN Inhibitor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [4]
BH3-interacting domain death agonist (BID) OTOSHSHU BID_HUMAN Protein Interaction/Cellular Processes [5]
E3 ubiquitin-protein ligase XIAP OT24GP9B XIAP_HUMAN Gene/Protein Processing [4]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Protein Interaction/Cellular Processes [5]
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Molecular Expression Atlas of This Drug

The Studied Disease Osteoporosis
ICD Disease Classification FB83.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Steryl-sulfatase (STS) DTT STS 1.80E-38 -0.79 -1.15
Carbonic anhydrase II (CA-II) DTT CA2 7.95E-08 0.52 0.33
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00592579) A Phase 2 Study With Panzem in Patients With Relapsed or Plateau Phase Multiple Myeloma. U.S. National Institutes of Health.
2 Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents. J Med Chem. 2008 Mar 13;51(5):1295-308.
3 2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity. J Med Chem. 2006 Dec 28;49(26):7683-96.
4 STX140 and STX641 cause apoptosis via the intrinsic mitochondrial pathway and down-regulate survivin and XIAP expression in ovarian and prostate cancer cells. Anticancer Res. 2009 Oct;29(10):3751-7.
5 2-MeOE2bisMATE induces caspase-dependent apoptosis in CAL51 breast cancer cells and overcomes resistance to TRAIL via cooperative activation of caspases. Apoptosis. 2004 May;9(3):323-32. doi: 10.1023/b:appt.0000025809.80684.bd.