Details of the Drug

General Information of Drug (ID: DMFQX1U)

Drug Name
EMATE
Synonyms
Emate compound; Estrone 3-O-Sulfamate; EMATE; Estrone-3-O-sulfamate; Oestrone-3-O-sulphamate; 148672-09-7; Estra-1,3,5(10)-trien-17-one-3-sulfamate; CHEMBL122708; 3-((Aminosulfonyl)oxy)estra-1,3,5(10)-trien-17-one; C18H23NO4S; 3-[(Aminosulfonyl)oxy]estra-1,3,5(10)-trien-17-one; Estra-1,3,5(10)-trien-17-one, 3-((aminosulfonyl)oxy)-; Estrone Sulfamate; estrone3-O-sulfamate; NSC685426; Estrone O-Sulfamate; Estrone 3-Sulfamate; AC1L2SFZ; SCHEMBL305660; CTK8F0296; RVKFQAJIXCZXQY-CBZIJGRNSA-N; ZINC5832614; BDBM50134329; AKOS030241107
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 349.4
Topological Polar Surface Area (xlogp) 2.4
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C18H23NO4S
IUPAC Name
[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] sulfamate
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)OS(=O)(=O)N
InChI
InChI=1S/C18H23NO4S/c1-18-9-8-14-13-5-3-12(23-24(19,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16H,2,4,6-9H2,1H3,(H2,19,21,22)/t14-,15-,16+,18+/m1/s1
InChIKey
RVKFQAJIXCZXQY-CBZIJGRNSA-N
Cross-matching ID
PubChem CID
127676
CAS Number
148672-09-7
TTD ID
D0R7QY

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 [1]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
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

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2 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.
3 Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8.
4 Sulfonamide linked neoglycoconjugates--a new class of inhibitors for cancer-associated carbonic anhydrases. J Med Chem. 2010 Apr 8;53(7):2913-26.
5 Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorg Med Chem. 2009 Jul 15;17(14):5054-8.
6 Localization of diuretic effects along the loop of Henle: an in vivo microperfusion study in rats. Clin Sci (Lond). 2000 Apr;98(4):481-8.
7 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
8 Selective effect of thiazides on the human osteoblast-like cell line MG-63. Kidney Int. 1996 Nov;50(5):1476-82.
9 Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50.
10 Nature of the inhibition of carbonic anhydrase by acetazolamide and benzthiazide. J Pharmacol Exp Ther. 1961 Mar;131:271-4.
11 Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5050-3.
12 Review of estrone sulfatase and its inhibitors--an important new target against hormone dependent breast cancer. Curr Med Chem. 2002 Jan;9(2):263-73.
13 Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template. J Med Chem. 2010 Mar 11;53(5):2155-70.
14 Synergistic effects of E2MATE and norethindrone acetate on steroid sulfatase inhibition: a randomized phase I proof-of-principle clinical study in women of reproductive age. Reprod Sci. 2014 Oct;21(10):1256-65.
15 Phase I study of STX 64 (667 Coumate) in breast cancer patients: the first study of a steroid sulfatase inhibitor. Clin Cancer Res. 2006 Mar 1;12(5):1585-92.
16 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
17 Estrogenic potential of 2-alkyl-4-(thio)chromenone 6-O-sulfamates: potent inhibitors of human steroid sulfatase. J Med Chem. 2003 Nov 6;46(23):5091-4.
18 Inhibition of estrone sulfatase (ES) by alkyl and cycloalkyl ester derivatives of 4-[(aminosulfonyl)oxy] benzoic acid. Bioorg Med Chem Lett. 2004 Feb 9;14(3):605-9.