Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0653)
Drug Name
MK-595
Synonyms
Acide etacrynique; Acide etacrynique [INN-French]; Acido etacrinico; Acido etacrinico [INN-Spanish]; Acidum etacrynicum; Acidum etacrynicum [INN-Latin]; Crinuryl; ETHACRYNIC ACID; Edecril; Edecrin; Edecrina; Endecril; Etacrinic acid; Etacrynic Acid; Etakrinic acid; Ethacrinique (acide); Ethacryinic Acid; Hidromedin; Hydromedin; Kyselina ethakrynova; Kyselina ethakrynova [Czech]; MK-595; Mingit; Otacril; Reomax; Taladren; Uregit; ethacrynate; 58-54-8; Methylenebutyrylphenoxyacetic acid
Indication Congenital heart anomaly [ICD11: LA8Z] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 303.13 Topological Polar Surface Area 63.6
Heavy Atom Count 19 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
3278
PubChem SID
122995 ; 491575 ; 798369 ; 834701 ; 855762 ; 5208062 ; 7847379 ; 7887267 ; 8149337 ; 8152080 ; 10321631 ; 11112144 ; 11336075 ; 11361314 ; 11363707 ; 11366269 ; 11368831 ; 11371330 ; 11374346 ; 11376993 ; 11446250 ; 11462286 ; 11466287 ; 11467407 ; 11483790 ; 11486033 ; 11487913 ; 11490241 ; 11492359 ; 11494627 ; 14776240 ; 17389016 ; 24894577 ; 26611737 ; 26680116 ; 26706137 ; 26746983 ; 26746984 ; 29222417 ; 46392033 ; 46394202 ; 46507562 ; 47662347 ; 47736552 ; 47959820 ; 47959821 ; 47959822 ; 48110508 ; 48185057 ; 48423385
ChEBI ID
ChEBI:4876
CAS Number
58-54-8
TTD Drug ID
D06TNL
Formula
C13H12Cl2O4
Canonical SMILES
CCC(=C)C(=O)C1=C(C(=C(C=C1)OCC(=O)O)Cl)Cl
InChI
1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17)
InChIKey
AVOLMBLBETYQHX-UHFFFAOYSA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
MK-595 M1 PDM007446 N. A. Reduction - Reduction of carbonyl 1 Human
MK-595 M2 PDM007447
13958730
Conjugation - Glycine conjugation 1 Human
MK-595 M3 PDM007448 N. A. Conjugation - O-Glucuronidation of aliphatic acid 1 Human
MK-595 M4 PDM007449 N. A. Conjugation - Carnitine conjugation 1 Human
MK-595 M5 PDM007450
165310
Reduction - Reduction of alpha,beta-unsaturated carbon-carbon double bond adjacent to electron withdrawing group 1 Gut microbial environment
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Glutathione S-transferase alpha-1 (GSTA1) DME0011 Homo sapiens
GSTA1_HUMAN
2.5.1.18
[3]
References
1 ClinicalTrials.gov (NCT01628731) Furosemide Versus Ethacrynic Acid in Children With Congenital Heart Disease.
2 Xenobiotic metabolizing and antioxidant enzymes in normal and neoplastic human breast tissue. Eur J Drug Metab Pharmacokinet. 1998 Oct-Dec;23(4):497-500.
3 Purification and biochemical properties of glutathione S-transferase from Lactuca sativa. J Biochem Mol Biol. 2005 Mar 31;38(2):232-7.

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