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Chemistry

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Also known as: Sodium ethacrynate, 6500-81-8, Ethacrynic acid sodium, Ethacrynate sodium [usan:usp], Etacrynate sodium, K41myv7mpm

Molecular Formula

C₁₃H₁₁Cl₂NaO₄

Molecular Weight

325.12 g/mol

InChI Key

CWCSCNSKBSCYCS-UHFFFAOYSA-M

FDA UNII

K41MYV7MPM

A compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.

1 2D Structure

Ethacrynate Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetate

2.1.2 InChI

InChI=1S/C13H12Cl2O4.Na/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);/q;+1/p-1

2.1.3 InChI Key

CWCSCNSKBSCYCS-UHFFFAOYSA-M

2.1.4 Canonical SMILES

CCC(=C)C(=O)C1=C(C(=C(C=C1)OCC(=O)[O-])Cl)Cl.[Na+]

2.2 Other Identifiers

2.2.1 UNII

K41MYV7MPM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acid, Etacrynic

2. Acid, Ethacrinic

3. Acid, Ethacrynic

4. Edecrin

5. Etacrynic Acid

6. Ethacrinic Acid

7. Ethacrynic Acid

8. Ethacrynic Acid, Sodium Salt

9. Hydromedin

10. Sodium, Ethacrynate

2.3.2 Depositor-Supplied Synonyms

1. Sodium Ethacrynate

2. 6500-81-8

3. Ethacrynic Acid Sodium

4. Ethacrynate Sodium [usan:usp]

5. Etacrynate Sodium

6. K41myv7mpm

7. Ethacrynic Acid Sodium Salt

8. Sodium (2,3-dichloro-4-(2-methylenebutyryl)phenoxy)acetate

9. Edecrin Sodium

10. Sodium;2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetate

11. Acetic Acid, (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)-, Sodium Salt

12. Sodium Edecrin

13. Ethacrynate Sodium [usan]

14. Unii-k41myv7mpm

15. Sodium Etacrynate

16. Ethacrynate Sodium (usp)

17. Schembl42210

18. Chembl1200487

19. Dtxsid10215320

20. Sodium Etacrynate [mart.]

21. Ethacrynate Sodium [vandf]

22. Etacrynate Sodium [who-dd]

23. Ethacrynate Sodium [orange Book]

24. Ethacrynate Sodium [usp Impurity]

25. Ethacrynic Acid Sodium Salt [mi]

26. D04079

27. Q27281933

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₁Cl₂NaO₄
Molecular Weight	325.12 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	323.9932085 g/mol
Monoisotopic Mass	323.9932085 g/mol
Topological Polar Surface Area	66.4 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	375
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Diuretics

Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

4.2 FDA Pharmacological Classification

4.2.1 Pharmacological Classes

Loop Diuretic [EPC]; Increased Diuresis at Loop of Henle [PE]

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