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Chemistry

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Also known as: 1616690-16-4, Desidustat [inn], Zyan-1, Zyan1, Y962pqa4ks, 1,2-dihydroquinoline-3-carbonyl]glycine

Molecular Formula

C₁₆H₁₆N₂O₆

Molecular Weight

332.31 g/mol

InChI Key

IKRKQQLJYBAPQT-UHFFFAOYSA-N

FDA UNII

Y962PQA4KS

Desidustat is an orally bioavailable, hypoxia-inducible factor prolyl hydroxylase (HIF-PH) inhibitor (HIF-PHI), with potential anti-anemic and anti-inflammatory activities. Upon administration, desidustat binds to and inhibits HIF-PH, an enzyme responsible for the degradation of transcription factors in the HIF family under normal oxygen conditions. This prevents HIF breakdown and promotes HIF activity. Increased HIF activity leads to an increase in endogenous erythropoietin production, thereby enhancing erythropoiesis. It also reduces the expression of the peptide hormone hepcidin, improves iron availability, and boosts hemoglobin (Hb) levels. HIF regulates the expression of genes in response to reduced oxygen levels, including genes required for erythropoiesis and iron metabolism. In addition, HIF 1-alpha (HIF1A) may play a role in reducing inflammation during acute lung injury (ALI) through HIF-dependent control of glucose metabolism in the alveolar epithelium.

1 2D Structure

Desidustat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[[1-(cyclopropylmethoxy)-4-hydroxy-2-oxoquinoline-3-carbonyl]amino]acetic acid

2.1.2 InChI

InChI=1S/C16H16N2O6/c19-12(20)7-17-15(22)13-14(21)10-3-1-2-4-11(10)18(16(13)23)24-8-9-5-6-9/h1-4,9,21H,5-8H2,(H,17,22)(H,19,20)

2.1.3 InChI Key

IKRKQQLJYBAPQT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CC1CON2C3=CC=CC=C3C(=C(C2=O)C(=O)NCC(=O)O)O

2.2 Other Identifiers

2.2.1 UNII

Y962PQA4KS

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(1-(cyclopropylmethoxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic Acid

2. Glycine, N-((1-(cyclopropylmethoxy)-1,2-dihydro-4-hydroxy-2-oxo-3-quinolinyl)carbonyl)-

3. N-(1-(cyclopropylmethoxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonyl)glycine

4. Zyan1 Compound

2.3.2 Depositor-Supplied Synonyms

1. 1616690-16-4

2. Desidustat [inn]

3. Zyan-1

4. Zyan1

5. Y962pqa4ks

6. 1,2-dihydroquinoline-3-carbonyl]glycine

7. N-[1-(cyclopropylmethoxy)-4-hydroxy-2-oxo-

8. 2-(1-(cyclopropylmethoxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic Acid

9. Glycine, N-((1-(cyclopropylmethoxy)-1,2-dihydro-4-hydroxy-2-oxo-3-quinolinyl)carbonyl)-

10. N-(1-(cyclopropylmethoxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonyl)glycine

11. Zyan1 Compound

12. Unii-y962pqa4ks

13. Desidustat [who-dd]

14. Chembl4650314

15. Schembl15846922

16. Dtxsid901337362

17. Bcp29692

18. Ex-a2999

19. S9699

20. Zb1514

21. Akos037515648

22. Cs-8034

23. Ac-36284

24. Bs-16050

25. Hy-103227

26. A16921

27. D80699

28. (1-(cyclopropylmethoxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonyl)glycine

29. 2-[[1-(cyclopropylmethoxy)-4-hydroxy-2-oxoquinoline-3-carbonyl]amino]acetic Acid

2.4 Create Date

2014-07-14

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₆N₂O₆
Molecular Weight	332.31 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	332.10083623 g/mol
Monoisotopic Mass	332.10083623 g/mol
Topological Polar Surface Area	116 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	583
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	1

4 Pharmacology and Biochemistry

4.1 Mechanism of Action

The small molecule hypoxia-inducible factor, desidustat, inhibits the prolyl hydrozylase and stimulates erythropoiesis. It is currently being investigated against anemia of inflammation and COVID-19.

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