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Deupirfenidone

Deupirfenidone

Synopsis, Chemistry

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Also known as: 1qc36bhi6s, Lyt-100, 1093951-85-9, 2(1h)-pyridinone, 5-(methyl-d3)-1-phenyl-, 1-phenyl-5-(trideuteriomethyl)-1,2-dihydropyridin-2-one, Deupirfenidone [usan]

Molecular Formula

C₁₂H₁₁NO

Molecular Weight

188.24 g/mol

InChI Key

ISWRGOKTTBVCFA-FIBGUPNXSA-N

FDA UNII

1QC36BHI6S

Deupirfenidone is an orally bioavailable and deuterated form of the synthetic antifibrotic agent pirfenidone, with potential anti-inflammatory and anti-fibrotic activities. Upon administration, deupirfenidone inhibits a variety of pro-inflammatory mediators, such as interleukin-6 (IL-6), tumor necrosis factor-alpha (TNF-a) and transforming growth factor-beta (TGF-b). This may reduce fibrosis, inflammation and infection, and may repair the impaired lymphatic flow, decrease lymphedema and restore lymphatic function. In the lungs, deupirfenidone may abrogate impaired lung function, lymphoedema and pulmonary fibrosis.

1 2D Structure

Deupirfenidone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-phenyl-5-(trideuteriomethyl)pyridin-2-one

2.1.2 InChI

InChI=1S/C12H11NO/c1-10-7-8-12(14)13(9-10)11-5-3-2-4-6-11/h2-9H,1H3/i1D3

2.1.3 InChI Key

ISWRGOKTTBVCFA-FIBGUPNXSA-N

2.1.4 Canonical SMILES

CC1=CN(C(=O)C=C1)C2=CC=CC=C2

2.1.5 Isomeric SMILES

[2H]C([2H])([2H])C1=CN(C(=O)C=C1)C2=CC=CC=C2

2.2 Other Identifiers

2.2.1 UNII

1QC36BHI6S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-phenyl-5-(trideuteriomethyl)-1,2-dihydropyridin-2-one

2. 5-methyl-1-phenyl-2-(1h)-pyridone

3. Deskar

4. Esbriet

5. Pirfenidone

2.3.2 Depositor-Supplied Synonyms

1. 1qc36bhi6s

2. Lyt-100

3. 1093951-85-9

4. 2(1h)-pyridinone, 5-(methyl-d3)-1-phenyl-

5. 1-phenyl-5-(trideuteriomethyl)-1,2-dihydropyridin-2-one

6. Deupirfenidone [usan]

7. Unii-1qc36bhi6s

8. Lyt100

9. Schembl4059454

10. Deupirfenidone [who-dd]

11. Sd-560

12. Who 12460

13. At18410

2.4 Create Date

2009-02-09

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₁NO
Molecular Weight	188.24 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Exact Mass	188.102894212 g/mol
Monoisotopic Mass	188.102894212 g/mol
Topological Polar Surface Area	20.3 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	285
Isotope Atom Count	3
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 MeSH Pharmacological Classification

Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)