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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
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 Weight 188.24 g/mol
Molecular Formula C12H11NO
XLogP31.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass188.102894212 g/mol
Monoisotopic Mass188.102894212 g/mol
Topological Polar Surface Area20.3 Ų
Heavy Atom Count14
Formal Charge0
Complexity285
Isotope Atom Count3
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.)


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