Oxaquin

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Also known as: Mcb-3837, 1221r21zrq, Mcb 3837, 790704-50-6, 3-quinolinecarboxylic acid, 7-(4-((4-((5s)-5-((acetylamino)methyl)-2-oxo-3-oxazolidinyl)-2-fluorophenoxy)methyl)-4-(phosphonooxy)-1-piperidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-, 7-(4-((4-((5s)-5-(acetamidomethyl)-2-oxo-oxazolidin-3-yl)-2-fluoro-phenoxy)methyl)-4-phosphonooxy-1-piperidyl)-1-cyclopropyl-6-fluoro-4-oxo-quinoline-3-carboxylic acid

Molecular Formula

C₃₁H₃₃F₂N₄O₁₁P

Molecular Weight

706.6 g/mol

InChI Key

MNABRWLVTSGIMU-FQEVSTJZSA-N

FDA UNII

1221R21ZRQ

Quinolonyl-oxazolidinone Antibiotic DNV3837 is a prodrug of DNV3681, a small molecule quinolonyl-oxazolidinone antibiotic with activity against Gram-positive bacteria, including Clostridioides difficile. Upon intravenous administration, DNV3837 crosses the gastrointestinal barrier to reach the C. difficile infection site. The active drug DNV3681 may affect four bacterial targets including DNA-gyrase, topoisomerase IV, protein synthesis and aminoacyl-t-RNA synthetases, which leads to bacterial cell death. DNV3681 does not have antibacterial activity against aerobic and anaerobic Gram-negative bacteria, sparing intestinal Bacteroides spp. that provide colonization resistance in the digestive tract.

1 2D Structure

Oxaquin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-[4-[[4-[(5S)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenoxy]methyl]-4-phosphonooxypiperidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid

2.1.2 InChI

InChI=1S/C31H33F2N4O11P/c1-17(38)34-13-20-14-37(30(42)47-20)19-4-5-27(24(33)10-19)46-16-31(48-49(43,44)45)6-8-35(9-7-31)26-12-25-21(11-23(26)32)28(39)22(29(40)41)15-36(25)18-2-3-18/h4-5,10-12,15,18,20H,2-3,6-9,13-14,16H2,1H3,(H,34,38)(H,40,41)(H2,43,44,45)/t20-/m0/s1

2.1.3 InChI Key

MNABRWLVTSGIMU-FQEVSTJZSA-N

2.1.4 Canonical SMILES

CC(=O)NCC1CN(C(=O)O1)C2=CC(=C(C=C2)OCC3(CCN(CC3)C4=C(C=C5C(=C4)N(C=C(C5=O)C(=O)O)C6CC6)F)OP(=O)(O)O)F

2.1.5 Isomeric SMILES

CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)OCC3(CCN(CC3)C4=C(C=C5C(=C4)N(C=C(C5=O)C(=O)O)C6CC6)F)OP(=O)(O)O)F

2.2 Other Identifiers

2.2.1 UNII

1221R21ZRQ

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Mcb-3837

2. 1221r21zrq

3. Mcb 3837

4. 790704-50-6

5. 3-quinolinecarboxylic Acid, 7-(4-((4-((5s)-5-((acetylamino)methyl)-2-oxo-3-oxazolidinyl)-2-fluorophenoxy)methyl)-4-(phosphonooxy)-1-piperidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-

6. 7-(4-((4-((5s)-5-(acetamidomethyl)-2-oxo-oxazolidin-3-yl)-2-fluoro-phenoxy)methyl)-4-phosphonooxy-1-piperidyl)-1-cyclopropyl-6-fluoro-4-oxo-quinoline-3-carboxylic Acid

7. 7-[4-[[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenoxy]methyl]-4-phosphonooxypiperidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic Acid

8. Unii-1221r21zrq

9. Schembl2109002

10. Gtpl10997

11. Dnv3837

12. Mcb3837

13. Dnv-3837

14. Hy-100435

15. Cs-0018921

16. Q27251356

17. 7-(4-{4-[(5s)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-4-phosphonooxy-piperidin-1-yl) -1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic Acid

18. 7-(4-{4-[(5s)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-4-phosphonooxy-piperidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic Acid

2.4 Create Date

2009-09-22

3 Chemical and Physical Properties

Molecular Formula	C₃₁H₃₃F₂N₄O₁₁P
Molecular Weight	706.6 g/mol
XLogP3	2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	11
Exact Mass	706.18515120 g/mol
Monoisotopic Mass	706.18515120 g/mol
Topological Polar Surface Area	196 Å²
Heavy Atom Count	49
Formal Charge	0
Complexity	1390
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1