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Chemistry

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Also known as: 1000296-70-7, 2-ethylbutanoyloxymethyl (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(1r,3s)-1-oxothiolan-3-yl]sulfanyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, Sulopenem etzadroxil (usan), Sulopenem etzadroxil [usan], Pf-03709270, 492m3i304t
Molecular Formula
C19H27NO7S3
Molecular Weight
477.6  g/mol
InChI Key
NBPVNGWRLGHULH-CSOWVJSESA-N
FDA UNII
492M3I304T

Sulopenem Etzadroxil
Sulopenem Etzadroxil is an orally available ester prodrug form of sulopenem, a thiopenem with broad-spectrum antibacterial activity against most gram-positive and gram-negative bacteria. After oral administration of sulopenem etzadroxil, the ester bond is cleaved, releasing active sulopenem. Sulopenem is not active against Pseudomonas aeruginosa. In addition, this agent is fairly stable against hydrolysis by various beta-lactamases.
1 2D Structure

Sulopenem Etzadroxil

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-ethylbutanoyloxymethyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(1R,3S)-1-oxothiolan-3-yl]sulfanyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
2.1.2 InChI
InChI=1S/C19H27NO7S3/c1-4-11(5-2)17(23)26-9-27-18(24)14-19(28-12-6-7-30(25)8-12)29-16-13(10(3)21)15(22)20(14)16/h10-13,16,21H,4-9H2,1-3H3/t10-,12+,13+,16-,30-/m1/s1
2.1.3 InChI Key
NBPVNGWRLGHULH-CSOWVJSESA-N
2.1.4 Canonical SMILES
CCC(CC)C(=O)OCOC(=O)C1=C(SC2N1C(=O)C2C(C)O)SC3CCS(=O)C3
2.1.5 Isomeric SMILES
CCC(CC)C(=O)OCOC(=O)C1=C(S[C@H]2N1C(=O)[C@@H]2[C@@H](C)O)S[C@H]3CC[S@@](=O)C3
2.2 Other Identifiers
2.2.1 UNII
492M3I304T
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 1000296-70-7

2. 2-ethylbutanoyloxymethyl (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(1r,3s)-1-oxothiolan-3-yl]sulfanyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

3. Sulopenem Etzadroxil (usan)

4. Sulopenem Etzadroxil [usan]

5. Pf-03709270

6. 492m3i304t

7. Sulopenem-etzadroxil

8. Pf 03709270

9. Schembl3412832

10. Dtxsid80635293

11. 4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-((1r)-1-hydroxyethyl)-7-oxo-3-(((1r,3s)-tetrahydro-1-oxido-3-thienyl)thio)-, (2-ethyl-1-oxobutoxy)methyl Ester, (5r,6s)-

12. Ex-a3685

13. Pf 03709270 (ulopenem Etzadroxil)

14. Ac-33246

15. Hy-109754

16. Cs-0033925

17. D09672

18. Q27259210

19. (2-ethyl-1-oxobutoxy)methyl (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[[(1r,3s)-tetrahydro-1-oxido-3-thienyl]thio]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

20. (2-ethyl-1-oxobutoxy)methyl (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[[(1r,3s)-tetrahydro-1-oxido-3-thienyl]thio]-4thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

21. Methylene 2-ethylbutanoate (5r,6s)-6-((1r)-1-hydroxyethyl)-7-oxo-3-(((1r,3s)-1-oxotetrahydro-1h-1.lamba.(sup 4)-thiophen-3-yl)sulfanyl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

2.4 Create Date
2008-01-14
3 Chemical and Physical Properties
Molecular Weight 477.6 g/mol
Molecular Formula C19H27NO7S3
XLogP32.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count10
Rotatable Bond Count11
Exact Mass477.09496572 g/mol
Monoisotopic Mass477.09496572 g/mol
Topological Polar Surface Area180 Ų
Heavy Atom Count30
Formal Charge0
Complexity767
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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