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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 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 Formula	C₁₉H₂₇NO₇S₃
Molecular Weight	477.6 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	11
Exact Mass	477.09496572 g/mol
Monoisotopic Mass	477.09496572 g/mol
Topological Polar Surface Area	180 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	767
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1