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Also known as: 149951-16-6, Lenapenem [inn], Unii-d6nbq3h12u, D6nbq3h12u, (4r,5s,6s)-6-[(1r)-1-hydroxyethyl]-3-[(3s,5s)-5-[(1r)-1-hydroxy-3-(methylamino)propyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, Bo2727

Molecular Formula

C₁₈H₂₉N₃O₅S

Molecular Weight

399.5 g/mol

InChI Key

PZLOCBSBEUDCPF-YJIVIRPOSA-N

FDA UNII

D6NBQ3H12U

Lenapenem is a broad-spectrum, carbapenem antibiotic with bactericidal activity. Lenapenem binds to penicillin binding proteins (PBPs) located on the bacterial cell wall, thereby inhibiting the final transpeptidation step in the synthesis of peptidoglycan, an essential component of the bacterial cell wall. This inhibition weakens the bacterial cell wall and leads to lytic cell death in a wide range of Gram-positive and Gram-negative aerobic and anaerobic pathogens.

1 2D Structure

Lenapenem

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(1R)-1-hydroxy-3-(methylamino)propyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C18H29N3O5S/c1-8-14-13(9(2)22)17(24)21(14)15(18(25)26)16(8)27-10-6-11(20-7-10)12(23)4-5-19-3/h8-14,19-20,22-23H,4-7H2,1-3H3,(H,25,26)/t8-,9-,10+,11+,12-,13-,14-/m1/s1

2.1.3 InChI Key

PZLOCBSBEUDCPF-YJIVIRPOSA-N

2.2 Other Identifiers

2.2.1 UNII

D6NBQ3H12U

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6-(1-hydroxyethyl)-2-(5-(1-hydroxy-3-n-methylaminopropyl)pyrrolidin-3-ylthio)1-methyl-1-carbapen-2-em-3-carboxylic Acid Hydrochloride Hydrate

2. Bo 2727

3. Bo-2727

4. L 739,428

5. L 739428

6. L-739,428

7. L-739428

2.3.2 Depositor-Supplied Synonyms

1. 149951-16-6

2. Lenapenem [inn]

3. Unii-d6nbq3h12u

4. D6nbq3h12u

5. (4r,5s,6s)-6-[(1r)-1-hydroxyethyl]-3-[(3s,5s)-5-[(1r)-1-hydroxy-3-(methylamino)propyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

6. Bo2727

7. (+)-(4r,5s,6s)-6-((r)-1-hydroxyethyl)-3-(((3s,5s)-5-((r)-1-hydroxy-3-(methylamino)propyl)-3-pyrrolidinyl)thio)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid

8. L-739,428

9. L-739428

10. Lenapenemum

11. (4r,5s,6s)-6-((1r)-1-hydroxyethyl)-3-((3s,5s)-5-((1r)-1-hydroxy-3-(methylamino)propyl)pyrrolidin-3-yl)sulfanyl-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid

12. Bo-2727

13. (4r,5s,6s)-3-(((3s,5s)-5-((r)-1-hydroxy-3-(methylamino)propyl)pyrrolidin-3-yl)thio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

14. 6-(1-hydroxyethyl)-2-(5-(1-hydroxy-3-n-methylaminopropyl)pyrrolidin-3-ylthio)1-methyl-1-carbapen-2-em-3-carboxylic Acid Hydrochloride Hydrate

15. Schembl75702

16. Chembl3989459

17. Gtpl10825

18. Dtxsid701031259

19. Da-64916

20. Hy-105180

21. Cs-0025215

22. Ns00124580

23. Q27276182

24. (+)-(4r,5s,6s)-6-((r)-1-hydroxyethyl)-3-((3s,5s)-5-((r)-1-hydroxy-3-(methyl-amino)propyl)-3-pyrrolidinyl)thio)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid

25. (1r,5s,6s)-6-[1(r)-hydroxyethyl]-2-[2(s)-[1(r)-hydroxy-3-(methylamino)propyl]pyrrolidin-4(s)-ylthio]-1-methyl-1-carba-2-penem-3-carboxylic Acid Monohydrochloride Monohydrate

26. 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid, 6-[(1r)-1-hydroxyethyl]-3-[[(3s,5s)-5-[(1r)-1-hydroxy-3-(methylamino)propyl]-3-pyrrolidinyl]thio]-4-methyl-7-oxo-, (4r,5s,6s)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₉N₃O₅S
Molecular Weight	399.5 g/mol
XLogP3	-2.5
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	8
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	147
Heavy Atom Count	27
Formal Charge	0
Complexity	642
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1