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Also known as: 87726-17-8, Cs-533, Rs-533, Papm, (5r,6s)-3-[(3s)-1-ethanimidoylpyrrolidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, (5r,6s)-6-((r)-1-hydroxyethyl)-3-(((s)-1-(1-iminoethyl)pyrrolidin-3-yl)thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Molecular Formula

C₁₅H₂₁N₃O₄S

Molecular Weight

339.4 g/mol

InChI Key

TYMABNNERDVXID-DLYFRVTGSA-N

FDA UNII

W9769W09JF

Panipenem is a broad-spectrum parenteral carbapenem with activity against aerobic, anaerobic, gram-positive and gram-negative organisms including non-fermenters. Panipenem is often co-administered with betamipron to prevent nephrotoxicity.

1 2D Structure

Panipenem

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5R,6S)-3-[(3S)-1-ethanimidoylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C15H21N3O4S/c1-7(19)12-10-5-11(13(15(21)22)18(10)14(12)20)23-9-3-4-17(6-9)8(2)16/h7,9-10,12,16,19H,3-6H2,1-2H3,(H,21,22)/t7-,9+,10-,12-/m1/s1

2.1.3 InChI Key

TYMABNNERDVXID-DLYFRVTGSA-N

2.1.4 Canonical SMILES

CC(C1C2CC(=C(N2C1=O)C(=O)O)SC3CCN(C3)C(=N)C)O

2.1.5 Isomeric SMILES

C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)S[C@H]3CCN(C3)C(=N)C)O

2.2 Other Identifiers

2.2.1 UNII

W9769W09JF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6-(1-hydroxyethyl)-2-(1--acetimidoylpyrrolidin-3-ylthio)-1-carbapen-2-em-3-carboxylic Acid

2. Carbapenem Rs 533

3. Carbapenem Rs-533

4. Cs 533

5. Cs-533

2.3.2 Depositor-Supplied Synonyms

1. 87726-17-8

2. Cs-533

3. Rs-533

4. Papm

5. (5r,6s)-3-[(3s)-1-ethanimidoylpyrrolidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

6. (5r,6s)-6-((r)-1-hydroxyethyl)-3-(((s)-1-(1-iminoethyl)pyrrolidin-3-yl)thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

7. W9769w09jf

8. Carbapenem Rs-533

9. Panipenemum

10. (+)-(5r,6s)-3-(((s)-1-acetimidoyl-3-pyrrolidinyl)thio)-6-((r)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid

11. Cs 533

12. Panipenem [inn:jan]

13. Panipenemum [inn-latin]

14. Rs 533

15. Penipanem

16. Unii-w9769w09jf

17. 6-(1-hydroxyethyl)-2-(1-acetimidoylpyrrolidin-3-ylthio)-1-carbaren-2-em-3-carboxylic Acid

18. Panipenem [inn]

19. Panipenem [jan]

20. Panipenem [mi]

21. Panipenem (jp17/inn)

22. Panipenem [mart.]

23. Panipenem [who-dd]

24. Schembl150517

25. Chebi:7911

26. Chembl339323

27. Gtpl12184

28. Dtxsid20868982

29. Carbenin (panipenem + Betamipron)

30. Zinc3780837

31. Akos015895977

32. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-(1-hydroxyethyl)-3-((1-(1-iminoethyl)-3-pyrrolidinyl)thio)-7-oxo-, (5r-(3(s*),5-alpha,6-alpha(r*)))-

33. Ac-22713

34. A13096

35. D01048

36. Q7131192

37. (5r,6s)-2-[1-acetamidoylpyrrolidin-3(s)-ylthio]-6-[1(r)-hydroxyethyl]-2-carbapenem-3-carboxylic Acid

38. (5r,6s)-6-((r)-1-hydroxyethyl)-3-(((s)-1-(1-iminoethyl)pyrrolidin-3-yl)thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₁N₃O₄S
Molecular Weight	339.4 g/mol
XLogP3	0
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	339.12527733 g/mol
Monoisotopic Mass	339.12527733 g/mol
Topological Polar Surface Area	130 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	606
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1