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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 222400-20-6, Cs-023, Ro-4908463, R-1558, R-115685, R-1l5685

Molecular Formula

C₂₃H₃₅N₇O₆S

Molecular Weight

537.6 g/mol

InChI Key

KEDAXBWZURNCHS-GPODMPQUSA-N

FDA UNII

1654W9611T

Tomopenem is a 1-beta-methylcarbapenem antibiotic with broad-spectrum activity against gram-positive and gram-negative bacteria. Tomopenem has a longer half-life than imipenem-cilastatin or meropenem and shows activity against methicillin-resistant S. aureus.

1 2D Structure

Cs 023

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4R,5S,6S)-3-[(3S,5S)-5-[(3S)-3-[[2-(diaminomethylideneamino)acetyl]amino]pyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C23H35N7O6S/c1-10-17-16(11(2)31)21(34)30(17)18(22(35)36)19(10)37-13-6-14(28(3)9-13)20(33)29-5-4-12(8-29)27-15(32)7-26-23(24)25/h10-14,16-17,31H,4-9H2,1-3H3,(H,27,32)(H,35,36)(H4,24,25,26)/t10-,11-,12+,13+,14+,16-,17-/m1/s1

2.1.3 InChI Key

KEDAXBWZURNCHS-GPODMPQUSA-N

2.1.4 Canonical SMILES

CC1C2C(C(=O)N2C(=C1SC3CC(N(C3)C)C(=O)N4CCC(C4)NC(=O)CN=C(N)N)C(=O)O)C(C)O

2.1.5 Isomeric SMILES

C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](N(C3)C)C(=O)N4CC[C@@H](C4)NC(=O)CN=C(N)N)C(=O)O)[C@@H](C)O

2.2 Other Identifiers

2.2.1 UNII

1654W9611T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cs 023

2. Cs-023

3. Cs023 Cpd

4. R 115685

5. R-115685

6. R115685

7. Ro4908463

2.3.2 Depositor-Supplied Synonyms

1. 222400-20-6

2. Cs-023

3. Ro-4908463

4. R-1558

5. R-115685

6. R-1l5685

7. Ro4908463

8. Antibiotic Cs 023

9. 1654w9611t

10. R115685

11. (4r,5s,6s)-3-[(3s,5s)-5-[(3s)-3-[[2-(diaminomethylideneamino)acetyl]amino]pyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

12. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 3-(((3s,5s)-5-(((3s)-3-((((aminoiminomethyl)amino)acetyl)amino)-1-pyrrolidinyl)carbonyl)-1-methyl-3-pyrrolidinyl)thio)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-, (4r,5s,6s)-

13. Tomopenem [usan]

14. Tomopenem [usan:inn]

15. R 115685

16. Ro 4908463

17. R 1558

18. Unii-1654w9611t

19. (4r,5s,6s)-3-(((3s,5s)-5-((s)-3-(2-guanidinoacetamido)pyrrolidine-1-carbonyl)-1-methylpyrrolidin-3-yl)thio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[

20. Cs 023

21. Tomopenem [inn]

22. Cs023 Cpd

23. Tomopenem (usan/inn)

24. Tomopenem [who-dd]

25. Schembl304829

26. Chembl389847

27. Gtpl10869

28. Dtxsid70873384

29. Cs023

30. Zinc3993831

31. Bdbm50483019

32. Hy-123022

33. Cs-0079886

34. D09022

35. Q15427876

36. (1r,5s,6s)-2-[(2s,4s)-2-[(3s)-3-(2-guanidinoacetylamino)pyrrolidin-1-ylcarbonyl]-1-methylpyrrolidin-4-ylthio]-6-[(1r)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic Acid

37. (1r,5s,6s)-6-[(1r)-1-hydroxyethyl]-1-methyl-2-[(2s,4s)-2-[(3s)-3-(2-guanidinoacetylamino)pyrrolidin-1-ylcarbonyl]-1-methylpyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylic Acid

38. (4r,5s,6s)-3-(((3s,5s)-5-(((3s)-3-((2-guanidinoacetyl)amino)pyrrolidin-1-yl)carbonyl)-1-methylpyrrolidin-3-yl)sulfanyl)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid

39. (4r,5s,6s)-3-(((3s,5s)-5-((3s)-3-(carbamimidamidoacetamido)pyrrolidine-1-carbonyl)-1-methylpyrrolidin-3-yl)sulfanyl)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid

40. (4r,5s,6s)-3-(((3s,5s)-5-((s)-3-(2-guanidinoacetamido)pyrrolidine-1-carbonyl)-1-methylpyrrolidin-3-yl)thio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

41. (4r,5s,6s)-3-[(3s,5s)-5-[(3s)-3-[(2-guanidinoacetyl)amino]pyrrolidine-1-carbonyl]-1-methyl-pyrrolidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

42. (4r,5s,6s)-3-{[(3s,5s)-5-{[(3s)-3-{[n-(diaminomethylidene)glycyl]amino}pyrrolidin-1-yl]carbonyl}-1-methylpyrrolidin-3-yl]sulfanyl}-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₃₅N₇O₆S
Molecular Weight	537.6 g/mol
XLogP3	-3.7
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	8
Exact Mass	537.23695304 g/mol
Monoisotopic Mass	537.23695304 g/mol
Topological Polar Surface Area	220 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	1050
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