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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 426253-04-5, Smp-601, Sm-216601, Pz-601, 26020h3q1l, (4r,5s,6s)-3-[[4-[(5s)-2,5-dihydro-5-methyl-1h-pyrrol-3-yl]-2-thiazolyl]thio]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Molecular Formula

C₁₈H₂₁N₃O₄S₂

Molecular Weight

407.5 g/mol

InChI Key

XFGOMLIRJYURLQ-GOKYHWASSA-N

FDA UNII

26020H3Q1L

Razupenem is a broad-spectrum carbapenem with activity against gram-positive bacteria, including methicillin-resistant S. aureus.

1 2D Structure

Sm-216601

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[[4-[(5S)-5-methyl-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl]sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C18H21N3O4S2/c1-7-4-10(5-19-7)11-6-26-18(20-11)27-15-8(2)13-12(9(3)22)16(23)21(13)14(15)17(24)25/h4,6-9,12-13,19,22H,5H2,1-3H3,(H,24,25)/t7-,8+,9+,12+,13+/m0/s1

2.1.3 InChI Key

XFGOMLIRJYURLQ-GOKYHWASSA-N

2.1.4 Canonical SMILES

CC1C=C(CN1)C2=CSC(=N2)SC3=C(N4C(C3C)C(C4=O)C(C)O)C(=O)O

2.1.5 Isomeric SMILES

C[C@H]1C=C(CN1)C2=CSC(=N2)SC3=C(N4[C@H]([C@H]3C)[C@H](C4=O)[C@@H](C)O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

26020H3Q1L

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Sm-216601

2.3.2 Depositor-Supplied Synonyms

1. 426253-04-5

2. Smp-601

3. Sm-216601

4. Pz-601

5. 26020h3q1l

6. (4r,5s,6s)-3-[[4-[(5s)-2,5-dihydro-5-methyl-1h-pyrrol-3-yl]-2-thiazolyl]thio]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

7. (4r,5s,6s)-6-((r)-1-hydroxyethyl)-4-methyl-3-((4-((s)-5-methyl-2,5-dihydro-1h-pyrrol-3-yl)thiazol-2-yl)thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

8. (4r,5s,6s)-6-[(1r)-1-hydroxyethyl]-4-methyl-3-[[4-[(5s)-5-methyl-2,5-dihydro-1h-pyrrol-3-yl]-1,3-thiazol-2-yl]sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

9. (4r,5s,6s)-3-[[4-[(5s)-2,5-dihydro-5-methyl-1h-pyrrol-3-yl]-2-thiazolyl]thio]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid

10. (4r,5s,6s)-6-((1r)-1-hydroxyethyl)-4-methyl-3-((4-((5s)-5-methyl-2,5-dihydro-1h-pyrrol-3-yl)thiazol-2-yl)sulfanyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid

11. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 3-((4-((5s)-2,5-dihydro-5-methyl-1h-pyrrol-3-yl)-2-thiazolyl)thio)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-, (4r,5s,6s)-

12. Razupenem [usan]

13. (4r,5s,6s)-6-((r)-1-hydroxyethyl)-4-methyl-3-((4-((s)-5-methyl-2,5-dihydro-1h-pyrrol-3-yl)thiazol-2-yl)thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic A

14. Razupenem [usan:inn]

15. Unii-26020h3q1l

16. (4r,5s,6s)-6-[(1r)-1-hydroxyethyl]-4-methyl-3-({4-[(5s)-5-methyl-2,5-dihydro-1h-pyrrol-3-yl]-1,3-thiazol-2-yl}sulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

17. (4r,5s,6s)-6-[(1r)-1-hydroxyethyl]-4-methyl-3-({4-[(5s)-5-methyl-2,5-dihydro-1h-pyrrol-3-yl}-1,3-thiazol-2-yl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

18. Razupenem [inn]

19. Razupenem (usan/inn)

20. Razupenem [who-dd]

21. Schembl2894324

22. Chembl1256722

23. Gtpl10851

24. Dtxsid801045429

25. Zinc3986713

26. Db12587

27. D09658

28. 253d045

29. Q15410192

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₁N₃O₄S₂
Molecular Weight	407.5 g/mol
XLogP3	-1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	407.09734851 g/mol
Monoisotopic Mass	407.09734851 g/mol
Topological Polar Surface Area	156 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	740
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