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Chemistry

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Also known as: Carindacillin sodium, 26605-69-6, Indanyl carbenicillin sodium salt, Sodium indanylcarbinicillin, Sodium 5-indanylcarbenicillin, Carindacillin (sodium)

Molecular Formula

C₂₆H₂₅N₂NaO₆S

Molecular Weight

516.5 g/mol

InChI Key

QFWPXOXWAUAYAB-XZVIDJSISA-M

FDA UNII

4OUL81K2RT

Carbenicillin Indanyl Sodium is the sodium salt of indanyl carbenicillin, a broad-spectrum, semi-synthetic carboxypenicillin antibiotic with bactericidal activity. Carbenicillin acylates C-terminal domain of penicillin-sensitive transpeptidase, resulting in opening the lactam ring of the antibiotic. This inactivation prevents the formation of the cross-linkage of peptidoglycan strands, thereby inhibiting the third and last stage of bacterial cell wall synthesis. As a result, cell wall integrity is compromised and cell lysis may follow. This agent is used mainly for gram-negative infections, and has limited gram-positive coverage.

1 2D Structure

Carbenicillin Indanyl

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(2S,5R,6R)-6-[[3-(2,3-dihydro-1H-inden-5-yloxy)-3-oxo-2-phenylpropanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.1.2 InChI

InChI=1S/C26H26N2O6S.Na/c1-26(2)20(24(31)32)28-22(30)19(23(28)35-26)27-21(29)18(15-7-4-3-5-8-15)25(33)34-17-12-11-14-9-6-10-16(14)13-17;/h3-5,7-8,11-13,18-20,23H,6,9-10H2,1-2H3,(H,27,29)(H,31,32);/q;+1/p-1/t18?,19-,20+,23-;/m1./s1

2.1.3 InChI Key

QFWPXOXWAUAYAB-XZVIDJSISA-M

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)OC4=CC5=C(CCC5)C=C4)C(=O)[O-])C.[Na+]

2.1.5 Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)OC4=CC5=C(CCC5)C=C4)C(=O)[O-])C.[Na+]

2.2 Other Identifiers

2.2.1 UNII

4OUL81K2RT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Carbenicillin Indanyl

2. Carbenicillin Indanyl, 2s-(2alpha,5alpha,6beta)-isomer

3. Carindacillin

4. Carindacillin Sodium

5. Carindapen

6. Cp 15,464-2

7. Cp 15464

8. Cp-15,464-2

9. Cp-15464

10. Geocillin

11. Indanyl Carbenicillin

12. N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamate

13. Sodium Carindacillin

2.3.2 Depositor-Supplied Synonyms

1. Carindacillin Sodium

2. 26605-69-6

3. Indanyl Carbenicillin Sodium Salt

4. Sodium Indanylcarbinicillin

5. Sodium 5-indanylcarbenicillin

6. Carindacillin (sodium)

7. Carindacillin Sodium Salt

8. Carindacillin Sodium (jan)

9. Carindacillin Sodium [jan]

10. 4oul81k2rt

11. I-cbpc

12. Chebi:31358

13. Cp-15,464-2

14. Cp-15464-2

15. 1-(5-indanyl)(2s,5r,6r)-n-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamate Monosodium Salt

16. Sodium;(2s,5r,6r)-6-[[3-(2,3-dihydro-1h-inden-5-yloxy)-3-oxo-2-phenylpropanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

17. Urobac

18. Gu-pen

19. Unii-4oul81k2rt

20. Geocillin (tn)

21. Einecs 247-845-3

22. Carbenicillin Indanyl Sodium [usan]

23. Carbenicillin Indanyl Sodium [usan:usp]

24. Cp 15464-2

25. Schembl33856

26. Chembl1200991

27. Carbenicillin Indanyl Sodium (usp)

28. Carindacillin Sodium [mart.]

29. Carindacillin Sodium [who-dd]

30. Carindacillin Sodium Salt [mi]

31. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((3-((2,3-dihydro-1h-inden-5-yl)oxy)-1,3-dioxo-2-phenylpropyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, (2s-(2alpha,5alpha,6beta))-

32. Carbenicillin Indanyl Sodium [vandf]

33. Hy-108880

34. Carbenicillin Indanyl Sodium [usp-rs]

35. Cs-0031237

36. D01283

37. Carbenicillin Indanyl Sodium [orange Book]

38. Carbenicillin Indanyl Sodium [usp Impurity]

39. Q3658672

40. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((3-((2,3-dihydro-1h-inden-5-yl)oxy)-1,3-dioxo-2-phenylpropyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, (2s-(2.alpha.,5.alpha.,6.beta.))-.

41. Malonamic Acid, N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenyl-, 1-(5-indanyl) Ester, Monosodium Salt

42. Sodium (2s,5r,6r)-6-{[3-(2,3-dihydro-1h-inden-5-yloxy)-3-oxo-2-phenylpropanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

43. Sodium 6beta-[3-(2,3-dihydro-1h-inden-5-yloxy)-3-oxo-2-phenylpropanamido]-2,2-dimethylpenam-3alpha-carboxylate

44. Sodium 6beta-{2-[(2,3-dihydro-1h-inden-5-yloxy)carbonyl]-2-phenylacetamido}-2,2-dimethylpenam-3alpha-carboxylate

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₅N₂NaO₆S
Molecular Weight	516.5 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	7
Exact Mass	516.13310198 g/mol
Monoisotopic Mass	516.13310198 g/mol
Topological Polar Surface Area	141 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	894
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2