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Synopsis

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Chemistry

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Also known as: 37091-66-0, Azlocilina, Azlocilline, Azlocillinum, Azlocilina [inn-spanish], Azlocilline [inn-french]

Molecular Formula

C₂₀H₂₃N₅O₆S

Molecular Weight

461.5 g/mol

InChI Key

JTWOMNBEOCYFNV-NFFDBFGFSA-N

FDA UNII

HUM6H389W0

A semisynthetic ampicillin-derived acylureido penicillin.

1 2D Structure

Azlocillin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

2.1.2 InChI

InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1

2.1.3 InChI Key

JTWOMNBEOCYFNV-NFFDBFGFSA-N

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)O)C

2.1.5 Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)O)C

2.2 Other Identifiers

2.2.1 UNII

HUM6H389W0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Azlin

2. Azlocillin Sodium

3. Azlocillin, Sodium

4. Bay E 6905

5. Bay-e 6905

6. Baye 6905

7. Securopen

8. Sodium Azlocillin

9. Sodium, Azlocillin

2.3.2 Depositor-Supplied Synonyms

1. 37091-66-0

2. Azlocilina

3. Azlocilline

4. Azlocillinum

5. Azlocilina [inn-spanish]

6. Azlocilline [inn-french]

7. Azlocillinum [inn-latin]

8. Chebi:2956

9. Azlocillin Sodium Salt

10. Hum6h389w0

11. J01ca09

12. Nsc-758227

13. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-((r)-2-(2-oxo-1-imidazolidinecarboxamido)-2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

14. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-{[(2r)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

15. 37091-65-9

16. Azlocillin (usan/inn)

17. Unii-hum6h389w0

18. Azlocillin [usan:inn:ban]

19. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-(((2r)-2-(((2-oxoimidazolidin-1-yl)carbonyl)amino)-2-phenylacetyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

20. Einecs 253-348-2

21. Azlocillin [mi]

22. Azlocillin [inn]

23. Prestwick3_000821

24. Azlocillin [usan]

25. Azlocillin [vandf]

26. Epitope Id:141185

27. 6-((r)-2-(2-oxoimidazolidin-1-carboxamido)-2-phenylacetamido)penicillansaeure

28. Azlocillin [mart.]

29. Azlocillin [who-dd]

30. Chembl1537

31. Schembl34150

32. Bspbio_000741

33. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2r)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

34. Bpbio1_000817

35. Dtxsid1022639

36. Zinc3830261

37. Akos025402328

38. Ac-8140

39. Db01061

40. Ds-3291

41. Nsc 758227

42. 2,2-dimethyl-6beta-[(2r)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetamido]penam-3alpha-carboxylic Acid

43. 91a659

44. C06839

45. D02339

46. D81792

47. A823527

48. Q510154

49. Brd-k60663764-236-02-1

50. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-((r)-2-(2-oxoimidazolidine-1-carboxamido)-2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

51. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2r)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

52. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2r)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenyl-acetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

53. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2s)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenyl-acetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid;azlocillin

54. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-(((((2-oxo-1-imidazolidinyl)carbonyl)amino)phenylacetyl)amino)-, (2s-(2.alpha.,5.alpha.,6.beta.(s*)))-

55. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-(((((2-oxo-1-imidazolidinyl)carbonyl)amino)phenylacetyl)amino)-, (2s-(2alpha,5alpha,6beta(s*)))-

56. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-[[[[((r)-2-oxo-1-imidazolidinyl)carbonyl]amino]phenylacetyl]amino]-, (2s,5r,6r)-

57. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid,3,3-dimethyl-7-oxo-6-[[[[(2-oxo-1-imidazolidinyl)carbonyl]amino]phenylacetyl]amino]-, [2s-[2a,5a,6b(s*)]]-

2.4 Create Date

2006-04-29

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₃N₅O₆S
Molecular Weight	461.5 g/mol
XLogP3	0.1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	461.13690464 g/mol
Monoisotopic Mass	461.13690464 g/mol
Topological Polar Surface Area	173 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	844
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

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of infections caused by Pseudomonas aeruginosa, Escherichia coli, and Haemophilus influenzae.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Similar to [mezlocillin] and [piperacillin], azlocillin is an acylampicillin that exhibits an extended-spectrum of activity and _in vitro_ potency that is greater than that of the carboxy penicillins. Azlocillin is shown to be effective against a broad spectrum of bacteria, including Pseudomonas aeruginosa and enterococci.

5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CA - Penicillins with extended spectrum

J01CA09 - Azlocillin

5.4 Absorption, Distribution and Excretion

Absorption

Not significantly absorbed from the gastrointestinal tract.

5.5 Metabolism/Metabolites

Eliminated predominantly by renal mechanisms, but also undergoes biotransformation within body tissues and intraintestinal degradation by bowel bacteria, with high concentrations found in bile.

5.6 Biological Half-Life

Mean elimination half-life is 1.3 to 1.5 hours. Longer in neonates, and 2 to 6 hours in patients with renal impairment.

5.7 Mechanism of Action

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, azlocillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that azlocillin interferes with an autolysin inhibitor.

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