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Chemistry

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Also known as: 51481-65-3, Mezlin, Mezlocilina, Mezlocillinum, Mezlocilline, Mezlocillin sodium

Molecular Formula

C₂₁H₂₅N₅O₈S₂

Molecular Weight

539.6 g/mol

InChI Key

YPBATNHYBCGSSN-VWPFQQQWSA-N

FDA UNII

OH2O403D1G

Semisynthetic ampicillin-derived acylureido penicillin. It has been proposed for infections with certain anaerobes and may be useful in inner ear, bile, and CNS infections.

1 2D Structure

Mezlocillin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C21H25N5O8S2/c1-21(2)14(18(29)30)26-16(28)13(17(26)35-21)22-15(27)12(11-7-5-4-6-8-11)23-19(31)24-9-10-25(20(24)32)36(3,33)34/h4-8,12-14,17H,9-10H2,1-3H3,(H,22,27)(H,23,31)(H,29,30)/t12-,13-,14+,17-/m1/s1

2.1.3 InChI Key

YPBATNHYBCGSSN-VWPFQQQWSA-N

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)NC(=O)N4CCN(C4=O)S(=O)(=O)C)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)N4CCN(C4=O)S(=O)(=O)C)C(=O)O)C

2.2 Other Identifiers

2.2.1 UNII

OH2O403D1G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bay F 1353

2. Bay-f 1353

3. Bayf 1353

4. Baypen

5. Melocin

6. Meslocillin

7. Mezlin

8. Mezlocillin Sodium

9. Mezlocilline

10. Sodium, Mezlocillin

2.3.2 Depositor-Supplied Synonyms

1. 51481-65-3

2. Mezlin

3. Mezlocilina

4. Mezlocillinum

5. Mezlocilline

6. Mezlocillin Sodium

7. Mezlocillin Acid

8. Chebi:6919

9. Oh2o403d1g

10. (2s,5r,6r)-3,3-dimethyl-6-[[(2r)-2-[(3-methylsulfonyl-2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

11. (2s,5r,6r)-3,3-dimethyl-6-{[(2r)-2-({[3-(methylsulfonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

12. Multocillin

13. Bay-f-1353

14. 6beta-{(2r)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic Acid

15. Ncgc00167470-01

16. (2s,5r,6r)-3,3-dimethyl-6-((r)-2-(3-(methylsulfonyl)-2-oxo-1-imidazolidinecarboxamido)-2-phenylacetamido)-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

17. (2s,5r,6r)-3,3-dimethyl-6-((r)-2-(3-(methylsulfonyl)-2-oxoimidazolidine-1-carboxamido)-2-phenylacetamido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

18. Mezlocillin (usan/inn)

19. Mezlocilina [inn-spanish]

20. Mezlocilline [inn-french]

21. Mezlocillinum [inn-latin]

22. Unii-oh2o403d1g

23. Mezlocillin [usan:inn:ban]

24. 59798-30-0

25. Mezlocillin,(s)

26. Einecs 257-233-8

27. Mezlocillin [mi]

28. Mezlocillin [inn]

29. Dsstox_cid_3316

30. Mezlocillin [usan]

31. Epitope Id:120371

32. Mezlocillin [vandf]

33. Chembl1731

34. Dsstox_rid_76973

35. Mezlocillin [mart.]

36. Dsstox_gsid_23316

37. Schembl34075

38. Mezlocillin [who-dd]

39. Dtxsid1023316

40. Hy-b1466a

41. Zinc3831120

42. Tox21_112474

43. Db00948

44. (methylsulfonyl)-2-oxoimidazolidine-1-

45. Carboxamido)-2-phenylacetamido)-7-oxo-

46. Ncgc00167470-03

47. Ncgc00167470-05

48. 6beta-{(2r)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}-2,2-dimethylpenam-3alpha-carboxylic Acid

49. As-11668

50. Cas-51481-65-3

51. Cs-0013695

52. C07221

53. D05021

54. 481m653

55. A828617

56. (2s,5r,6r)-3,3-dimethyl-6-((r)-2-(3-

57. Q3307752

58. (2s,5r,6r)-3,3-dimethyl-6-[[(2r)-2-[(3-methylsulfonyl-2-oxidanylidene-imidazolidin-1-yl)carbonylamino]-2-phenyl-ethanoyl]amino]-7-oxidanylidene-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

59. (2s,5r,6r)-3,3-dimethyl-6-[[(2r)-2-[[(3-methylsulfonyl-2-oxo-1-imidazolidinyl)-oxomethyl]amino]-1-oxo-2-phenylethyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

60. (2s,5r,6r)-6-[(2r)-2-{[(3-methanesulfonyl-2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

61. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-6-(((((3-(methylsulfonyl)-2-oxo-1-imidazolidinyl)carbonyl)amino)phenylacetyl)amino)-7-oxo-, (2s-(2.alpha.,5.alpha.,6.beta.(s*)))

62. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-6-(((((3-(methylsulfonyl)-2-oxo-1-imidazolidinyl)carbonyl)amino)phenylacetyl)amino)-7-oxo-, (2s-(2alpha,5alpha,6beta(s*)))

63. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 3,3-dimethyl-6-[[(2r)-2-[[[3-(methylsulfonyl)-2-oxo-1-imidazolidinyl]carbonyl]amino]-2-phenylacetyl]amino]-7-oxo-, (2s,5r,6r)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₅N₅O₈S₂
Molecular Weight	539.6 g/mol
XLogP3	-0.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	6
Exact Mass	539.11445512 g/mol
Monoisotopic Mass	539.11445512 g/mol
Topological Polar Surface Area	207 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	1080
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

Used to treat serious gram–negative infections of the lungs, urinary tract, and skin.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Mezlocillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Mezlocillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of mezlocillin results from the inhibition of cell wall synthesis and is mediated through mezlocillin binding to penicillin binding proteins (PBPs). Mezlocillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. Mezlocillin can be used to treat susceptible strains of H. influenzae, Klebsiella species, Pseudomonas species, Proteus mirabilis, E. coli, Enterobacter species, Streptococcus faecelis, Peptococcus species, Peptostreptococcus species, Bacteriodes species (including B. fragilis), Morganella morganii, Serratia species, N. gonorrhoeae, P. vulgaris, and Providencia rettgeri. This drug is discontinued in the U.S.

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

J01CA10 - Mezlocillin

5.4 Metabolism/Metabolites

Unlike many other penicillins, mezlocillin is either extensively metabolized or is subject to biliary excretion, as only about 50% of the dose was accounted for in normal urine.

5.5 Biological Half-Life

1.3 to 4.4 hours

5.6 Mechanism of Action

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, mezlocillin 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 mezlocillin interferes with an autolysin inhibitor.

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