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2D Structure
Also known as: Oxazocillin, 66-79-5, Oxazocilline, Mpi-penicillin, Oxacilina, Bactocill
Molecular Formula
C19H19N3O5S
Molecular Weight
401.4  g/mol
InChI Key
UWYHMGVUTGAWSP-JKIFEVAISA-N
FDA UNII
UH95VD7V76

An antibiotic similar to FLUCLOXACILLIN used in resistant staphylococci infections.
Oxacillin is a Penicillin-class Antibacterial.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
2.1.2 InChI
InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1
2.1.3 InChI Key
UWYHMGVUTGAWSP-JKIFEVAISA-N
2.1.4 Canonical SMILES
CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
2.1.5 Isomeric SMILES
CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
UH95VD7V76
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Methylphenylisoxazolyl Penicillin

2. Oxacillin Sodium

3. Oxacillin, Monosodium Salt, Anhydrous

4. Oxacillin, Monosodium Salt, Monohydrate

5. Oxacillin, Sodium

6. Oxazocilline

7. Penicillin, Methylphenylisoxazolyl

8. Prostaphlin

9. Sodium Oxacillin

10. Sodium, Oxacillin

2.3.2 Depositor-Supplied Synonyms

1. Oxazocillin

2. 66-79-5

3. Oxazocilline

4. Mpi-penicillin

5. Oxacilina

6. Bactocill

7. Prostaphlin

8. Oxacillin Sodium

9. 5-methyl-3-phenyl-4-isoxazolyl-penicillin

10. Oxacillin (inn)

11. Chebi:7809

12. (2s,5r,6r)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

13. (5-methyl-3-phenyl-4-isoxazolyl)penicillin

14. Penicillin, (5-methyl-3-phenyl-4-isoxazolyl)-

15. 6beta-(5-methyl-3-phenylisoxazol-4-yl)penicillanic Acid

16. Uh95vd7v76

17. (2s,5r,6r)-3,3-dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

18. Ossacillina

19. Oxacilline

20. Oxacillinum

21. Prostaphlyn

22. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 3,3-dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-, (2s,5r,6r)-

23. Ossacillina [dcit]

24. Oxacillin [inn]

25. Mpi-pc

26. Oxacillin [inn:ban]

27. Oxacilina [inn-spanish]

28. Oxacilline [inn-french]

29. Oxacillinum [inn-latin]

30. 1173-88-2

31. Oxacilina (tn)

32. Einecs 200-635-5

33. Unii-uh95vd7v76

34. Oxacillin,(s)

35. (2s,5r,6r)-3,3-dimethyl-6-[(5-methyl-3-phenyl-isoxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

36. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-6-(((5-methyl-3-phenyl-4-isoxazolyl)carbonyl)amino)-7-oxo-, (2s-(2alpha,5alpha,6beta))-

37. Oxacillin [mi]

38. Oxacillin [vandf]

39. Chembl819

40. Epitope Id:181859

41. Oxacillin [mart.]

42. Oxacillin [who-dd]

43. Schembl3817

44. Dtxsid8023397

45. Gtpl10943

46. Hy-b0925a

47. Phenylisoxazole-4-carboxamido)-7-

48. Zinc3875439

49. Bdbm50350483

50. Db00713

51. 2,2-dimethyl-6beta-(5-methyl-3-phenyl-1,2-oxazole-4-carboxamido)penam-3alpha-carboxylic Acid

52. (2s,5r,6r)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

53. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-6-(5-methyl-3-phenyl-4-isoxazolecarboxamide)-7-oxo-

54. 5-methyl-3-phenyl-4-isooxazolylpenicillin

55. Oxo-4-thia-1-azabicyclo[3.2.0]heptane-

56. Cs-0013715

57. C07334

58. D08307

59. (2s,5r,6r)-3,3-dimethyl-6-(5-methyl-3-

60. Q418725

61. Brd-k96786677-236-01-6

62. Brd-k96786677-236-02-4

63. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-6-(((5-methyl-3-phenyl-4-isoxazolyl)carbonyl)amino)-7-oxo-,(2s,5r,6r)-

64. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 3,3-dimethyl-6-(((5-methyl-3-phenyl-4-isoxazolyl)carbonyl)amino)-7-oxo-, (2s-(2.alpha.,5.alpha.,6.beta.))-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 401.4 g/mol
Molecular Formula C19H19N3O5S
XLogP32.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass401.10454189 g/mol
Monoisotopic Mass401.10454189 g/mol
Topological Polar Surface Area138 Ų
Heavy Atom Count28
Formal Charge0
Complexity681
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameOxacillin sodium
Drug LabelOxacillin for Injection, USP is a semisynthetic penicillin antibiotic derived from the penicillin nucleus, 6-amino-penicillanic acid. It is resistant to inactivation by the enzyme penicillinase (beta-lactamase). It is the sodium salt in parenteral do...
Active IngredientOxacillin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyAurobindo Pharma; Sandoz; Sagent Pharms; Agila Speclts

2 of 2  
Drug NameOxacillin sodium
Drug LabelOxacillin for Injection, USP is a semisynthetic penicillin antibiotic derived from the penicillin nucleus, 6-amino-penicillanic acid. It is resistant to inactivation by the enzyme penicillinase (beta-lactamase). It is the sodium salt in parenteral do...
Active IngredientOxacillin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyAurobindo Pharma; Sandoz; Sagent Pharms; Agila Speclts

4.2 Drug Indication

Used in the treatment of resistant staphylococci infections.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Oxacillin 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. Oxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Oxacillin results from the inhibition of cell wall synthesis and is mediated through Oxacillin binding to penicillin binding proteins (PBPs). Oxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.


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 FDA Pharmacological Classification
5.3.1 Active Moiety
OXACILLIN
5.3.2 FDA UNII
UH95VD7V76
5.3.3 Pharmacological Classes
Penicillins [CS]; Penicillin-class Antibacterial [EPC]
5.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CF - Beta-lactamase resistant penicillins

J01CF04 - Oxacillin


5.5 Absorption, Distribution and Excretion

Route of Elimination

Oxacillin Sodium is rapidly excreted as unchanged drug in the urine by glomerular filtration and active tubular secretion.


5.6 Biological Half-Life

20 to 30 minutes


5.7 Mechanism of Action

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