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2D Structure
Also known as: Oxacillin sodium salt, 1173-88-2, Oxabel, Prostaphlin, Bactocill, Sodium oxacillin
Molecular Formula
C19H18N3NaO5S
Molecular Weight
423.4  g/mol
InChI Key
VDUVBBMAXXHEQP-SLINCCQESA-M
FDA UNII
4TWD2995UP

An antibiotic similar to FLUCLOXACILLIN used in resistant staphylococci infections.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(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-carboxylate
2.1.2 InChI
InChI=1S/C19H19N3O5S.Na/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);/q;+1/p-1/t13-,14+,17-;/m1./s1
2.1.3 InChI Key
VDUVBBMAXXHEQP-SLINCCQESA-M
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-].[Na+]
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-].[Na+]
2.2 Other Identifiers
2.2.1 UNII
4TWD2995UP
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Methylphenylisoxazolyl Penicillin

2. Oxacillin

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. Oxacillin Sodium Salt

2. 1173-88-2

3. Oxabel

4. Prostaphlin

5. Bactocill

6. Sodium Oxacillin

7. Oxacillin Sodium Anhydrous

8. Bristopen

9. Micropenin

10. Resistopen

11. Staphcillin V

12. Oxacillin (sodium Salt)

13. Chebi:52134

14. 4twd2995up

15. Oxabel Sodium Salt

16. Monosodium Oxacillin

17. Sq-16423

18. Anhydrous Oxacillin Sodium

19. Sodium Methylphenylisoaxazolylpenicillin

20. Oxacillin Sodium (van)

21. Sodium (2s,5r,6r)-3,3-dimethyl-6-(5-methyl-3-phenylisoxazole-4-carboxamido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

22. 5-methyl-3-phenyl-4-isoxazolyl Penicillin, Sodium

23. Nsc-527712

24. Brl 1400

25. Oxacillin Sodium [usp]

26. 7240-38-2

27. Einecs 214-636-3

28. Nsc 527712

29. Unii-4twd2995up

30. Bactocill In Plastic Container

31. Ncgc00183361-01

32. Chembl693

33. Dsstox_cid_28906

34. Dsstox_rid_83174

35. Dsstox_gsid_48980

36. Schembl41165

37. 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-, Monosodium Salt, (2s-(2alpha,5alpha,6beta))-

38. Mls000069542

39. Dtxsid9048980

40. Oxacillin Sodium [who-dd]

41. Hms3714g11

42. Hy-b0925

43. Sodium;(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-carboxylate

44. Tox21_113439

45. Bdbm50248015

46. Akos015896457

47. Ccg-220675

48. 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-, Monosodium Salt, (2s,5r,6r)-

49. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-6-(5-methyl-3-phenyl-4-isoxazolecarboxamido)-7-oxo-, Monosodium Salt

50. As-82071

51. Smr000058841

52. Sodium (2s-(2alpha,5alpha,6beta))-3,3-dimethyl-6-(((5-methyl-3-phenylisoxazol-4-yl)carbonyl)amino)-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

53. Anhydrous Oxacillin Sodium [mart.]

54. Cas-1173-88-2

55. O0353

56. D97506

57. W-108566

58. Q27123265

59. Oxacillin Sodium, Antibiotic For Culture Media Use Only

60. Sodium 6beta-(5-methyl-3-phenylisoxazol-4-yl)penicillanate

61. 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-, Sodium Salt (1:1), (2s,5r,6r)-

62. Sodium 2,2-dimethyl-6beta-(5-methyl-3-phenyl-1,2-oxazole-4-carboxamido)penam-3alpha-carboxylate

2.4 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 423.4 g/mol
Molecular Formula C19H18N3NaO5S
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass423.08648614 g/mol
Monoisotopic Mass423.08648614 g/mol
Topological Polar Surface Area141 Ų
Heavy Atom Count29
Formal Charge0
Complexity687
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameBactocill in plastic container
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 20mg base/ml; eq 40mg base/ml
Market StatusPrescription
CompanyBaxter Hlthcare

2 of 4  
Drug NameOxacillin sodium
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

3 of 4  
Drug NameBactocill in plastic container
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 20mg base/ml; eq 40mg base/ml
Market StatusPrescription
CompanyBaxter Hlthcare

4 of 4  
Drug NameOxacillin sodium
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

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

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


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Penicillins [CS]; Penicillin-class Antibacterial [EPC]