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Oxacillin

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

1 API Suppliers, 1 USDMF

PRICE INFORMATION

API Reference Price, API Exports, API Imports, FDF Exports, FDF Imports

DOSSIERs // Finished Dosage Formulations

6 Dossiers, 1 Europe, 5 Listed Dossiers

GLOBAL SALES INFORMATION

3 US Medicaid Prescriptions, 1 Finished Drug Prices

MARKET PLACE

1 APIs, 5 DOSSIERS // FDF

ANALYTICAL SOLUTION(s)

1 Other Ref. Standards

1 Other Ref. Standards

DIGITAL CONTENT

1 Data Compilations & Company Tracker #PharmaFlow, 1 News

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

Oxacillin

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 Formula	C₁₉H₁₉N₃O₅S
Molecular Weight	401.4 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	401.10454189 g/mol
Monoisotopic Mass	401.10454189 g/mol
Topological Polar Surface Area	138 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	681
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
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 Information

1 of 2
Drug Name	Oxacillin sodium
Drug Label	Oxacillin 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 Ingredient	Oxacillin sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Aurobindo Pharma; Sandoz; Sagent Pharms; Agila Speclts

2 of 2
Drug Name	Oxacillin sodium
Drug Label	Oxacillin 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 Ingredient	Oxacillin sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Aurobindo 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.