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Chemistry

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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

Oxacillin
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 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.


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ABOUT THIS PAGE

Looking for 66-79-5 / Oxacillin API manufacturers, exporters & distributors?

Oxacillin manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Oxacillin API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Oxacillin manufacturer or Oxacillin supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Oxacillin manufacturer or Oxacillin supplier.

PharmaCompass also assists you with knowing the Oxacillin API Price utilized in the formulation of products. Oxacillin API Price is not always fixed or binding as the Oxacillin Price is obtained through a variety of data sources. The Oxacillin Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Oxacillin

Synonyms

Oxazocillin, 66-79-5, Oxazocilline, Mpi-penicillin, Oxacilina, Bactocill

Cas Number

66-79-5

Unique Ingredient Identifier (UNII)

UH95VD7V76

About Oxacillin

An antibiotic similar to FLUCLOXACILLIN used in resistant staphylococci infections.

Oxacillin Manufacturers

A Oxacillin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Oxacillin, including repackagers and relabelers. The FDA regulates Oxacillin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Oxacillin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Oxacillin Suppliers

A Oxacillin supplier is an individual or a company that provides Oxacillin active pharmaceutical ingredient (API) or Oxacillin finished formulations upon request. The Oxacillin suppliers may include Oxacillin API manufacturers, exporters, distributors and traders.

click here to find a list of Oxacillin suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Oxacillin USDMF

A Oxacillin DMF (Drug Master File) is a document detailing the whole manufacturing process of Oxacillin active pharmaceutical ingredient (API) in detail. Different forms of Oxacillin DMFs exist exist since differing nations have different regulations, such as Oxacillin USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Oxacillin DMF submitted to regulatory agencies in the US is known as a USDMF. Oxacillin USDMF includes data on Oxacillin's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Oxacillin USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Oxacillin suppliers with USDMF on PharmaCompass.

Oxacillin GMP

Oxacillin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Oxacillin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Oxacillin GMP manufacturer or Oxacillin GMP API supplier for your needs.

Oxacillin CoA

A Oxacillin CoA (Certificate of Analysis) is a formal document that attests to Oxacillin's compliance with Oxacillin specifications and serves as a tool for batch-level quality control.

Oxacillin CoA mostly includes findings from lab analyses of a specific batch. For each Oxacillin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Oxacillin may be tested according to a variety of international standards, such as European Pharmacopoeia (Oxacillin EP), Oxacillin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Oxacillin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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