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

    Oxacillin Sodium

    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]

    API Reference Price

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