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    Also known as: 985-16-0, Sodium nafcillin, Nafcillin sodium salt, Nafcillin sodium anhydrous, Nafcillin sodium, Nafcillin (sodium)
    Molecular Formula
    C21H21N2NaO5S
    Molecular Weight
    436.5  g/mol
    InChI Key
    AYAPZOUDXCDGIF-FRFVDRIFSA-M
    FDA UNII
    SY07234TTS
    Nafcillin Sodium
    A semi-synthetic antibiotic related to penicillin.
    1 2D Structure

    Nafcillin Sodium

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    sodium;(2S,5R,6R)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
    2.1.2 InChI
    InChI=1S/C21H22N2O5S.Na/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23;/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27);/q;+1/p-1/t15-,16+,19-;/m1./s1
    2.1.3 InChI Key
    AYAPZOUDXCDGIF-FRFVDRIFSA-M
    2.1.4 Canonical SMILES
    CCOC1=C(C2=CC=CC=C2C=C1)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].[Na+]
    2.1.5 Isomeric SMILES
    CCOC1=C(C2=CC=CC=C2C=C1)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
    SY07234TTS
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Nafcil

    2. Nafcillin

    3. Nafcillin, Monosodium Salt, Anhydrous

    4. Nafcillin, Sodium

    5. Naphthamidopenicillin

    6. Sodium Nafcillin

    7. Sodium, Nafcillin

    2.3.2 Depositor-Supplied Synonyms

    1. 985-16-0

    2. Sodium Nafcillin

    3. Nafcillin Sodium Salt

    4. Nafcillin Sodium Anhydrous

    5. Nafcillin Sodium

    6. Nafcillin (sodium)

    7. 6-(2-ethoxy-1-naphthamido)penicillin Sodium

    8. Sodium 6-(2-ethoxy-1-naphthamido)penicillanate

    9. Mls000069582

    10. Chebi:7448

    11. Sy07234tts

    12. 6-[2-ethoxy-1-naphthamido]-penicillin Sodium Salt

    13. Naftopen

    14. Smr000058840

    15. Sodium;(2s,5r,6r)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

    16. Anhydrous Nafcillin Sodium

    17. Brl 1383

    18. Einecs 213-574-4

    19. Unii-sy07234tts

    20. Nallpen In Plastic Container

    21. Unipen In Plastic Container

    22. Sodium (2s,5r,6r)-6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

    23. Opera_id_510

    24. Schembl34125

    25. Chembl1200344

    26. Hy-b0555b

    27. Dtxsid00904716

    28. Nafcillin Sodium [who-dd]

    29. Hms2236l03

    30. Hms3259o22

    31. Str11060

    32. Mfcd00056863

    33. Nc00606

    34. Ncgc00386250-01

    35. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amido)-3,3-dimethyl-7-oxo-, Monosodium Salt, (2s,5r,6r)-

    36. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-, Monosodium Salt

    37. Sodium (2s-(2alpha,5alpha,6beta))-6-(((2-ethoxy-1-naphthyl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

    38. Anhydrous Nafcillin Sodium [mart.]

    39. Cs-0129337

    40. Nafcillin Sodium Salt Anhydrous [mi]

    41. C08124

    42. Ab01566906_01

    43. 6-(2-ethoxy-1-naphthamido)penicillin Sodium Salt

    44. W-100077

    45. Q27107495

    46. Sodium 6beta-(2-ethoxynaphthalene-1-carboxamido)-2,2-dimethylpenam-3alpha-carboxylate

    47. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, (2s,5r,6r)-

    48. Sodium (2s,5r,6r)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

    49. Sodium (2s,5r,6r)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

    2.4 Create Date
    2008-02-05
    3 Chemical and Physical Properties
    Molecular Weight 436.5 g/mol
    Molecular Formula C21H21N2NaO5S
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count5
    Exact Mass436.10688723 g/mol
    Monoisotopic Mass436.10688723 g/mol
    Topological Polar Surface Area124 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity705
    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 NameNafcillin sodium
    Drug LabelNafcillin for Injection, USP is a semisynthetic antibiotic substance derived from 6-amino-penicillanic acid. It is the sodium salt in a parenteral dosage form. The chemical name of nafcillin sodium is monosodium (2S,5R,6R)-6-(2-ethoxy-1-naphthamido)-...
    Active IngredientNafcillin sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
    Market StatusPrescription
    CompanyIstituto Bio Ita Spa; Aurobindo Pharma; Sandoz; Antibiotice; Sagent Pharms; Agila Speclts

    2 of 4  
    Drug NameNallpen in plastic container
    Active IngredientNafcillin sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/100ml; eq 20mg base/ml
    Market StatusPrescription
    CompanyBaxter Hlthcare

    3 of 4  
    Drug NameNafcillin sodium
    Drug LabelNafcillin for Injection, USP is a semisynthetic antibiotic substance derived from 6-amino-penicillanic acid. It is the sodium salt in a parenteral dosage form. The chemical name of nafcillin sodium is monosodium (2S,5R,6R)-6-(2-ethoxy-1-naphthamido)-...
    Active IngredientNafcillin sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
    Market StatusPrescription
    CompanyIstituto Bio Ita Spa; Aurobindo Pharma; Sandoz; Antibiotice; Sagent Pharms; Agila Speclts

    4 of 4  
    Drug NameNallpen in plastic container
    Active IngredientNafcillin sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/100ml; eq 20mg base/ml
    Market StatusPrescription
    CompanyBaxter Hlthcare

    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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    06-May-2021
    19-Jan-2024
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