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    Chemistry

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    Also known as: 34642-77-8, Acuotricina, Ibiamox, Sodium amoxicillin, Amoxicillin natrium, Amoxicillin (sodium)
    Molecular Formula
    C16H18N3NaO5S
    Molecular Weight
    387.4  g/mol
    InChI Key
    BYHDFCISJXIVBV-YWUHCJSESA-M
    FDA UNII
    544Y3D6MYH
    Amoxicillin Sodium
    A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.
    1 2D Structure

    Amoxicillin Sodium

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    sodium;(2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
    2.1.2 InChI
    InChI=1S/C16H19N3O5S.Na/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7;/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24);/q;+1/p-1/t9-,10-,11+,14-;/m1./s1
    2.1.3 InChI Key
    BYHDFCISJXIVBV-YWUHCJSESA-M
    2.1.4 Canonical SMILES
    CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)[O-])C.[Na+]
    2.1.5 Isomeric SMILES
    CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)C(=O)[O-])C.[Na+]
    2.2 Other Identifiers
    2.2.1 UNII
    544Y3D6MYH
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Actimoxi

    2. Amoxicillin

    3. Amoxicillin Anhydrous

    4. Amoxicillin Monopotassium Salt

    5. Amoxicillin Monosodium Salt

    6. Amoxicillin Trihydrate

    7. Amoxicillin, (r*)-isomer

    8. Amoxicilline

    9. Amoxil

    10. Amoxycillin

    11. Brl 2333

    12. Brl-2333

    13. Brl2333

    14. Clamoxyl

    15. Clamoxyl G.a.

    16. Clamoxyl Parenteral

    17. Hydroxyampicillin

    18. Penamox

    19. Polymox

    20. Trimox

    21. Wymox

    2.3.2 Depositor-Supplied Synonyms

    1. 34642-77-8

    2. Acuotricina

    3. Ibiamox

    4. Sodium Amoxicillin

    5. Amoxicillin Natrium

    6. Amoxicillin (sodium)

    7. Amoxicillin Sodium Salt

    8. Amoxicillin Sodium [usan]

    9. Novabritine

    10. Brl-2333ab-b

    11. Amoxycillin (as Sodium)

    12. Amoxicillin Sodium (amox)

    13. 544y3d6myh

    14. Riotapen

    15. Chebi:51255

    16. Amoxicillin Sodium (usan)

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

    18. Sodium;(2s,5r,6r)-6-[[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    19. Danoxillin

    20. Amitron

    21. Penamox

    22. Quimiopen

    23. Trifamox

    24. Alfida

    25. Lamoxy

    26. Alfoxil Enjektabl

    27. Agram Im

    28. Riotapen [inj.]

    29. Ibiamox [inj.]

    30. Moxacin [inj.]

    31. Penamox [inj.]

    32. Danoxillin [inj.]

    33. Lamoxy [inj.]

    34. Novabritine [inj.]

    35. Brl 23333ab-b

    36. Unii-544y3d6myh

    37. Einecs 252-124-1

    38. Schembl973672

    39. Chembl2105950

    40. Amoxicillin Sodium [mart.]

    41. Amoxicillin Sodium [who-dd]

    42. Bcp12668

    43. Hy-b0467

    44. Sodium (2s,5r,6r)-6-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

    45. Amoxicillin Sodium Salt [mi]

    46. Mfcd08063910

    47. S2565

    48. Akos015951334

    49. Ccg-268488

    50. Amoxicillin Sodium [ep Monograph]

    51. (2s-(2alpha,5alpha,6beta(s*)))-6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid Monosodium Salt

    52. Monosodium (-)-(2s,5r,6r)-6-((r)-2-amino(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

    53. D02925

    54. F20449

    55. Q27122484

    56. Na-6-[d-a-amino-p-hydroxyphenylacetamido]penicillanic Acid

    57. (2s-(2alpha,5alpha.6beta(s*)))-6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid Monosodium Salt

    58. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 6-[[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-, Sodium Salt, (2s,5r,6r)- (1:1)

    59. Monosodium (-)-(2s,5r,6r)-6-((r)-2-amino-2-(p-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

    60. Sodium (2s-(2alpha,5alpha,6beta(s*)))-6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

    61. Sodium 6beta-[(2r)-2-amino-2-(4-hydroxyphenyl)acetamido]-2,2-dimethylpenam-3alpha-carboxylate

    62. Sodium(2s,5r,6r)-6-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-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 387.4 g/mol
    Molecular Formula C16H18N3NaO5S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass387.08648614 g/mol
    Monoisotopic Mass387.08648614 g/mol
    Topological Polar Surface Area161 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity596
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

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

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