Amoxicillin Sodium

Synopsis, 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

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 Formula	C₁₆H₁₈N₃NaO₅S
Molecular Weight	387.4 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	387.08648614 g/mol
Monoisotopic Mass	387.08648614 g/mol
Topological Polar Surface Area	161 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	596
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2