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Ampicillin Trihydrate
Also known as: 615-347-9, 7177-48-2, Aminobenzylpenicillin trihydrate, Penbritin, Nci-c56086, Ampicillin/ampicillin trihydrate
Molecular Formula
C16H25N3O7S
Molecular Weight
403.5  g/mol
InChI Key
RXDALBZNGVATNY-CWLIKTDRSA-N
FDA UNII
HXQ6A1N7R6

Ampicillin Trihydrate is the trihydrate form of ampicillin, a broad-spectrum semisynthetic derivative of aminopenicillin. Ampicillin trihydrate inhibits bacterial cell wall synthesis by binding to penicillin binding proteins, thereby inhibiting peptidoglycan synthesis, a critical component of the bacterial cell wall.
1 2D Structure

Ampicillin Trihydrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;trihydrate
2.1.2 InChI
InChI=1S/C16H19N3O4S.3H2O/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8;;;/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23);3*1H2/t9-,10-,11+,14-;;;/m1.../s1
2.1.3 InChI Key
RXDALBZNGVATNY-CWLIKTDRSA-N
2.1.4 Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C.O.O.O
2.1.5 Isomeric SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C.O.O.O
2.2 Other Identifiers
2.2.1 UNII
HXQ6A1N7R6
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 615-347-9

2. 7177-48-2

3. Aminobenzylpenicillin Trihydrate

4. Penbritin

5. Nci-c56086

6. Ampicillin/ampicillin Trihydrate

7. Hxq6a1n7r6

8. (2s,5r,6r)-6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Trihydrate

9. Chebi:31209

10. Poly-cillin

11. Ampicillin Hydrate

12. Amperil

13. Ampinova

14. Trafarbiot

15. Amcap

16. Cymbi

17. D-(-)-alpha-aminobenzylpenicillin

18. (2s,5r,6r)-6-{[(2r)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Trihydrate

19. Ampicillin 3-wasser

20. Alpha-aminobenzylpenicillin Trihydrate

21. (2s,5r,6r)-6-[(2r)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

22. (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Trihydrate

23. (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid;trihydrate

24. Ccris 267

25. Unii-hxq6a1n7r6

26. (d-(-)-alpha-aminobenzyl)penicillin Trihydrate

27. Cas-7177-48-2

28. Amcill (tn)

29. Ampicilline Trihydrate

30. Dsstox_cid_83

31. Ampicillin Hydrate (jp17)

32. Dsstox_rid_75354

33. Dsstox_gsid_20083

34. Ampicillin Trihydrate, Sodium

35. Chembl453388

36. Ampicillin Hydrate [jan]

37. Ampicillin/ampicillin Monohydrate

38. Dtxsid9020083

39. Ampicillin Trihydrate [mi]

40. Hms1568g10

41. Hms2095g10

42. Hms3712g10

43. Tox21_201148

44. Ampicillin Trihydrate [vandf]

45. Mfcd00072036

46. S4148

47. Ampicillin Trihydrate [mart.]

48. Akos015915153

49. Ampicillin Trihydrate [usp-rs]

50. Ampicillin Trihydrate [who-dd]

51. Ampicillin Trihydrate [who-ip]

52. Ccg-220114

53. Ks-5251

54. Ncgc00023282-03

55. Ncgc00258700-01

56. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((2r)-aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, Trihydrate, (2s,5r,6r)-

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

58. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, Trihydrate, D- (-)-

59. Ampicillin Trihydrate [green Book]

60. Ampicillin Trihydrate [ep Monograph]

61. Ampicillin, Meets Usp Testing Specifications

62. D01251

63. 005a175

64. Sr-01000000061

65. Sr-01000000061-4

66. Ampicillin/ampicillin Trihydrate [orange Book]

67. Q27114210

68. Ampicillin Trihydrate, Vetranal(tm), Analytical Standard

69. Ampicillin Trihydrate, 96.0-100.5% Anhydrous Basis (hplc)

70. Ampicillin Trihydrate, British Pharmacopoeia (bp) Reference Standard

71. Ampicillin Trihydrate, European Pharmacopoeia (ep) Reference Standard

72. Ampicillin Trihydrate, United States Pharmacopeia (usp) Reference Standard

73. 6beta-[(2r)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylic Acid Trihydrate

74. Ampicillin Trihydrate, Pharmaceutical Secondary Standard; Certified Reference Material

75. (2s,5r,6r)-6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacidtrihydrate

76. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((2r)-2-amino-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-, Hydrate (1:3), (2s,5r,6r)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 403.5 g/mol
Molecular Formula C16H25N3O7S
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Exact Mass403.14132132 g/mol
Monoisotopic Mass403.14132132 g/mol
Topological Polar Surface Area141 Ų
Heavy Atom Count27
Formal Charge0
Complexity562
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count4
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameAmpicillin trihydrate
Drug LabelAmpicillin trihydrate is a semisynthetic penicillin derived from the basic penicillin nucleus, 6-aminopenicillanic acid. Ampicillin is designed chemically as (2S, 5R, 6R)-6-[(R)-2-Amino-2-phenylacetamido]-3, 3-dimethyl-7-oxo-4-this-l-azabicyclo[3.2.0...
Active IngredientAmpicillin/ampicillin trihydrate
Dosage FormCapsule; For suspension
RouteOral
Strengtheq 250mg base/5ml; eq 500mg base; eq 250mg base; eq 125mg base/5ml
Market StatusPrescription
CompanySandoz; Dava Pharms

2 of 2  
Drug NameAmpicillin trihydrate
Drug LabelAmpicillin trihydrate is a semisynthetic penicillin derived from the basic penicillin nucleus, 6-aminopenicillanic acid. Ampicillin is designed chemically as (2S, 5R, 6R)-6-[(R)-2-Amino-2-phenylacetamido]-3, 3-dimethyl-7-oxo-4-this-l-azabicyclo[3.2.0...
Active IngredientAmpicillin/ampicillin trihydrate
Dosage FormCapsule; For suspension
RouteOral
Strengtheq 250mg base/5ml; eq 500mg base; eq 250mg base; eq 125mg base/5ml
Market StatusPrescription
CompanySandoz; Dava Pharms

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