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Pivampicillin

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Chemistry

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Also known as: Pivaloylampicillin, 33817-20-8, Pivaloyloxymethyl ampicillinate, Pivampicilina, Pivampicilline, Pivampicillinum

Molecular Formula

C₂₂H₂₉N₃O₆S

Molecular Weight

463.5 g/mol

InChI Key

ZEMIJUDPLILVNQ-ZXFNITATSA-N

FDA UNII

0HLM346LL7

Pivalate ester analog of AMPICILLIN.

1 2D Structure

Pivampicillin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.1.2 InChI

InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1

2.1.3 InChI Key

ZEMIJUDPLILVNQ-ZXFNITATSA-N

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)OCOC(=O)C(C)(C)C)C

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)OCOC(=O)C(C)(C)C)C

2.2 Other Identifiers

2.2.1 UNII

0HLM346LL7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ampicillin Pivaloyl Ester

2. Berocillin

3. Ester, Ampicillin Pivaloyl

4. Hydrochloride, Pivampicillin

5. Monohydrochloride, Pivampicillin

6. Pivamiser

7. Pivampicillin Hydrochloride

8. Pivampicillin Monohydrochloride

9. Pondocillin

2.3.2 Depositor-Supplied Synonyms

1. Pivaloylampicillin

2. 33817-20-8

3. Pivaloyloxymethyl Ampicillinate

4. Pivampicilina

5. Pivampicilline

6. Pivampicillinum

7. Ampicillin Pivaloyloxymethyl Ester

8. Pivampicilina [inn-spanish]

9. Pivampicilline [inn-french]

10. Pivampicillinum [inn-latin]

11. Pivampicillin (inn)

12. 0hlm346ll7

13. Chebi:8255

14. 2,2-dimethylpropanoyloxymethyl (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

15. Mk-191

16. Pivampicillin [inn]

17. Dsstox_cid_25459

18. Dsstox_rid_80890

19. Dsstox_gsid_45459

20. 2,2-dimethylpropanoyloxymethyl (2s,5r,6r)-6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

21. Pivampicillin [inn:ban]

22. Mk 191

23. Pondocillin (tn)

24. Einecs 251-688-6

25. Unii-0hlm346ll7

26. Ncgc00016823-01

27. Cas-33817-20-8

28. Prestwick0_001009

29. Prestwick1_001009

30. Prestwick2_001009

31. Prestwick3_001009

32. Pivampicillin [mi]

33. Schembl34182

34. Bspbio_001137

35. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (2s-(2alpha,5alpha,6beta(s*)))-

36. Pivampicillin [mart.]

37. Spbio_003018

38. Pivampicillin [who-dd]

39. Bpbio1_001251

40. Chembl3182343

41. Dtxsid1045459

42. Hms1571i19

43. Hms2098i19

44. Hms3715i19

45. Pivampicillin [ep Monograph]

46. Tox21_110631

47. Zinc34967244

48. Tox21_110631_1

49. Ccg-221009

50. Db01604

51. Ncgc00179290-01

52. Ncgc00179290-03

53. [(2,2-dimethylpropanoyl)oxy]methyl 6beta-[(2r)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylate

54. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, Hydroxymethyl Ester, Pivalate (ester), D-(-)-

55. Ab00513999

56. D08396

57. Sr-01000872693

58. Q3122143

59. Sr-01000872693-1

60. (2s,5r,6r)-pivaloyloxymethyl 6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

61. {[(2s,5r,6r)-6-[(2r)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbonyloxy}methyl 2,2-dimethylpropanoate

62. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester (2s-(2.alpha.,5.alpha.,6.beta.(s*)))-

63. Hydroxymethyl D-(-)-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate Pivalate (ester)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₉N₃O₆S
Molecular Weight	463.5 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Exact Mass	463.17770683 g/mol
Monoisotopic Mass	463.17770683 g/mol
Topological Polar Surface Area	153 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	774
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	1

4 Drug and Medication Information

4.1 Drug Indication

or the treatment of respiratory tract infections (including acute bronchitis, acute exacerbations of chronic bronchitis and pneumonia); ear, nose and throat infections; gynecological infections; urinary tract infections (including acute uncomplicated gonococcal urethritis) when caused by non penicillinase-producing susceptible strains of the following organisms: gram-positive organisms, e.g., streptococci, pneumococci and staphylococci; gram-negative organisms, e.g., H. influenzae, N. gonorrhoeae, E. coli, P. mirabilis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Pivampicillin is the pivaloyloxymethyl ester of (the semi-synthetic penicillin) ampicillin. It is an inactive pro-drug, which is converted during its absorption from the gastrointestinal tract to the microbiologically active ampicillin, together with formaldehyde and pivalic acid, by non-specific esterases present in most body tissues. Amounts in excess of 99% of the pivampicillin absorbed are converted to ampicillin within 15 minutes of absorption.

5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

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

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CA - Penicillins with extended spectrum

J01CA02 - Pivampicillin

5.4 Absorption, Distribution and Excretion

Absorption

Absorbed following oral administration.