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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

Pivampicillin
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 Weight 463.5 g/mol
Molecular Formula C22H29N3O6S
XLogP32.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Exact Mass463.17770683 g/mol
Monoisotopic Mass463.17770683 g/mol
Topological Polar Surface Area153 Ų
Heavy Atom Count32
Formal Charge0
Complexity774
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.


5.5 Biological Half-Life

Approximately 1 hour.


5.6 Mechanism of Action

Ampicillin (the active metabolite of pivampicillin) has a bactericidal action resulting from inhibition of cell wall mucopeptide biosynthesis.


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ABOUT THIS PAGE

Pivampicillin Manufacturers

A Pivampicillin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Pivampicillin, including repackagers and relabelers. The FDA regulates Pivampicillin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Pivampicillin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Pivampicillin Suppliers

A Pivampicillin supplier is an individual or a company that provides Pivampicillin active pharmaceutical ingredient (API) or Pivampicillin finished formulations upon request. The Pivampicillin suppliers may include Pivampicillin API manufacturers, exporters, distributors and traders.

click here to find a list of Pivampicillin suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Pivampicillin CEP

A Pivampicillin CEP of the European Pharmacopoeia monograph is often referred to as a Pivampicillin Certificate of Suitability (COS). The purpose of a Pivampicillin CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Pivampicillin EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Pivampicillin to their clients by showing that a Pivampicillin CEP has been issued for it. The manufacturer submits a Pivampicillin CEP (COS) as part of the market authorization procedure, and it takes on the role of a Pivampicillin CEP holder for the record. Additionally, the data presented in the Pivampicillin CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Pivampicillin DMF.

A Pivampicillin CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Pivampicillin CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Pivampicillin suppliers with CEP (COS) on PharmaCompass.

Pivampicillin GMP

Pivampicillin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Pivampicillin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Pivampicillin GMP manufacturer or Pivampicillin GMP API supplier for your needs.

Pivampicillin CoA

A Pivampicillin CoA (Certificate of Analysis) is a formal document that attests to Pivampicillin's compliance with Pivampicillin specifications and serves as a tool for batch-level quality control.

Pivampicillin CoA mostly includes findings from lab analyses of a specific batch. For each Pivampicillin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Pivampicillin may be tested according to a variety of international standards, such as European Pharmacopoeia (Pivampicillin EP), Pivampicillin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Pivampicillin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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