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ACTIVE PHARMA INGREDIENTS

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Synopsis

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Chemistry

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Also known as: Amdinocillin pivoxil, 32886-97-8, Pivmecilinamo, Pivmecillinamum, Selexid, Amdinocillin pivoxil [usan]

Molecular Formula

C₂₁H₃₃N₃O₅S

Molecular Weight

439.6 g/mol

InChI Key

NPGNOVNWUSPMDP-HLLBOEOZSA-N

FDA UNII

1WAM1OQ30B

Pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin.

1 2D Structure

Pivmecillinam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1

2.1.3 InChI Key

NPGNOVNWUSPMDP-HLLBOEOZSA-N

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)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)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C

2.2 Other Identifiers

2.2.1 UNII

1WAM1OQ30B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Amdinocillin Pivoxil

2. Fl 1039

3. Fl-1039

4. Fl1039

5. Hydrochloride, Pivmecillinam

6. Mecillinam Pivaloyl Ester

7. Pivaloyl Ester, Mecillinam

8. Pivamdinocillin

9. Pivmecillinam Hydrochloride

10. Pivoxil, Amdinocillin

11. Selexid

2.3.2 Depositor-Supplied Synonyms

1. Amdinocillin Pivoxil

2. 32886-97-8

3. Pivmecilinamo

4. Pivmecillinamum

5. Selexid

6. Amdinocillin Pivoxil [usan]

7. Pivmecilinamo [inn-spanish]

8. Pivmecillinamum [inn-latin]

9. Ro 10-9071

10. Amdinocillin, Pivaloyloxymethyl Ester

11. Pivmecillinam (inn)

12. Pivmecillinam [inn]

13. 1wam1oq30b

14. Amdinocillin Pivoxil (usan)

15. Ro-10-9071

16. Chebi:51210

17. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (2s-(2alpha,5alpha,6beta))-

18. Hydroxymethyl (2s,5r,6r)-6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate Pivalate (ester)

19. Coactabs

20. [(2,2-dimethylpropanoyl)oxy]methyl (2s,5r,6r)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

21. [(2,2-dimethylpropanoyl)oxy]methyl 6beta-[(azepan-1-ylmethylidene)amino]-2,2-dimethylpenam-3alpha-carboxylate

22. Coactabs (tn)

23. 2,2-dimethylpropanoyloxymethyl (2s,5r,6r)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

24. Ncgc00016813-01

25. Cas-32887-03-9

26. Unii-1wam1oq30b

27. Sr-01000838842

28. Einecs 251-276-6

29. Prestwick0_001053

30. Prestwick1_001053

31. Prestwick2_001053

32. Prestwick3_001053

33. Pivmecillinam [jan]

34. Schembl33907

35. Schembl33908

36. Bspbio_001006

37. Pivmecillinam [mart.]

38. Spbio_002933

39. Pivmecillinam [who-dd]

40. Bpbio1_001108

41. Chembl1525183

42. Chembl1616433

43. Chembl1650818

44. Dtxsid7048538

45. Gtpl10922

46. Amdinocillin Pivoxil [mi]

47. Pivmecillinam, >=98% (hplc)

48. Bcp07843

49. Hy-b0810

50. Zinc4214799

51. Zinc13704173

52. Db01605

53. Ro-109071

54. Ncgc00179344-01

55. Ncgc00179344-04

56. Ncgc00179344-07

57. Ab00514713

58. D02889

59. A918810

60. Q418086

61. Sr-01000838842-2

62. Brd-k67100011-003-03-0

63. (2s,6r)-pivaloyloxymethyl 6-((e)-azepan-1-ylmethyleneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

64. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (2s-(2.alpha.,5.alpha.,6.beta.))-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₃₃N₃O₅S
Molecular Weight	439.6 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	8
Exact Mass	439.21409234 g/mol
Monoisotopic Mass	439.21409234 g/mol
Topological Polar Surface Area	114 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	710
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
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

Used to treat infections due to mecillinam-sensitive organisms such as urinary tract infections, salmonellosis and typhoid fever.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Pivmecillinam is a pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin.

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.)

Anti-Infective Agents, Urinary

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CA - Penicillins with extended spectrum

J01CA08 - Pivmecillinam

5.4 Absorption, Distribution and Excretion

Absorption

Well absorbed following oral administration.

5.5 Mechanism of Action

Pivmecillinam interferes with the biosynthesis of the bacterial cell wall however its activity is slightly different from that of other penicillins and cephalosporins

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