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    Pivmecillinam

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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 Weight 439.6 g/mol
    Molecular Formula C21H33N3O5S
    XLogP33.1
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count8
    Exact Mass439.21409234 g/mol
    Monoisotopic Mass439.21409234 g/mol
    Topological Polar Surface Area114 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity710
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    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

    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