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    Cefpirome Sulphate

    ACTIVE PHARMA INGREDIENTS

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    FINISHED DOSAGE FORMULATIONS

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    PharmaCompass
    $ API Ref.Price (USD/KG) : 630Xls

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    2D Structure
    Also known as: 84957-29-9, Cefpiroma, Cefpiromum, Cefrom, Cefir, Cefpirome sulfate
    Molecular Formula
    C22H22N6O5S2
    Molecular Weight
    514.6  g/mol
    InChI Key
    DKOQGJHPHLTOJR-WHRDSVKCSA-N
    FDA UNII
    S72Q2F09HY
    Cefpirome is a semisynthetic, broad-spectrum, fourth-generation cephalosporin with antibacterial activity. Cefpirome binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C22H22N6O5S2/c1-33-26-15(13-10-35-22(23)24-13)18(29)25-16-19(30)28-17(21(31)32)12(9-34-20(16)28)8-27-7-3-5-11-4-2-6-14(11)27/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32)/b26-15-/t16-,20-/m1/s1
    2.1.3 InChI Key
    DKOQGJHPHLTOJR-WHRDSVKCSA-N
    2.1.4 Canonical SMILES
    CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCC5)C(=O)[O-]
    2.1.5 Isomeric SMILES
    CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCC5)C(=O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    S72Q2F09HY
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3-((2,3-cyclopenteno-1-pyridinium)methyl)-7-(2-syn-methoximino-2-(2-aminothiazole-4-yl)acetamido)ceph-3-em-4-carboxylate

    2. Cefpirome Sulfate

    3. Cefrom

    4. Hr 810

    5. Hr-810

    6. Metran

    2.3.2 Depositor-Supplied Synonyms

    1. 84957-29-9

    2. Cefpiroma

    3. Cefpiromum

    4. Cefrom

    5. Cefir

    6. Cefpirome Sulfate

    7. Hr 810

    8. Hr-810 Free Base

    9. Chebi:3503

    10. S72q2f09hy

    11. Hr-810

    12. Cefpirome (inn)

    13. (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5h-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    14. Cefpirome Sulphate

    15. Cefpirome [inn]

    16. (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(6,7-dihydro-5h-cyclopenta[b]pyridinium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    17. 5h-cyclopenta[b]pyridinium,1-[[(6r,7r)-7-[[(2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-, Inner Salt

    18. Cefpiromum [latin]

    19. Cefpiroma [spanish]

    20. Cefpirome [inn:ban]

    21. Ncgc00181339-01

    22. Unii-s72q2f09hy

    23. Broact

    24. Keiten

    25. Keiten, Cefpiroma

    26. Cefir (tn)

    27. Cefpirome [mi]

    28. Cefpirome [who-dd]

    29. Schembl49406

    30. Mls006010792

    31. Chembl65794

    32. Dtxsid2048244

    33. Schembl22207951

    34. Akos016013926

    35. Db13682

    36. 1-(((6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-5h-1-pyridinium Hydroxide, Inner Salt

    37. 5h-1-pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-, Hydroxide, Inner Salt, (6r-(6alpha,7beta(z)))-

    38. Smr004701476

    39. 98753-19-6

    40. D07649

    41. (6r,7r)-7-((2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)-8-oxo-3-(2beta-trimethylenpyridinio)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carboxylat

    42. 1-(((6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-5h-1-pyrindinium Hydroxide, Inner Salt, 72-(z)-(o-methyloxime)

    43. 1-{[(6r,7r)-2-carboxylato-7-{[(2z)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5h,6h,7h-cyclopenta[b]pyridin-1-ium

    44. 5h-1-pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydro-, Hydroxide, Inner Salt, (6r-(6alpha,7beta(z)))-

    45. 5h-1-pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-, Hydroxide, Inner Salt, (6r-(6.alpha.,7.beta.(z)))-

    46. 7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(6,7-dihydro-5h-cyclopenta[b]pyridinium-1-ylmethyl)-3,4-didehydrocepham-4-carboxylic Acid

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 514.6 g/mol
    Molecular Formula C22H22N6O5S2
    XLogP30.9
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count6
    Exact Mass514.10931017 g/mol
    Monoisotopic Mass514.10931017 g/mol
    Topological Polar Surface Area208 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity955
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

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

    4.2 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DE - Fourth-generation cephalosporins

    J01DE02 - Cefpirome