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    Ceforanide

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    $ API Ref.Price (USD/KG) : 1,864Xls

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    2D Structure
    Also known as: 60925-61-3, Precef, Ceforanido, Ceforanidum, Ceforanidum [inn-latin], Ceforanido [inn-spanish]
    Molecular Formula
    C20H21N7O6S2
    Molecular Weight
    519.6  g/mol
    InChI Key
    SLAYUXIURFNXPG-CRAIPNDOSA-N
    FDA UNII
    8M1YF8951V
    Ceforanide is a semi-synthetic, broad-spectrum, beta-lactam, second-generation cephalosporin antibiotic with bactericidal activity. Ceforanide causes inhibition of bacterial cell wall synthesis by inactivating penicillin binding proteins (PBPs) thereby interfering with the final transpeptidation step required for cross-linking of peptidoglycan units which are a component of the cell wall. This results in a reduction of cell wall stability and causes cell lysis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C20H21N7O6S2/c21-6-11-4-2-1-3-10(11)5-13(28)22-15-17(31)27-16(19(32)33)12(8-34-18(15)27)9-35-20-23-24-25-26(20)7-14(29)30/h1-4,15,18H,5-9,21H2,(H,22,28)(H,29,30)(H,32,33)/t15-,18-/m1/s1
    2.1.3 InChI Key
    SLAYUXIURFNXPG-CRAIPNDOSA-N
    2.1.4 Canonical SMILES
    C1C(=C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3CN)C(=O)O)CSC4=NN=NN4CC(=O)O
    2.1.5 Isomeric SMILES
    C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3CN)C(=O)O)CSC4=NN=NN4CC(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    8M1YF8951V
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 7-(alpha-(2-aminomethylphenyl)acetamido)-3-((1-carboxymethyltetrazol-5-ylthio)methyl)-3-cephem-4-carboxylic Acid

    2. Bl-s 786

    3. Bl-s786r

    4. Cefaronide

    5. Ceforanide, Monosodium Salt

    2.3.2 Depositor-Supplied Synonyms

    1. 60925-61-3

    2. Precef

    3. Ceforanido

    4. Ceforanidum

    5. Ceforanidum [inn-latin]

    6. Ceforanido [inn-spanish]

    7. Bl-s786

    8. (6r,7r)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    9. Chebi:3495

    10. 7-(o-(aminomethyl)phenylacetamido)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic Acid

    11. 8m1yf8951v

    12. Nsc-760049

    13. (6r,7r)-7-{2-[2-(aminomethyl)phenyl]acetamido}-3-({[1-(carboxymethyl)-1h-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    14. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-(aminomethyl)phenyl)acetyl)amino)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-trans)-

    15. 7-[o-(aminomethyl)phenylacetamido]-3-[[[1-(carboxymethyl)-1h-tetrazol-5-yl]thio]methyl]-3-cephem-4-carboxylic Acid

    16. 7beta-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1h-tetrazol-5-yl]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylic Acid

    17. Bl-s 786

    18. Precef (tn)

    19. Ceforanide (usp/inn)

    20. Sr-01000872614

    21. Unii-8m1yf8951v

    22. Ceforanide [usan:usp:inn:ban]

    23. Ncgc00016897-01

    24. Cas-60925-61-3

    25. (6r,7r)-7-(2-(alpha-amino-o-tolyl)acetamido)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

    26. Ceforanide [mi]

    27. Ceforanide [inn]

    28. Prestwick0_000470

    29. Prestwick1_000470

    30. Prestwick2_000470

    31. Prestwick3_000470

    32. Ceforanide [usan]

    33. Dsstox_cid_2760

    34. Ceforanide [vandf]

    35. Ceforanide [mart.]

    36. Ceforanide(200mg)

    37. Ceforanide [usp-rs]

    38. Ceforanide [who-dd]

    39. Dsstox_rid_76719

    40. Dsstox_gsid_22760

    41. Bspbio_000580

    42. (6r-trans)-7-(((2-(aminomethyl)phenyl)acetyl)amino)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

    43. Schembl122072

    44. Spbio_002519

    45. Bpbio1_000638

    46. Ceforanide [orange Book]

    47. Chembl1201046

    48. Dtxsid1022760

    49. Gtpl12218

    50. Ceforanide [usp Impurity]

    51. Hms1569m22

    52. Hms2096m22

    53. Hms3713m22

    54. (6r,7r)-7-(2-(2-(aminomethyl)phenyl)acetamido)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    55. Hy-b1297

    56. Zinc3830434

    57. Tox21_110670

    58. Ccg-220470

    59. Db00923

    60. Nsc 760049

    61. Ncgc00179514-05

    62. (6r,7r)-7-({[2-(aminomethyl)phenyl]acetyl}amino)-3-({[1-(carboxymethyl)-1h-tetrazol-5-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    63. (6r,7r)-7-({[2-(aminomethyl)phenyl]acetyl}amino)-3-({[1-(carboxymethyl)-1h-tetrazol-5-yl]thio}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    64. As-15783

    65. Ab00513845

    66. Cs-0013066

    67. S5081

    68. C06884

    69. D00259

    70. D81832

    71. 925c613

    72. A913663

    73. Q5057287

    74. Sr-01000872614-2

    75. Sr-01000872614-3

    76. Brd-k37848908-001-03-1

    77. (6r,7r)-7-(2-(.alpha.-amino-o-tolyl)acetamido)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

    78. (6r,7r)-7-(2-(2-(aminomethyl)phenyl)acetamido)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid

    79. 7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 519.6 g/mol
    Molecular Formula C20H21N7O6S2
    XLogP3-3.2
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count10
    Exact Mass519.09947376 g/mol
    Monoisotopic Mass519.09947376 g/mol
    Topological Polar Surface Area244 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity905
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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

    For the treatment of infections caused by susceptible organisms.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Ceforanide is a semisynthetic second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins.

    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

    J01D - Other beta-lactam antibacterials

    J01DC - Second-generation cephalosporins

    J01DC11 - Ceforanide

    5.4 Absorption, Distribution and Excretion

    Absorption

    Rapidly absorbed following intramuscular injection.

    5.5 Metabolism/Metabolites

    The major drug elimination route was urinary excretion with 85% of the dose being excreted unchanged in the urine within 12 hr, and no metabolites with antibiotic activity were observed in urine.

    5.6 Biological Half-Life

    2.6 to 2.98 hours

    5.7 Mechanism of Action

    The bactericidal activity of ceforanide results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).