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    Cefotiam

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    $ API Ref.Price (USD/KG) : 499Xls

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    2D Structure
    Also known as: 61622-34-2, Cefotiamum, Cefotiamum [inn-latin], Ceradon, Aspil, Ctm
    Molecular Formula
    C18H23N9O4S3
    Molecular Weight
    525.6  g/mol
    InChI Key
    QYQDKDWGWDOFFU-IUODEOHRSA-N
    FDA UNII
    91W6Z2N718
    One of the CEPHALOSPORINS that has a broad spectrum of activity against both gram-positive and gram-negative microorganisms.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-[[1-[2-(dimethylamino)ethyl]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/C18H23N9O4S3/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31)/t12-,15-/m1/s1
    2.1.3 InChI Key
    QYQDKDWGWDOFFU-IUODEOHRSA-N
    2.1.4 Canonical SMILES
    CN(C)CCN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)CC4=CSC(=N4)N)SC2)C(=O)O
    2.1.5 Isomeric SMILES
    CN(C)CCN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)CC4=CSC(=N4)N)SC2)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    91W6Z2N718
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Abbott 48999

    2. Abbott-48999

    3. Abbott48999

    4. Cefotiam Hydrochloride

    5. Ceradolan

    6. Cgp 14221 E

    7. Cgp-14221-e

    8. Cgp14221e

    9. Haloapor

    10. Halospor

    11. Hydrochloride, Cefotiam

    12. Sce 963

    13. Sce-963

    14. Sce963

    2.3.2 Depositor-Supplied Synonyms

    1. 61622-34-2

    2. Cefotiamum

    3. Cefotiamum [inn-latin]

    4. Ceradon

    5. Aspil

    6. Ctm

    7. Cefotiam (inn)

    8. J01dc07

    9. Chebi:355510

    10. 91w6z2n718

    11. Cefotiam [inn]

    12. Cefotiam [inn:ban]

    13. (6r,7r)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-[[1-[2-(dimethylamino)ethyl]tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    14. (6r,7r)-7-[2-(2-amino-thiazol-4-yl)-acetylamino]-3-[1-(2-dimethylamino-ethyl)-1h-tetrazol-5-ylsulfanylmethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    15. Cgp 14221e

    16. 66309-69-1

    17. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[(2-amino-4-thiazolyl)acetyl]amino]-3-[[[1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl]thio]methyl]-8-oxo-, (6r,7r)-

    18. Aspil (tn)

    19. Sr-01000841230

    20. Unii-91w6z2n718

    21. Cefotiam,(s)

    22. (6r,7r)-7-(2-(2-aminothiazol-4-yl)acetamido)-3-((1-(2-(dimethylamino)ethyl)-1h-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    23. Cefotiam [jan]

    24. Cefotiam [mi]

    25. Prestwick0_000482

    26. Prestwick1_000482

    27. Prestwick2_000482

    28. Prestwick3_000482

    29. Cefotiam [who-dd]

    30. Chembl1296

    31. Bspbio_000343

    32. Schembl149538

    33. Spbio_002264

    34. Bpbio1_000379

    35. Dtxsid6022763

    36. Schembl11224134

    37. Hy-b0734

    38. Zinc3830445

    39. Bdbm50485561

    40. Db00229

    41. Ncgc00179594-01

    42. (6r,7r)-7-{[(2-amino-1,3-thiazol-4-yl)acetyl]amino}-3-[({1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl}sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    43. (6r,7r)-7-{[(2-amino-1,3-thiazol-4-yl)acetyl]amino}-3-[({1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl}thio)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    44. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)acetyl)amino)-3-(((1-(2-(dimethylamino)ethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-trans)-

    45. 7beta-(2-amino-1,3-thiazol-4-yl)acetamido-3-[({1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl}sulfanyl)methyl]-3,4-didehydrocepham-4-carboxylic Acid

    46. Ab00514684

    47. Cs-0009630

    48. C21544

    49. D07648

    50. 622c342

    51. J-700162

    52. Q3009984

    53. Sr-01000841230-2

    54. Brd-k02275692-003-03-4

    55. (6r,7r)-7-[2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-[({1-[2-(dimethylamino)ethyl]-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

    56. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[(2-amino-4-thiazolyl)acetyl]amino]-3-[[[1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl]thio]methyl]-8-oxo-,(6r,7r)-

    57. 7beta-(2-imino-4-thiazolin-4-yl)acetamido-3-{1-[2-(n,n-dimethylamino)ethyl]-1h-tetrazol-5-yl}thiomethyl-3-cephem-4-carboxylic Acid

    58. 7beta-[ 2-(2-aminothiazol-4-yl) Acetamido]-3-[1-(2-dimethylaminoethyl)-1h-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic Acid

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 525.6 g/mol
    Molecular Formula C18H23N9O4S3
    XLogP3-2.4
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count10
    Exact Mass525.10351377 g/mol
    Monoisotopic Mass525.10351377 g/mol
    Topological Polar Surface Area251 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity848
    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 treatment of severe infections caused by susceptible bacteria.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Cefotiam is a third generation beta-lactam cephalosporin antibiotic that works by inhibiting bacterial cell wall biosynthesis. It is a broad spectrum antibiotic that is effective against Gram positive and Gram negative bacteria.

    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

    J01DC07 - Cefotiam

    5.4 Absorption, Distribution and Excretion

    Absorption

    Rapidly absorbed following intramuscular injection. Bioavailability is 60% following intramuscular injection.

    5.5 Biological Half-Life

    Approximately 1 hour.

    5.6 Mechanism of Action

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