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    Temocillin Disodium

    ACTIVE PHARMA INGREDIENTS

    DIGITAL CONTENT

    MARKET PLACE

    PharmaCompass
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    2D Structure
    Also known as: 66148-78-5, Temocillinum, Temocillina, Temocilline, Negaban, Brl 17421
    Molecular Formula
    C16H18N2O7S2
    Molecular Weight
    414.5  g/mol
    InChI Key
    BVCKFLJARNKCSS-DWPRYXJFSA-N
    FDA UNII
    03QB156W6I
    Temocillin is a semisynthetic, narrow-spectrum, beta-lactamase-resistant penicillin with antibacterial activity. Temocillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,5R,6S)-6-[(2-carboxy-2-thiophen-3-ylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C16H18N2O7S2/c1-15(2)9(12(22)23)18-13(24)16(25-3,14(18)27-15)17-10(19)8(11(20)21)7-4-5-26-6-7/h4-6,8-9,14H,1-3H3,(H,17,19)(H,20,21)(H,22,23)/t8?,9-,14+,16-/m0/s1
    2.1.3 InChI Key
    BVCKFLJARNKCSS-DWPRYXJFSA-N
    2.1.4 Canonical SMILES
    CC1(C(N2C(S1)C(C2=O)(NC(=O)C(C3=CSC=C3)C(=O)O)OC)C(=O)O)C
    2.1.5 Isomeric SMILES
    CC1([C@@H](N2[C@H](S1)[C@@](C2=O)(NC(=O)C(C3=CSC=C3)C(=O)O)OC)C(=O)O)C
    2.2 Other Identifiers
    2.2.1 UNII
    03QB156W6I
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Brl 17421

    2. Disodium 6beta-(2-carboxy-2-thien-3-ylacetamido)-6alpha-methoxypenicillanate

    3. Temocillin, (2s-(2alpha,5alpha,6alpha))-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. 66148-78-5

    2. Temocillinum

    3. Temocillina

    4. Temocilline

    5. Negaban

    6. Brl 17421

    7. Brl-17421

    8. N-((2s,5r,6s)-2-carboxy-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-3-thiophenemalonamic Acid

    9. Brl 17421 [as Sodium]

    10. (2s,5r,6s)-6-[(3-hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    11. Brl 17421 Free Acid

    12. Brl-17421 Free Acid

    13. Chebi:51817

    14. 03qb156w6i

    15. Temocillin (usan)

    16. (2s,5r,6s)-6-[(2-carboxy-2-thiophen-3-ylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    17. Temocillin [usan]

    18. Temocilline [inn-french]

    19. Temocillinum [inn-latin]

    20. Temocillina [inn-spanish]

    21. 6beta-[carboxy(thiophen-3-yl)acetamido]-6-methoxy-2,2-dimethylpenam-3alpha-carboxylic Acid

    22. (2s,5r,6s)-6-{[carboxy(3-thienyl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    23. (2s,5r,6s)-6-{[carboxy(thiophen-3-yl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    24. Einecs 266-184-1

    25. Temocillin [usan:inn:ban]

    26. Unii-03qb156w6i

    27. Temocillin [mi]

    28. Temocillin [inn]

    29. Temocillin [mart.]

    30. Temocillin [who-dd]

    31. Schembl34084

    32. Chembl1276310

    33. Gtpl10926

    34. Dtxsid201009398

    35. Brl17421

    36. Db12343

    37. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((carboxy-3-thienylacetyl)amino)-6-methoxy-3,3-dimethyl-7-oxo-, (2s-(2alpha,5alpha,6alpha))-

    38. Hy-145158

    39. Cs-0356857

    40. D06064

    41. 148t785

    42. A900942

    43. Q3983108

    44. (2s,5r,6s)-6-(2-carboxy-2-(thiophen-3-yl)acetamido)-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    45. (2s,5r,6s)-6-[2-carboxy(thiophen-3-yl)acetamido]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    46. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((carboxy-3-thienylacetyl)amino)-6-methoxy-3,3-dimethyl-7-oxo-, (2s-(2.alpha.,5.alpha.,6.alpha.))-

    2.4 Create Date
    2005-08-09
    3 Chemical and Physical Properties
    Molecular Weight 414.5 g/mol
    Molecular Formula C16H18N2O7S2
    XLogP31.1
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count6
    Exact Mass414.05554326 g/mol
    Monoisotopic Mass414.05554326 g/mol
    Topological Polar Surface Area187 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity700
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    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

    J01CA17

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01C - Beta-lactam antibacterials, penicillins

    J01CA - Penicillins with extended spectrum

    J01CA17 - Temocillin