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    Sultamicillin

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

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    2D Structure
    Also known as: 76497-13-7, Sultamicilina, Sultamicillinum, Sultamicillin tosylate, Vd 1827, Cp-49,952
    Molecular Formula
    C25H30N4O9S2
    Molecular Weight
    594.7  g/mol
    InChI Key
    OPYGFNJSCUDTBT-PMLPCWDUSA-N
    FDA UNII
    65DT0ML581
    Sultamicillin is a combination formulation of the sodium salts of the antibiotic ampicillin and the beta-lactamase inhibitor sulbactam with antibacterial activity. Ampicillin, a broad-spectrum, semisynthetic penicillin, binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall, thereby interfering with the cross-linking of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. As a result, the cell wall is weakened and the cell lyses. The sulbactam component irreversibly binds to bacterial beta-lactamase at or near its active site, thereby interfering with substrate binding and inhibiting bacterial metabolism of penicillin and cephalosporin beta-lactam antibiotics, effectively extending their antibiotic spectrum to include many beta-lactam-resistant bacteria.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2S,5R)-3,3-dimethyl-4,4,7-trioxo-46-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
    2.1.2 InChI
    InChI=1S/C25H30N4O9S2/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1
    2.1.3 InChI Key
    OPYGFNJSCUDTBT-PMLPCWDUSA-N
    2.1.4 Canonical SMILES
    CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)OCOC(=O)C4C(S(=O)(=O)C5N4C(=O)C5)(C)C)C
    2.1.5 Isomeric SMILES
    CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)OCOC(=O)[C@H]4C(S(=O)(=O)[C@H]5N4C(=O)C5)(C)C)C
    2.2 Other Identifiers
    2.2.1 UNII
    65DT0ML581
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ampicillin-sulbactam

    2. Combisid

    3. Cp 49,952

    4. Cp 49952

    5. Unasyn

    2.3.2 Depositor-Supplied Synonyms

    1. 76497-13-7

    2. Sultamicilina

    3. Sultamicillinum

    4. Sultamicillin Tosylate

    5. Vd 1827

    6. Cp-49,952

    7. Chebi:51770

    8. 65dt0ml581

    9. 76497-13-7 (free)

    10. Unacid

    11. Vd-1827

    12. Cp-49952

    13. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-,[[[(2s,5r)-3,3-dimethyl-4,4-dioxido-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-yl]carbonyl]oxy]methylester, (2s,5r,6r)-

    14. Hydroxymethyl (2s,5r,6r)-6-((r)-(2-amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate, (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate (ester) S,s-dioxide

    15. (((2s,5r,6r)-6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl)oxy)methyl (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide

    16. ({6beta-[(2r)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carbonyl}oxy)methyl 2,2-dimethylpenam-3alpha-carboxylate 1,1-dioxide

    17. [(2,2-dimethyl-1,1-dioxidopenam-3alpha-carbonyl)oxy]methyl 6beta-[(2r)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylate

    18. Sultamicilina [spanish]

    19. Sultamicillinum [latin]

    20. Cp 49952

    21. Unii-65dt0ml581

    22. Sultamicillin [usan:inn:ban]

    23. Sultamicillin [mi]

    24. Sultamicillin [inn]

    25. Sultamicillin (usan/inn)

    26. Sultamicillin [usan]

    27. Schembl34392

    28. Sultamicillin [mart.]

    29. Sultamicillin [who-dd]

    30. Chembl506110

    31. Dtxsid501010077

    32. Hy-n7115

    33. Sultamicillin [ep Monograph]

    34. Sultamicillin For Peak Identification

    35. S5411

    36. Zinc42834847

    37. Akos015963376

    38. Ccg-270182

    39. Db12127

    40. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonyloxymethyl (2s,5r,6r)-6-((r)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carboxylat

    41. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (((3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-2-yl)carbonyl)oxy)methyl Ester, S,s-dioxide, (2s-(2alpha(2r*,5s*),5alpha,6beta(s*)))-

    42. As-14087

    43. Cs-0082687

    44. D05972

    45. 497s137

    46. 6'-(2-amino-2-phenylacetamido)penicillanoyloxymethyl Penicillanate 1,1-dioxide

    47. [(2s,5r)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

    48. 1,1-dioxopenicillanoyloxymethyl 6-(d-.alpha.-amino-.alpha.-phenylacetamido)penicillanate

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 594.7 g/mol
    Molecular Formula C25H30N4O9S2
    XLogP30.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count9
    Exact Mass594.14542089 g/mol
    Monoisotopic Mass594.14542089 g/mol
    Topological Polar Surface Area216 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity1240
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    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

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01C - Beta-lactam antibacterials, penicillins

    J01CR - Combinations of penicillins, incl. beta-lactamase inhibitors

    J01CR04 - Sultamicillin