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    Chemistry

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    Also known as: 37661-08-8, Bacampicillin hcl, Spectrobid, Bacampicillin (hydrochloride), Becampicillin hydrochloride, Bapc
    Molecular Formula
    C21H28ClN3O7S
    Molecular Weight
    502.0  g/mol
    InChI Key
    IWVTXAGTHUECPN-ANBBSHPLSA-N
    FDA UNII
    PM034U953T
    Bacampicillin
    Bacampicillin Hydrochloride is the hydrochloride salt of bacampicillin, a prodrug of ampicillin, a broad-spectrum, semisynthetic, beta-lactam aminopenicillin antibiotic with bactericidal activity. Bacampicillin is hydrolyzed in vivo by esterases to its active metabolite ampicillin. Ampicillin binds to and inactivates penicillin-binding proteins (PBP) 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 and causes cell lysis.
    1 2D Structure

    Bacampicillin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-ethoxycarbonyloxyethyl (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;hydrochloride
    2.1.2 InChI
    InChI=1S/C21H27N3O7S.ClH/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12;/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25);1H/t11?,13-,14-,15+,18-;/m1./s1
    2.1.3 InChI Key
    IWVTXAGTHUECPN-ANBBSHPLSA-N
    2.1.4 Canonical SMILES
    CCOC(=O)OC(C)OC(=O)C1C(SC2N1C(=O)C2NC(=O)C(C3=CC=CC=C3)N)(C)C.Cl
    2.1.5 Isomeric SMILES
    CCOC(=O)OC(C)OC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)[C@@H](C3=CC=CC=C3)N)(C)C.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    PM034U953T
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Bacampicillin

    2. Bacampicillin Monohydrochloride

    3. Bacampicine

    4. Carampicillin

    5. Ethoxycarbonyloxyethyl Ester Of Ampicillin

    6. Penglobe

    2.3.2 Depositor-Supplied Synonyms

    1. 37661-08-8

    2. Bacampicillin Hcl

    3. Spectrobid

    4. Bacampicillin (hydrochloride)

    5. Becampicillin Hydrochloride

    6. Bapc

    7. Chebi:2969

    8. Pm034u953t

    9. Nsc-758228

    10. 37661-08-8 (hcl)

    11. Dsstox_cid_25466

    12. Dsstox_rid_80897

    13. Dsstox_gsid_45466

    14. (2s,5r,6r)-6-((r)-(2-amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid Ester With Ethyl 1-hydroxyethyl Carbonate, Monohydrochloride

    15. 1-ethoxycarbonyloxyethyl (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;hydrochloride

    16. Ambacamp

    17. Ambaxin

    18. Bacacil

    19. Velbacil

    20. Bacampicillin Hydrochoride

    21. Unii-pm034u953t

    22. Spectrobid (tn)

    23. Prestwick_776

    24. Einecs 253-580-4

    25. Bacampicillin Hydrochloride [usan:usp:jan]

    26. Ncgc00016837-01

    27. Surecn721373

    28. Cas-37661-08-8

    29. 4-propyloxybenzylamine

    30. Mls002153801

    31. Schembl124593

    32. Chembl1200965

    33. Dtxsid0045466

    34. Hy-b1149a

    35. Hms1569c14

    36. Tox21_110640

    37. Akos016014246

    38. Tox21_110640_1

    39. Ccg-220416

    40. Cs-4754

    41. Nsc 758228

    42. Bacampicillin Hydrochloride [mi]

    43. Bacampicillin Hydrochloride [jan]

    44. Ncgc00179582-03

    45. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1-((ethoxycarbonyl)oxy)ethyl Ester, Monohydrochloride, (2s-(2alpha,5alpha,6beta(s*)))-

    46. Bacampicillin Hydrochloride (jp17/usan)

    47. Bacampicillin Hydrochloride [usan]

    48. Smr001233177

    49. Bacampicillin Hydrochloride [mart.]

    50. Bacampicillin Hydrochloride [vandf]

    51. Bacampicillin Hydrochloride [who-dd]

    52. C08123

    53. D00927

    54. Bacampicillin Hydrochloride [orange Book]

    55. A823813

    56. Bacampicillin Hydrochloride [ep Monograph]

    57. Bacampicillin Hydrochloride [usp Impurity]

    58. Q27105902

    59. (2s,5r,6r)-6-[[(2r)-2-amino-1-oxo-2-phenylethyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 1-ethoxycarbonyloxyethyl Ester Hydrochloride

    60. 1-((ethoxycarbonyl)oxy)ethyl (2s-(2alpha,5alpha,6beta(s*)))-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate Monohydrochloride

    61. 1-ethoxycarbonyloxyethyl (2s,5r,6r)-6-[[(2r)-2-amino-2-phenyl-acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

    62. 1-ethoxycarbonyloxyethyl (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;hydron;chloride

    63. 1-ethoxycarbonyloxyethyl (2s,5r,6r)-6-[[(2r)-2-azanyl-2-phenyl-ethanoyl]amino]-3,3-dimethyl-7-oxidanylidene-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Hydrochloride

    64. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1-((ethoxycarbonyl)oxy)ethyl Ester, Hydrochloride

    65. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1-((ethoxycarbonyl)oxy)ethyl Ester, Monohydrochloride, (2s-(2.alpha.,5.alpha.,6.beta.(s*)))-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 502.0 g/mol
    Molecular Formula C21H28ClN3O7S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count10
    Exact Mass501.1336491 g/mol
    Monoisotopic Mass501.1336491 g/mol
    Topological Polar Surface Area163 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity756
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    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.)

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