Bacampicillin

Synopsis, 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 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 Formula	C₂₁H₂₈ClN₃O₇S
Molecular Weight	502.0 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	10
Exact Mass	501.1336491 g/mol
Monoisotopic Mass	501.1336491 g/mol
Topological Polar Surface Area	163 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	756
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2