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Technical details about Biapenem, learn more about the structure, uses, toxicity, action, side effects and more

Biapenem

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

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1. Also known as: 120410-24-4, Omegacin, Biapenern, L-627, Ljc-10627, Lj c10,627

Molecular Formula

C₁₅H₁₈N₄O₄S

Molecular Weight

350.4 g/mol

InChI Key

MRMBZHPJVKCOMA-YJFSRANCSA-N

FDA UNII

YR5U3L9ZH1

Biapenem is a 1-beta-methylcarbapenem antibiotic with a wide range of antibacterial activity. Biapenem has similar antibacterial activity to that of imipenem, but is more stable against human renal dehydropeptidase-I and with less neurotoxicity.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylsulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

2.1.2 InChI

InChI=1S/C15H18N4O4S/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)24-9-3-17-5-16-6-18(17)4-9/h5-11,20H,3-4H2,1-2H3/t7-,8-,10-,11-/m1/s1

2.1.3 InChI Key

MRMBZHPJVKCOMA-YJFSRANCSA-N

2.1.4 Canonical SMILES

CC1C2C(C(=O)N2C(=C1SC3CN4C=NC=[N+]4C3)C(=O)[O-])C(C)O

2.1.5 Isomeric SMILES

C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1SC3CN4C=NC=[N+]4C3)C(=O)[O-])[C@@H](C)O

2.2 Other Identifiers

2.2.1 UNII

YR5U3L9ZH1

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-((6,7-dihydro-5h-pyrazolo(1,2-a)(1,2,4)triazol-4-ium-6-yl)thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3,2,0)hept-2-ene-2-carboxylate

2. Cli 86,815

3. Cli 86815

4. Cli-86815

5. L 627

6. L-627

7. Ljc 10627

8. Ljc-10627

9. Ljc10,627

2.3.2 Depositor-Supplied Synonyms

1. 120410-24-4

2. Omegacin

3. Biapenern

4. L-627

5. Ljc-10627

6. Lj C10,627

7. Cl 186,815

8. L 627

9. Cl-186815

10. Rpx2003

11. (4r,5s,6s)-3-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylsulfanyl)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

12. Yr5u3l9zh1

13. Chebi:3089

14. Lj-c10627

15. (4r,5s,6s)-3-((6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-yl)thio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

16. 6-(((4r,5s,6s)-2-carboxy-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-en-3-yl)thio)-6,7-dihydro-5h-pyrazolo(1,2-a)-s-triazol-4-ium Hydroxide, Inner Salt

17. Biapenem [usan:inn]

18. Omegacin (tn)

19. (4r,5s,6s)-3-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylthio)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

20. (6s)-2-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylsulfanyl)-6-[(1r)-1-hydroxyethyl]-1beta-methyl-2,3-didehydro-1-carbapenam-3-carboxylate

21. Biapenem;(4r,5s,6s)-3-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylthio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

22. Ljc 10627

23. Unii-yr5u3l9zh1

24. Bipenem

25. Ncgc00164551-01

26. Ljc10627

27. Cli 86815

28. Ljc10,627

29. Mfcd00864863

30. Biapenem [usan]

31. Biapenem [inn]

32. Biapenem [jan]

33. Biapenem [mi]

34. Biapenem [mart.]

35. Biapenem [who-dd]

36. Dsstox_cid_26435

37. Dsstox_rid_81612

38. Dsstox_gsid_46435

39. Schembl49242

40. Biapenem (jan/usan/inn)

41. Chembl285347

42. Biapenem, >=98% (hplc)

43. Dtxsid5046435

44. Gtpl12022

45. Ex-a4945

46. Tox21_112180

47. S1370

48. Akos025149478

49. Ccg-268031

50. Cs-2071

51. Db13028

52. Ncgc00164551-02

53. Ncgc00164551-05

54. As-14655

55. Hy-13573

56. L627

57. Cas-120410-24-4

58. D01057

59. A804499

60. Q-101421

61. Q4902548

62. (4r,5s,6s)-3-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylthio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

63. (4r,5s,6s)-3-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylthio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

64. 5h-pyrazolo(1,2-a)(1,2,4)triazol-4-ium, 6-((2-carboxy-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-en-3-yl)thio)-6,7-dihydro-, Hydroxide, Inner Salt, (4r-(4.alpha.,5.beta.,6.beta.(r*)))-

65. 6-(((4r,5s,6s)-2-carboxy-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-en-3-yl)thio)-6,7-dihydro-5h-pyrazolo(1,2-a)(1,2,4)triazol-4-ium Inner Salt

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₈N₄O₄S
Molecular Weight	350.4 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	350.10487624 g/mol
Monoisotopic Mass	350.10487624 g/mol
Topological Polar Surface Area	128 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	609
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	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

4.2 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DH - Carbapenems

J01DH05 - Biapenem

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