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Amdinocillin

Synopsis, Chemistry

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Also known as: Amdinocillin, 32887-01-7, Penicillin hx, Coactin, Hexacillin, Mecillinamum

Molecular Formula

C₁₅H₂₃N₃O₃S

Molecular Weight

325.4 g/mol

InChI Key

BWWVAEOLVKTZFQ-NTZNESFSSA-N

FDA UNII

V10579P3QZ

An amidinopenicillanic acid derivative with broad spectrum antibacterial action.

1 2D Structure

Amdinocillin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

2.1.2 InChI

InChI=1S/C15H23N3O3S/c1-15(2)11(14(20)21)18-12(19)10(13(18)22-15)16-9-17-7-5-3-4-6-8-17/h9-11,13H,3-8H2,1-2H3,(H,20,21)/t10-,11+,13-/m1/s1

2.1.3 InChI Key

BWWVAEOLVKTZFQ-NTZNESFSSA-N

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)C(=O)O)C

2.1.5 Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)O)C

2.2 Other Identifiers

2.2.1 UNII

V10579P3QZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Amdinocillin

2. Fl 1060

3. Fl-1060

4. Fl1060

5. Penicillin Hx

2.3.2 Depositor-Supplied Synonyms

1. Amdinocillin

2. 32887-01-7

3. Penicillin Hx

4. Coactin

5. Hexacillin

6. Mecillinamum

7. Selexidin

8. Mecilinamo

9. Fl 1060

10. Amdinocillin [usan]

11. Ro 10-9070

12. Fl-1060

13. Mecillinam (inn)

14. Mecillinam [inn]

15. Amdinocillin (usan)

16. Ro-10-9070

17. (2s,5r,6r)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

18. V10579p3qz

19. (2s,5r,6r)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

20. Dsstox_cid_2584

21. Dsstox_rid_76643

22. Dsstox_gsid_22584

23. Mecilinamo [inn-spanish]

24. Mecillinamum [inn-latin]

25. (2s,5r,6r)-6-{[(1e)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

26. 79580-20-4

27. Smr000466361

28. Coactin (tn)

29. Ro 109070

30. Cas-32887-01-7

31. Micillinam

32. Einecs 251-277-1

33. 6-((hexahydro-1h-azepin-1-yl)methyleneamino)penicillanic Acid

34. Amdinocillin [usan:usp]

35. Unii-v10579p3qz

36. (2s,5r,6r)-6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

37. Ncgc00164583-01

38. Selecidin

39. Mecillinam [jan]

40. Amdinocillin [mi]

41. Chembl530

42. Mecillinam [mart.]

43. Mecillinam [who-dd]

44. Schembl34387

45. Schembl34388

46. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, (2s-(2alpha,5alpha,6beta))-

47. Mls000759478

48. Mls001424041

49. Mecillinam;coactin;fl 1060

50. Chembl258646

51. Dtxsid3022584

52. Amdinocillin [orange Book]

53. Hms2051e14

54. Act03258

55. Hy-a0269

56. Zinc3830206

57. Tox21_112209

58. Mfcd00056869

59. S6584

60. Zinc12469558

61. Tox21_112209_1

62. Ccg-100873

63. Db01163

64. Fs-4354

65. Nc00123

66. 6beta-[(azepan-1-ylmethylidene)amino]-2,2-dimethylpenam-3alpha-carboxylic Acid

67. Ncgc00164583-02

68. Ncgc00188988-01

69. Ac-32602

70. Cs-0017618

71. C21545

72. D02888

73. Mecillinam, Vetranal(tm), Analytical Standard

74. Ab01209740-01

75. Brd-k41051431-001-01-6

76. Q13019044

77. 6beta-{[(azepan-1-yl)methylidene]amino}-2,2-dimethylpenam-3alpha-carboxylic Acid

78. (2s,5r,6r)-6-(((e)-azepan-1-ylmethylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

79. (2s,5r,6r)-6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid.

80. (2s,5r,6r)-6-((e)-azepan-1-ylmethyleneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

81. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, (2s-(2.alpha.,5.alpha.,6.beta.)0-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₃N₃O₃S
Molecular Weight	325.4 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	325.14601278 g/mol
Monoisotopic Mass	325.14601278 g/mol
Topological Polar Surface Area	98.5 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	500
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used in the treatment of urinary tract infections caused by some strains of E. coli and klebsiella and enterobacter species. Used mainly against Gram negative organisms.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Amdinocillin is a novel, semisynthetic penicillin effective against many gram-negative bacteria. The antibacterial activity of amdinocillin is derived from its ability to bind specifically and avidly to Penicillin Binding Protein-2 (PBP 2). Amdinocillin is active alone against many gram-negative organisms. Pseudomonas and non-fermenting gram-negative bacteria, however, are usually resistant. Amdinocillin, in combination with many beta-lactams, exhibits marked synergy against many enterobacteriaceae. No such synergy can be demonstrated for gram-positive organisms or pseudomonas species. Amdinocillin is not beta-lactamase stable. Organisms which produce high levels of plasma-mediated beta-lactamase are resistant to the drug. Co-administration of probenecid results in markedly elevated plasma levels of amdinocillin and delays its excretion.

5.2 MeSH Pharmacological Classification

Anti-Infective Agents, Urinary

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CA - Penicillins with extended spectrum

J01CA11 - Mecillinam

5.4 Absorption, Distribution and Excretion

Absorption

Poorly absorbed if given orally.

5.5 Biological Half-Life

Approximately 1 hour in patients with normal renal function. Increases to 3 to 6 hours in anephric patients.

5.6 Mechanism of Action

Amdinocillin is a stong and specific antagonist of Penicillin Binding Protein-2 (PBP 2). It is active against gram negative bacteria, preventing cell wall synthesis by inhibiting the activity of PBP2. PBP2 is a peptidoglycan elongation initiating enzyme. Peptidoglycan is a polymer of sugars and amino acids that is the main component of bacterial cell walls.