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DSSTox_CID_3143

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Also known as: 64221-86-9, Imipemide, N-formimidoylthienamycin, Imipenem anhydrous, Tienamycin, Imipenemum

Molecular Formula

C₁₂H₁₇N₃O₄S

Molecular Weight

299.35 g/mol

InChI Key

ZSKVGTPCRGIANV-ZXFLCMHBSA-N

FDA UNII

Q20IM7HE75

Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with CILASTATIN, a renal dipeptidase inhibitor.

Imipenem anhydrous is a Penem Antibacterial.

1 2D Structure

DSSTox_CID_3143

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1

2.1.3 InChI Key

ZSKVGTPCRGIANV-ZXFLCMHBSA-N

2.1.4 Canonical SMILES

CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O

2.1.5 Isomeric SMILES

C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O

2.2 Other Identifiers

2.2.1 UNII

Q20IM7HE75

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Anhydrous Imipenem

2. Anhydrous, Imipenem

3. Imipemide

4. Imipenem Anhydrous

5. Imipenem, Anhydrous

6. Mk 0787

7. Mk-0787

8. Mk0787

9. N Formimidoylthienamycin

10. N-formimidoylthienamycin

2.3.2 Depositor-Supplied Synonyms

1. 64221-86-9

2. Imipemide

3. N-formimidoylthienamycin

4. Imipenem Anhydrous

5. Tienamycin

6. Imipenemum

7. N-formimidoyl Thienamycin

8. Imipenem Hydrate

9. Mk 0787

10. Chebi:471744

11. 74431-23-5

12. Imipenem, N-formimidoyl Thienamycin

13. (5r,6s)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

14. Imipenem (inn)

15. Imipenem [inn]

16. (5r,6s)-6-((r)-1-hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure

17. (5r,6s)-3-((2-(formimidoylamino)ethyl)thio)-6-((r)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid

18. Mk-0787

19. Chembl148

20. Q20im7he75

21. (5r,6s)-3-(2-formimidoylamino-ethylsulfanyl)-6-((r)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

22. Imipenen

23. Dsstox_cid_3143

24. Dsstox_rid_76888

25. Dsstox_gsid_23143

26. Anhydrous Imipenem

27. Imipenem, Anhydrous

28. Imipenemum [latin]

29. Cas-64221-86-9

30. Sr-05000000294

31. Imipen

32. Unii-q20im7he75

33. Ncgc00016928-01

34. (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-(2-methanimidamidoethylsulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

35. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-((1r)-1-hydroxyethyl)-3-((2-((iminomethyl)amino)ethyl)thio)-7-oxo-, (5r,6s)-

36. 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid, 6-[(1r)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-, (5r,6s)-

37. Prestwick_844

38. Einecs 264-734-5

39. Mk-787

40. Mk0787

41. Imipenem [mi]

42. Imipenem Anhydrate

43. Prestwick0_000519

44. Prestwick1_000519

45. Prestwick2_000519

46. Prestwick3_000519

47. Epitope Id:120384

48. Imipenem [who-dd]

49. Bspbio_000477

50. Bidd:gt0686

51. Spbio_002398

52. Bpbio1_000525

53. Schembl1649260

54. Schembl8781920

55. Dtxsid2023143

56. Gtpl10821

57. Hy-b1369a

58. Primaxin (imipenem + Cilastatin)

59. Hms1569h19

60. Hms2090a15

61. Hms2096h19

62. Hms3260h20

63. Hms3713h19

64. Pharmakon1600-01506001

65. Bcp13012

66. Zinc4097225

67. Tox21_110689

68. Tox21_500279

69. Bdbm50049708

70. Bdbm50213266

71. Nsc717864

72. Nsc759901

73. Akos016010844

74. Tox21_110689_1

75. Ccg-220519

76. Ccg-221583

77. Db01598

78. Lp00279

79. Nsc-717864

80. Sdccgsbi-0633697.p001

81. Ncgc00167958-01

82. Ncgc00167958-02

83. Ncgc00167958-03

84. Ncgc00167958-05

85. Ncgc00167958-09

86. Ncgc00260964-01

87. (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-({2-[(iminomethyl)amino]ethyl}thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

88. 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid,6-[(1r)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-,(5r,6s)-

89. As-75130

90. Cs-0077844

91. C06665

92. D04515

93. D96091

94. Ab01563339_01

95. Recarbrio (imipenem + Cilastatin + Relebactam).

96. 847i667

97. Q425152

98. Sr-05000000294-2

99. Sr-05000000294-5

100. Thienamycin P-nitrobenzylester Hydrochloride(n-methylpyrrolidinonesolvate)

101. (5r,6s)-3-((2-formimidamidoethyl)thio)-6-((r)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

102. (5r,6s)-3-({2-[(e)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

103. (5r,6s)-3-(2-formimidamidoethylthio)-6-((r)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

104. (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-[(2-methanimidamidoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

105. [5r-[5.alpha.,6.alpha.(r*)]]-6-(1-hydroxyethyl)-3-[[2- [(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2- Ene-2-carboxylic Acid Monohydrate

106. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-(1-hydroxyethyl)-3-((2-((iminomethyl)amino)ethyl)thio)-7-oxo-, (5r-(5-alpha,6-alpha(r*)))-

107. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-(1-hydroxyethyl)-3-((2-((iminomethyl)amino)ethyl)thio)-7-oxo-, (5r-(5.alpha.,6.alpha.(r*)))-

108. 103730-39-8

109. 3-[(2-aminoethyl)thio]-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid (4-nitrophenyl)methylester Monohydrochloride Compd. With 1-methyl-2-pyrrolidinone (1:1)

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₇N₃O₄S
Molecular Weight	299.35 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	299.09397721 g/mol
Monoisotopic Mass	299.09397721 g/mol
Topological Polar Surface Area	142 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	491
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 Information

1 of 2
Drug Name	Primaxin
PubMed Health	Imipenem/Cilastatin (Injection)
Drug Classes	Antibiotic
Active Ingredient	imipenem; Cilastatin sodium
Dosage Form	Injectable
Route	Injection
Strength	500mg/vial; 250mg/vial; eq 500mg base/vial; eq 250mg base/vial
Market Status	Prescription
Company	Merck

2 of 2
Drug Name	Primaxin
PubMed Health	Imipenem/Cilastatin (Injection)
Drug Classes	Antibiotic
Active Ingredient	imipenem; Cilastatin sodium
Dosage Form	Injectable
Route	Injection
Strength	500mg/vial; 250mg/vial; eq 500mg base/vial; eq 250mg base/vial
Market Status	Prescription
Company	Merck

4.2 Drug Indication

Imipenem is indicated, in combination with [cilastatin] with or without [relebactam], for the treatment of bacterial infections including respiratory, skin, bone, gynecologic, urinary tract, and intra-abdominal as well as septicemia and endocarditis.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Imipenem is a beta-lactam antibiotic belongings to the subgroup of carbapenems. Imipenem is active against aerobic and anaerobic Gram positive as well as Gram negative bacteria including Pseudomonas aeruginosa and the Enterococcus. It exerts a bactericidal effects by disrupting cell wall synthesis.

5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

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

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

IMIPENEM ANHYDROUS

5.3.2 FDA UNII

Q20IM7HE75

5.3.3 Pharmacological Classes

Established Pharmacologic Class [EPC] - Penem Antibacterial

5.4 ATC Code

J01DH51

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

5.5 Absorption, Distribution and Excretion

Absorption

Imipenem is not effectively absorbed from the gastrointestinal tract and therefore must be administered parenterally. The bioavailability of the IM injection is 89%.

Route of Elimination

Approximately 70% of imipenem is excreted in the urine as the parent drug.

Volume of Distribution

The reported volume of distribution for imipenem ranges from 0.23-0.31 L/kg.

Clearance

The total clearance of imipenem is 0.2 L/h/kg. When used alone, the renal clearance is 0.05 L/h/kg. In combination with cilastatin the renal clearance of imipenem is 0.15 L/h/kg, likely due to the increased concentration of the parent drug.

5.6 Metabolism/Metabolites

Imipenem is metabolized by renal dehydropeptidase.

5.7 Biological Half-Life

When given via IV injection imipenem has a half-life of 1 h. The apparent half-life of the IM injection ranges from 1.3-5.1 h, likely due to slower absorption form the injection site.

5.8 Mechanism of Action

Imipenem acts as an antimicrobial through the inhibition of cell wall synthesis of various gram-positive and gram-negative bacteria. This inhibition of cell wall synthesis in gram-negative bateria is attained by binding to penicillin-binding proteins (PBPs). In E. coli and selected strains of P. aeruginosa, imipenem has shown to have the highest affinity to PBP-2, PBP-1a, and PBP-1b. This inhibition of PBPs prevents the bacterial cell from adding to the peptidoglycan polymer which forms the bacterial cell wall eventually leading to cell death.