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Chemistry

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Also known as: 82009-34-5, Cilastatina, Cilastatine, Cilastatinum, Mk-791, Cilastatin (inn)

Molecular Formula

C₁₆H₂₆N₂O₅S

Molecular Weight

358.5 g/mol

InChI Key

DHSUYTOATWAVLW-WFVMDLQDSA-N

FDA UNII

141A6AMN38

A renal dehydropeptidase-I and leukotriene D4 dipeptidase inhibitor. Since the antibiotic, IMIPENEM, is hydrolyzed by dehydropeptidase-I, which resides in the brush border of the renal tubule, cilastatin is administered with imipenem to increase its effectiveness. The drug also inhibits the metabolism of leukotriene D4 to leukotriene E4.

Cilastatin is a Renal Dehydropeptidase Inhibitor. The mechanism of action of cilastatin is as a Dipeptidase Inhibitor.

1 2D Structure

Cilastatin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid

2.1.2 InChI

InChI=1S/C16H26N2O5S/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23)/b12-6-/t10-,11+/m1/s1

2.1.3 InChI Key

DHSUYTOATWAVLW-WFVMDLQDSA-N

2.1.4 Canonical SMILES

CC1(CC1C(=O)NC(=CCCCCSCC(C(=O)O)N)C(=O)O)C

2.1.5 Isomeric SMILES

CC1(C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N)/C(=O)O)C

2.2 Other Identifiers

2.2.1 UNII

141A6AMN38

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cilastatin Monosodium Salt

2. Cilastatin Sodium

3. Mk 0791

4. Mk 791

5. Mk-791

6. Mk0791

7. Mk791

8. Monosodium Salt, Cilastatin

9. Salt, Cilastatin Monosodium

10. Sodium, Cilastatin

2.3.2 Depositor-Supplied Synonyms

1. 82009-34-5

2. Cilastatina

3. Cilastatine

4. Cilastatinum

5. Mk-791

6. Cilastatin (inn)

7. Mk0791

8. Chebi:3697

9. Cilastatin Acid

10. 141a6amn38

11. Mk 0791

12. (2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1s)-2,2-dimethylcyclopropyl]formamido}hept-2-enoic Acid

13. Cilastatine [french]

14. Cilastatinum [latin]

15. Cilastatin [inn]

16. Cilastatina [spanish]

17. Cilastatin [inn:ban]

18. (z)-(s)-6-carboxy-6-[(s)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-l-cysteine

19. (z)-7-(((r)-2-amino-2-carboxyethyl)thio)-2-((s)-2,2-dimethylcyclopropane-1-carboxamido)hept-2-enoic Acid

20. Cilastin

21. (l)-7-(2-amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic Acid

22. (z)-7-((r)-2-amino-2-carboxy-ethylsulfanyl)-2-[((s)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic Acid

23. Ncgc00181346-01

24. Einecs 279-875-8

25. Unii-141a6amn38

26. Mk791

27. (z)-7-[(2s)-2-amino-3-hydroxy-3-oxopropyl]sulfanyl-2-[[(1s)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic Acid

28. Cilastatin [mi]

29. 81129-83-1

30. Cilastatin [vandf]

31. Chembl766

32. Cilastatin [who-dd]

33. Schembl37051

34. 2-heptenoic Acid, 7-((2-amino-2-carboxyethyl)thio)-2-(((2,2-dimethylcyclopropyl)carbonyl)amino)-, (r-(r*,s*-(z)))-

35. Bidd:gt0782

36. Gtpl5166

37. Dtxsid8048238

38. Ex-a4954

39. Hy-a0166

40. Zinc4095696

41. Ac-268

42. Bdbm50367502

43. Mfcd00867379

44. Akos015962144

45. Cs-8177

46. Db01597

47. (2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic Acid

48. Ds-11972

49. A16977

50. C01675

51. D07698

52. A840230

53. Q418201

54. Sr-01000781260

55. Sr-01000781260-3

56. (z)-7-[(2r)-2-azanyl-3-oxidanyl-3-oxidanylidene-propyl]sulfanyl-2-[[(1s)-2,2-dimethylcyclopropyl]carbonylamino]hept-2-enoic Acid

57. (z)-7-[[(2r)-2-amino-2-carboxyethyl]thio]-2-[[[(1s)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic Acid

58. 2-heptenoic Acid, 7-[[(2r)-2-amino-2-carboxyethyl]thio]-2-[[[(1s)-2,2-dimethylcyclopropyl]carbonyl]amino]-, (2z)-

2.4 Create Date

2006-04-28

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₆N₂O₅S
Molecular Weight	358.5 g/mol
XLogP3	-1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	11
Exact Mass	358.15624311 g/mol
Monoisotopic Mass	358.15624311 g/mol
Topological Polar Surface Area	155 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	519
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Cilastatin is indicated, in combination with [imipenem] 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

Cilastatin is a chemical compound which inhibits the human enzyme dehydropeptidase. Renal Dehydropeptidase degrades the antibiotic [imipenem]. Cilastatin is therefore combined intravenously with imipenem in order to protect it from dehydropeptidase and prolong its antibacterial effect. However, cilastatin in and of itself does not have any antibacterial activity. The increased renal excretion of unchanged imipenem appears to prevent proximal tubular necrosis associated with high doses of imipenem.

5.2 MeSH Pharmacological Classification

Protease Inhibitors

Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

CILASTATIN

5.3.2 FDA UNII

141A6AMN38

5.3.3 Pharmacological Classes

Established Pharmacologic Class [EPC] - Renal Dehydropeptidase Inhibitor

5.4 Absorption, Distribution and Excretion

Route of Elimination

Cilastatin is reported by official FDA labeling to be 70% excreted in the urine, however published literature has reported values as high as 98%.

Volume of Distribution

Cilastatin has a volume of distribution of 14.6-20.1L.

Clearance

Cilastatin has a total clearance of 0.2 L/h/kg and a renal clearance of 0.10-0.16 L/h/kg.

5.5 Biological Half-Life

The half-life of cilastatin is approximately 1h.

5.6 Mechanism of Action

Cilastatin is a renal dehydropeptidase-I inhibitor. Since the antibiotic, imipenem, is hydrolyzed by dehydropeptidase-I, which resides in the brush border of the renal tubule, cilastatin is administered with imipenem to block the metabolism of imipenem.

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