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    Cilastatin

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    2D Structure
    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

    2D Structure

    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 Weight 358.5 g/mol
    Molecular Formula C16H26N2O5S
    XLogP3-1
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count11
    Exact Mass358.15624311 g/mol
    Monoisotopic Mass358.15624311 g/mol
    Topological Polar Surface Area155 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity519
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.