Home > Name List By other > (Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2, 2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid

CAS No 82009-34-5 , (Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,
2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid

  • Name: (Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,
    2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid
  • Synonyms: Cilastatine [French]; Cilastatinum;Cilastatina; Cilastatine; Cilastatin acid; Cilastatinum [Latin]; CHEBI:3697; Cilastatina [Spanish];(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,
    2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid;
  • CAS Registry Number:
  • Density: 1.275 g/cm3
  • Refractive index: 1.569
  • EINECS: 279-875-8
  • Molecular Weight: 358.45304
  • InchiKey: DHSUYTOATWAVLW-WFVMDLQDSA-N
  • 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
  • Molecular Formula: C16H26N2O5S
  • Molecular Structure:CAS No:82009-34-5 (Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,<br />2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid

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References of (Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,
2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid
Title: Cilastatin
CAS Registry Number: 82009-34-5
CAS Name: (2Z)-7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic acid
Manufacturers' Codes: MK-791
Molecular Formula: C16H26N2O5S
Molecular Weight: 358.45
Percent Composition: C 53.61%, H 7.31%, N 7.82%, O 22.32%, S 8.95%
Literature References: Prevents renal metabolism of penem and carbapenem antibiotics by specific and reversible dehydropeptidase I inhibition. Synthesis and combination with thienamycins: D. W. Graham et al., EP 48301; H. Kropp et al., EP 48025 (both 1982 to Merck & Co.), C.A. 97, 145271b, 145270a (1982). Combination with penems: F. M. Kahan, H. Kropp, EP 72014 (1983 to Merck & Co.), C.A. 99, 70272h (1983). The articles cited below discuss the activity of cilastatin alone and in combination with imipenem, q.v. Dipeptidase inhibition, pharmacokinetics: S. R. Norrby et al., Antimicrob. Agents Chemother. 23, 300 (1983). Stimulation of granulocyte function: H. Gnarpe et al., ibid. 25, 179 (1984). HPLC determn in serum: C. M. Myers, J. L. Blumer, ibid. 26, 78 (1984). Enhances intrathecal and ocular penetration of imipenem: A. W. Chow et al., ibid. 23, 634 (1983) and K. R. Finlay et al., Invest. Ophthalmol. Visual Sci. 24, 1147 (1983), respectively. In experimental meningitis: D. E. Washburn et al., J. Antimicrob. Chemother. 12, 39 (1983). Series of articles on pharmacokinetics, safety and tolerance and efficacy of cilastatin/imipenem: ibid. 12, Suppl. D, 1-155 (1983); Infection 14, Suppl. 2, S111-S180 (1986).
 
Derivative Type: Sodium salt
CAS Registry Number: 81129-83-1
Synonyms: Cilastatin sodium
Molecular Formula: C16H25N2NaO5S
Molecular Weight: 380.43
Percent Composition: C 50.51%, H 6.62%, N 7.36%, Na 6.04%, O 21.03%, S 8.43%
Properties: Off-white to yellowish-white hygroscopic, amorphous solid. pKa1 2.0; pKa2 4.4; pKa3 9.2. Very sol in water, methanol.
pKa: pKa1 2.0; pKa2 4.4; pKa3 9.2
 
Therap-Cat: Antibacterial adjunct (dipeptidase inhibitor).
Keywords: Antibacterial Adjuncts; Renal Dipeptidase Inhibitors.