7-[(2-Amino-2-carboxyethyl)thio]-2-[[(2,2-dimethylcyclopropyl)-oxomethyl]amino]-2-heptenoic acid

Base Information

• Chemical Name: 7-[(2-Amino-2-carboxyethyl)thio]-2-[[(2,2-dimethylcyclopropyl)-oxomethyl]amino]-2-heptenoic acid
• CAS No.: 82009-34-5
• Molecular Formula: C16H26N2O5S
• Molecular Weight: 358.459
• European Community (EC) Number: 279-875-8
• Wikipedia: Cilastatin
• Wikidata: Q27163748
• NCI Thesaurus Code: C61679
• RXCUI: 2540
• Mol file: 82009-34-5.mol

Synonyms:Cilastatin;Cilastatin Monosodium Salt;Cilastatin Sodium;MK 0791;MK 791;MK-791;MK0791;MK791;Monosodium Salt, Cilastatin;Salt, Cilastatin Monosodium;Sodium, Cilastatin

Chemical Property of 7-[(2-Amino-2-carboxyethyl)thio]-2-[[(2,2-dimethylcyclopropyl)-oxomethyl]amino]-2-heptenoic acid

Chemical Property:

• Appearance/Colour: White to light-yellow crystalline powder
• Vapor Pressure: 7.13E-19mmHg at 25°C
• Melting Point: 156-158°C
• Refractive Index: 1.569
• Boiling Point: 655.5 °C at 760 mmHg
• PKA: 2.09±0.10(Predicted)
• Flash Point: 350.2 °C
• PSA: 155.02000
• Density: 1.275 g/cm³
• LogP: 2.52380
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: -1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 358.15624311
• Heavy Atom Count: 24
• Complexity: 519

Purity/Quality:

99% ^*data from raw suppliers

Cilastatin ammonium salt United States Pharmacopeia (USP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC1C(=O)NC(=CCCCCSCC(C(=O)O)N)C(=O)O)C
• Description: Cilastatin is an inhibitor of dipeptidase (dehydropeptidase I), a renal dipeptidase. It inhibits human renal dipeptidase (Ki = 0.7 μM), porcine dipeptidase (IC50 = 0.11 μM), and bacterial metallo-β-lactamase CphA from A. hydrophila (IC50 = 178 μM). Cilastatin (200 μg/ml) protects primary porcine renal proximal tubular epithelial cells from nephrotoxicity and apoptosis induced by vancomycin . In a mouse model of systemic infection, cilastatin in combination with imipenem protects mice from S. aureus, E. coli, and P. aeruginosa infection. Cilastatin was designed to inhibit renal metabolism of imipenem and prolong its half-life. Formulations containing cilastatin in combination with imipenem have been used to treat susceptible bacterial infections.
• Uses: Prevents renal metabolism of penem and carbapenem antibiotics by specific and reversible dehydropeptidase I inhibition. Antibacterial adjunct spectrum antibiotic Cilastatin is used for treating diseases caused by polyresistant Gram-negative microorganisms and serious complex infections, including infection of S. aureus. Because of its strong activity against anaerobic bacteria, cilastatin is effective in monotherapy of intraabdominal infections. It is used for infectious diseases of the lower respiratory tract, urinary tract, gynecological infections, bacterial septicemia, and infections of the bones, skin, and so on.

Technology Process of 7-[(2-Amino-2-carboxyethyl)thio]-2-[[(2,2-dimethylcyclopropyl)-oxomethyl]amino]-2-heptenoic acid

There total 14 articles about 7-[(2-Amino-2-carboxyethyl)thio]-2-[[(2,2-dimethylcyclopropyl)-oxomethyl]amino]-2-heptenoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

(Z)-7-chloro-2 ((2s)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid (877674-77-6,166037-21-4) + l-cysteine hydrochloride (52-89-1) → cilastatine (82009-34-5,78852-98-9)

Guidance literature:

(Z)-7-chloro-2 ((2s)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid; With sodium hydroxide; In water; at 5 ℃; for 0.166667h;

l-cysteine hydrochloride; In water; at 45 - 50 ℃; for 0.166667h; Temperature;

Reference yield:

cilastatin calcium → cilastatine (82009-34-5,78852-98-9)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; pH=3; Inert atmosphere;

Reference yield:

(Z)-7-chloro-2 ((2s)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid (877674-77-6,166037-21-4) + L-cysteine hydrochloride → cilastatine (82009-34-5,78852-98-9)

Guidance literature:

(Z)-7-chloro-2 ((2s)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid; L-cysteine hydrochloride; With sodium hydroxide; In methanol; Reflux;

In water; butan-1-ol; at 25 - 30 ℃; pH=3 - 3.5;

upstream raw materials:

L-Cysteine

(Z)-7-bromo-2 ((2s)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid

1,5-dibromo-pentane

2,2-dimethylcyclopropane-1-carboxylic acid

Refernces

• 1、 -. "Preparation method of cilastatin sodium active pharmaceutical ingredient". Paragraph 0087; 0088; 0092; 0093; 0097; 0098; 0102-0163. . Retrieved 2017/06/02.
• 2、 -. "An improved process for the preparation of cilastatin acid". . . Retrieved 2012/02/04.