ChemicalBook > CAS DataBase List > Cilastatin

Cilastatin

Product Name
Cilastatin
CAS No.
82009-34-5
Chemical Name
Cilastatin
Synonyms
Cilastatin acid;Cilastatin AMMoniuM Salt;(Z)-7-(((R)-2-Amino-2-carboxyethyl)thio)-2-((S)-2,2-dimethylcyclopropane-1-carboxamido)hept-2-enoic acid;mk-791;Cilastain;CILASTATIN;Cilistatin Acid;Cilastatinic acid;CILASTATIN (MK0791);Cilastatin USP/EP/BP
CBNumber
CB2781013
Molecular Formula
C16H26N2O5S
Formula Weight
358.45
MOL File
82009-34-5.mol
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Cilastatin Property

Melting point:
156-158°C
Boiling point:
655.5±55.0 °C(Predicted)
Density 
1.275±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility 
DMSO (Slightly), Methanol (Slightly, Sonicated)
form 
Solid
pka
2.09±0.10(Predicted)
color 
White to Light Brown
CAS DataBase Reference
82009-34-5(CAS DataBase Reference)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
23511
Product name
Cilastatin
Purity
≥98%
Packaging
10mg
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
23511
Product name
Cilastatin
Purity
≥98%
Packaging
50mg
Price
$216
Updated
2024/03/01
Cayman Chemical
Product number
23511
Product name
Cilastatin
Purity
≥98%
Packaging
100mg
Price
$403
Updated
2024/03/01
Cayman Chemical
Product number
23511
Product name
Cilastatin
Purity
≥98%
Packaging
250mg
Price
$770
Updated
2024/03/01
American Custom Chemicals Corporation
Product number
API0002010
Product name
CILASTATIN
Purity
95.00%
Packaging
25MG
Price
$498
Updated
2021/12/16
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Cilastatin Chemical Properties,Usage,Production

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.

Chemical Properties

White to Light-Yellow Crystalline Powder

Uses

Prevents renal metabolism of penem and carbapenem antibiotics by specific and reversible dehydropeptidase I inhibition. Antibacterial adjunct

Uses

spectrum antibiotic

Uses

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.

Definition

ChEBI: Cilastatin is the thioether resulting from the formal oxidative coupling of the thiol group of L-cysteine with the 7-position of (2Z)-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid. It is an inhibitor of dehydropeptidase I (membrane dipeptidase, 3.4.13.19), an enzyme found in the brush border of renal tubes and responsible for degrading the antibiotic imipenem. Cilastatin is therefore administered (as the sodium salt) with imipenem to prolong the antibacterial effect of the latter by preventing its renal metabolism to inactive and potentially nephrotoxic products. Cilastatin also acts as a leukotriene D4 dipeptidase inhibitor, preventing the metabolism of leukotriene D4 to leukotriene E4. It has a role as a protease inhibitor, an EC 3.4.13.19 (membrane dipeptidase) inhibitor, a xenobiotic and an environmental contaminant. It is a non-proteinogenic L-alpha-amino acid, a L-cysteine derivative, an organic sulfide and a carboxamide. It is a conjugate acid of a cilastatin(1-).

Synthesis

Cilastatin, (Z)-7-[(2-amino-2-carboethoxyethyl)thio]-2-[[2,2-dimethylcyclopropyl) carbonyl] amino]-2-heptenoic acid (32.1.3.6), is synthesized from the ethyl ester of 1,3-dithian-2-carboxylic acid (which is ethyl glyoxylate, protected at the aldehyde group with 1,3-propanedithiol), which is alkylated by 1,5-dibromopentane in the presence of sodium amide, forming the ethyl ester of 7-bromo-2-[2-(1,3-dithiano)]hepthanoic acid (32.1.3.2). Oxidative hydrolysis of this product with N-bromosuccinimide in a mixture of acetonitrile¨Cwater solvents leads to the formation of the ethyl ester of 7-bromo-|á-ketoheptanoic acid (32.1.3.3). Acidic hydrolysis of this product using hydrogen bromide in acetic acid gives 7-bromo-|á-ketoheptanoic acid (32.1.3.4). This is reacted with 2,2-dimethylcyclopropancarboxylic acid amide to form the corresponding enamide, (Z)-7-bromo-2-(2, 2-dimethylcycloprotancarboxamido)-2-heptenoic acid (32.1.3.5). The resulting product is used for S-alkylation of L-cysteine, which results in the production of the desired cilastatin (32.1.3.6).

Cilastatin Preparation Products And Raw materials

Raw materials

N,N'-DIOCTADECYLOXACARBOCYANINE P-TOLUENESULFONATE, 99 Amine compound 1,5-Dibromopentane Ethyl heptanoate p-Toluenesulfonic acid 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester Potassium hydroxide Ethyl diethoxyacetate (S)-(+)-2,2-Dimethylcyclopropanecarboxamide ACETYL FLUORIDE Succinimide 1,3-Dithiane-2-carboxylic acid Tosyl chloride L-Cystine 1,3-Dimercaptopropane Cyclopropanecarboxylic acid 2,2-Dimethylcyclopropylcyanide POTASSIUM CYANIDE Quinine Activ Ester

Preparation Products

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Cilastatin Suppliers

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View Lastest Price from Cilastatin manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cilastatin 82009-34-5
Price
US $1.00/g
Min. Order
1g
Purity
98%
Supply Ability
10kg/month
Release date
2021-12-27
Shaanxi Dideu Medichem Co. Ltd
Product
Cilastatin 82009-34-5
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-07
Hebei Chuanghai Biotechnology Co,.LTD
Product
Cilastatin 82009-34-5
Price
US $80.70/kg
Min. Order
10kg
Purity
99%
Supply Ability
10000kg
Release date
2024-08-21

82009-34-5, CilastatinRelated Search:

Glycine Dimethyl sulfoxide CHLOROPHOSPHONAZO III Poly(dimethylsiloxane) Betahistine Betaine N,N-Dimethylacetamide ALTRENOGEST N,N-Dimethyl-1,4-phenylenediamine Lithium diisopropylamide N,N-Dimethylformamide Dimethyl sulfone Dimethicone ULINASTATIN Cilastatin Sodium Impurity E(EP) Methyl 3-Oxo-4-(2,4,5-trifluorophenyl)butanoate 1-Bromo-5-chloropentane Ethyl 7-chloro-2-oxoheptanoate

  • Cilistatin Acid
  • (z)-7-[(2s)-2-amino-3-hydroxy-3-oxopropyl]sulfanyl-2-[[(1s)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid
  • (r-(r*,s*-(z)))-)carbonyl)amino)
  • mk-791
  • CILASTATIN
  • Cilastain
  • (2Z)-7-[[(2R)-2-amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic Acid
  • Cilastatin acid
  • [R-[R^<*>^，S^<*>^(Z)]]-7-[(2-Amino-2-carboxyethyl)thio]-2-[[(2，2-dimethylcyclopropyl)carbonyl]amino]-2-heptenoic acid
  • (Z)-7-[[(R)-2-Amino-2-carboxyethyl]thio]-2-[[[(S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic acid
  • Cilastatin AMMoniuM Salt
  • CILASTATIN (MK0791)
  • 2-Heptenoic acid, 7-[[(2R)-2-amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-, (2Z)-
  • (Z)-7-(((R)-2-Amino-2-carboxyethyl)thio)-2-((S)-2,2-dimethylcyclopropane-1-carboxamido)hept-2-enoic acid
  • Cilastatin USP/EP/BP
  • CilastatinQ: What is Cilastatin Q: What is the CAS Number of Cilastatin Q: What is the storage condition of Cilastatin Q: What are the applications of Cilastatin
  • 5-(4-hydroxyphenyl)isoxazole-8-carboxylicacid
  • Cilastatinic acid
  • (Z)-7-(((R)-2-amino-2-carboxyethyl)thio)-2-((S)-2,2-dimethylcyclopropanecarboxamido)hept-2-enoic acid
  • 82009-34-5
  • C16H26N2O5S
  • Inhibitors
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pharmaceuticals