[R-[R,S(Z)]]-7-[(2-氨基-2-羧基乙基)硫]-2-[[(2,2-二甲基环丙基)羰基]氨基]-2-庚烯酸
Cilastatin
CAS: 82009-34-5;166037-21-4
Molecular Formula: C16H26N2O5S
[R-[R,S(Z)]]-7-[(2-氨基-2-羧基乙基)硫]-2-[[(2,2-二甲基环丙基)羰基]氨基]-2-庚烯酸 - Names and Identifiers
| Name | Cilastatin |
| Synonyms | mk-791 Cilastain Cilastatin CILASTATIN Cilastatin acid Cilistatin Acid (r-(r*,s*-(z)))-)carbonyl)amino) (z)-(s)-7-Chloro-2-(2,2-Dimethylcyclopropane carboxamido)-2-Heptenoic acid (2Z)-7-[[(2R)-2-amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic Acid (2Z)-7-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid (z)-7-[(2s)-2-amino-3-hydroxy-3-oxopropyl]sulfanyl-2-[[(1s)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid (Z)-7-[(2S)-2-Amino-3-hydroxy-3-oxopropyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid |
| CAS | 82009-34-5 166037-21-4 |
| EINECS | 279-875-8 |
| InChI | InChI=1/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 |
[R-[R,S(Z)]]-7-[(2-氨基-2-羧基乙基)硫]-2-[[(2,2-二甲基环丙基)羰基]氨基]-2-庚烯酸 - Physico-chemical Properties
| Molecular Formula | C16H26N2O5S |
| Molar Mass | 358.45 |
| Density | 1.275±0.06 g/cm3(Predicted) |
| Melting Point | 156-158°C |
| Boling Point | 655.5±55.0 °C(Predicted) |
| Flash Point | 350.2°C |
| Solubility | DMSO (Slightly), Methanol (Slightly, Sonicated) |
| Vapor Presure | 7.13E-19mmHg at 25°C |
| Appearance | Solid |
| Color | White to Light Brown |
| pKa | 2.09±0.10(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.569 |
| Physical and Chemical Properties | Cilastatin SodiuIn: C16H25N2NaO5S. [86109-83-1]. Off-white to off-white amorphous solid, hygroscopic. Very soluble in water or methanol. Pka = 2.0,pKa = 24.4,pKa = 39.2. |
| Use | Renal peptidase inhibitors. It can be used in combination with carbapenem antibiotic imine. Because of its specific inhibition of renal peptidase, the latter is protected from the degradation of renal peptidase, and the activity of imine ligand is improved. The mixture of cilastatin sodium and imine ligand (1:1) was Tienan (Primaxin). |
| In vivo study | In a mouse model (female mice, strain CD-1, 20 g) of systemic infection, Imipenem plus Cilastatin can protect mice from S. aureus , E. coli , and P. aeruginosa infection. |
[R-[R,S(Z)]]-7-[(2-氨基-2-羧基乙基)硫]-2-[[(2,2-二甲基环丙基)羰基]氨基]-2-庚烯酸 - Reference
| Reference Show more | 1. [IF=3.681] Rao Zhi et al."Determination of Total and Unbound Meropenem, Imipenem/Cilastatin, and Cefoperazone/Sulbactam in Human Plasma: Application for Therapeutic Drug Monitoring in Critically Ill Patients."Ther Drug Monit. 2020 Aug;42(4):578-587 |
[R-[R,S(Z)]]-7-[(2-氨基-2-羧基乙基)硫]-2-[[(2,2-二甲基环丙基)羰基]氨基]-2-庚烯酸 - Reference Information
| biological activity | Cilastatin (MK0791) is a reversible competitive renal dehydropeptidase I. Inhibitor, IC50 0.1 μm. Cilastin inhibits the bacterial Metallo-leaf lactamase CphA with an IC50 of 178 μm. Cilastatin can be used as an antibacterial adjuvant. |
| Target | Value |
| Cell Line: | Renal proximal tubular epithelial cells (RPTECs) |
| Concentration: | 200 μg/mL |
| Incubation Time: | 24 hours |
| Result: | Significantly ameliorated Vancomycin-induced nuclear apoptosis. |
| Use | Renal peptidase inhibitor. It can be used in combination with carbapenem antibiotic imine. Because of its specific inhibition of renal peptidase, the latter is protected from the degradation of renal peptidase, and the activity of imine ligand is improved. The mixture of cilastatin sodium and imine ligand (1:1) was Tienan (Primaxin). |
| production method | the reaction of ethyl 2, 2-diethoxyacetate and 1, 3-propanedithiol gave 1, ethyl 3-dithiane-2-carboxylate, yield 69.4%. It is then reacted with 1, 5-dibromopentane in the presence of sodium hydride to give ethyl 2-(5-bromopentyl)-1, 3-dithiane-2-carboxylate. This is followed by reaction with brominated succinimide (NBS) to give ethyl 7-bromo-2-oxoheptanoate. Acidic hydrolysis gave 7-bromo-2-oxoheptanoic acid in 69% yield (based on 1, 3-dithiane-2-carboxylic acid ethyl ester). 2, 2-dimethyl-1, 3-propanediol was esterified with P-Toluenesulfonyl chloride to form bis-p-toluenesulfonate in a yield of 94.3%. Under the action of potassium cyanide, 2, 2-dimethylcyclopropane carbonitrile was obtained by cyclization in a yield of 64.9%. Alkaline hydrolysis of aqueous potassium hydroxide solution, Racemic 2, 2-dimethylcyclopropane carboxylic acid was obtained in almost quantitative yield. The racemate was resolved with L-quinine to give the pure (S) configuration in 14.1% yield. It is then reacted with N-trifluoroacetoxysuccinimide to give (+)-N-[(2,2-dimethylcyclopropane) formyloxy] succinimide in a yield of 90.5%. The imine compound is an active ester compound with high reactivity, and (+)-(S)-2, 2-dimethylcyclopropanecarboxamide is obtained by aminolysis in a yield of 83%. The product of 7-bromo-2-oxoheptanoic acid and (+)-(S)-2, 2-dimethylcyclopropanecarboxamide refluxed in toluene (Yield 25%) further reaction with L-cystine gave cilastatin in a yield of 63% [α]D23 +18.0 °(C = 0.54, methanol). |
Last Update：2024-04-09 20:48:19
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[R-[R,S(Z)]]-7-[(2-氨基-2-羧基乙基)硫]-2-[[(2,2-二甲基环丙基)羰基]氨基]-2-庚烯酸
3,3-二氟-4-羟基吡咯烷-1-羧酸叔丁酯
5-(4-氯丁基)-1-环己基-1H-四氮唑
5-溴-4-氯-2-甲硫-7H-吡咯[2,3-D]嘧啶
Methacrylic acid 2-(2-hexyloxyethoxy)ethyl ester
1-甲基-1H-苯并咪唑-2-硫醇
2-溴-2-甲基丙酰溴(2-溴异丁酰溴)
4-氨基-1-哌啶甲酸叔丁酯
3,3-二氟-4-羟基吡咯烷-1-羧酸叔丁酯
5-(4-氯丁基)-1-环己基-1H-四氮唑
5-溴-4-氯-2-甲硫-7H-吡咯[2,3-D]嘧啶
Methacrylic acid 2-(2-hexyloxyethoxy)ethyl ester
1-甲基-1H-苯并咪唑-2-硫醇
2-溴-2-甲基丙酰溴(2-溴异丁酰溴)
4-氨基-1-哌啶甲酸叔丁酯