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10mg |
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25mg |
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50mg |
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100mg |
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250mg |
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Purity: ≥98%
Ertapenem (L-749345; Invanoz; MK-0826; Invanz) is a 1-β-methyl carbapenem antibiotic marketed by Merck as Invanz. Ertapenem is a long-acting, broad-spectrum antibiotic of β-lactam subclass. Ertapenem has a broad spectrum of antibacterial activity including common aerobic and anaerobic bacteria and organisms with extended-spectrum β-lactamases. Ertapenem is an inhibitor of bacteria cell-wall synthesis, it acts by binding to penicillin binding proteins located on the bacterial cell wall, in particular PBPs 2 and 3, thereby inhibiting the final transpeptidation step in the synthesis of peptidoglycan, an essential component of the bacterial cell wall. Inhibition of peptidoglycan synthesis results in weakening and lysis of the cell wall and cell death. Erapenem is resistant to hydrolysis by a variety of beta-lactamases, including penicillinases, cephalosporinases and extended-spectrum beta-lactamases.
Targets |
β-lactam
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ln Vitro |
Ertapenem (0-100 μg/mL approximately, 48 hours) is effective against 99.1% of all anaerobes, with MICs for B.fragilis and B.vulgatus species of ≥8 μg/mL and a mode MIC of 0.12 μg/mL and MIC90 of 1 μg/mL, respectively[1].
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ln Vivo |
In a S. aureus thigh tissue infection model, ertapenem (subcutaneous injection, 0–10 mg/kg, 0-120 h after infection) reduces the organism by > 3 log10 CFU at 10 mg/kg and keeps the activity at 3.3 and 4.4 log10 CFU eliminated at 2 mg/kg[2].
In addition to being active against all gram-positive organisms, ertapenem (subcutaneous injection, 4 hours after infection, systemic infection model) is also active against gram-negative organisms with ED50s of less than 0.25 mg/kg/dose[2]. |
Cell Assay |
Cell Line: B. fragilis (ATCC 25285), B. thetaiotaomicron (ATCC 29741), and Eubacterium lentum (ATCC 43055)
Concentration: 0-100 μg/mL approximately Incubation Time: 48 h Result: 98.8% of the isolates in the B. fragilis group were susceptible, and 99.1% of all isolates were inhibited with a mode MIC of 0.12 μg/mL and MIC90 of 1 μg/mL. |
Animal Protocol |
Animal Model: S. aureus thigh tissue infection model (DBA/2 mice)[2]
Dosage: 0.5,1, 2, 5, 10 mg/kg (given at 2, 6, 10, 24, 48, 72, 96, 120 h) Administration: Subcutaneous injection (0.5 mL after infection) Result: showed a reduction in organism of > 3 log10 CFU at 10 mg/kg when compared to controls not treated with antibiotics. kept up the activity at 2 mg/kg, eliminating 3.3 and 4.4 log10 CFU. |
References |
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Additional Infomation |
Ertapenem is meropenem in which the one of the two methyl groups attached to the amide nitrogen is replaced by hydrogen while the other is replaced by a 3-carboxyphenyl group. The sodium salt is used for the treatment of moderate to severe susceptible infections including intra-abdominal and acute gynaecological infections, pneumonia, and infections of the skin and of the urinary tract. It has a role as an antibacterial drug. It is a carbapenemcarboxylic acid and a pyrrolidinecarboxamide. It is a conjugate acid of an ertapenem(1-).
Ertapenem is a 1-β methyl-carbapenem that is structurally related to beta-lactam antibiotics. It was first authorized for use in the US in November 2001 and in Europe in April 2002. Shown to be effective against a wide range of Gram-positive and Gram-negative aerobic and anaerobic bacteria, ertapenem is used to treat various bacterial infections. Ertapenem is a Penem Antibacterial. Ertapenem is a broad spectrum carbapenem antibiotic used primarily for the treatment of aerobic gram-negative bacterial infections. Ertapenem, like other carbapenems, is associated with transient and asymptomatic elevations in serum enzymes. The carbapenems have also been linked to rare instances of clinically apparent, acute cholestatic liver injury. Ertapenem is a 1-beta-methyl carbapenem and broad-spectrum beta-lactam antibiotic with bactericidal property. Ertapenem binds to penicillin binding proteins (PBPs) located on the bacterial cell wall, in particular PBPs 2 and 3, thereby inhibiting the final transpeptidation step in the synthesis of peptidoglycan, an essential component of the bacterial cell wall. Inhibition results in a weakening and subsequent lysis of the cell wall leading to cell death of Gram-positive and Gram-negative aerobic and anaerobic pathogens. This agent is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, cephalosporinases and extended-spectrum beta-lactamases. A carbapenem derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of Gram-positive and Gram-negative bacterial infections including intra-abdominal infections, acute gynecological infections, complicated urinary tract infections, skin infections, and respiratory tract infections. It is also used to prevent infection in colorectal surgery. |
Molecular Formula |
C22H25N3O7S
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Molecular Weight |
475.5
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Exact Mass |
475.14
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Elemental Analysis |
C, 55.57; H, 5.30; N, 8.84; O, 23.55; S, 6.74
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CAS # |
153832-46-3
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Related CAS # |
Ertapenem sodium;153773-82-1;Ertapenem disodium;153832-38-3
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PubChem CID |
150610
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Appearance |
Solid powder
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Density |
1.6±0.1 g/cm3
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Boiling Point |
813.9±65.0 °C at 760 mmHg
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Flash Point |
446.0±34.3 °C
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Vapour Pressure |
0.0±3.1 mmHg at 25°C
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Index of Refraction |
1.7
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LogP |
-1.07
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tPSA |
181.57
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SMILES |
O=C(C(N12)=C(S[C@@H]3CN[C@H](C(NC4=CC=CC(C(O)=O)=C4)=O)C3)[C@H](C)[C@]2([H])[C@@H]([C@H](O)C)C1=O)O
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InChi Key |
JUZNIMUFDBIJCM-ANEDZVCMSA-N
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InChi Code |
InChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1
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Chemical Name |
(4R,5S,6S)-3-[(3S,5S)-5-[(3-Carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
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Synonyms |
MK 826; L-749345; MK-826; L749345; MK826; L 749345; MK-0826; MK 0826; MK0826; Ertapenem Sodium; Trade Name: Invanoz; Invanz
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HS Tariff Code |
2934.99.9001
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
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Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400  (Please use freshly prepared in vivo formulations for optimal results.) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 2.1030 mL | 10.5152 mL | 21.0305 mL | |
5 mM | 0.4206 mL | 2.1030 mL | 4.2061 mL | |
10 mM | 0.2103 mL | 1.0515 mL | 2.1030 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Efficacy of MK-826 and other agents in the mouse thigh model: experiment 1. DBA/2 mice were challenged (0.2 ml; i.p.) with S. aureus MB2985 in the right thigh at 0 h. Antibiotic treatment (0.5 ml; s.c.) was given at 2, 6, 10, 24, 48, 72, 96, and 120 h after challenge.[2].Antimicrob Agents Chemother. 1998 Aug;42(8):1996-2001. td> |
Efficacy of MK-826 and other agents in the mouse thigh model: experiment 2. DBA/2 mice were challenged (0.2 ml; i.p.) with S. aureus MB2985 in the right thigh at 0 h. Antibiotic treatment (0.5 ml; s.c.) was given at 2, 6, 10, 24, 48, 72, 96, and 120 h after challenge. [2].Antimicrob Agents Chemother. 1998 Aug;42(8):1996-2001. td> |