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Ertapenem sodium

Product Name
Ertapenem sodium
CAS No.
153773-82-1
Chemical Name
Ertapenem sodium
Synonyms
Invanz;ErtapeneM MonosodiuM;3-(((3S;L 749345;EtapeneM;Etapenem sodium;ErtapeneM Crude;Ertapenem Sodium;Ertapenem Impurity 16;TIANFU CHEM---EtapeneM
CBNumber
CB11238838
Molecular Formula
C22H26N3NaO7S
Formula Weight
499.51
MOL File
153773-82-1.mol
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Ertapenem sodium Property

Melting point:
>174oC (dec.)
storage temp. 
-70°C
solubility 
DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
form 
powder
color 
white to beige
Water Solubility 
Fully miscible in water. Soluble in DMSO.
Stability:
Hygroscopic, Temperature Sensitive
InChIKey
FYIATPOZJSVTLD-KBQNSVMINA-N
SMILES
C(C1=C([C@H](C)[C@]2([H])[C@@]([H])([C@H](O)C)C(=O)N12)S[C@@H]1CN[C@H](C(=O)NC2C=CC=C(C(=O)O)C=2)C1)(=O)O.[NaH] |&1:3,5,7,9,16,19,r|
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

Precautionary statements

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

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML1238
Product name
Ertapenem sodium
Purity
≥90% (HPLC)
Packaging
10MG
Price
$118
Updated
2025/07/31
Sigma-Aldrich
Product number
SML1238
Product name
Ertapenem sodium
Purity
≥90% (HPLC)
Packaging
50MG
Price
$475
Updated
2025/07/31
TRC
Product number
E635080
Product name
ErtapenemMonosodium(90%)
Packaging
250mg
Price
$105
Updated
2021/12/16
TRC
Product number
E635080
Product name
ErtapenemMonosodium(90%)
Packaging
2.5g
Price
$625
Updated
2021/12/16
ChemScene
Product number
CS-8020
Product name
Ertapenemsodium
Purity
99.09%
Packaging
1g
Price
$328
Updated
2021/12/16
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Ertapenem sodium Chemical Properties,Usage,Production

Uses

Ertapenem sodium has been used as a carbapenem in the NitroSpeed-Carba NP test in minimum inhibitory concentration (MIC) testing for differentiation of carbapenemases in Enterobacterales and Pseudomonas aeruginosa. It has also been used as an antibiotic to study its effects on the survival of septic mice.

Definition

ChEBI: The monosodium salt of ertapenem. It 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 is more stable to renal dehydropeptidase I tham imipenem, and so unlike imipenem, its use with cilastatin, which inhibits the enzyme, is not required.

Biochem/physiol Actions

Ertapenem is a broad spectrum carbopenem antibiotic. Ertapenem is active against both gram-positive and gram-negative bacteria. Ertapenem shows an extended duration of action in vivo due to its reversible binding to serum protein.

Synthesis

202467-70-7

153773-82-1

Synthesis of (4R,5S,6S)-3-(((3S,5S)-5-((3-carboxyphenyl)carbamoyl)pyrrolidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(R)), according to the methodology described in CN102731508A, based on the compound (CAS: 202467-70-7) The general procedure for the monosodium salt of [3.2.0]hept-2-ene-2-carboxylic acid was as follows: to a solvent mixture of 750 mL of ethyl acetate and 500 mL of water was added the doubly protected crystalline form of Ertapenem (10 g, 0.017 mol) prepared in Example 1. The pH was adjusted to 7.1-7.2 with 5% aqueous sodium hydroxide, followed by the addition of 15 g of palladium carbon catalyst. The hydrogenation reaction was carried out under hydrogen pressure of 20.0-30.0 MPa for 2 hours. After completion of the reaction, the catalyst was removed by filtration and the filtrate was extracted with dichloromethane (100 mL x 2) to separate the aqueous layer. The aqueous layer was adsorbed through a macroporous adsorbent resin, followed by washing the resin with 2 L of deionized water. Next, the resin was eluted with acetone solution containing 0.05 M sodium bicarbonate, and after the eluate was acidified to pH 5.5, it was concentrated by nanofiltration to 50 mL. 100 g of a solvent mixture of methanol and n-propanol (W/W = 1:1) was added to the concentrated solution, and it was further concentrated to promote crystallization. The temperature of the crystallization process was controlled at 10-20 °C, and the product was collected by filtration upon completion of crystallization. The product was dried under vacuum at <0.09 MPa for 3 h. The final product was 3.4 g of Ertapenem monosodium salt in 40.2% yield and 99.2% purity by HPLC.

in vivo

Ertapenem sodium (Subcutaneous injection, 0-10 mg/kg, 0-120 h after infection, S. aureus thigh tissue infection model) shows > 3 log10 CFU reduction of organism at 10 mg/kg, and maintains the activity with 3.3 and 4.4 log10 CFU eliminated at 2 mg/kg[2]. Ertapenem sodium (Subcutaneous injection, 4h after infection, systemic infection model) is active against all gram-positive organisms, and is also active against gram-negative organisms tested with ED50s of <0.25 mg/kg/dose[2].

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:Displayed > 3 log10 CFU reduction of organism compared to non-antibiotic-treated controls at 10 mg/kg. Maintained the activity with 3.3 and 4.4 log10 CFU eliminated at 2 mg/kg.
Animal Model:Systemic infection model (DBA/2 female mice, viral antibody-free CD-1 female mice)[2]
Dosage:0-3 mg/kg approximately
Administration:Subcutaneous injection (0.5 mL, begin immediately and 4 h after infection)
Result:Showed activity against all gram-positive organisms, and also ram-negative organisms tested with ED50s of <0.25 mg/kg/dose.
Animal Model:CD-1 mice, rats[2]
Dosage:10 mg/kg approximately
Administration:Intraperitoneal injection (pharmacokinetic assay)
Result:Exhibited an AUC0-∞ ranging from 1.8-21.82 μg?hr/mL in tissue in mice following a 10-mg/kg i.p. dose. Exhibited slow clearance rate with a t1/2β of 3.2 h, Clp of 0.47 mL/min/kg, AUC0-8 of 284.15 μg?hr/mL.

IC 50

β-lactam

References

[1] Patent: CN104788452, 2017, B. Location in patent: Paragraph 0067; 0068
[2] Patent: WO2013/121279, 2013, A2. Location in patent: Page/Page column 15

Ertapenem sodium Preparation Products And Raw materials

Raw materials

Preparation Products

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Ertapenem sodium Suppliers

China 228 India 10 United Kingdom 2 United States 10 Global 250
Wuhan Wsem Biological Co., Ltd.
Tel
027-83778876 13667159345
Fax
027-83778876
Email
13667159345@163.com
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China
ProdList
1997
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JINAN SHENGQI PHARMACEUTICAL CO., LTD
Tel
0531-0531-88892685 18660160628
Email
15069007290@163.com
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China
ProdList
154
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58
Hubei Yanke Times Technology Co., Ltd
Tel
15780669880 15727070860
Email
15780669880@163.com
Country
China
ProdList
997
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58
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006356688 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
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Beijing Ouhe Technology Co., Ltd
Tel
010-010-82967028 13522913783
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12000
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Shanghai Buddy Bio-pharm Intermediates Ltd
Tel
021-50460499 13120992296
Fax
021-50460489
Email
xinxiaojuan513@163.com
Country
China
ProdList
24
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Beijing Lunarsun Pharmaceutical Co.,LTD.
Tel
86-10-64911848-8020.8010
Fax
86-10-64946614
Email
sales@lunarsun.com.cn
Country
China
ProdList
95
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60
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
15883
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64
China Langchem Inc.
Tel
0086-21-58956006
Fax
0086-21-58956100
Country
China
ProdList
7811
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57
Wuhan Kemi-Works Chemical Co., Ltd
Tel
027-85736489
Fax
86-27-85736485
Email
info@kemiworks.net
Country
China
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540
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View Lastest Price from Ertapenem sodium manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Ertapenem Sodium 153773-82-1
Price
US $0.00-0.00/g/Bag
Min. Order
25g
Purity
97%min
Supply Ability
500G
Release date
2021-07-19
Shaanxi Dideu Medichem Co. Ltd
Product
Ertapenem Sodium 153773-82-1
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-07
Shaanxi Dideu Medichem Co. Ltd
Product
Ertapenem sodium 153773-82-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
1000KG
Release date
2024-08-07

153773-82-1, Ertapenem sodiumRelated Search:

Ertapenem Methyl Ester Sodium Salt Ertapenem Dimer Form D Impurity Ertapenem Disodium Ertapenem Impurity 11 Ertapenem Impurity 10 ATXZKQUYOZAYTG-BIHIRSSMSA-N (4R,5S,6S)-3-[[(3S,5S)-5-[[(Aminosulfonyl)amino]methyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester Meropenem ACS-PNZ-PYRROLIDYL-(BOC)-NSO2NH2 BIAPENEM SIDE CHAIN 3-[(2S,4S)-4-Mercaptopyrrolidine-2-carboxamido]benzoic acid hydrochloride 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid Doripenem Doripenem hydrate Side chain for meropenem Biapenem Ertapenem ErtapeneM IMpurity DIPP

  • 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-(((3S,5S)-5-(((3-ca rboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-((1R)-1-hydroxyethy l)-4-methyl-7-oxo-, monosodium salt, (4R,5S,6S)-
  • (4R,5S,6S)-3-[[(3S,5S)-5-[[(3-Carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt (1:1)
  • ErtapeneM MonosodiuM
  • Invanz
  • L 749345
  • EtapeneM,Invanz,MK-0826,L-749,345
  • EtapeneM
  • ErtapeneM Crude
  • Etapenem sodium
  • Ertapenem sodium, >=97%
  • He Seoul sodium imipenem
  • Ertapenem Monosodium (90%)
  • 3-(((3S
  • 5S)-5-(((3-ca rboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-((1R)-1-hydroxyethy l)-4-methyl-7-oxo-
  • [4R-[3(3S*,5S*),4α,5β,6β(R*)]]-3-[[-5-[[(3-carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monosodium
  • sodium 3-[[[(2S,4S)-4-[[(4R,5S,6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-2-pyrrolidinyl]-oxomethyl]amino]benzoate
  • Ertapenem monosodium salt
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  • 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-(((3S,5S)-5-(((3-ca rboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-((1R)-1-hydroxyethy l)-4-methyl-7-oxo-, monosodium salt, (4R,5S,6S)- USP/EP/BP
  • Sodium (4R,5S,6S)-3-(((3S,5S)-5-((3-carboxyphenyl)carbamoyl)pyrrolidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  • 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-(((3S,5S)...
  • Ertapenem sodiumQ: What is Ertapenem sodium Q: What is the CAS Number of Ertapenem sodium Q: What is the storage condition of Ertapenem sodium Q: What are the applications of Ertapenem sodium
  • TIANFU CHEM---EtapeneM
  • Ertapenem Sodium
  • (4R,5S,6S)-3-(((3S,5S)-5-(((3-ca Rboxy-phenyl)amino)carbonyl)-pyrrolidin-3-yl)thio)-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-en-2-carboxylic acid monosodium salt
  • (4R,5S,6S)-3-(((3S,5S)-5-((3-carboxyphenyl)carbamoyl)pyrrolidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, sodium salt
  • Ertapenem sodium, 10 mM in DMSO
  • (4R,5S,6S)-3-(((3S,5S)-5-((3-Carboxy-phenyl)-carbamoyl)-pyrrolidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-2-carboxylic acid sodium salt
  • 153773-82-1
  • C22H24N3NaO7S
  • C22H25N3O7SNa
  • C22H24N3O7SNa
  • API