Invanz

Base Information

• Chemical Name: Invanz
• CAS No.: 153773-82-1
• Molecular Formula: C22H24N3NaO7S
• Molecular Weight: 497.504
• European Community (EC) Number: 836-232-1
• NCI Thesaurus Code: C61753
• RXCUI: 353107
• Mol file: 153773-82-1.mol

Synonyms:ertapenem;ertapenem sodium;Invanoz;Invanz

Chemical Property of Invanz

Chemical Property:

• Appearance/Colour: White or off-white powder
• Vapor Pressure: 5.26E-28mmHg at 25°C
• Boiling Point: 813.9 °C at 760 mmHg
• Flash Point: 446 °C
• PSA: 184.40000
• LogP: -0.05430
• Storage Temp.: -70°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• Water Solubility.: Fully miscible in water. Soluble in DMSO.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 497.12326557
• Heavy Atom Count: 34
• Complexity: 882

Purity/Quality:

98% ^*data from raw suppliers

ErtapenemMonosodium(90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(C(=O)N2C(=C1SC3CC([NH2+]C3)C(=O)NC4=CC=CC(=C4)C(=O)[O-])C(=O)[O-])C(C)O.[Na+]
• Isomeric SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H]([NH2+]C3)C(=O)NC4=CC=CC(=C4)C(=O)[O-])C(=O)[O-])[C@@H](C)O.[Na+]
• Recent ClinicalTrials: Ertapenem Sodium (MK-0826) Versus Piperacillin/Tazobactam Sodium for the Treatment of Diabetic Foot Infections in Chinese Adults (MK-0826-061)
• Recent EU Clinical Trials: Short course antibiotic treatment of Gram-negative bacteremia: A multicenter, randomized, non-blinded, non-inferiority interventional study
• 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.

Technology Process of Invanz

There total 3 articles about Invanz 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: 40.2%

(4-nitrophenyl)methyl (4R,5S,6S)-3-[[(3S,5S)-5-[[(-carboxyphenyl)amino]carbonyl]-1-[[(4-nitrophenyl)methyoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (202467-70-7) → [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 (153773-82-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; sodium hydroxide; In water; ethyl acetate; for 2h; under 150015 - 225023 Torr; pH=7.1 - Ca. 7.2;

Reference yield:

(4-nitrophenyl)methyl (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-carboxylate → [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 (153773-82-1)

Guidance literature:

(4-nitrophenyl)methyl (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-carboxylate; With 4-methyl-morpholine; 2,6-dimethylpyridine; palladium 10% on activated carbon; hydrogen; In water; ethyl acetate; at 0 - 10 ℃; under 5250.53 - 7500.75 Torr;

With sodium hydrogencarbonate; In water; Reagent/catalyst;

Reference yield:

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (93711-81-0,90776-59-3,189188-38-3) + (2S-cis)-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride (219909-83-8) → [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 (153773-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: diisopropylamine / N,N-dimethyl-formamide / 3 h / -30 - -10 °C

2: 2,6-dimethylpyridine; hydrogen; 4-methyl-morpholine; palladium 10% on activated carbon / water; ethyl acetate / 0 - 10 °C / 5250.53 - 7500.75 Torr

With 4-methyl-morpholine; 2,6-dimethylpyridine; palladium 10% on activated carbon; hydrogen; diisopropylamine; In water; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

(4-nitrophenyl)methyl (4R,5S,6S)-3-[[(3S,5S)-5-[[(-carboxyphenyl)amino]carbonyl]-1-[[(4-nitrophenyl)methyoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

(2S-cis)-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride