153832-38-3 Usage
Description
Disodium (4R,5R,6S)-3-[(3S,5S)-5-[(3-carboxylatophenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate is a complex organic compound with a unique chemical structure. It is characterized by its molecular formula and stereochemistry, which contribute to its specific properties and potential applications.
Uses
1. Used in Pharmaceutical Industry:
Disodium (4R,5R,6S)-3-[(3S,5S)-5-[(3-carboxylatophenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate is used as an active pharmaceutical ingredient for the development of new drugs targeting various medical conditions. Its unique chemical structure allows for potential interactions with biological targets, making it a promising candidate for drug discovery and development.
2. Used in Chemical Research:
disodium (4R,5R,6S)-3-[(3S,5S)-5-[(3-carboxylatophenyl)carbamoyl]pyrro lidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2 .0]hept-2-ene-2-carboxylate can also be utilized in chemical research for understanding its reactivity, stability, and potential applications in the synthesis of other complex organic molecules. Its unique structure may provide insights into new reaction pathways and mechanisms, contributing to the advancement of chemical science.
3. Used in Material Science:
The compound's properties, such as its solubility, stability, and potential for self-assembly, may make it suitable for applications in material science. It could be explored for use in the development of new materials with specific properties, such as improved mechanical strength, thermal stability, or chemical resistance.
Originator
Astra Zeneca (UK)
Synthesis
Following a conventional carbapenem synthetic strategy,
ertapenem sodium (6) can be assembled from 4-nitrobenzylprotected
β-methyl carbapenemenolphosphate 71 and 2-
aminocarbonylpyrrolidine-4-ylthio-containing side chain 70.
Many efficient approaches to 71 have been reported in the
literature , and this compound is now commercially
available on a large scale. The synthesis of 70 is
outlined in the scheme. Protection of the amino group
in trans-4-hydroxy-L-proline (62) with diisopropyl
phosphite followed by NaClO oxidation gave N-DIPP
protected hydroxyl proline 63 in 80% yield. The carboxyl
group in 63 was activated via reaction with
diphenylphosphinic chloride (DPPC) in the presence of
diisopropylethylamine (DIPEA). This intermediate 64 was
directly reacted with methanesulfonyl chloride in the presence of pyridine to furnish mesylate 65. Mesylate 65
was then quenched with aqueous sodium sulfide yielding 66
instantaneously, which then slowly cyclized to 67.
Aminolysis of 67 with m-aminobenzoic acid (68) and
subsequent deprotection of the DIPP group with
concentrated HCl provided 70 in 90-95% yield in a one-pot
process. The coupling reaction between 70 and 71 followed
by deprotection of PNB group was completed in one
reaction vessel to furnish ertapenem sodium (6) (yield was
not disclosed).
in vitro
in e.coli, ertapenem binds to penicillin binding proteins (pbps) 1a, 1b, 2, 3, 4 and 5, showing highest affinity for pbps 2 and 3 [1]. mic90s for most species of enterobacteriaceae were < 1 mg/l. mic90s for most bacteroides fragilis group isolates ranged from 1 to 4 mg/l, and mic90s were species specific for clostridium, ranging from 0.06 mg/l for clostridium perfringens to 4 mg/l for clostridiumclostridioforme [2].
in vivo
in healthy young men and women volunteers, the mean concentration of ertapenem in plasma ranged from ~145 to 175 μg/ml at the end of a 30-min infusion, from ~30 to 34 μg/ml at 6 h, and from ~9 to 11 μg/ml at 12 h. the mean plasma t1/2 ranged from 3.8 to 4.4 h. about 45% of the plasma clearance (clp) was via renal clearance [3].
references
[1]. shah p m, isaacs r d. ertapenem, the first of a new group of carbapenems[j]. journal of antimicrobial chemotherapy, 2003, 52(4): 538-542.[2]. wexler h m. in vitro activity of ertapenem: review of recent studies[j]. journal of antimicrobial chemotherapy, 2004, 53(suppl 2): ii11-ii21.[3]. majumdar a k, musson d g, birk k l, et al. pharmacokinetics of ertapenem in healthy young volunteers[j]. antimicrobial agents and chemotherapy, 2002, 46(11): 3506-3511.
Check Digit Verification of cas no
The CAS Registry Mumber 153832-38-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,3,8,3 and 2 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 153832-38:
(8*1)+(7*5)+(6*3)+(5*8)+(4*3)+(3*2)+(2*3)+(1*8)=133
133 % 10 = 3
So 153832-38-3 is a valid CAS Registry Number.
InChI:InChI=1/C22H25N3O7S.2Na/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);;/q;2*+1/p-2/t9-,10-,13+,14+,15-,16-;;/m1../s1
