153832-46-3 Usage
Brand Name(s) in US
Invanz
Uses
Different sources of media describe the Uses of 153832-46-3 differently. You can refer to the following data:
1. Ertapenem is a long-acting parenteral cabapenem. Ertapenem has bactericidal activity against a variety of gram-negative pathogens, some gram positive strains, and Haemopilus influenzae. Ertapenem has shown to inactivate L,D-transpeptidase, an enzyme responsible for in vitro cross-linking of Mycobacterium tuberculosis peptidoglycan.
2. Antibacterial. Invanz (Merck).
Definition
ChEBI: 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 includ
ng intra-abdominal and acute gynaecological infections, pneumonia, and infections of the skin and of the urinary tract.
Antimicrobial activity
Activity against aerobic and anaerobic pathogens is comparable
to that of imipenem: MIC values for Gramnegative
bacilli (with the exception of Ps. aeruginosa) are
generally lower and those for Gram-positive cocci higher.
Ertapenem is stable to most serine β-lactamases, but
is hydrolyzed by serine carbapenemases and metallo-
β-lactamases.
General Description
Ertapenem (Invanz, for injection) is a synthetic 1-β-methylcarbapenem that is structurally related to β-lactam antibiotics,particularly the thienamycin group. Its mechanism ofaction is the same as that of other β-lactam antibiotics. Thestructure resists β-lactamases and dehydropeptidases.Ertapenem is indicated for the treatment of moderate tosevere infections caused by susceptible strains causing complicatedintra-abdominal infections such as Escherichia,Clostridium, Peptostreptococcus, and Bacteroides. Theantibiotic is also indicated for complicated skin and skinstructure infections including diabetic foot infections (withoutosteomyelitis). Treatable strains include Staphylococcus(MSSA), Streptococcus, Escherichia, Klebsiella, Proteus,and Bacteroides. Ertapenem is also indicated for community-acquired pneumonia caused by S. pneumoniae,Haemophilus infljuenzae, and M. catarrhalis. Complicatedurinary tract infections and acute pelvic infections round outthe indications for ertapenem.
Pharmacokinetics
Cmax 1 g intramuscular: c. 67 mg/L after 2 h
1 g intravenous infusion (30 min): c. 155 mg/L end infusion
Plasma half-life: c. 4 h
Volume of distribution: c. 0.12 L/kg (steady state)
Plasma protein binding: 85–95%
Absorption after intramuscular injection is essentially complete
with 90% bioavailability. The modestly extended plasma
half-life allows once-daily dosing.
Excretion is predominantly by the renal route, about 80%
being recovered in the urine within 24 h. About 40% is eliminated
unchanged, the rest as a biologically inactive ringopened
metabolite. Dosage should be reduced in severe renal
impairment.
Clinical Use
Complicated intra-abdominal infections
Complicated skin and skin structure infections, including diabetic foot
infections without osteomyelitis
Community acquired pneumonia
Complicated urinary tract infections including pyelonephritis
Acute pelvic infections including postpartum endomyometritis, septic
abortion and postsurgical gynecologic infections
Prophylaxis of surgical site infection following elective colorectal surgery
Side effects
Ertapenem appears to be generally well tolerated. The most
common drug-related adverse experiences are diarrhea (5.5%),
infused vein complication (3.7%), nausea (3.1%), headache
(2.2%), vaginitis (2.1%), phlebitis/thrombophlebitis (1.3%)
and vomiting (1.1%). Seizures have occasionally been reported
(0.5%) in patients with a history of disorders of the CNS.
Drug interactions
Potentially hazardous interactions with other drugs
Antiepileptics: concentration of valproate reduced -
avoid concomitant use
Metabolism
After intravenous infusion of radiolabelled 1 g ertapenem,
the plasma radioactivity consists predominantly (94%)
of ertapenem. The major metabolite of ertapenem is the
ring-opened derivative formed by dehydropeptidaseI-mediated hydrolysis of the beta-lactam ring. Approximately 80% of a dose is recovered in urine
and 10% in faeces. Of the 80% recovered in urine,
approximately 38% is excreted as unchanged ertapenem
and approximately 37% as the ring-opened metabolite.
Check Digit Verification of cas no
The CAS Registry Mumber 153832-46-3 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, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 153832-46:
(8*1)+(7*5)+(6*3)+(5*8)+(4*3)+(3*2)+(2*4)+(1*6)=133
133 % 10 = 3
So 153832-46-3 is a valid CAS Registry Number.
InChI:InChI=1/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
153832-46-3Relevant articles and documents
A luer Ertapenem, luer he lateral chain and its preparation method
-
Paragraph 0143; 0144; 0145; 0146; 0147; 0148; 0149, (2017/07/14)
The invention discloses ertapenem and ertapenem side chains, as well as preparation methods of ertapenem and ertapenem side chains. L-hydroxyproline is protected by p-nitrobenzyl ester to obtain (2S,4R)-4-hydroxyl-1-(((4-Nitrobenzformyl)-oxyl)caboyl)pyrrolidine-2-carboxylic acid; then 4-nitro(1S,4S)-3-oxo-2-thia-5-azabicyclo[2.2.1]heptan-5-carboxylic anhydride can be obtained, and reacts with m-aminobenzoic acid p-nitrobenzyl ester to obtain ertapenem side chain III; and the ertapenem can be synthesized through two-step chemical reaction of condensation and deprotection to the ertapenem side chain III and a raw material MAP. An ertapenem side chain I (10), an ertapenem side chain II (13) and the ertapenem side chain III (2) which are prevailing in the market can be synthesized through simple steps, without the need of ultralow temperature, industrialization is easy, and the product purity is high, and the operation is simple and convenient.
Improved process for the preparation of carbapenem using carbapenem intermediates and recovery of carbapenem
-
, (2011/12/03)
The present invention relates to preparing carbapenem intermediates that are useful to produce Ertapenem, Meropenem and Doripenem; and provides an effective process for recovering ertapenem compounds.
Antibiotic compounds
-
, (2008/06/13)
The present invention relates to carbapenems and provides a compound of the formula (I): STR1 or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof wherein: R1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl; R2 is hydrogen or C1-4 alkyl; R3 is hydrogen or C1-4 alkyl; R4 and R5 are the same or different and are selected from hydrogen, halo, cyano, C1-4 alkyl, nitro, hydroxy, carboxy, C1-4 alkoxy, C1-4 alkoxycarbonyl, aminosulphonyl, C1-4 alkylaminosulphonyl, di-C1-4 alkylaminosulphonyl, carbamoyl, C1-4 alkylcarbamoyl, di-C1-4 alkylcarbamoyl, trifluoromethyl, sulphonic acid, amino, C1-4 alkylamino, di-C1-4 alkylamino, C1-4 alkanoylamino, C1-4 alkanoyl(N-C1-4 alkyl)amino, C1-4 alkanesulphonamido and C1-4 alkylS(O)n -- wherein n is zero, one or two: with the proviso that there is no hydroxy or carboxy substituent in a position ortho to the --NR2 --. Processes for their preparation, intermediates in their preparation, their use as therapeutic agents and pharmaceutical compositions containing them.
