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Relebactam

Relebactam structure

CAS No.: 1174018-99-5

Chemical Name:: Relebactam

Synonyms: MK7655;CS-2637;RELEBACTAM;Relibactam;2H4]-Relebactam;Cefadroxil Monomer;MK-7655(Relebactam);Relebactam(MK-7655);MK-7655;MK 7655;MK7655;(2S,5R)-7-oxo-2-(piperidin-1-ium-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate

CBNumber:: CB82546782

Molecular Formula:: C12H20N4O6S

Molecular Weight:: 348.38

MDL Number:: MFCD28502833

MOL File:: 1174018-99-5.mol

Last updated:2024-03-29 16:09:00

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Relebactam Properties

Melting point	>252°C (dec.)
Density	1.59
storage temp.	Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility	DMSO (Slightly), Water (Slightly)
pka	-4.59±0.18(Predicted)
form	Solid
color	Off-White to Light Yellow
Stability	Hygroscopic
InChI	InChI=1S/C12H20N4O6S/c17-11(14-8-3-5-13-6-4-8)10-2-1-9-7-15(10)12(18)16(9)22-23(19,20)21/h8-10,13H,1-7H2,(H,14,17)(H,19,20,21)/t9-,10+/m1/s1
InChIKey	SMOBCLHAZXOKDQ-ZJUUUORDSA-N
SMILES	S(O)(ON1C(=O)[N@@]2C[C@@]1([H])CC[C@H]2C(NC1CCNCC1)=O)(=O)=O
FDA UNII	1OQF7TT3PF

Relebactam price More Price(22)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Cayman Chemical	23890	MK-7655 ≥98%	1174018-99-5	1mg	$37	2024-03-01	Buy
Cayman Chemical	23890	MK-7655 ≥98%	1174018-99-5	5mg	$169	2024-03-01	Buy
Cayman Chemical	23890	MK-7655 ≥98%	1174018-99-5	10mg	$319	2024-03-01	Buy
Cayman Chemical	23890	MK-7655 ≥98%	1174018-99-5	25mg	$704	2024-03-01	Buy
Usbiological	464603	Relebactam	1174018-99-5	1mg	$305	2021-12-16	Buy

Product number	Packaging	Price	Buy
23890	1mg	$37	Buy
23890	5mg	$169	Buy
23890	10mg	$319	Buy
23890	25mg	$704	Buy
464603	1mg	$305	Buy

Relebactam Chemical Properties,Uses,Production

Description

Relebactam (formerly known as MK-7655) is a novel,intravenous,class A and class C B-lactamase inhibitor and is currently under evaluation in combination with imipenem/cilastatin for the treatment of resistant Gram-negative infections.In vitro studies demonstrated that relebactam restored imipenem's activity against KPC-producing Enterobacteriacae，lowering imipenem MICs from 16-64 to 0.12-1mg/L at a concentration of 4 mg/L. Moreover, relebactam is able to lower imipenem MICs for P. aeruginosa，particularly in strains with depressed OprD expression and increased AmpC expression.Conversely, the addition of relebactam to imipenem does not seem to provide any adjunctive benefit against A.baumanii or S.maltophilia or against MBL-producing Enterobacteriacae.A non-inferiority, Phase 3 trial evaluating the efficacy and safety of imipenem/relebactam compared to piperacillin/tazobactam for the treatment of HAP and VAP(ClinicalTrials.gov Identifier: NCT02493764) is currently recruiting. A Phase 3 study evaluating the efficacy and safety of imipenem/relebactam (200/100-500/250 mg depending on renal function) compared to colistimethate sodium plus imipenem/cilastatin for the treatment of imipenem-resistant bacterial infections,including HAP, VAP, cIAIs and cUTIs, has recently been completed and results are pending(ClinicalTrials.gov Identifier: NCTO2452047).In Phase 2 trials, imipenem/relebactam was well tolerated, with diarrhea, nausea, vomiting and headache being the most commonly reported adverse events.

Uses

Relebactam is a novel β-lactamase inhibitor in combination with Primaxin. It has also demonstrated the potential to enhance the activity of imipenem against P.aeruginosa, including those strains with depressed OprD expression and increased AmpC expression.

Mechanism of action

Relebactam is a beta-lactamase inhibitor known to inhibit many types of beta-lactamases including Ambler class A and Ambler class C enzymes, helping to prevent imipenem from degrading in the body.Label,Similar to the structurally-related avibactam, first, relebactam binds non-covalently to a beta-lactamase binding site, then, it covalently acylates the serine residue in the active site of the enzyme.In contrast to some other beta-lactamase inhibitors, once relebactam de-acylates from the active site, it can reform it's 5 membered ring and is capable of rebinding to target enzymes.
https://go.drugbank.com/drugs/DB12377

Clinical Use

Recently, another carbapenem-β-lactamase inhibitor, imipenem/cilastatin-relebactam (RecarbrioTM), was approved by the FDA. Relebactam, a bicyclic diazabicyclooctane, is structurally related to avibactam but differs by the addition of a piperidine ring to the 2-position carbonyl group. Like meropenem- vaborbactam (VabomereTM), imipenem-relebactam(RecarbrioTM) is active against class A and class C carbapenemases and is approved for the treatment of multidrug-resistant intraabdominal infections secondary to Bacteroides caccae, Bacteroides fragilis, Bacteroides ovatus, Bacteroides thetaiotaomicron, Bacteroides uniformis, Bacteroides vulgatus, Bifidobacterium stercoris, Citrobacter freundii, Enterobacter cloacae, Escherichia coli, Fusobacterium nucleatum, Klebsiella aerogenes, Klebsiella oxytoca, Klebsiella pneumoniae, Parabacteroides distasonis, and Pseudomonas aeruginosa and multidrug-resistant complicated urinary tract infections secondary to E. cloacae, E. coli, K. aerogenes, K. pneumoniae and P. aeruginosa.

Synthesis

Relebactam is a β-lactamase inhibitor in clinical trials as a combination therapy for the treatment of bacterial infection resistant to β-lactam antibiotics. Its unusual structural challenges have inspired a rapid synthesis featuring an iridium-catalyzed N–H insertion and a series of late stage transformations designed around the reactivity of the labile bicyclo[3.2.1]urea at the core of the target.
Synthesis of Relebactam
In 2014, Qualified Infectious Disease Product (QIDP) and Fast Track designations were assigned by the FDA for the treatment of complicated urinary tract infections, complicated intra-abdominal infections and hospital-acquired bacterial pneumonia/ventilator-associated bacterial pneumonia.
A Concise Synthesis of a β-Lactamase Inhibitor

Relebactam synthesis

Synthesis of Relebactam from N,N,N-tributylbutan-1-aminium [({(2S,5R)-7-oxo-2-[(piperidin-4-ylamino)carbonyl]-1,6-diazabicyclo[3.2.1]oct-6-yl}oxy)sulfonyl]oxidanide

Relebactam Preparation Products And Raw materials

Raw materials

tert-butyl 4-((1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate N,N,N-tributylbutan-1-aminium [({(2S,5R)-7-oxo-2-[(piperidin-4-ylamino)carbonyl]-1,6-diazabicyclo[3.2.1]oct-6-yl}oxy)sulfonyl]oxidanide

Preparation Products

Relebactam Suppliers

Global( 123)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Heading （Nanjing）Pharmtechnologies Co., Ltd.	+86-25-58467899-832 +86-13382406280	liucheng@headingpharm.com	China	46	58
Anhui Ruihan Technology Co., Ltd	+8617756083858	daisy@anhuiruihan.com	China	994	58
Henan Fengda Chemical Co., Ltd	+86-371-86557731 +86-13613820652	info@fdachem.com	China	18223	58
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	32686	60
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58
BOC Sciences	+1-631-485-4226	inquiry@bocsci.com	United States	19553	58
Chongqing Chemdad Co., Ltd	+86-023-61398051 +8613650506873	sales@chemdad.com	China	39916	58
HANGZHOU CLAP TECHNOLOGY CO.,LTD	86-571-88216897,88216896 13588875226	sales@hzclap.com	CHINA	6313	58
Zhejiang J&C Biological Technology Co.,Limited	+1-2135480471 +1-2135480471	sales@sarms4muscle.com	China	10523	58
ChemExpress	+86-021-58950125	info@chemexpress.com	China	566	58

Supplier	Advantage
Heading （Nanjing）Pharmtechnologies Co., Ltd.	58
Anhui Ruihan Technology Co., Ltd	58
Henan Fengda Chemical Co., Ltd	58
ATK CHEMICAL COMPANY LIMITED	60
career henan chemical co	58
BOC Sciences	58
Chongqing Chemdad Co., Ltd	58
HANGZHOU CLAP TECHNOLOGY CO.,LTD	58
Zhejiang J&C Biological Technology Co.,Limited	58
ChemExpress	58

How to synthesize Relebactam?
Relebactam, formerly MK-7655, is a DBO that promises to contribute to the renaissance in antimicrobial chemotherapy.
Jan 5，2024

View Lastest Price from Relebactam manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-03-29	Relebactam 1174018-99-5	US $8.00-1.00 / KG	1KG	99%	g-kg-tons, free sample is available	Henan Fengda Chemical Co., Ltd
2023-09-08	Relebactam 1174018-99-5	US $30.00 / kg	1kg	99%	1000t/year	Anhui Ruihan Technology Co., Ltd
2019-07-06	Sulfuric acid Mono-[7-oxo-2-(piperidin-4-ylcarbaMoyl)-1,6-diaza-bicyclo[3.2.1]oct-6-yl] ester 1174018-99-5	US $1.00 / kg	1kg	95%-99%	100kg	Career Henan Chemical Co

Relebactam
1174018-99-5
US $8.00-1.00 / KG
99%
Henan Fengda Chemical Co., Ltd

Relebactam
1174018-99-5
US $30.00 / kg
99%
Anhui Ruihan Technology Co., Ltd

Sulfuric acid Mono-[7-oxo-2-(piperidin-4-ylcarbaMoyl)-1,6-diaza-bicyclo[3.2.1]oct-6-yl] ester
1174018-99-5
US $1.00 / kg
95%-99%
Career Henan Chemical Co

1174018-99-5(Relebactam)Related Search:

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Relugolix Impurity 5 Ammonium bisulfate

1of4

Sulfuric acid Mono-[7-oxo-2-(piperidin-4-ylcarbaMoyl)-1,6-diaza-bicyclo[3.2.1]oct-6-yl] ester Sulfuric acid mono[(1R,2S,5R)-7-oxo-2-[(4-piperidinylamino)carbonyl]-1,6-diazabicyclo[3.2.1]oct-6-yl] ester MK-7655(Relebactam) RELEBACTAM MK7655 (2S,5R)-sulfuric acid mono{[(4-aminopiperidin-4-yl)carbonyl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl}ester (2S,5R)-7-oxo-2-(piperidin-1-ium-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate Relebactam(MK-7655) MK-7655;MK 7655;MK7655 CS-2637 (1R,2S,5R)-7-Oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate 2H4]-Relebactam Relibactam (2S,5R)-7-oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate （Relebactam） Cefadroxil Monomer 1174018-99-5 C12H20N4O6S