Relebactam
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MedKoo CAT#: 319570

CAS#: 1174018-99-5 (free acid)

Description: Relebactam, also known as MK-7655, a potent and selective β-lactamase inhibitor. At a concentration of 4 mg/L, MK-7655 reduced imipenem MICs for Enterobacteriaceae with KPC carbapenemases from 16-64 mg/L to 0.12-1 mg/L. MK-7655 potentiated imipenem against Enterobacteriaceae with KPC carbapenemases or combinations of β-lactamase and impermeability, but not those with metallo-carbapenemases. It augmented the activity of imipenem against P. aeruginosa in general and OprD mutants in particular.


Chemical Structure

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Relebactam
CAS# 1174018-99-5 (free acid)

Theoretical Analysis

MedKoo Cat#: 319570
Name: Relebactam
CAS#: 1174018-99-5 (free acid)
Chemical Formula: C12H20N4O6S
Exact Mass: 348.1104
Molecular Weight: 348.37
Elemental Analysis: 41.37; H, 5.79; N, 16.08; O, 27.55; S, 9.20

Size Price Shipping out time Quantity
10mg USD 90 Same day
25mg USD 190 Same day
50mg USD 350 Same day
100mg USD 550 Same day
200mg USD 950 Same day
500mg USD 1650 Same day
1g USD 2950 Same day
2g USD 5250 2 Weeks
5g USD 79506 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-08. Prices are subject to change without notice.

Relebactam, purity > 98%, is in stock. The same day shipping after order is received.

Related CAS #: 1174020-13-3 (hydrate)   1174018-99-5 (free acid)   1502858-91-4 (sodium)  

Synonym: MK-7655; MK 7655; MK7655; Relebactam;

IUPAC/Chemical Name: (1R,2S,5R)-7-oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate

InChi Key: SMOBCLHAZXOKDQ-ZJUUUORDSA-N

InChi Code: 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

SMILES Code: O=S(O)(ON1[C@]2([H])CC[C@@H](C(NC3CCNCC3)=O)[N@@](C2)C1=O)=O

Appearance:
White to off-white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO and water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO or water

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 348.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Chung JYL, Meng D, Shevlin M, Gudipati V, Chen Q, Liu Y, Lam YH, Dumas A, Scott J, Tu Q, Xu F. Diastereoselective FeCl3·6H2O / NaBH4 Reduction of Oxime Ether for the Synthesis of β-Lactamase Inhibitor Relebactam. J Org Chem. 2019 Dec 18. doi: 10.1021/acs.joc.9b02948. [Epub ahead of print] PubMed PMID: 31850754.

2: Fraile-Ribot P, Zamorano L, Orellana R, Barrio-Tofiño ED, Sánchez-Diener I, Cortes-Lara S, López-Causapé C, Cabot G, Bou G, Martínez-Martínez L, Oliver A; GEMARA-SEIMC/REIPI Pseudomonas study Group. Activity of imipenem/relebactam against a large collection of Pseudomonas aeruginosa clinical isolates and isogenic β-lactam resistant mutants. Antimicrob Agents Chemother. 2019 Nov 18. pii: AAC.02165-19. doi: 10.1128/AAC.02165-19. [Epub ahead of print] PubMed PMID: 31740559.

3: Karlowsky JA, Lob SH, Kazmierczak KM, Young K, Motyl MR, Sahm DF. In vitro activity of imipenem-relebactam and key β-lactam agents against Gram-negative bacilli isolated from lower respiratory tract infection samples of intensive care unit patients - SMART Surveillance United States 2015-2017. Int J Antimicrob Agents. 2019 Nov 5. pii: S0924-8579(19)30302-4. doi: 10.1016/j.ijantimicag.2019.10.022. [Epub ahead of print] PubMed PMID: 31704217.

4: Karlowsky JA, Lob SH, Kazmierczak KM, Young K, Motyl MR, Sahm DF. In vitro activity of imipenem-relebactam against Enterobacteriaceae and Pseudomonas aeruginosa isolated from intraabdominal and urinary tract infection samples - SMART Surveillance United States 2015-2017. J Glob Antimicrob Resist. 2019 Nov 4. pii: S2213-7165(19)30290-5. doi: 10.1016/j.jgar.2019.10.028. [Epub ahead of print] PubMed PMID: 31698105.

5: Le Run E, Atze H, Arthur M, Mainardi JL. Impact of relebactam-mediated inhibition of Mycobacterium abscessus BlaMab β-lactamase on the in vitro and intracellular efficacy of imipenem. J Antimicrob Chemother. 2019 Oct 21. pii: dkz433. doi: 10.1093/jac/dkz433. [Epub ahead of print] PubMed PMID: 31637424.

6: Bhagunde P, Patel P, Lala M, Watson K, Copalu W, Xu M, Kulkarni P, Young K, Rizk ML. Population Pharmacokinetic Analysis for Imipenem-Relebactam in Healthy Volunteers and Patients With Bacterial Infections. CPT Pharmacometrics Syst Pharmacol. 2019 Oct;8(10):748-758. doi: 10.1002/psp4.12462. Epub 2019 Oct 4. PubMed PMID: 31508899; PubMed Central PMCID: PMC6813166.

7: Bhagunde P, Zhang Z, Racine F, Carr D, Wu J, Young K, Rizk ML. A translational pharmacokinetic/pharmacodynamic model to characterize bacterial kill in the presence of imipenem-relebactam. Int J Infect Dis. 2019 Dec;89:55-61. doi: 10.1016/j.ijid.2019.08.026. Epub 2019 Aug 31. PubMed PMID: 31479762.

8: Carpenter J, Neidig N, Campbell A, Thornsberry T, Truex T, Fortney T, Zhang Y, Bush K. Activity of imipenem/relebactam against carbapenemase-producing Enterobacteriaceae with high colistin resistance. J Antimicrob Chemother. 2019 Nov 1;74(11):3260-3263. doi: 10.1093/jac/dkz354. PubMed PMID: 31430370.

9: Motsch J, Murta de Oliveira C, Stus V, Köksal I, Lyulko O, Boucher HW, Kaye KS, File TM, Brown ML, Khan I, Du J, Joeng HK, Tipping RW, Aggrey A, Young K, Kartsonis NA, Butterton JR, Paschke A. RESTORE-IMI 1: A Multicenter, Randomized, Double-blind Trial Comparing Efficacy and Safety of Imipenem/Relebactam vs Colistin Plus Imipenem in Patients With Imipenem-nonsusceptible Bacterial Infections. Clin Infect Dis. 2019 Aug 10. pii: ciz530. doi: 10.1093/cid/ciz530. [Epub ahead of print] PubMed PMID: 31400759.

10: Tooke CL, Hinchliffe P, Lang PA, Mulholland AJ, Brem J, Schofield CJ, Spencer J. Molecular Basis of Class A β-Lactamase Inhibition by Relebactam. Antimicrob Agents Chemother. 2019 Sep 23;63(10). pii: e00564-19. doi: 10.1128/AAC.00564-19. Print 2019 Oct. PubMed PMID: 31383664; PubMed Central PMCID: PMC6761529.

11: Kulengowski B, Burgess DS. Imipenem/relebactam activity compared to other antimicrobials against non-MBL-producing carbapenem-resistant Enterobacteriaceae from an academic medical center. Pathog Dis. 2019 Jun 1;77(4). pii: ftz040. doi: 10.1093/femspd/ftz040. PubMed PMID: 31365075.

12: Chen Y, Xu M, Xu W, Song H, Hu L, Xue S, Zhang S, Qian X, Xie H. Highly selective and wash-free visualization of resistant bacteria with a relebactam-derived fluorogenic probe. Chem Commun (Camb). 2019 Aug 28;55(67):9919-9922. doi: 10.1039/c9cc04533c. Epub 2019 Jul 22. PubMed PMID: 31328197.

13: Young K, Painter RE, Raghoobar SL, Hairston NN, Racine F, Wisniewski D, Balibar CJ, Villafania A, Zhang R, Sahm DF, Blizzard T, Murgolo N, Hammond ML, Motyl MR. In vitro studies evaluating the activity of imipenem in combination with relebactam against Pseudomonas aeruginosa. BMC Microbiol. 2019 Jul 4;19(1):150. doi: 10.1186/s12866-019-1522-7. PubMed PMID: 31272373; PubMed Central PMCID: PMC6610938.

14: Asempa TE, Nicolau DP, Kuti JL. In Vitro Activity of Imipenem-Relebactam Alone or in Combination with Amikacin or Colistin against Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2019 Aug 23;63(9). pii: e00997-19. doi: 10.1128/AAC.00997-19. Print 2019 Sep. PubMed PMID: 31262769; PubMed Central PMCID: PMC6709505.

15: Canver MC, Satlin MJ, Westblade LF, Kreiswirth BN, Chen L, Robertson A, Fauntleroy K, La Spina M, Callan K, Jenkins SG. Activity of Imipenem-Relebactam and Comparator Agents against Genetically Characterized Isolates of Carbapenem-Resistant Enterobacteriaceae. Antimicrob Agents Chemother. 2019 Aug 23;63(9). pii: e00672-19. doi: 10.1128/AAC.00672-19. Print 2019 Sep. PubMed PMID: 31262761; PubMed Central PMCID: PMC6709495.

16: Noel AR, Bowker KE, Attwood M, MacGowan AP. Antibacterial effect of imipenem/relebactam on aerobic Gram-negative bacilli: in vitro simulations of 7 or 14 day human exposures. J Antimicrob Chemother. 2019 Jul 1;74(7):1945-1951. doi: 10.1093/jac/dkz114. PubMed PMID: 31220257.

17: Karlowsky JA, Lob SH, Young K, Motyl MR, Sahm DF. Activity of imipenem-relebactam against multidrug-resistant Pseudomonas aeruginosa from the United States - SMART 2015-2017. Diagn Microbiol Infect Dis. 2019 Oct;95(2):212-215. doi: 10.1016/j.diagmicrobio.2019.05.001. Epub 2019 May 8. PubMed PMID: 31174995.

18: Lob SH, Karlowsky JA, Young K, Motyl MR, Hawser S, Kothari ND, Gueny ME, Sahm DF. Activity of imipenem/relebactam against MDR Pseudomonas aeruginosa in Europe: SMART 2015-17. J Antimicrob Chemother. 2019 Aug 1;74(8):2284-2288. doi: 10.1093/jac/dkz191. PubMed PMID: 31086960.

19: Galani I, Souli M, Nafplioti K, Adamou P, Karaiskos I, Giamarellou H, Antoniadou A; Study Collaborators. Correction to: In vitro activity of imipenem-relebactam against non-MBL carbapenemase-producing Klebsiella pneumoniae isolated in Greek hospitals in 2015-2016. Eur J Clin Microbiol Infect Dis. 2019 Jun;38(6):1151-1152. doi: 10.1007/s10096-019-03553-8. PubMed PMID: 31037478.

20: Horner C, Mushtaq S, Livermore DM; BSAC Resistance Surveillance Standing Committee . Potentiation of imipenem by relebactam for Pseudomonas aeruginosa from bacteraemia and respiratory infections. J Antimicrob Chemother. 2019 Jul 1;74(7):1940-1944. doi: 10.1093/jac/dkz133. PubMed PMID: 31032858.