RG-6080
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 327016

CAS#: 1452458-86-4 (free acid)

Description: Nacubactam, also known as RG-6080, FPI-1459, and OP-0595, is a beta-lactamase inhibitor used for treating bacterial infections.


Chemical Structure

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RG-6080
CAS# 1452458-86-4 (free acid)

Theoretical Analysis

MedKoo Cat#: 327016
Name: RG-6080
CAS#: 1452458-86-4 (free acid)
Chemical Formula: C9H16N4O7S
Exact Mass: 324.074
Molecular Weight: 324.308
Elemental Analysis: C, 33.33; H, 4.97; N, 17.28; O, 34.53; S, 9.89

Price and Availability

Size Price Availability Quantity
5.0mg USD 90.0 Ready to ship
10.0mg USD 150.0 Ready to ship
25.0mg USD 250.0 Ready to ship
50.0mg USD 450.0 Ready to ship
100.0mg USD 750.0 Ready to ship
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Related CAS #: 2007923-17-1 (hydrate)   1452458-86-4 (free acid)    

Synonym: RG-6080; RG 6080; RG6080; FPI-1459; FPI 1459; FPI1459; OP-0595; OP 0595; OP0595; Nacubactam;

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

InChi Key: RSBPYSTVZQAADE-RQJHMYQMSA-N

InChi Code: InChI=1S/C9H16N4O7S/c10-3-4-19-11-8(14)7-2-1-6-5-12(7)9(15)13(6)20-21(16,17)18/h6-7H,1-5,10H2,(H,11,14)(H,16,17,18)/t6-,7+/m1/s1

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

Appearance: Off-white to beige 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

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

Biological target: Nacubactam (OP0595 free acid) is a potent non-β-lactam-β-lactamase inhibitor with activity against class A and class C β-lactamases.
In vitro activity: To assess the functional concentration of OP0595 for use with β-lactam agents, the MICs (the lowest concentration to prevent visible growth after incubation at 35°C for 18 to 20 h) of piperacillin, cefepime, and meropenem in combination with different concentrations of OP0595 were determined against five strains of CTX-M-15-positive E. coli and five strains of KPC-positive K. pneumoniae. The log averages of MICs were plotted as the geometric mean MICs (Fig. 1). For all β-lactam agents, the geometric mean MICs decreased as the OP0595 concentrations increased, regardless of the type of partner β-lactam agent or the bacterial species. In each case, the MIC reached a plateau at 2 to 4 μg/ml of OP0595. These results suggest that a concentration of 4 μg/ml of OP0595 against these strains is sufficient to result in maximal MIC reduction in in vitro studies. Reference: Antimicrob Agents Chemother. 2016 Apr 22;60(5):3001-6. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4862534/
In vivo activity: A neutropenic murine model of thigh infection was used to clarify the efficacy of OP0595 alone and in combination with cefepime in vivo. The strains tested were CTX-M-15-positive E. coli MSC20653 and MSC20662 and KPC-positive K. pneumoniae ATCC BAA-1705 and ATCC BAA-1904, which have been confirmed to grow in the thigh of neutropenic Crlj:CD1 (ICR) mice. The viable cell counts of CTX-M-15-positive E. coli MSC20653 or MSC20662 in control mice and in mice after administration of the test compounds are shown in Fig. 3A. The viable cell count in mice treated with cefepime (10 mg/kg) or OP0595 (2.5 mg/kg) was not significantly lower than that in mice treated with vehicle at 23 h after the start of treatment. However, mice in the cefepime-OP0595 groups (5/1.25 mg/kg and 10/2.5 mg/kg) had significantly (P < 0.05) lower bacterial counts than those in the saline vehicle group. Cefepime-OP0595 showed stronger efficacy than cefepime alone against all β-lactamase-positive strains tested, whereas OP0595 alone showed weaker or no efficacy. Taken together, these data indicate that combinational use of OP0595 and a β-lactam agent is important to exert the antimicrobial functions of OP0595. Reference: Antimicrob Agents Chemother. 2016 Apr 22;60(5):3001-6. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4862534/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 62.5 192.72

Preparing Stock Solutions

The following data is based on the product molecular weight 324.308 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.

Recalculate based on batch purity %
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
Formulation protocol: 1. Morinaka A, Tsutsumi Y, Yamada K, Takayama Y, Sakakibara S, Takata T, Abe T, Furuuchi T, Inamura S, Sakamaki Y, Tsujii N, Ida T. In vitro and in vivo activities of the diazabicyclooctane OP0595 against AmpC-derepressed Pseudomonas aeruginosa. J Antibiot (Tokyo). 2017 Mar;70(3):246-250. doi: 10.1038/ja.2016.150. Epub 2016 Dec 21. PMID: 27999441. 2. Morinaka A, Tsutsumi Y, Yamada K, Takayama Y, Sakakibara S, Takata T, Abe T, Furuuchi T, Inamura S, Sakamaki Y, Tsujii N, Ida T. In Vitro and In Vivo Activities of OP0595, a New Diazabicyclooctane, against CTX-M-15-Positive Escherichia coli and KPC-Positive Klebsiella pneumoniae. Antimicrob Agents Chemother. 2016 Apr 22;60(5):3001-6. doi: 10.1128/AAC.02704-15. PMID: 26953205; PMCID: PMC4862534.
In vitro protocol: 1. Morinaka A, Tsutsumi Y, Yamada K, Takayama Y, Sakakibara S, Takata T, Abe T, Furuuchi T, Inamura S, Sakamaki Y, Tsujii N, Ida T. In vitro and in vivo activities of the diazabicyclooctane OP0595 against AmpC-derepressed Pseudomonas aeruginosa. J Antibiot (Tokyo). 2017 Mar;70(3):246-250. doi: 10.1038/ja.2016.150. Epub 2016 Dec 21. PMID: 27999441. 2. Morinaka A, Tsutsumi Y, Yamada K, Takayama Y, Sakakibara S, Takata T, Abe T, Furuuchi T, Inamura S, Sakamaki Y, Tsujii N, Ida T. In Vitro and In Vivo Activities of OP0595, a New Diazabicyclooctane, against CTX-M-15-Positive Escherichia coli and KPC-Positive Klebsiella pneumoniae. Antimicrob Agents Chemother. 2016 Apr 22;60(5):3001-6. doi: 10.1128/AAC.02704-15. PMID: 26953205; PMCID: PMC4862534.
In vivo protocol: 1. Morinaka A, Tsutsumi Y, Yamada K, Takayama Y, Sakakibara S, Takata T, Abe T, Furuuchi T, Inamura S, Sakamaki Y, Tsujii N, Ida T. In vitro and in vivo activities of the diazabicyclooctane OP0595 against AmpC-derepressed Pseudomonas aeruginosa. J Antibiot (Tokyo). 2017 Mar;70(3):246-250. doi: 10.1038/ja.2016.150. Epub 2016 Dec 21. PMID: 27999441. 2. Morinaka A, Tsutsumi Y, Yamada K, Takayama Y, Sakakibara S, Takata T, Abe T, Furuuchi T, Inamura S, Sakamaki Y, Tsujii N, Ida T. In Vitro and In Vivo Activities of OP0595, a New Diazabicyclooctane, against CTX-M-15-Positive Escherichia coli and KPC-Positive Klebsiella pneumoniae. Antimicrob Agents Chemother. 2016 Apr 22;60(5):3001-6. doi: 10.1128/AAC.02704-15. PMID: 26953205; PMCID: PMC4862534.

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