AAI-101
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MedKoo CAT#: 527715

CAS#: 1001404-83-6

Description: AAI-101, also known as Enmetazobactam, is a beta lactamase inhibitor potentially for the treatment of multi-drug resistant gram-negative bacterial infections.


Chemical Structure

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AAI-101
CAS# 1001404-83-6

Theoretical Analysis

MedKoo Cat#: 527715
Name: AAI-101
CAS#: 1001404-83-6
Chemical Formula: C11H14N4O5S
Exact Mass: 314.0685
Molecular Weight: 314.32
Elemental Analysis: C, 42.03; H, 4.49; N, 17.83; O, 25.45; S, 10.20

Price and Availability

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10.0mg USD 120.0 Ready to ship
25.0mg USD 240.0 Ready to ship
50.0mg USD 400.0 Ready to ship
100.0mg USD 650.0 Ready to ship
200.0mg USD 1150.0 Ready to ship
500.0mg USD 2450.0 Ready to ship
1.0g USD 3450.0 Ready to ship
2.0g USD 6250.0 Ready to ship
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Synonym: AAI-101; AAI-101; AAI-101, Enmetazobactam

IUPAC/Chemical Name: (2S,3S,5R)-3-methyl-3-((3-methyl-1H-1,2,3-triazol-3-ium-1-yl)methyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide

InChi Key: HFZITXBUTWITPT-YWVKMMECSA-N

InChi Code: InChI=1S/C11H14N4O5S/c1-11(6-14-4-3-13(2)12-14)9(10(17)18)15-7(16)5-8(15)21(11,19)20/h3-4,8-9H,5-6H2,1-2H3/t8-,9+,11+/m1/s1

SMILES Code: C[N+]1=NN(C[C@@](S([C@]2([H])C3)(=O)=O)(C)[C@H](C([O-])=O)N2C3=O)C=C1

Appearance: 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

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: AAI101 is an extended-spectrum β-lactamase inhibitor, against many resistant Gram-negative pathogens.
In vitro activity: MICs for cefepime-enmetazobactam were determined using a fixed enmetazobactam concentration of 8 μg/ml. For the complete Enterobacteriaceae panel of 1,696 isolates, the addition of enmetazobactam to cefepime lowered the MIC90 compared to cefepime alone by seven doubling dilutions from 32 to 0.25 μg/ml. The same MIC90 diminution was observed for E. coli isolates, with a shift from 16 to 0.12 μg/ml. The MIC90s for K. pneumoniae were reduced by at least eight doubling dilutions from >64 to 0.5 μg/ml. E. cloacae and E. aerogenes MIC90s were reduced by four and by one doubling dilution, from 16 to 1 μg/ml and from 0.5 to 0.25 μg/ml, respectively. Enmetazobactam did not enhance the potency of cefepime against P. aeruginosa, the MIC90 for both cefepime and cefepime-enmetazobactam being 16 μg/ml. Enmetazobactam did not show intrinsic activity against Enterobacteriaceae or P. aeruginosa (data not shown). Reference: Antimicrob Agents Chemother. 2019 Jul; 63(7): e00514-19. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6591593/
In vivo activity: For the three Enterobacteriaceae isolates resistant to cefepime (MICs of ≥32 μg/ml) due to the expression of ≥2 β-lactamases, the addition of AAI101 had a remarkable ameliorative effect. AAI101 restored the protective efficacy of cefepime more than 10-fold toward the mice infected with the K. pneumoniae strain coproducing an ESBL and a class D carbapenemase and approximately 20- fold toward the K. pneumoniae and E. cloacae strains each coproducing an ESBL and an AmpC (Fig. 9, ,10,10, and 11). For all three cefepime-resistant Enterobacteriaceae, the PD50s for cefepime-AAI101 (2:1, wt/wt) were similar (range, 12.77 to 15.97 mg/kg). Cefepime-AAI101 afforded protection comparable to that of meropenem toward the mice infected with E. cloacae B-143 and better protection than meropenem toward the mice infected with K. pneumoniae B-124, though meropenem proved more protective than cefepime-AAI101 toward the mice infected with K. pneumoniae R-43. Reference: Antimicrob Agents Chemother. 2019 May; 63(5): e00105-19. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6496078/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 113.3 360.46

Preparing Stock Solutions

The following data is based on the product molecular weight 314.32 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. Crandon JL, Nicolau DP. In Vitro Activity of Cefepime/AAI101 and Comparators against Cefepime Non-susceptible Enterobacteriaceae. Pathogens. 2015 Aug 18;4(3):620-5. doi: 10.3390/pathogens4030620. PMID: 26295262; PMCID: PMC4584277. 2. Morrissey I, Magnet S, Hawser S, Shapiro S, Knechtle P. In Vitro Activity of Cefepime-Enmetazobactam against Gram-Negative Isolates Collected from U.S. and European Hospitals during 2014-2015. Antimicrob Agents Chemother. 2019 Jun 24;63(7):e00514- 19. doi: 10.1128/AAC.00514-19. PMID: 30988152; PMCID: PMC6591593. 3. Crandon JL, Nicolau DP. In vivo activities of simulated human doses of cefepime and cefepime-AAI101 against multidrug-resistant Gram-negative Enterobacteriaceae. Antimicrob Agents Chemother. 2015 May;59(5):2688-94. doi: 10.1128/AAC.00033-15. Epub 2015 Feb 23. PMID: 25712356; PMCID: PMC4394792. 4. Papp-Wallace KM, Bethel CR, Caillon J, Barnes MD, Potel G, Bajaksouzian S, Rutter JD, Reghal A, Shapiro S, Taracila MA, Jacobs MR, Bonomo RA, Jacqueline C. Beyond Piperacillin-Tazobactam: Cefepime and AAI101 as a Potent β-Lactam-β-Lactamase Inhibitor Combination. Antimicrob Agents Chemother. 2019 Apr 25;63(5):e00105-19. doi: 10.1128/AAC.00105-19. PMID: 30858223; PMCID: PMC6496078.
In vitro protocol: 1. Crandon JL, Nicolau DP. In Vitro Activity of Cefepime/AAI101 and Comparators against Cefepime Non-susceptible Enterobacteriaceae. Pathogens. 2015 Aug 18;4(3):620-5. doi: 10.3390/pathogens4030620. PMID: 26295262; PMCID: PMC4584277. 2. Morrissey I, Magnet S, Hawser S, Shapiro S, Knechtle P. In Vitro Activity of Cefepime-Enmetazobactam against Gram-Negative Isolates Collected from U.S. and European Hospitals during 2014-2015. Antimicrob Agents Chemother. 2019 Jun 24;63(7):e00514- 19. doi: 10.1128/AAC.00514-19. PMID: 30988152; PMCID: PMC6591593.
In vivo protocol: 1. Crandon JL, Nicolau DP. In vivo activities of simulated human doses of cefepime and cefepime-AAI101 against multidrug-resistant Gram-negative Enterobacteriaceae. Antimicrob Agents Chemother. 2015 May;59(5):2688-94. doi: 10.1128/AAC.00033-15. Epub 2015 Feb 23. PMID: 25712356; PMCID: PMC4394792. 2. Papp-Wallace KM, Bethel CR, Caillon J, Barnes MD, Potel G, Bajaksouzian S, Rutter JD, Reghal A, Shapiro S, Taracila MA, Jacobs MR, Bonomo RA, Jacqueline C. Beyond Piperacillin-Tazobactam: Cefepime and AAI101 as a Potent β-Lactam-β-Lactamase Inhibitor Combination. Antimicrob Agents Chemother. 2019 Apr 25;63(5):e00105-19. doi: 10.1128/AAC.00105-19. PMID: 30858223; PMCID: PMC6496078.

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1: Crandon JL, Nicolau DP. In vivo activities of simulated human doses of cefepime and cefepime-AAI101 against multidrug-resistant Gram-negative Enterobacteriaceae. Antimicrob Agents Chemother. 2015 May;59(5):2688-94. doi: 10.1128/AAC.00033-15. PubMed PMID: 25712356; PubMed Central PMCID: PMC4394792.

2: Crandon JL, Nicolau DP. In Vitro Activity of Cefepime/AAI101 and Comparators against Cefepime Non-susceptible Enterobacteriaceae. Pathogens. 2015 Aug 18;4(3):620-5. doi: 10.3390/pathogens4030620. PubMed PMID: 26295262; PubMed Central PMCID: PMC4584277.

3: Bush K. A resurgence of β-lactamase inhibitor combinations effective against multidrug-resistant Gram-negative pathogens. Int J Antimicrob Agents. 2015 Nov;46(5):483-93. doi: 10.1016/j.ijantimicag.2015.08.011. Review. PubMed PMID: 26498989.

AAI-101

10.0mg / USD 120.0