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MedKoo Cat#: 414525 | Name: Avibactam free acid
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Description:

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

Avibactam is a non-β-lactam β-lactamase inhibitor that restores the efficacy of β-lactam antibiotics against resistant Gram-negative bacteria by inhibiting class A (including KPC), class C (AmpC), and some class D (OXA-48-like) β-lactamases. It is not effective against metallo-β-lactamases (class B). Avibactam, when combined with ceftazidime (as in the drug ceftazidime-avibactam), significantly lowers the minimum inhibitory concentrations (MICs) of ceftazidime against multidrug-resistant Enterobacterales and Pseudomonas aeruginosa. For example, MIC values for Klebsiella pneumoniae carbapenemase (KPC)-producing strains can drop from >64 µg/mL with ceftazidime alone to ≤4 µg/mL with the combination, often restoring susceptibility.

Chemical Structure

Avibactam free acid
Avibactam free acid
CAS#1192500-31-4 (free acid)

Theoretical Analysis

MedKoo Cat#: 414525

Name: Avibactam free acid

CAS#: 1192500-31-4 (free acid)

Chemical Formula: C7H11N3O6S

Exact Mass: 265.0369

Molecular Weight: 265.24

Elemental Analysis: C, 31.70; H, 4.18; N, 15.84; O, 36.19; S, 12.09

Price and Availability

Size Price Availability Quantity
10mg USD 300.00 2 Weeks
50mg USD 650.00 2 Weeks
100mg USD 950.00 2 Weeks
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Related CAS #
1192491-61-4 (sodium) 1192500-31-4 (free acid)
Synonym
Avibactam Free Acid; NXL-104; NXL104; NXL 104
IUPAC/Chemical Name
(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate
InChi Key
NDCUAPJVLWFHHB-UHNVWZDZSA-N
InChi Code
InChI=1S/C7H11N3O6S/c8-6(11)5-2-1-4-3-9(5)7(12)10(4)16-17(13,14)15/h4-5H,1-3H2,(H2,8,11)(H,13,14,15)/t4-,5+/m1/s1
SMILES Code
NC([C@@H]1CC[C@@H]2CN1C(N2OS(=O)(O)=O)=O)=O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info
The compound functions by forming a reversible covalent bond with the active site serine of β-lactamases, inhibiting their hydrolytic activity without being degraded, and has shown clinical utility in complicated intra-abdominal and urinary tract infections caused by resistant pathogens

Preparing Stock Solutions

The following data is based on the product molecular weight 265.24 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
1: Das S, Li J, Riccobene T, Carrothers TJ, Newell P, Melnick D, Critchley IA, Stone GG, Nichols WW. Dose Selection and Validation for Ceftazidime-Avibactam in Adults with Complicated Intra-abdominal Infections, Complicated Urinary Tract Infections, and Nosocomial Pneumonia. Antimicrob Agents Chemother. 2019 Mar 27;63(4). pii: e02187-18. doi: 10.1128/AAC.02187-18. Print 2019 Apr. Review. PubMed PMID: 30670413; PubMed Central PMCID: PMC6437548. 2: Giri P, Patel H, Srinivas NR. Review of Clinical Pharmacokinetics of Avibactam, A Newly Approved non-β lactam β-lactamase Inhibitor Drug, In Combination Use With Ceftazidime. Drug Res (Stuttg). 2019 May;69(5):245-255. doi: 10.1055/a-0748-5548. Epub 2018 Oct 8. Review. PubMed PMID: 30296806. 3: Sy SKB, Zhuang L, Sy S, Derendorf H. Clinical Pharmacokinetics and Pharmacodynamics of Ceftazidime-Avibactam Combination: A Model-Informed Strategy for its Clinical Development. Clin Pharmacokinet. 2019 May;58(5):545-564. doi: 10.1007/s40262-018-0705-y. Review. PubMed PMID: 30097887. 4: Zhong H, Zhao XY, Zhang ZL, Gu ZC, Zhang C, Gao Y, Cui M. Evaluation of the efficacy and safety of ceftazidime/avibactam in the treatment of Gram-negative bacterial infections: a systematic review and meta-analysis. Int J Antimicrob Agents. 2018 Oct;52(4):443-450. doi: 10.1016/j.ijantimicag.2018.07.004. Epub 2018 Aug 31. Review. PubMed PMID: 30012440. 5: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK500953/ PubMed PMID: 30000012. 6: Shirley M. Ceftazidime-Avibactam: A Review in the Treatment of Serious Gram-Negative Bacterial Infections. Drugs. 2018 Apr;78(6):675-692. doi: 10.1007/s40265-018-0902-x. Review. PubMed PMID: 29671219. 7: Nichols WW, Newell P, Critchley IA, Riccobene T, Das S. Avibactam Pharmacokinetic/Pharmacodynamic Targets. Antimicrob Agents Chemother. 2018 May 25;62(6). pii: e02446-17. doi: 10.1128/AAC.02446-17. Print 2018 Jun. Review. PubMed PMID: 29610208; PubMed Central PMCID: PMC5971577. 8: Sherry N, Howden B. Emerging Gram negative resistance to last-line antimicrobial agents fosfomycin, colistin and ceftazidime-avibactam - epidemiology, laboratory detection and treatment implications. Expert Rev Anti Infect Ther. 2018 Apr;16(4):289-306. doi: 10.1080/14787210.2018.1453807. Epub 2018 Mar 21. Review. PubMed PMID: 29543500. 9: Rodriguez BA, Girotto JE, Nicolau DP. Ceftazidime/Avibactam and Ceftolozane/Tazobactam: Novel Therapy for Multidrug Resistant Gram Negative Infections in Children. Curr Pediatr Rev. 2018;14(2):97-109. doi: 10.2174/1573396314666180308150908. Review. PubMed PMID: 29521242. 10: Falcone M, Viale P, Tiseo G, Pai M. Pharmacokinetic drug evaluation of avibactam + ceftazidime for the treatment of hospital-acquired pneumonia. Expert Opin Drug Metab Toxicol. 2018 Mar;14(3):331-340. doi: 10.1080/17425255.2018.1434142. Epub 2018 Jan 31. Review. PubMed PMID: 29373935. 11: Tuon FF, Rocha JL, Formigoni-Pinto MR. Pharmacological aspects and spectrum of action of ceftazidime-avibactam: a systematic review. Infection. 2018 Apr;46(2):165-181. doi: 10.1007/s15010-017-1096-y. Epub 2017 Nov 7. Review. PubMed PMID: 29110143. 12: Yaeger A, Kappes J. Pharmacotherapy Review of Ceftazidime-Avibactam. S D Med. 2017 May;70(5):229-231. Review. PubMed PMID: 28813756. 13: Barber KE, Ortwine JK, Akins RL. Ceftazidime/Avibactam: Who Says You Can't Teach an Old Drug New Tricks? J Pharm Pharm Sci. 2016 Oct - Dec;19(4):448-464. doi: 10.18433/J3X31R. Review. PubMed PMID: 28057163. 14: Goodlet KJ, Nicolau DP, Nailor MD. Ceftolozane/tazobactam and ceftazidime/avibactam for the treatment of complicated intra-abdominal infections. Ther Clin Risk Manag. 2016 Dec 1;12:1811-1826. eCollection 2016. Review. PubMed PMID: 27942218; PubMed Central PMCID: PMC5140030. 15: Buckman SA, Krekel T, Muller AE, Mazuski JE. Ceftazidime-avibactam for the treatment of complicated intra-abdominal infections. Expert Opin Pharmacother. 2016 Dec;17(17):2341-2349. Epub 2016 Oct 31. Review. PubMed PMID: 27758148. 16: Hidalgo JA, Vinluan CM, Antony N. Ceftazidime/avibactam: a novel cephalosporin/nonbeta-lactam beta-lactamase inhibitor for the treatment of complicated urinary tract infections and complicated intra-abdominal infections. Drug Des Devel Ther. 2016 Jul 26;10:2379-86. doi: 10.2147/DDDT.S110946. eCollection 2016. Review. PubMed PMID: 27528799; PubMed Central PMCID: PMC4970634. 17: Falcone M, Paterson D. Spotlight on ceftazidime/avibactam: a new option for MDR Gram-negative infections. J Antimicrob Chemother. 2016 Oct;71(10):2713-22. doi: 10.1093/jac/dkw239. Epub 2016 Jul 17. Review. PubMed PMID: 27432599. 18: Wang DY, Abboud MI, Markoulides MS, Brem J, Schofield CJ. The road to avibactam: the first clinically useful non-β-lactam working somewhat like a β-lactam. Future Med Chem. 2016 Jun;8(10):1063-84. doi: 10.4155/fmc-2016-0078. Epub 2016 Jun 21. Review. PubMed PMID: 27327972. 19: van Duin D, Bonomo RA. Ceftazidime/Avibactam and Ceftolozane/Tazobactam: Second-generation β-Lactam/β-Lactamase Inhibitor Combinations. Clin Infect Dis. 2016 Jul 15;63(2):234-41. doi: 10.1093/cid/ciw243. Epub 2016 Apr 20. Review. PubMed PMID: 27098166; PubMed Central PMCID: PMC4928383. 20: Gardiner BJ, Golan Y. Ceftazidime-avibactam (CTZ-AVI) as a treatment for hospitalized adult patients with complicated intra-abdominal infections. Expert Rev Anti Infect Ther. 2016;14(5):451-63. doi: 10.1586/14787210.2016.1173542. Review. PubMed PMID: 27042762.