WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 598226
CAS#: 107167-31-7
Description: Lactivicin is a non-beta-lactam antibiotic that binds to penicillin-binding proteins.
MedKoo Cat#: 598226
Name: Lactivicin
CAS#: 107167-31-7
Chemical Formula: C10H12N2O7
Exact Mass: 272.0645
Molecular Weight: 272.21
Elemental Analysis: C, 44.12; H, 4.44; N, 10.29; O, 41.14
This product is not in stock, which may be available by custom synthesis.
For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge).
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Synonym: Lactivicin;
IUPAC/Chemical Name: 2-(4-acetamido-3-oxoisoxazolidin-2-yl)-5-oxotetrahydrofuran-2-carboxylic acid
InChi Key: ZUEKKUYIXILDAF-UHFFFAOYSA-N
InChi Code: InChI=1S/C10H12N2O7/c1-5(13)11-6-4-18-12(8(6)15)10(9(16)17)3-2-7(14)19-10/h6H,2-4H2,1H3,(H,11,13)(H,16,17)
SMILES Code: O=C(C(CC1)(N2OCC(NC(C)=O)C2=O)OC1=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: Soluble in DMSO
Shelf Life: >3 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: 2934.99.03.00
The following data is based on the product molecular weight 272.21 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.
| 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: Starr J, Brown MF, Aschenbrenner L, Caspers N, Che Y, Gerstenberger BS, Huband M, Knafels JD, Lemmon MM, Li C, McCurdy SP, McElroy E, Rauckhorst MR, Tomaras AP, Young JA, Zaniewski RP, Shanmugasundaram V, Han S. Siderophore receptor-mediated uptake of lactivicin analogues in gram-negative bacteria. J Med Chem. 2014 May 8;57(9):3845-55. doi: 10.1021/jm500219c. Epub 2014 Apr 21. PubMed PMID: 24694215.
2: Nozaki Y, Katayama N, Harada S, Ono H, Okazaki H. Lactivicin, a naturally occurring non-beta-lactam antibiotic having beta-lactam-like action: biological activities and mode of action. J Antibiot (Tokyo). 1989 Jan;42(1):84-93. PubMed PMID: 2493440.
3: Calvopiña K, Umland KD, Rydzik AM, Hinchliffe P, Brem J, Spencer J, Schofield CJ, Avison MB. Sideromimic Modification of Lactivicin Dramatically Increases Potency against Extensively Drug-Resistant Stenotrophomonas maltophilia Clinical Isolates. Antimicrob Agents Chemother. 2016 Jun 20;60(7):4170-5. doi: 10.1128/AAC.00371-16. Print 2016 Jul. PubMed PMID: 27139464; PubMed Central PMCID: PMC4914698.
4: Tamura N, Matsushita Y, Kawano Y, Yoshioka K. Synthesis and antibacterial activity of lactivicin derivatives. Chem Pharm Bull (Tokyo). 1990 Jan;38(1):116-22. PubMed PMID: 2337934.
5: Brown T Jr, Charlier P, Herman R, Schofield CJ, Sauvage E. Structural basis for the interaction of lactivicins with serine beta-lactamases. J Med Chem. 2010 Aug 12;53(15):5890-4. doi: 10.1021/jm100437u. PubMed PMID: 20593835.
6: Holzgrabe U. [Lactivicin--an antibiotic against penicillin-resistant pneumococci]. Pharm Unserer Zeit. 2007;36(6):421-2. German. PubMed PMID: 17957683.
7: Nozaki Y, Katayama N, Ono H, Tsubotani S, Harada S, Okazaki H, Nakao Y. Binding of a non-beta-lactam antibiotic to penicillin-binding proteins. Nature. 1987 Jan 8-14;325(7000):179-80. PubMed PMID: 3543695.
8: 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.
9: Macheboeuf P, Fischer DS, Brown T Jr, Zervosen A, Luxen A, Joris B, Dessen A, Schofield CJ. Structural and mechanistic basis of penicillin-binding protein inhibition by lactivicins. Nat Chem Biol. 2007 Sep;3(9):565-9. Epub 2007 Aug 5. PubMed PMID: 17676039.
10: Kumar KM, Anitha P, Sivasakthi V, Bag S, Lavanya P, Anbarasu A, Ramaiah S. In silico study on Penicillin derivatives and Cephalosporins for upper respiratory tract bacterial pathogens. 3 Biotech. 2014 Jun;4(3):241-251. doi: 10.1007/s13205-013-0147-z. Epub 2013 Jun 11. PubMed PMID: 28324428; PubMed Central PMCID: PMC4026453.
11: Kovacic P, Ames JR, Ryan MD. Minimum essential structural requirements for lactam antibiotic action. Free Radic Res Commun. 1989;7(1):19-26. PubMed PMID: 2806952.
12: Baldwin JE, Lynch GP, Pitlik J. Gamma-lactam analogues of beta-lactam antibiotics. J Antibiot (Tokyo). 1991 Jan;44(1):1-24. Review. PubMed PMID: 2001979.
13: Zervosen A, Sauvage E, Frère JM, Charlier P, Luxen A. Development of new drugs for an old target: the penicillin binding proteins. Molecules. 2012 Oct 24;17(11):12478-505. doi: 10.3390/molecules171112478. Review. PubMed PMID: 23095893.
