Lactivicin | CAS#107167-31-7 | antibiotic

MedKoo Cat#: 598226 | Name: Lactivicin

Description:

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

Lactivicin is a non-beta-lactam antibiotic that binds to penicillin-binding proteins.

Chemical Structure

Lactivicin

CAS#107167-31-7

Theoretical Analysis

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

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

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.