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MedKoo Cat#: 329874 | Name: Tigemonam free acid

Description:

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

Tigemonam is an orally administered monobactam. At less than or equal to 1 microgram/ml it inhibited the majority of strains of Escherichia coli, Klebsiella spp., Enterobacter aerogenes, Citrobacter diversus, Proteus spp., Providencia spp., Aeromonas hydrophila, Salmonella spp., Shigella spp., Serratia marcescens, and Yersinia enterocolitica.

Chemical Structure

Tigemonam free acid
Tigemonam free acid
CAS#102507-71-1 (free acid)

Theoretical Analysis

MedKoo Cat#: 329874

Name: Tigemonam free acid

CAS#: 102507-71-1 (free acid)

Chemical Formula: C12H15N5O9S2

Exact Mass: 437.0311

Molecular Weight: 437.40

Elemental Analysis: C, 32.95; H, 3.46; N, 16.01; O, 32.92; S, 14.66

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.
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Related CAS #
102916-21-2 (dicholine) 102507-71-1 (free acid)
Synonym
Tigemonam,
IUPAC/Chemical Name
2-[[1-(2-Amino-1,3-thiazol-4-yl)- 2-[[(3S)-2,2-dimethyl-4-oxo-1- sulfooxyazetidin-3-yl]amino]-2- oxoethylidene]amino]oxyacetic acid
InChi Key
VAMSVIZLXJOLHZ-XUNMKLQISA-N
InChi Code
InChI=1S/C12H15N5O9S2/c1-12(2)8(10(21)17(12)26-28(22,23)24)15-9(20)7(16-25-3-6(18)19)5-4-27-11(13)14-5/h4,8H,3H2,1-2H3,(H2,13,14)(H,15,20)(H,18,19)(H,22,23,24)/b16-7+/t8-/m1/s1
SMILES Code
O=C(O)CO/N=C(C1=CSC(N)=N1)/C(N[C@H]2C(C)(C)N(OS(=O)(O)=O)C2=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
>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
More Info
Tigemonam was not hydrolyzed by the common plasmid beta-lactamases such as TEM-1 and SHV-1 or by the chromosomal beta-lactamases of Enterobacter, Morganella, Pseudomonas, and Bacteroides spp. Tigemonam inhibited beta-lactamases of E. cloacae and Pseudomonas aeruginosa but did not induce beta-lactamases. The growth medium had a minimal effect on the in vitro activity of tigemonam, and there was a close agreement between the MICs and MBCs.

Preparing Stock Solutions

The following data is based on the product molecular weight 437.40 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: Nélet F, Gutmann L, Kitzis MD, Acar JF. Tigemonam activity against clinical isolates of Enterobacteriaceae and Enterobacteriaceae with known mechanisms of resistance to beta-lactam antibiotics. J Antimicrob Chemother. 1989 Aug;24(2):173-81. PubMed PMID: 2676940. 2: Rylander M, Gezelius L, Norrby SR. Comparative in-vitro activity of tigemonam, a new monobactam. J Antimicrob Chemother. 1988 Sep;22(3):307-13. PubMed PMID: 3182428. 3: Clark JM, Olsen SJ, Weinberg DS, Dalvi M, Whitney RR, Bonner DP, Sykes RB. In vivo evaluation of tigemonam, a novel oral monobactam. Antimicrob Agents Chemother. 1987 Feb;31(2):226-9. PubMed PMID: 3551830; PubMed Central PMCID: PMC174696. 4: Chin NX, Neu HC. Tigemonam, an oral monobactam. Antimicrob Agents Chemother. 1988 Jan;32(1):84-91. PubMed PMID: 3279906; PubMed Central PMCID: PMC172104. 5: Fuchs PC, Jones RN, Barry AL. In vitro antimicrobial activity of tigemonam, a new orally administered monobactam. Antimicrob Agents Chemother. 1988 Mar;32(3):346-9. PubMed PMID: 3259122; PubMed Central PMCID: PMC172173. 6: Tanaka SK, Summerill RA, Minassian BF, Bush K, Visnic DA, Bonner DP, Sykes RB. In vitro evaluation of tigemonam, a novel oral monobactam. Antimicrob Agents Chemother. 1987 Feb;31(2):219-25. PubMed PMID: 3105448; PubMed Central PMCID: PMC174695. 7: van Ogtrop ML, Mattie H, Guiot HF, van Strijen E, Sekh BR, van Furth R. Comparison of the effects of aztreonam and tigemonam against Escherichia coli and Klebsiella pneumoniae in vitro and in vivo. Antimicrob Agents Chemother. 1991 Mar;35(3):417-22. PubMed PMID: 2039191; PubMed Central PMCID: PMC245025. 8: Yourassowsky E, Linden MP, Lismont MJ, Crokaert F. Growth Curve Patterns of Escherichia coli, Serratia marcescens, and Proteus vulgaris Submitted to Different Tigemonam Concentrations. J Chemother. 1989 May;1(sup2):49-53. PubMed PMID: 27416151. 9: Schito GC, Debbia E, Bandelloni R, Paglia P, Pesce A. Antibacterial activity in vitro of tigemonam, a new oral monobactam. J Chemother. 1989 May;1 Suppl 2:41-4. PubMed PMID: 2809702. 10: Andrews JM, Wise R. The in vitro activity of tigemonam: a comparison with other antimicrobial agents. J Chemother. 1989 May;1 Suppl 2:5-12. PubMed PMID: 2509645. 11: Giamarellou H, Pephanis A, Grammatikou M, Avlamis A, Papoulias G. In vitro activity of tigemonam against multiresistant nosocomial Enterobacteriaceae. J Chemother. 1989 May;1 Suppl 2:32-5. PubMed PMID: 2809700. 12: van Ogtrop ML, Guiot HF, Mattie H, van Strijen E, Sekh BR, van Furth R. Modulation of the intestinal flora of mice by treatment with aztreonam and tigemonam. Antimicrob Agents Chemother. 1991 May;35(5):983-5. PubMed PMID: 1854181; PubMed Central PMCID: PMC245140. 13: Shah PM, Gänger-Farshid G, Mulert R, Stille W. Bactericidal activity of tigemonam, alone and in combination with gentamicin. J Chemother. 1989 May;1 Suppl 2:45-8. PubMed PMID: 2809703. 14: Garcia-Rodriguez JA, Garcia-Sanchez JE. In vitro activity of tigemonam against urinary tract pathogens. J Chemother. 1989 May;1 Suppl 2:28-31. PubMed PMID: 2809699. 15: Shah PM, Gànger-Farshid G, Mulert R, Stille W. Bactericidal Activity of Tigemonam, Alone and in Combination with Gentamicin. J Chemother. 1989 May;1(sup2):45-46. PubMed PMID: 27416150. 16: Raimondi A, Cocuzza CE. Antibacterial activity of tigemonam dicholate (SQ 30836) and interaction with beta-lactamases of gram-negative bacteria. J Chemother. 1989 May;1 Suppl 2:13-21. PubMed PMID: 2809698. 17: Giamarellou H, Pephanis A, Grammatikou M, Avlamis A, Papoulias G. In Vitro Activity of Tigemonam Against Multiresistant Nosocomial Enterobacteriaceae. J Chemother. 1989 May;1(sup2):32-35. PubMed PMID: 27416147. 18: Yourassowsky E, van der Linden MP, Lismont MJ, Crokaert F. Growth curve patterns of Escherichia coli, Serratia marcescens, and Proteus vulgaris submitted to different tigemonam concentrations. J Chemother. 1989 May;1 Suppl 2:49-53. PubMed PMID: 2681561. 19: Schito GC, Debbia E, Bandelloni R, Paglia P, Pesce A. Antibacterial Activity In Vitro of Tigemonam, a New Oral Monobactam. J Chemother. 1989 May;1(sup2):41-44. PubMed PMID: 27416149. 20: Andrews JM, Wise R. The In Vitro Activity of Tigemonam: a Comparison with Other Antimicrobial Agents. J Chemother. 1989 May;1(sup2):5-12. PubMed PMID: 27416143.

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