Synonym
Mecillinam; AMDINOCILLIN; Coactin; Penicillin HX; Mecillinamum; Hexacillin; FL 1060; FL-1060; FL1060;
IUPAC/Chemical Name
(2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChi Key
BWWVAEOLVKTZFQ-CXUHLZMHSA-N
InChi Code
InChI=1S/C15H23N3O3S/c1-15(2)11(14(20)21)18-12(19)10(13(18)22-15)16-9-17-7-5-3-4-6-8-17/h9-11,13H,3-8H2,1-2H3,(H,20,21)/b16-9+
SMILES Code
CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)C(=O)O)C
Purity
>95% (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, not in water
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
325.43
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 |
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2: Neu HC. Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use. Pharmacotherapy. 1985 Jan-Feb;5(1):1-10. doi: 10.1002/j.1875-9114.1985.tb04448.x. PMID: 3885172.
3: Gordin FM, Sande MA. Amdinocillin therapy of experimental animal infections. Am J Med. 1983 Aug 29;75(2A):48-53. doi: 10.1016/0002-9343(83)90093-1. PMID: 6311005.
4: Demos CH, Green E. Review of clinical experience with amdinocillin monotherapy and comparative studies. Am J Med. 1983 Aug 29;75(2A):72-81. doi: 10.1016/0002-9343(83)90098-0. PMID: 6311009.
5: Thulin E, Sundqvist M, Andersson DI. Amdinocillin (Mecillinam) resistance mutations in clinical isolates and laboratory-selected mutants of Escherichia coli. Antimicrob Agents Chemother. 2015 Mar;59(3):1718-27. doi: 10.1128/AAC.04819-14. Epub 2015 Jan 12. PMID: 25583718; PMCID: PMC4325821.
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7: Neu HC. Penicillin-binding proteins and role of amdinocillin in causing bacterial cell death. Am J Med. 1983 Aug 29;75(2A):9-20. doi: 10.1016/0002-9343(83)90089-x. PMID: 6311012.
8: Lawson RD, Estey EH, Bodey GP. Amdinocillin: use alone or in combination with cefoxitin or carbenicillin-ticarcillin. Am J Med. 1983 Aug 29;75(2A):113-8. doi: 10.1016/0002-9343(83)90105-5. PMID: 6310998.
9: Ward TT, Amon MB, Krause LK. Combination amdinocillin and cefoxitin therapy of multiply-resistant Serratia marcescens urinary tract infections. Am J Med. 1983 Aug 29;75(2A):85-9. doi: 10.1016/0002-9343(83)90100-6. PMID: 6311011.
10: Olson ME, Nickel JC, Khoury AE, Morck DW, Cleeland R, Costerton JW. Amdinocillin treatment of catheter-associated bacteriuria in rabbits. J Infect Dis. 1989 Jun;159(6):1065-72. doi: 10.1093/infdis/159.6.1065. PMID: 2656876.
11: File TM Jr, Tan JS. Amdinocillin plus cefoxitin versus cefoxitin alone in therapy of mixed soft tissue infections (including diabetic foot infections). Am J Med. 1983 Aug 29;75(2A):100-5. doi: 10.1016/0002-9343(83)90103-1. PMID: 6310996.
12: Kramer MJ, Mauriz YR, Timmes MD, Robertson TL, Cleeland R. Morphologic changes produced by amdinocillin alone and in combination with beta-lactam antibiotics: in vitro and in vivo. Am J Med. 1983 Aug 29;75(2A):30-41. doi: 10.1016/0002-9343(83)90091-8. PMID: 6311003.
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14: Mecillinam. Lancet. 1976 Sep 4;1(7984):503-5. PMID: 74467.
15: Gambertoglio JG, Barriere SL, Lin ET, Conte JE Jr. Amdinocillin pharmacokinetics. Simultaneous administration with cephalothin and cerebrospinal fluid penetration. Am J Med. 1983 Aug 29;75(2A):54-9. doi: 10.1016/0002-9343(83)90094-3. PMID: 6311006.
16: de Louvois J, Mulhall A. Efficacy, pharmacology, and safety of amdinocillin in treatment of neonates. Am J Med. 1983 Aug 29;75(2A):119-24. doi: 10.1016/0002-9343(83)90106-7. PMID: 6310999.
17: Cho H, Uehara T, Bernhardt TG. Beta-lactam antibiotics induce a lethal malfunctioning of the bacterial cell wall synthesis machinery. Cell. 2014 Dec 4;159(6):1300-11. doi: 10.1016/j.cell.2014.11.017. PMID: 25480295; PMCID: PMC4258230.
18: Freyhult E, Bremell D, Tängden T. Pivmecillinam – ett osäkert alternativ vid pyelonefrit. Lakartidningen. 2020 Aug 21;117:20048. Swedish. PMID: 32852775.
19: Yourassowsky E, van der Linden MP, Lismont MJ, Crokaert F, Glupczynski Y. Protective effect of amdinocillin against emergence of resistance to ceftazidime in Enterobacter cloacae. Antimicrob Agents Chemother. 1988 Nov;32(11):1632-5. doi: 10.1128/AAC.32.11.1632. PMID: 3075433; PMCID: PMC175942.
20: Bakhtiar M, Selwyn S. Mecillinam. Lancet. 1978 Feb 11;1(8059):337. doi: 10.1016/s0140-6736(78)90115-0. PMID: 75379.
