Synonym
Methicillin Free Base; HSDB3121; HSDB-3121; HSDB 3121, Meticillin, Methicillin, Dimethoxyphenyl Penicillin, Metin, Staphcillin
IUPAC/Chemical Name
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((2,6-dimethoxybenzoyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
InChi Key
RJQXTJLFIWVMTO-TYNCELHUSA-N
InChi Code
InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1
SMILES Code
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC(C3=C(OC)C=CC=C3OC)=O)N1C2=O)O
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
Biological target:
Methicillin is a narrow-spectrum β-lactam antibiotic, acts by inhibiting penicillin-binding proteins (PBPs).
In vitro activity:
Cell-bound and extracellular autolytic activity was studied in a tolerant and a non-tolerant Staphylococcus aureus strain after exposure to low (10 mg/l) and high (80 mg/l) concentrations of methicillin. In both types of strains extracellular activity was less after exposure to a high concentration of methicillin than after exposure to a low concentration.
Reference: J Antimicrob Chemother. 1986 Oct;18(4):459-66. https://pubmed.ncbi.nlm.nih.gov/3639873/
In vivo activity:
Ceftazidime, cefuroxime and methicillin proved equally effective in the therapy of experimental Staphylococcus aureus endocarditis in rabbits with a dosing regimen of 40 mg/kg intramuscularly at 8-hourly intervals for three days. Treated animals all demonstrated a thousand to 10,000-fold reduction in the levels of bacteria in the vegetations compared with untreated controls.
Reference: J Antimicrob Chemother. 1984 Oct;14(4):373-7. https://pubmed.ncbi.nlm.nih.gov/6389474/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
380.42
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 |
Formulation protocol:
1. Goessens WH, Wouters JT, Fontijne P, Michel MF. Cell-bound and extracellular autolytic activity of a tolerant and a nontolerant Staphylococcus aureus strain exposed to methicillin. J Antimicrob Chemother. 1986 Oct;18(4):459-66. doi: 10.1093/jac/18.4.459. PMID: 3639873.
2. Frimodt-Møller N, Rosdahl VT, Sørensen G, Hartzen SH, Bentzon MW. Relationship between penicillinase production and the in-vitro activity of methicillin, oxacillin, cloxacillin, dicloxacillin, flucloxacillin, and cephalothin against strains of Staphylococcus aureus of different phage patterns and penicillinase activity. J Antimicrob Chemother. 1986 Jul;18(1):27-33. doi: 10.1093/jac/18.1.27. PMID: 3489704.
3. McColm AA, Ryan DM, Acred P. Comparison of ceftazidime, cefuroxime and methicillin in the treatment of Staphylococcus aureus endocarditis in rabbits. J Antimicrob Chemother. 1984 Oct;14(4):373-7. doi: 10.1093/jac/14.4.373. PMID: 6389474.
In vitro protocol:
1. Goessens WH, Wouters JT, Fontijne P, Michel MF. Cell-bound and extracellular autolytic activity of a tolerant and a nontolerant Staphylococcus aureus strain exposed to methicillin. J Antimicrob Chemother. 1986 Oct;18(4):459-66. doi: 10.1093/jac/18.4.459. PMID: 3639873.
2. Frimodt-Møller N, Rosdahl VT, Sørensen G, Hartzen SH, Bentzon MW. Relationship between penicillinase production and the in-vitro activity of methicillin, oxacillin, cloxacillin, dicloxacillin, flucloxacillin, and cephalothin against strains of Staphylococcus aureus of different phage patterns and penicillinase activity. J Antimicrob Chemother. 1986 Jul;18(1):27-33. doi: 10.1093/jac/18.1.27. PMID: 3489704.
In vivo protocol:
1. McColm AA, Ryan DM, Acred P. Comparison of ceftazidime, cefuroxime and methicillin in the treatment of Staphylococcus aureus endocarditis in rabbits. J Antimicrob Chemother. 1984 Oct;14(4):373-7. doi: 10.1093/jac/14.4.373. PMID: 6389474.
1: Methicillin-resistant Staphylococcus aureus. Nat Rev Dis Primers. 2018 May 31;4:18034. doi: 10.1038/nrdp.2018.34. PMID: 29849126.
2: Aguayo-Reyes A, Quezada-Aguiluz M, Mella S, Riedel G, Opazo-Capurro A, Bello- Toledo H, Domínguez M, González-Rocha G. Bases moleculares de la resistencia a meticilina en Staphylococcus aureus [Molecular basis of methicillin-resistance in Staphylococcus aureus]. Rev Chilena Infectol. 2018;35(1):7-14. Spanish. doi: 10.4067/s0716-10182018000100007. PMID: 29652966.
3: Thornsberry C. Methicillin-resistant staphylococci. Clin Lab Med. 1989 Jun;9(2):255-67. PMID: 2659244.
4: Ditlove J, Weidmann P, Bernstein M, Massry SG. Methicillin nephritis. Medicine (Baltimore). 1977 Nov;56(6):483-91. doi: 10.1097/00005792-197711000-00003. PMID: 335187.
5: Brumfitt W, Hamilton-Miller J. Methicillin-resistant Staphylococcus aureus. N Engl J Med. 1989 May 4;320(18):1188-96. doi: 10.1056/NEJM198905043201806. PMID: 2651925.
6: Siebert WT, Moreland N, Williams TW Jr. Methicillin-resistant Staphylococcus epidermidis. South Med J. 1978 Nov;71(11):1353-5. doi: 10.1097/00007611-197811000-00011. PMID: 251348.
7: Baum SE, Dooley DP. Preventing methicillin-resistant Staphylococcus aureus infections in cardiovascular surgery patients: can we do any better? Clin Infect Dis. 2004 Jun 1;38(11):1561-3. doi: 10.1086/420828. Epub 2004 May 12. PMID: 15156443.
8: Methicillin-resistant Staphylococcus aureus. J Hosp Infect. 1983 Dec;4(4):327-9. doi: 10.1016/0195-6701(83)90001-4. PMID: 6198361.
9: Harkins CP, Pichon B, Doumith M, Parkhill J, Westh H, Tomasz A, de Lencastre H, Bentley SD, Kearns AM, Holden MTG. Methicillin-resistant Staphylococcus aureus emerged long before the introduction of methicillin into clinical practice. Genome Biol. 2017 Jul 20;18(1):130. doi: 10.1186/s13059-017-1252-9. PMID: 28724393; PMCID: PMC5517843.
10: Gilbert DN, Sanford JP. Methicillin: critical appraisal after a decade of experience. Med Clin North Am. 1970 Sep;54(5):1113-25. PMID: 4248509.
