Metampicillin

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

MedKoo CAT#: 584252

CAS#: 6489-97-0 (free acid)

Description: Metampicillin is a penicillin antibiotic. It is prepared by the reaction of ampicillin with formaldehyde, and is hydrolysed in aqueous solution with the formation of ampicillin. Hydrolysis is rapid under acid conditions, e.g., in the stomach, less rapid in neutral media, and incomplete in solutions such as human serum.

Chemical Structure

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Metampicillin
CAS# 6489-97-0 (free acid)
Instruction

Theoretical Analysis

MedKoo Cat#: 584252
Name: Metampicillin
CAS#: 6489-97-0 (free acid)
Chemical Formula: Chemical Formula: C17H19N3O4S
Exact Mass: 361.11
Molecular Weight: 361.416
Elemental Analysis: Elemental Analysis: C, 56.50; H, 5.30; N, 11.63; O, 17.71; S, 8.87

Price and Availability

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). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 6489-97-0 (free acid)   6489-61-8 (sodium)    

Synonym: Fedacilina; Metampicillin; Methylenampicillin; Micinovo; Pravacilin; Rastomycin K; Ruticina; Viderpen;

IUPAC/Chemical Name: 6-((2-Methylenamino-2-phenyl)acetamido)penicillansaeure

InChi Key: FZECHKJQHUVANE-UKAJUAJCSA-N

InChi Code: InChI=1S/C17H19N3O4S/c1-17(2)12(16(23)24)20-14(22)11(15(20)25-17)19-13(21)10(18-3)9-7-5-4-6-8-9/h4-8,10-12,15H,3H2,1-2H3,(H,19,21)(H,23,24)/t10?,11-,12+,15-/m1/s1

SMILES Code: [H][C@@]1(SC2(C)C)[C@H](NC(C(N=C)C3=CC=CC=C3)=O)C(N1[C@H]2C(O)=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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 361.42 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.

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Reinbold R, John T, Spingardi P, Kawamura A, Schofield CJ, Hopkinson RJ. Metampicillin is a cyclic aminal produced by reaction of ampicillin with formaldehyde. Sci Rep. 2020 Oct 21;10(1):17955. doi: 10.1038/s41598-020-74990-1. PMID: 33087772; PMCID: PMC7577985.


2: Lam L, Sathirareuangchai S, Oyama J, Devendra G, Hong R. Lymphocytic Myocarditis and Cardiogenic Shock in Hawai'i: A Case Series. Hawaii J Health Soc Welf. 2019 Jul;78(7):223-229. PMID: 31475250; PMCID: PMC6697651.


3: Ardestani MM, Giska I, van Gestel CAM. The effect of the earthworm Lumbricus rubellus on the bioavailability of cadmium and lead to the springtail Folsomia candida in metal-polluted field soils. Environ Sci Pollut Res Int. 2019 Sep;26(27):27816-27822. doi: 10.1007/s11356-019-05969-3. Epub 2019 Jul 24. PMID: 31342354.


4: Luckner P, Brandsch M. Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. doi: 10.1016/j.ejpb.2004.07.008. PMID: 15567297.


5: Chin HS, Sim J, Seah KI, Sim TS. Deacetoxycephalosporin C synthase isozymes exhibit diverse catalytic activity and substrate specificity. FEMS Microbiol Lett. 2003 Jan 28;218(2):251-7. doi: 10.1111/j.1574-6968.2003.tb11525.x. PMID: 12586400.


6: Romano A, Torres MJ, Fernandez J, Vega JM, Mayorga C, Garcia J, Blanca M. Allergic reactions to ampicillin. Studies on the specificity and selectivity in subjects with immediate reactions. Clin Exp Allergy. 1997 Dec;27(12):1425-31. PMID: 9433938.


7: Lee H, Lee JS, Lee HS. Simultaneous determination of ampicillin and metampicillin in biological fluids using high-performance liquid chromatography with column switching. J Chromatogr B Biomed Appl. 1995 Feb 17;664(2):335-40. doi: 10.1016/0378-4347(94)00472-h. PMID: 7780585.


8: Wierzba CB, Maman L, Poidatz E. Expérimentation d'une pénicilline semi- synthétique en odonto-stomatologie. "La Métampicilline" [Experience with a semi- synthetic penicillin in oral medicine. Methampicillin]. Chir Dent Fr. 1985 Oct 24;55(310):47-8. French. PMID: 3867475.


9: Brogard JM, Pinget M, Dorner M, Blickle JF. Biliary elimination of beta- lactam antibiotics by the isolated perfused rabbit liver. Liver. 1985 Jun;5(3):147-55. doi: 10.1111/j.1600-0676.1985.tb00230.x. PMID: 4046753.


10: Casal M, Solis F, Gonzalez JM. Investigation of the beta-lactamase activity of Prototheca zopfii. Ann Microbiol (Paris). 1984 Nov-Dec;135B(3):359-62. doi: 10.1016/s0769-2609(84)80103-9. PMID: 6335827.


11: Brogard JM, Audhuy B, Pinget M, Dorner M. Evaluation du passage biliaire des antibiotiques bêta-lactaminiques [Evaluation of the biliary passage of beta- lactam antibiotics]. Ann Med Interne (Paris). 1984;135(7):512-8. French. PMID: 6517422.


12: Ziv G. Availability and usage of new antibacterial drugs in Europe. J Am Vet Med Assoc. 1980 May 15;176(10 Spec No):1122-8. PMID: 7216885.


13: Brogard JM, Arnaud JP, Dauchel J, Pinget M, Lavillaureix J. Evaluation du passage biliaire de la pénicilline G [Evaluation of the biliary excretion of penicillin G. (author's transl)]. Pathol Biol (Paris). 1979 Sep;27(7):403-10. French. PMID: 388319.


14: Dureux JB, Canton P, Pecqueux JL, Belleville F, Biava MF, Chanteclair G. Cinétique intra-rachidienne de la métampicilline [Cerebrospinal fluid distribution of metampicillin (author's transl)]. Pathol Biol (Paris). 1977 Dec;25(10):699-703. French. PMID: 349485.


15: Brogard JM, Pinget M, Adloff M, Dorner M, Lavillaureix J. Experimental and clinical pharmacology of metampicillin in the biliary tract. J Antimicrob Chemother. 1976 Dec;2(4):363-71. doi: 10.1093/jac/2.4.363. PMID: 1032647.


16: Leng B, Leng JJ, Lesgouarres MT, Dubecq JP. Etude des concentrations de métampicilline dans le sang maternel, foetal et dans le liquide amniotique [Concentration of metampicillin in the maternal blood, fetal blood and in the amniotic fluid]. Rev Fr Gynecol Obstet. 1976 Dec;71(12):775-7. French. PMID: 1023329.


17: Pinget M, Brogard JM, Dauchel J, Lavillaureix J. Biliary excretion of ampicillin, metampicillin and carbenicillin. J Antimicrob Chemother. 1976 Jun;2(2):195-201. doi: 10.1093/jac/2.2.195. PMID: 956082.


18: Mussini MP, Fleischmann L. Ricerche in vivo sulla stabilità della metampicillina (MTP) [In vivo research on the stability of methampicillin (MTP)]. Farmaco Prat. 1976 Apr;31(4):219-26. Italian. PMID: 1261660.


19: Ziv G. Absorption of ampicillin derivatives from the bovine udder. Isr J Med Sci. 1976 Mar;12(3):260-3. PMID: 931723.


20: Brogard JM, Pinget M, Meyer C, Brandt C, Lavillaureix J. Elimination biliaire de la métampicilline. Etude expérimentale et clinique [Biliary elimination of metampicillin. Experimental and clinical study (author's transl)]. Pathol Biol (Paris). 1976 Jan;24(1):17-23. French. PMID: 772563.