Maduramicin Ammonium
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| Category | Antibiotics |
| Catalog number | BBF-04627 |
| CAS | 84878-61-5 |
| Molecular Weight | 934.16 |
| Molecular Formula | C47H83O17N |
| Purity | >95% |
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Description
Maduramcin ammonium is prepared from maduramicin by taking advantage of the acidic carboxylic acid which ionises and readily forms the salt in ammonium hydroxide solutions. The ammonium salt is the preferred formulation in animals to prevent coccidiosis. It is a polyether antibiotic chemically related to the Lonomycins.
Specification
| Related CAS | 79356-08-4 (free base) |
| Synonyms | Cygro; Maduramicin α, Monoammonium Salt; Prinicin Ammonium; CL 259971; Lonomycin A, 23,27-didemethoxy-2,6,22-tridemethyl-11-O-demethyl-22-((2,6-dideoxy-3,4-di-O-methyl-beta-L-arabino-hexopyranosyl)oxy)-6-methoxy-, monoammonium salt, (3R,4S,5S,6R,7S,22S)- |
| Storage | Store at 2-8°C |
| IUPAC Name | azane;2-[(2R,3S,4S,5R,6S)-6-[(1R)-1-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-[(2R,3S,5R)-3-[(2R,4S,5S,6S)-4,5-dimethoxy-6-methyloxan-2-yl]oxy-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]-5-methyloxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-2-hydroxy-4,5-dimethoxy-3-methyloxan-2-yl]acetic acid |
| Canonical SMILES | CC1CC(C(OC1C2CC(C(O2)C3(CCC(O3)C4(CCC5(O4)CC(C(C(O5)C(C)C6C(C(C(C(O6)(CC(=O)O)O)C)OC)OC)C)O)C)C)OC7CC(C(C(O7)C)OC)OC)(C)O)C.N |
| InChI | InChI=1S/C47H80O17.H3N/c1-23-18-24(2)45(9,51)61-36(23)31-19-32(58-35-20-30(53-10)40(55-12)28(6)57-35)42(59-31)44(8)15-14-33(60-44)43(7)16-17-46(64-43)21-29(48)25(3)37(62-46)26(4)38-41(56-13)39(54-11)27(5)47(52,63-38)22-34(49)50;/h23-33,35-42,48,51-52H,14-22H2,1-13H3,(H,49,50);1H3/t23-,24+,25+,26+,27-,28-,29-,30-,31+,32-,33+,35+,36-,37-,38-,39-,40-,41-,42+,43-,44-,45-,46+,47+;/m0./s1 |
| InChI Key | WQGJEAMPBSZCIF-HKSLRPGUSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Solid |
| Application | Anti-Bacterial Agents |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 913.9°C at 760 mmHg |
| Melting Point | 173-176°C |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO, Chloroform |
Reference Reading
1. Efficacy of maduramicin against turkey coccidiosis in battery: a clinical and pathological study
M Castagnaro, A Agostini, S Cerruti Sola, A Leoni Schweiz Arch Tierheilkd . 1996;138(4):201-6.
Two groups of 24 three-day-old turkeys each were inoculated with Eimeria meleagrimitis sporulated oocytes and fed a diet containing respectively 5 and 6 ppm of maduramicin ammonium. Clinical signs, mortality rates, weight gain, intestinal lesions and replication of the parasite were compared to the data obtained from a group of infected, untreated birds kept in the same experimental conditions over a period of 17 days. The treated birds showed better performances and less severe intestinal damages; the replication and the development of the parasite in the intestinal mucosa were impaired and delayed by the drug. All the data were dose dependent.
2. Assessment of the feed additive consisting of Enterococcus faecium DSM 7134 (Bonvital®) for chickens for fattening for the renewal of its authorisation (Lactosan GmbH & Co. KG)
Mojca Fašmon Durjava, Secundino López Puente, Roberto Edoardo Villa, Matteo Innocenti, Fernando Ramos, Ruud Woutersen, Francesca Marcon, Maria de Lourdes Bastos, Vasileios Bampidis, Marta López-Alonso, Pier Sandro Cocconcelli, Maria Saarela, Maryline Kouba, Henrik Christensen, Maria Vittoria Vettori, Rosella Brozzi, Alena Pechová, Yolanda Sanz, Miguel Prieto Maradona, Mariana Petkova, Baltasar Mayo, EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP), Jaume Galobart, Lucilla Gregoretti, Birgit Dusemund, Boet Glandorf, Giovanna Azimonti, Gloria López-Gálvez EFSA J . 2021 Mar 8;19(3):e06451. doi: 10.2903/j.efsa.2021.6451.
Following a request from the European Commission, the Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) was asked to deliver a scientific opinion on the assessment of the application for renewal of authorisation of the additive consisting ofEnterococcus faeciumDSM 7134 (trade name: Bonvital®) as a zootechnical additive (gut flora stabiliser) for chickens for fattening. The additive is produced in powder and granulate (microencapsulated) forms. The applicant has provided data demonstrating that the additive currently in the market complies with the conditions of authorisation. The FEEDAP Panel confirms that the use of Bonvital®under the current authorised conditions of use is safe for the target species, the consumers and the environment. Bonvital®is not irritant to skin and eyes but should be considered a potential skin sensitiser and a respiratory sensitiser. There is no need to assess the efficacy of Bonvital®in the context of the renewal of the authorisation. The FEEDAP Panel reiterates its previous conclusions thatE. faeciumDSM 7134 is compatible with the coccidiostats robenidine hydrochloride, maduramicin ammonium, diclazuril, decoquinate, halofuginone hydrobromide, monensin sodium and lasalocid A sodium.
3. Optimization of Maduramicin Ammonium-Loaded Nanostructured Lipid Carriers Using Box-Behnken Design for Enhanced Anticoccidial Effect against Eimeria tenella in Broiler Chickens
Shanxiang Jiang, Xia Chen, Jiahao Gong, Xiuge Gao, Fengzhu Yang, Dawei Guo, Mengjuan Lin, Yan Zhang, Xinhao Song, Xingxing Cheng, Lin Peng, Junqi Wang, Hui Ji, Runan Zuo Pharmaceutics . 2022 Jun 23;14(7):1330. doi: 10.3390/pharmaceutics14071330.
Maduramicin ammonium (MAD) is one of the most frequently used anticoccidial agents in broiler chickens. However, the high toxicity and low solubility of MAD limit its clinical application. In this study, MAD-loaded nanostructured lipid carriers (MAD-NLCs) were prepared to overcome the defects of MAD by using highly soluble nanostructured lipid carriers (NLCs). The formulation was optimized via a three-level, three-factor Box-Behnken response surface method. Then, the optimal MAD-NLCs were evaluated according to their hydrodynamic diameter (HD), zeta potential (ZP), crystal structure, encapsulation efficiency (EE), drug loading (DL), in vitro release, and anticoccidial effect. The optimal MAD-NLCs had an HD of 153.6 ± 3.044 nm and a ZP of -41.4 ± 1.10 mV. The X-ray diffraction and Fourier-transform infrared spectroscopy results indicated that the MAD was encapsulated in the NLCs in an amorphous state. The EE and DL were 90.49 ± 1.05% and 2.34 ± 0.04%, respectively, which indicated that the MAD was efficiently encapsulated in the NLCs. In the in vitro study, the MAD-NLCs demonstrated a slow and sustained drug release behavior. Notably, MAD-NLCs had an excellent anticoccidial effect againstEimeria tenellain broiler chickens. In summary, MAD-NLCs have huge potential to form a new preparation administered via drinking water with a powerful anticoccidial effect.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
