Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C45H71NO17 |
Molecular Weight | 898.0417 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 16 / 16 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC(=O)O[C@H]1[C@H](C)O[C@H](C[C@@]1(C)OC(C)=O)O[C@@H]2[C@@H](C)O[C@@H](O[C@H]3[C@@H](CC=O)C[C@@H](C)[C@@H](OC(C)=O)\C=C\C=C\C[C@@H](C)OC(=O)C[C@@H](OC(=O)CC)[C@@H]3OC)[C@H](O)[C@H]2N(C)C
InChI
InChIKey=GQNZGCARKRHPOH-RQIKCTSVSA-N
InChI=1S/C45H71NO17/c1-13-34(50)59-33-23-36(52)55-26(4)18-16-15-17-19-32(58-29(7)48)25(3)22-31(20-21-47)41(42(33)54-12)62-44-39(53)38(46(10)11)40(27(5)57-44)61-37-24-45(9,63-30(8)49)43(28(6)56-37)60-35(51)14-2/h15-17,19,21,25-28,31-33,37-44,53H,13-14,18,20,22-24H2,1-12H3/b16-15+,19-17+/t25-,26-,27-,28+,31+,32+,33-,37+,38-,39-,40-,41+,42+,43+,44+,45-/m1/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/7506653Curator's Comment: http://link.springer.com/article/10.2165/00042310-200622060-00001 and http://www.meppo.com/pdf/drugs/1129-MIOCAMEN-1331886550.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7506653
Curator's Comment: http://link.springer.com/article/10.2165/00042310-200622060-00001 and http://www.meppo.com/pdf/drugs/1129-MIOCAMEN-1331886550.pdf
Midecamycin diacetate (a derivative of Midecamycin) is reported as an ingredient of Miocamycin in Japan. Miocamycin is an orally administered 16-membered macrolide antimicrobial drug. It has a spectrum of in vitro activity similar to that of erythromycin, inhibiting a range of Gram-positive and Gram-negative organisms, atypical microbes and some anaerobes. Importantly, miocamycin demonstrates greater in vitro potency than erythromycin against several pathogens including Legionella pneumophila, Mycoplasma hominis, and Ureaplasma urealyticum. Equally noteworthy is its activity against erythromycin-resistant staphylococcal and streptococcal species expressing inducible-type resistance. Miocamycin possesses poor overall activity against Haemophilus influenzae and is inactive against Enterobacteriaceae. Penetration of miocamycin into body tissues and fluids is both rapid and extensive. The 3 major metabolites of miocamycin possess antimicrobial activity and may contribute to the therapeutic efficacy of the drug. Clinical data indicate that miocamycin is useful in the treatment of upper and lower respiratory tract infections in both adult and paediatric patients. Miocamycin is also effective in the treatment of urogenital tract infections caused by Chlamydia trachomatis or U. urealyticum. Midecamycin binds reversibly to 50S ribosomal subunit causing blockade of transpeptidation/translocation reactions, inhibition of protein synthesis and thus inhibition of cell growth. Midecamycin diacetate is also known as MIOCAMEN, Merced Box of 8 sachets (900mg), Mosil, Myoxam.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Streptococcus pneumoniae growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/17405779 |
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Target ID: Streptococcus pyogenes growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/17405779 |
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Target ID: map03010 Sources: http://www.genome.jp/dbget-bin/www_bget?D01636 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | MIOCAMEN Approved UseInfections in adults and children caused by sensitive germs to midecamycin diacetate; bronchitis;
pneumonia; tonsillitis; pharyngitis; rhinopharyngitis; sinusitis; otitis; otitis media; scarlet fever; pimples;
pyodermitis; abscesses; phlegmons. It is also active in odontostomatological, urogenital infections and infections of the bile-duct from sensitive germs. It may also be administered to subjects who are allergic to penicillin. |
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Curative | MIOCAMEN Approved UseInfections in adults and children caused by sensitive germs to midecamycin diacetate; bronchitis;
pneumonia; tonsillitis; pharyngitis; rhinopharyngitis; sinusitis; otitis; otitis media; scarlet fever; pimples;
pyodermitis; abscesses; phlegmons. It is also active in odontostomatological, urogenital infections and infections of the bile-duct from sensitive germs. It may also be administered to subjects who are allergic to penicillin. |
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Curative | MIOCAMEN Approved UseInfections in adults and children caused by sensitive germs to midecamycin diacetate; bronchitis;
pneumonia; tonsillitis; pharyngitis; rhinopharyngitis; sinusitis; otitis; otitis media; scarlet fever; pimples;
pyodermitis; abscesses; phlegmons. It is also active in odontostomatological, urogenital infections and infections of the bile-duct from sensitive germs. It may also be administered to subjects who are allergic to penicillin. |
PubMed
Title | Date | PubMed |
---|---|---|
In vitro killing kinetics and postantibiotic effect of josamycin and other macrolides on several bacteria. | 1993 May-Jun |
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[Resistance to macrolide antibiotics found in methicillin-resistant Japanese clinical isolates of Staphylococcus aureus in 1996]. | 1998 Jul |
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Activities of 16-membered ring macrolides and telithromycin against different genotypes of erythromycin-susceptible and erythromycin-resistant Streptococcus pyogenes and Streptococcus pneumoniae. | 2007 Jun |
Patents
Sample Use Guides
Adults: 1200 to 1800mg daily, divided into 2-3
administrations.
Tablets: 2-3 tablets of 600mg daily.
Sachets: 1 sachet of 900mg every 12 hours.
Children: 50mg/kg/day, divided into 2-3 administrations,
according to the physician’s advice. The measuring
cap is graduated 1 to 10ml. Each ml contains
50mg of midecamycin diacetate.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1827101
MIDECAMYCIN ACETATE inhibited Chlamydia pneumoniae in cell culture with MIC 0.5 mg/l
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WHO-VATC |
QJ01FA11
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WHO-ATC |
J01FA11
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MIOCAMYCIN
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ALTERNATIVE |
SUBSTANCE RECORD