U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of MIDECAMYCIN ACETATE

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

HIDE SMILES / InChI

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Streptococcus pneumoniae growth
Target ID: Streptococcus pyogenes growth
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MIOCAMEN

Approved Use

Infections 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.
Curative
MIOCAMEN

Approved Use

Infections 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.
Curative
MIOCAMEN

Approved Use

Infections 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

PubMed

TitleDatePubMed
In vitro killing kinetics and postantibiotic effect of josamycin and other macrolides on several bacteria.
1993 May-Jun
[Resistance to macrolide antibiotics found in methicillin-resistant Japanese clinical isolates of Staphylococcus aureus in 1996].
1998 Jul
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
MIDECAMYCIN ACETATE inhibited Chlamydia pneumoniae in cell culture with MIC 0.5 mg/l
Name Type Language
MIDECAMYCIN ACETATE
WHO-DD  
Common Name English
LEUCOMYCIN V, 3B,9-DIACETATE 3,4B-DIPROPANOATE
Common Name English
MIDECAMYCIN ACETATE [JAN]
Common Name English
ACECAMYCIN
Common Name English
MIOCAMYCIN [MI]
Common Name English
MOM
Common Name English
9,3''-DI-O-ACETYLMIDECAMYCIN
Common Name English
3'',9-DIACETYLMYDECAMYCIN
Common Name English
MIDECAMYCIN DIACETATE
Common Name English
MIOCAMYCIN
MI  
Brand Name English
PONSINOMYCIN
Common Name English
Midecamycin acetate [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01FA11
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WHO-ATC J01FA11
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Code System Code Type Description
EPA CompTox
DTXSID60905087
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PRIMARY
SMS_ID
100000088900
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FDA UNII
3T48CPS7U2
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PRIMARY
DRUG BANK
DB13287
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PRIMARY
ChEMBL
CHEMBL1908336
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PRIMARY
DRUG CENTRAL
1815
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PRIMARY
ChEMBL
CHEMBL1091024
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PRIMARY
RXCUI
236200
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PUBCHEM
5282188
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PRIMARY
CAS
55881-07-7
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PRIMARY
MESH
D015644
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WIKIPEDIA
MIOCAMYCIN
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PRIMARY
EVMPD
SUB21789
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PRIMARY
RXCUI
6985
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ALTERNATIVE