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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

Molecular Formula C45H71NO17
Molecular Weight 898.0417
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 16 / 16
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MIOCAMEN
Curative
MIOCAMEN
Curative
MIOCAMEN

PubMed

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Record UNII
3T48CPS7U2
Record Status Validated (UNII)
Record Version