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

Details

Stereochemistry ABSOLUTE
Molecular Formula C41H67NO15
Molecular Weight 813.9684
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIDECAMYCIN

SMILES

[H][C@@]1(C[C@@](C)(O)[C@@H](OC(=O)CC)[C@H](C)O1)O[C@@H]2[C@@H](C)O[C@@]([H])(O[C@H]3[C@@H](CC=O)C[C@@H](C)[C@@H](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=DMUAPQTXSSNEDD-QALJCMCCSA-N
InChI=1S/C41H67NO15/c1-11-30(45)54-29-21-32(47)51-24(4)16-14-13-15-17-28(44)23(3)20-27(18-19-43)37(38(29)50-10)57-40-35(48)34(42(8)9)36(25(5)53-40)56-33-22-41(7,49)39(26(6)52-33)55-31(46)12-2/h13-15,17,19,23-29,33-40,44,48-49H,11-12,16,18,20-22H2,1-10H3/b14-13+,17-15+/t23-,24-,25-,26+,27+,28+,29-,33+,34-,35-,36-,37+,38+,39+,40+,41-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.antibiotic.ru/cmac/pdf/9_1_066.pdf

Midecamycin (Acetate) is a macrolide antibiotic with actions and uses similar to those of erythromycin but somewhat less active. It is synthesized from Streptomyces mycarofaciens. It has been given by mouth to treat variety of bacterial infections like respiratory tract, ear, skin infections etc. Antibiotics require constant drug level in body for therapeutic effect. This is achieved by taking the drug at regular interval of time throughout the day and night as prescribed. Midecamycin (Acetate) is primarily indicated in conditions like Bronchitis, Laryngopharyngitis, Otitis media, Periodontitis, Pneumonia, Respiratory tract infections, Skin infections, Subcutaneous abscess, Tonsillitis. Midecamycin inhibits bacterial growth by targeting the 50S ribosomal subunit preventing peptide bond formation and translocation during protein synthesis. Resistance to midecamycin is commonly attributed to mutations in 50S rRNA preventing midecamycin binding allowing the cell to synthesize proteins free of error.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: map03010
Target ID: Streptococcus pneumoniae growth
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Macropen

Approved Use

Macropen used to treat infectious and inflammatory diseases caused by susceptible microorganisms midecamycin: Infections of the genitourinary system caused by Chlamydia spp., Mycoplasma spp., Ureaplasma urealyticum, and Legionella spp.; Respiratory tract infections (including those caused by atypical pathogens Chlamydia spp, Mycoplasma spp, Ureaplasma urealyticum, and Legionella spp..): sinusitis, acute otitis media, community-acquired pneumonia, tonzillofaringit, exacerbation of chronic bronchitis; Infections of the skin and subcutaneous tissue; Enteritis caused by Campylobacter spp. Furthermore, the drug is used for treatment and prevention of pertussis and diphtheria.
Curative
Macropen

Approved Use

Macropen used to treat infectious and inflammatory diseases caused by susceptible microorganisms midecamycin: Infections of the genitourinary system caused by Chlamydia spp., Mycoplasma spp., Ureaplasma urealyticum, and Legionella spp.; Respiratory tract infections (including those caused by atypical pathogens Chlamydia spp, Mycoplasma spp, Ureaplasma urealyticum, and Legionella spp..): sinusitis, acute otitis media, community-acquired pneumonia, tonzillofaringit, exacerbation of chronic bronchitis; Infections of the skin and subcutaneous tissue; Enteritis caused by Campylobacter spp. Furthermore, the drug is used for treatment and prevention of pertussis and diphtheria.
Curative
Midecamycin Meiji

Approved Use

Resp tract, skin & soft tissue infections, UTI.

Launch Date

9.4607999E10
Curative
Midecamycin Meiji

Approved Use

Resp tract, skin & soft tissue infections, UTI.

Launch Date

9.4607999E10
PubMed

PubMed

TitleDatePubMed
Potential cholestatic activity of various therapeutic agents assessed by bile canalicular membrane vesicles isolated from rats and humans.
2003
Patents

Sample Use Guides

Adult 800-1200 mg. Children 600 mg daily. To be taken daily in 3-4 divided doses.
Route of Administration: Oral
In Vitro Use Guide
Midecamycin (10 uM) reduced Ca2+ uptake by rabbit terminal cisternae vesicles to approximately 76% without Ruthenium Red and to approximately 90 % with Ruthenium Red.
Name Type Language
MIDECAMYCIN
INN   MART.   WHO-DD  
INN  
Official Name English
MIDECAMYCIN A1
MI  
Common Name English
MEDECAMYCIN A1
Common Name English
NORMICINA
Common Name English
MEDEMYCIN
Common Name English
MIDECAMYCIN A1 [MI]
Common Name English
midecamycin [INN]
Common Name English
Midecamycin [WHO-DD]
Common Name English
SF-837
Code English
SF-837A1
Code English
MOMICINE
Brand Name English
MYDECAMYCIN A1
Common Name English
ABOREN
Brand Name English
YL-704B1
Code English
PLATENOMYCIN B1
Common Name English
MYDECAMYCIN
Common Name English
MIDECAMYCIN [JAN]
Common Name English
MIDECIN
Brand Name English
TURIMYCIN P3
Common Name English
NSC-154011
Code English
MEDEMYCIN A1
Common Name English
RUBIMYCIN
Common Name English
MACROPEN
Common Name English
LEUCOMYCIN V, 3,4B-DIPROPANOATE
Common Name English
ESPINOMYCIN A
Common Name English
MIDECAMYCIN [MART.]
Common Name English
MYOXAM
Brand Name English
Classification Tree Code System Code
WHO-ATC J01FA03
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
WHO-VATC QJ01FA03
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
Code System Code Type Description
PUBCHEM
5282169
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
DRUG CENTRAL
1861
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
WIKIPEDIA
MIDECAMYCIN
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
MERCK INDEX
m7532
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB13456
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
SMS_ID
100000080607
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
INN
3461
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
NSC
154011
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
RXCUI
30005
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C174736
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
MESH
C026483
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
ChEMBL
CHEMBL1908336
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
FDA UNII
N34Z0Y5UH7
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
ECHA (EC/EINECS)
252-578-0
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
EVMPD
SUB08951MIG
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
CAS
35457-80-8
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID5045463
Created by admin on Fri Dec 15 18:56:49 UTC 2023 , Edited by admin on Fri Dec 15 18:56:49 UTC 2023
PRIMARY