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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H41N5O7
Molecular Weight 463.5688
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MICRONOMICIN

SMILES

CNC[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1

InChI

InChIKey=DNYGXMICFMACRA-XHEDQWPISA-N
InChI=1S/C20H41N5O7/c1-20(28)8-29-19(14(27)17(20)25-3)32-16-12(23)6-11(22)15(13(16)26)31-18-10(21)5-4-9(30-18)7-24-2/h9-19,24-28H,4-8,21-23H2,1-3H3/t9-,10+,11-,12+,13-,14+,15+,16-,17+,18+,19+,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H41N5O7
Molecular Weight 463.5688
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 12 / 12
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Micronomicin is a new aminoglycosidic antibiotic discovered and developed by Kyowa Hakko Kogyo Co., Ltd. It is produced by Micromonospora sagamiensis var. nonreducans. Investigation of micronomicin performed in 134 research facilities in Japan led to the following results. 1) Micronomicin showed a broad antibacterial spectrum against Gram positive and Gram negative bacteria. 2) In susceptibility tests of clinical isolates, micronomicin was almost similarly active to GM. 3) Bactericidal activity of micronomicin against Pseudomonas aeruginosa and E. coli was higher than those of TOB and DKB. 4) Micronomicin showed a synergistic antibacterial activity against Pseudomonas aeruginosa and E. coli with CBPC and SBPC. 5) The therapeutic activity of micronomicin in mice infected with Pseudomonas aeruginosa and Serratia sp. was in high correlation with in vitro antibacterial activity similarly to that of GM. Micronomicin (sold under the brand names Sagamicin and Luxomicina among others) is an aminoglycoside antibiotic, and like others in its class, binds to the ribosomes of non-resistant cells causing mistranscription of mRNA which fatally inhibits production of essential proteins. Micronomicin sulfate can inhibit bacterial protein synthesis, while destroy the bacterial cell wall. Micronomicin has an antibacterial activity against gram-negative and gram-positive bacteria such as Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa, Shara, Escherichia coli, etc. Streptococcus pneumoniae and Pneumococcus are sensitive to it, but its activity on anaerobic bacteria and some hemolytic streptococcus is weak.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Sagamicin
Curative
Micronomicin sulfate
Curative
Micronomicin sulfate
Curative
Micronomicin sulfate

PubMed

Sample Use Guides

In Vivo Use Guide
Instillation of a drop or two drops, 3-8 times per day on average, in the cul-de-sac of the lower conjunctival eye to Treat. In the initial treatment of more serious infections, the dose may be increased, the product can be instilled every hour during the first days under medical supervision.
Route of Administration: Topical
In Vitro Use Guide
Sagamicin was highly effective against enterobacteriaceae with a MIC(90) of 2 mg/l.
Substance Class Chemical
Record UNII
S9AZ0R40QV
Record Status Validated (UNII)
Record Version