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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 12 / 12
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Sagamicin

Approved Use

Ocular infection
Curative
Micronomicin sulfate

Approved Use

Sepsis, bronchitis, bronchiectasis(in infection), pneumonia, peritonitis, pyelonephritis, cystitis

Launch Date

2001
Curative
Micronomicin sulfate

Approved Use

Sepsis, bronchitis, bronchiectasis(in infection), pneumonia, peritonitis, pyelonephritis, cystitis

Launch Date

2001
Curative
Micronomicin sulfate

Approved Use

Sepsis, bronchitis, bronchiectasis(in infection), pneumonia, peritonitis, pyelonephritis, cystitis

Launch Date

2001
PubMed

PubMed

TitleDatePubMed
[Review [new antibiotics series III]: micronomicin (author's transl)].
1982 Mar
In vitro activity of sagamicin against ocular bacterial isolates.
2002 Mar-Apr
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Could also be administered i.m.: Single- and multiple-dose pharmacokinetics have been investigated in patients affected by bronchopulmonary infections treated with 60 mg sagamicin i.m. every 12 h. https://www.ncbi.nlm.nih.gov/pubmed/3568801 I.V route is possible: IM or IV 120mg twice daily for adult pyelonephritis and cystitis 60mg 2-3 times daily for other infections http://eng.yuhan.co.kr/OVERSEAS/Products/Finished/?cid=516&Category=530
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
Sagamicin was highly effective against enterobacteriaceae with a MIC(90) of 2 mg/l.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:19:47 GMT 2023
Edited
by admin
on Fri Dec 15 17:19:47 GMT 2023
Record UNII
S9AZ0R40QV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MICRONOMICIN
INN   MI   WHO-DD  
INN  
Official Name English
Micronomicin [WHO-DD]
Common Name English
6'-N-METHYLGENTAMICIN C1A
Common Name English
micronomicin [INN]
Common Name English
MICRONOMICIN [MI]
Common Name English
O-2-AMINO-2,3,4,6-TETRADEOXY-6-(METHYLAMINO)-A-D-ERYTHRO-HEXOPYRANOSYL-(1->4)-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL-(1->6))-2-DEOXY-D-STREPTAMINE
Common Name English
GENTAMICIN C2B
Common Name English
O-2-AMINO-2,3,4,6-TETRADEOXY-6-(METHYLAMINO)-.ALPHA.-D-ERYTHRO-HEXOPYRANOSYL-(1->4)-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL-(1->6)-2-DEOXY-D-STREPTAMINE
Common Name English
Classification Tree Code System Code
WHO-VATC QS01AA22
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
WHO-ATC S01AA22
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
NCI_THESAURUS C2363
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
Code System Code Type Description
SMS_ID
100000080604
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
DRUG BANK
DB13274
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
CAS
52093-21-7
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
MERCK INDEX
m7530
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY Merck Index
PUBCHEM
3037206
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
NCI_THESAURUS
C90638
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
RXCUI
29996
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY RxNorm
INN
5036
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
ChEMBL
CHEMBL373081
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
DRUG CENTRAL
1801
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID401023736
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
MESH
C037545
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
WIKIPEDIA
MICRONOMICIN
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
FDA UNII
S9AZ0R40QV
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
EVMPD
SUB08945MIG
Created by admin on Fri Dec 15 17:19:47 GMT 2023 , Edited by admin on Fri Dec 15 17:19:47 GMT 2023
PRIMARY
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