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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C20H41N5O7.5H2O4S
Molecular Weight 1417.53
Optical Activity UNSPECIFIED
Defined Stereocenters 24 / 24
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MICRONOMICIN SULFATE

SMILES

OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.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.CNC[C@@H]4CC[C@@H](N)[C@@H](O[C@@H]5[C@@H](N)C[C@@H](N)[C@H](O[C@H]6OC[C@](C)(O)[C@H](NC)[C@H]6O)[C@H]5O)O4

InChI

InChIKey=KUIYUSGPDNRECG-OSPBMVHQSA-N
InChI=1S/2C20H41N5O7.5H2O4S/c2*1-20(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;5*1-5(2,3)4/h2*9-19,24-28H,4-8,21-23H2,1-3H3;5*(H2,1,2,3,4)/t2*9-,10+,11-,12+,13-,14+,15+,16-,17+,18+,19+,20-;;;;;/m00...../s1

HIDE SMILES / InChI

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 Sat Dec 16 07:15:21 GMT 2023
Edited
by admin
on Sat Dec 16 07:15:21 GMT 2023
Record UNII
09H5UKQ7TZ
Record Status Validated (UNII)
Record Version
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Name Type Language
MICRONOMICIN SULFATE
EP   JAN   MI   WHO-DD  
Common Name English
MICRONOMICIN SULFATE [EP IMPURITY]
Common Name English
Micronomicin sulfate [WHO-DD]
Common Name English
SANTEMYCIN
Brand Name English
MICRONOMICIN HEMIPENTASULFATE
Common Name English
6'-N-METHYLGENTAMICIN C1A HEMIPENTASULFATE
Common Name English
MICRONOMICIN SULFATE [JAN]
Common Name English
D-STREPTAMINE, 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-, SULFATE (SALT)
Common Name English
MICRONOMICIN SULFATE [MI]
Common Name English
VB11MZ2BJP
Common Name English
GENTAMICIN C2B SULFATE
Common Name English
SAGAMICIN
Brand Name English
D-STREPTAMINE, 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-, SULFATE
Common Name English
Code System Code Type Description
RXCUI
236199
Created by admin on Sat Dec 16 07:15:21 GMT 2023 , Edited by admin on Sat Dec 16 07:15:21 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL373081
Created by admin on Sat Dec 16 07:15:21 GMT 2023 , Edited by admin on Sat Dec 16 07:15:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID3048609
Created by admin on Sat Dec 16 07:15:21 GMT 2023 , Edited by admin on Sat Dec 16 07:15:21 GMT 2023
PRIMARY
SMS_ID
100000085961
Created by admin on Sat Dec 16 07:15:21 GMT 2023 , Edited by admin on Sat Dec 16 07:15:21 GMT 2023
PRIMARY
CAS
66803-19-8
Created by admin on Sat Dec 16 07:15:21 GMT 2023 , Edited by admin on Sat Dec 16 07:15:21 GMT 2023
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
9963894
Created by admin on Sat Dec 16 07:15:21 GMT 2023 , Edited by admin on Sat Dec 16 07:15:21 GMT 2023
PRIMARY
FDA UNII
09H5UKQ7TZ
Created by admin on Sat Dec 16 07:15:21 GMT 2023 , Edited by admin on Sat Dec 16 07:15:21 GMT 2023
PRIMARY
MERCK INDEX
m7530
Created by admin on Sat Dec 16 07:15:21 GMT 2023 , Edited by admin on Sat Dec 16 07:15:21 GMT 2023
PRIMARY Merck Index
EVMPD
SUB03286MIG
Created by admin on Sat Dec 16 07:15:21 GMT 2023 , Edited by admin on Sat Dec 16 07:15:21 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY