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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H41N5O7
Molecular Weight 475.5795
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NETILMICIN

SMILES

[H][C@]3(O[C@@H]1[C@@H](N)C[C@@H](NCC)[C@H](O[C@@]2([H])OC[C@](C)(O)[C@H](NC)[C@H]2O)[C@H]1O)OC(CN)=CC[C@H]3N

InChI

InChIKey=CIDUJQMULVCIBT-MQDUPKMGSA-N
InChI=1S/C21H41N5O7/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3/t11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20(General%20Monographs-%20N)/NETROMYCIN.html

Netilmicin is a semisynthetic, water soluble antibiotic of the aminoglycoside group, produced by the fermentation of Micromonospora inyoensis, a species of actinomycete. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. It is active at low concentrations against a wide variety of pathogenic bacteria including Escherichia coli, bacteria of the Klebsiella-Enterobacter-Serratia group, Citrobacter sp., Proteus sp. (indole-positive and indole-negative), including Proteus mirabilis, P. morganii, P. rettgrei, P. vulgaris, Pseudomonas aeruginosa and Neisseria gonorrhoea. Netilmicin is also active in vitro against isolates of Hemophilus influenzae, Salmonella sp., Shigella sp. and against penicillinase and non-penicillinase-producing Staphylococcus including methicillin-resistant strains. Some strains of Providencia sp., Acinetobacter sp. and Aeromonas sp. are also sensitive to netilmicin. Many strains of the above organisms which are found to be resistant to other aminoglycosides, such as kanamycin, gentamicin, tobramycin and sisomicin, are susceptible to netilmicin in vitro. Occasionally, strains have been identified which are resistant to amikacin but susceptible to netilmicin. The combination of netilmicin and penicillin G has a synergistic bactericidal effect against most strains of Streptococcus faecalis (enterococcus). The combined effect of netilmicin and carbenicillin or ticarcillin is synergistic for many strains of Pseudomonas aeruginosa. In addition, many isolates of Serratia, which are resistant to multiple antibiotics, are inhibited by synergistic combinations of netilmicin with carbenicillin, azlocillin, mezlocillin, cefamandole, cefotaxime or moxalactam. Netilmicin "irreversibly" binds to specific 30S-subunit proteins and 16S rRNA. Specifically netilmicin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes, leaving the bacterium unable to synthesize proteins vital to its growth.

Originator

Curator's Comment: No longer available in the U.S. http://www.hopkinsguides.com/hopkins/view/Johns_Hopkins_ABX_Guide/540382/all/Netilmicin

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Ornithine decarboxylase (guinea pig)
1.7 mM [Ki]
0.11565 mM [IC50]
Target ID: 16S rRNA
Target ID: HIV-1 replication
23.1 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
NETROMYCIN

Approved Use

In the US, Netilmicin is a member of the drug class aminoglycosides and is used to treat Bacterial Infection and Urinary Tract Infection.

Launch Date

4.1523839E11
Curative
Unknown

Approved Use

Unknown
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
76.9 mg × h/L
4.5 mg/kg single, intravenous
dose: 4.5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
NETILMICIN serum
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.1 h
4.5 mg/kg single, intravenous
dose: 4.5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
NETILMICIN serum
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
6 mg/kg 1 times / day steady, intravenous
Studied dose
Dose: 6 mg/kg, 1 times / day
Route: intravenous
Route: steady
Dose: 6 mg/kg, 1 times / day
Sources:
unhealthy, 26-42 weeks
n = 21
Health Status: unhealthy
Age Group: 26-42 weeks
Sex: M+F
Population Size: 21
Sources:
1.5 mg/kg 3 times / day steady, intravenous|intramuscular
Studied dose
Dose: 1.5 mg/kg, 3 times / day
Route: intravenous|intramuscular
Route: steady
Dose: 1.5 mg/kg, 3 times / day
Sources:
unhealthy, 36.8 years (range: 14-79 years)
n = 55
Health Status: unhealthy
Condition: appendicitis | other intra-abdominal infections
Age Group: 36.8 years (range: 14-79 years)
Sex: M+F
Population Size: 55
Sources:
Other AEs: Pain...
Other AEs:
Pain (mild)
Sources:
4.5 mg/kg 1 times / day steady, intravenous|intramuscular
Studied dose
Dose: 4.5 mg/kg, 1 times / day
Route: intravenous|intramuscular
Route: steady
Dose: 4.5 mg/kg, 1 times / day
Sources:
unhealthy, 40.3 years (range: 18-80 years)
n = 57
Health Status: unhealthy
Condition: appendicitis | other intra-abdominal infections
Age Group: 40.3 years (range: 18-80 years)
Sex: M+F
Population Size: 57
Sources:
Other AEs: Pain...
Other AEs:
Pain (mild)
Sources:
2.5 mg/kg 3 times / day steady, intramuscular
Studied dose
Dose: 2.5 mg/kg, 3 times / day
Route: intramuscular
Route: steady
Dose: 2.5 mg/kg, 3 times / day
Sources:
unhealthy, old
Health Status: unhealthy
Age Group: old
Sex: M
Sources:
3.6 mg/kg 3 times / day steady, intramuscular
Highest studied dose
Dose: 3.6 mg/kg, 3 times / day
Route: intramuscular
Route: steady
Dose: 3.6 mg/kg, 3 times / day
Sources:
unhealthy
n = 16
Health Status: unhealthy
Condition: chronic or recurrent urinary tract infections
Population Size: 16
Sources:
AEs

AEs

AESignificanceDosePopulation
Pain mild
1.5 mg/kg 3 times / day steady, intravenous|intramuscular
Studied dose
Dose: 1.5 mg/kg, 3 times / day
Route: intravenous|intramuscular
Route: steady
Dose: 1.5 mg/kg, 3 times / day
Sources:
unhealthy, 36.8 years (range: 14-79 years)
n = 55
Health Status: unhealthy
Condition: appendicitis | other intra-abdominal infections
Age Group: 36.8 years (range: 14-79 years)
Sex: M+F
Population Size: 55
Sources:
Pain mild
4.5 mg/kg 1 times / day steady, intravenous|intramuscular
Studied dose
Dose: 4.5 mg/kg, 1 times / day
Route: intravenous|intramuscular
Route: steady
Dose: 4.5 mg/kg, 1 times / day
Sources:
unhealthy, 40.3 years (range: 18-80 years)
n = 57
Health Status: unhealthy
Condition: appendicitis | other intra-abdominal infections
Age Group: 40.3 years (range: 18-80 years)
Sex: M+F
Population Size: 57
Sources:
PubMed

PubMed

TitleDatePubMed
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.
1987 Oct
In-vitro activity of seventeen antimicrobial compounds against seven species of mycobacteria.
1988 Dec
Discovery of selective bioactive small molecules by targeting an RNA dynamic ensemble.
2011 Jun 26
Patents

Patents

Sample Use Guides

Adult: 4-6 mg/kg once daily or in equally divided doses given every 8 or 12 hours. Life-threatening infections: Increase to up to 7.5 mg/kg daily every 8 hours. Treatment is usually given for 7-14 days. Child: Premature infants and neonates <1 week: 6 mg/kg daily in divided doses every 12 hours. Infants and neonates >1 week: 7.5-9 mg/kg daily in divided doses every 8 hours. Older children: 6-7.5 mg/kg daily in divided doses every 8 hours. Alternative regimen: Neonates <6 weeks: 4-6.5 mg/kg daily in divided doses every 12 hours. Older infants and children: 5.5-8 mg/kg daily in divided doses every 8 or 12 hours.
Route of Administration: Other
In Vitro Use Guide
Curator's Comment: In Ca2+- and Mg2+-adjusted broth, the netilmicin MIC for gentamicin-susceptible P. aeruginosa was 9.6 ug/ml, and for gentamicin-resistant strains it was 23.1 ug/ml, an 18-fold increase.
MIC (Minimum inhibitory concentration) of netilmicin against P. aeruginosa in unadjusted broth was 0.73 ug/ml for gentamicin-susceptible strains and 1.35 ug/ml for gentamicin-resistant strains
Name Type Language
NETILMICIN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
netilmicin [INN]
Common Name English
NETILMICIN [HSDB]
Common Name English
NETILMICIN [VANDF]
Common Name English
Netilmicin [WHO-DD]
Common Name English
NETIRA
Brand Name English
O-3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL-(1->4)-O-(2,6-DIAMINO-2,3,4,6-TETRADEOXY-.ALPHA.-D-GLYCERO-HEX-4-ENOPYRANOSYL-(1->6))-2-DEOXY-N(SUP 3)-ETHYL-L-STREPTAMINE
Common Name English
NETILMICIN [MI]
Common Name English
NSC-759586
Code English
D-STREPTAMINE, O-3-DEOXY-4-C-METHYL-3-(METHYLAMINO)- .BETA.-L-ARABINOPYRANOSYL-(1->6)-O-(2,6-DIAMINO-2,3,4,6-TETRADEOXY-.ALPHA.-D-GLYCERO-HEX-4-ENOPYRANOSYL-(1->4))-2-DEOXY-N(SUP 1)-ETHYL-
Common Name English
Classification Tree Code System Code
WHO-ATC S01AA23
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
NDF-RT N0000175477
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
WHO-ATC J01GB07
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
NDF-RT N0000007853
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
WHO-VATC QJ01GB07
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
NCI_THESAURUS C2363
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
WHO-VATC QS01AA23
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
Code System Code Type Description
WIKIPEDIA
Netilmicin
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
DRUG CENTRAL
1903
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
FDA UNII
4O5J85GJJB
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
HSDB
3584
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
ChEMBL
CHEMBL1572
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
DRUG BANK
DB00955
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
CAS
56391-56-1
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
SMS_ID
100000084160
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
MESH
D009428
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
INN
4093
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
PUBCHEM
441306
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
CHEBI
7528
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
RXCUI
7337
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID1048542
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
MERCK INDEX
M7834
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
260-146-8
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
NSC
759586
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
EVMPD
SUB09210MIG
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY
NCI_THESAURUS
C66236
Created by admin on Wed Jul 05 22:47:52 UTC 2023 , Edited by admin on Wed Jul 05 22:47:52 UTC 2023
PRIMARY