Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H37N5O7 |
Molecular Weight | 447.5264 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]3(O[C@@H]1[C@@H](N)C[C@@H](N)[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=URWAJWIAIPFPJE-YFMIWBNJSA-N
InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1
Molecular Formula | C19H37N5O7 |
Molecular Weight | 447.5264 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/6994206Curator's Comment: description was created based on several sources, including
http://www.drugsupdate.com/generic/view/479/Sisomicin
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6994206
Curator's Comment: description was created based on several sources, including
http://www.drugsupdate.com/generic/view/479/Sisomicin
Sisomicin is a new broad-spectrum aminoglycoside most closely related structurally to gentamicin C1a. In vitro and in experimental infections, sisomicin has been found to be more potent than or nearly as potent as the most active of the other available aminoglycosides. Although susceptible to many (but not all) aminoglycoside-inactivating enzymes, sisomicin is active against many microorganisms that are resistant to other aminoglycosides by nonenzymatic mechanisms. Sisomicin has been shown to interact synergistically with various beta-lactam antibiotics against enterococci, staphylocicci, Enterobacteriaceae, and nonfermentative gram-negative bacilli. The pharmacokinetics and toxicity of sisomicin in humans appear to be similar to those of gentamicin, despite earlier reports of greater acute toxicity in animals. Sisomicin binds to 30s and 50s ribosomal subunits of susceptible bacteria disrupting protein synthesis, thus rendering the bacterial cell membrane defective.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363135 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Ensamycin Cream Approved UseEnsamycin Cream is used in the treatment, control, prevention, and improvement of the following diseases, conditions and symptoms: • Chest infections; • Bacterial infection |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.15 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
50 mg single, intramuscular dose: 50 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
11.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
17.76 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
21.52 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.98 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
25 mg single, intramuscular dose: 25 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.39 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
50 mg single, intramuscular dose: 50 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.68 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.44 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.89 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
25 mg single, intramuscular dose: 25 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7334458 |
25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SISOMICIN serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
Title | Date | PubMed |
---|---|---|
Hypocalcemia with hypoparathyroidism and renal tubular dysfunction associated with aminoglycoside therapy. | 1977 Apr |
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[Comparative ototoxicity of aminoglycoside antibiotics in a guinea pig model (author's transl)]. | 1978 Nov 29 |
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Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. | 1993 Sep 24 |
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A comparative clinical study of sisomicin cream versus mupirocin ointment in pyodermas. | 2002 Mar-Apr |
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[Evaluation of outcomes of combined specific prophylaxis with the antibiotic resistant immunogenic plague pathogen strain and emergency prophylaxis with aminoglycosides in the experimental plague model in white mice]. | 2003 |
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Role of the acetyltransferase AAC(6')-Iz modifying enzyme in aminoglycoside resistance in Stenotrophomonas maltophilia. | 2003 Apr |
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Novel antibiotic-resistance markers in pGK12-derived vectors for Borrelia burgdorferi. | 2003 Jan 16 |
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A new micellar electrokinetic capillary chromatography method for separation of the components of the aminoglycoside antibiotics. | 2003 Sep |
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Determination of tobramycin in serum using liquid chromatography-tandem mass spectrometry and comparison with a fluorescence polarisation assay. | 2003 Sep 5 |
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Acid-base versus structural properties of an aminoglycoside antibiotic--sisomicin: NMR and potentiometric approach. | 2004 Aug 1 |
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Voltage-dependent inhibition of rat skeletal muscle sodium channels by aminoglycoside antibiotics. | 2004 May |
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Evaluation of combined deactivators-supplemented agar medium (CDSAM) for recovery of dermatophytes from patients with tinea pedis. | 2007 Jun |
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Inhibition of poly(A) polymerase by aminoglycosides. | 2007 Oct |
|
Aminoglycoside resistance in members of the Staphylococcus sciuri group. | 2007 Summer |
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Improved liquid chromatographic method with pulsed electrochemical detection for the analysis of gentamicin. | 2008 May 2 |
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Evaluation of the stability of gentamicin in different antibiotic carriers using a validated MEKC method. | 2008 Nov 4 |
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Deep recurrent infection of the hip after tumoral resection in an 18-years old male--a case report. | 2008 Oct-Dec |
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Molecular cloning and sequence analysis of the sisomicin biosynthetic gene cluster from Micromonospora inyoensis. | 2009 Mar |
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[Antibiotics given subcutaneously to elderly]. | 2009 Mar |
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Inactivation of the Ecs ABC transporter of Staphylococcus aureus attenuates virulence by altering composition and function of bacterial wall. | 2010 Dec 2 |
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Immunoassays for the rapid detection of gentamicin and micronomicin in swine muscle. | 2010 Jan-Feb |
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Determination of aminoglycoside and macrolide antibiotics in meat by pressurized liquid extraction and LC-ESI-MS. | 2010 Mar |
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Biomimetic synthesis and structural refinement of the macrocyclic dimer aminoglycoside 66-40C--the remarkably selective self-condensation of a putative aldehyde intermediate in the submerged culture medium producing sisomicin. | 2010 Mar 28 |
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Activity of a novel aminoglycoside, ACHN-490, against clinical isolates of Escherichia coli and Klebsiella pneumoniae from New York City. | 2010 Oct |
|
Discovery of selective bioactive small molecules by targeting an RNA dynamic ensemble. | 2011 Jun 26 |
Patents
Sample Use Guides
Adult: IM- Susceptible infections- 3 mg/kg/day in 2-3 divided doses.
Ophthalmic- Instill one or two drops into the affected eyes.
Toical-As 0.1% cream: Apply twice daily.
Route of Administration:
Other
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/2777351
540 strains of bacteria isolated from various clinical materials comprising 440 strains of Gram negative bacilli and 100 strains of Gram positive cocci were tested for their susceptibility in vitro to Sisomicin (Ensamycin). The sensitivity pattern revealed that 89.0% of the strains were sensitive to Sisomicin. The effectiveness of Sisomicin is comparatively greater (6.1%) than the other two aminoglycosides.
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 07:58:58 UTC 2023
by
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on
Sat Dec 16 07:58:58 UTC 2023
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Record UNII |
X55XSL74YQ
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QJ01GB08
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NCI_THESAURUS |
C2363
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WHO-ATC |
J01GB08
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CHEMBL221886
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100000083520
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2447
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C72569
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DB12604
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32385-11-8
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D012853
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251-018-2
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9806
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Sisomicin
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SUB10538MIG
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m9958
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY |
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ACTIVE MOIETY |
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