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Sisomicin information


Sisomicin
Clinical data
Trade namesBaymicin, bactoCeaze
AHFS/Drugs.comInternational Drug Names
Routes of
administration
topical
ATC code
  • J01GB08 (WHO)
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
CAS Number
  • 32385-11-8 ☒N
PubChem CID
  • 36119
ChemSpider
  • 33222 ☒N
UNII
  • X55XSL74YQ
KEGG
  • D02544 checkY
ChEBI
  • CHEBI:9169 ☒N
ChEMBL
  • ChEMBL221886 ☒N
CompTox Dashboard (EPA)
  • DTXSID0023583 Edit this at Wikidata
ECHA InfoCard100.046.365 Edit this at Wikidata
Chemical and physical data
FormulaC19H37N5O7
Molar mass447.533 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N)N)O
InChI
  • 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 ☒N
  • Key:URWAJWIAIPFPJE-YFMIWBNJSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Sisomicin (bactoCeaze, ensamycin, and initially antibiotic 6640[1] and rickamicin[1]), is an aminoglycoside antibiotic, isolated from the fermentation broth of Micromonospora inositola.[1] It is a newer broad-spectrum aminoglycoside most structurally related to gentamicin.

Sisomicin is the most predictably active aminoglycoside against Gram-positive bacteria.[2] Like most other aminoglycosides, sisomicin is bactericidal for sensitive clinical isolates. The minimum bactericidal concentrations (MBC) have been found to be equivalent or very close to the minimum inhibitory concentrations (MIC).[3] Like other aminoglycosides, most clinical isolates of Pseudomonas aeruginosa remain susceptible to sisomicin. Resistance to sisomicin may be enzymatically or non-enzymatically mediated. Sisomicin is inactivated by the same enzymes as gentamicin, but it is active against many organisms that resist gentamicin by non-enzymatic mechanisms.[4]

Some studies show that sisomicin has been effective in the treatment of infections that either had failed to respond to other drugs or were due to microorganisms resistant in vitro to other aminoglycosides.[5][6]

  1. ^ a b c Weinstein MJ, Marquez JA, Testa RT, Wagman GH, Oden EM, Waitz JA (November 1970). "Antibiotic 6640, a new Micromonospora-produced aminoglycoside antibiotic". The Journal of Antibiotics. 23 (11): 551–4. doi:10.7164/antibiotics.23.551. PMID 5487129.
  2. ^ Sanders WE, Sanders CC (Mar–Apr 1980). "Sisomicin: a review of eight years' experience". Reviews of Infectious Diseases. 2 (2): 182–95. doi:10.1093/clinids/2.2.182. PMID 6994206.
  3. ^ Levison ME, Kaye D (June 1974). "In vitro comparison of four aminoglycoside antibiotics: sisomicin, gentamicin, tobramycin, and BB-K8". Antimicrobial Agents and Chemotherapy. 5 (6): 667–9. doi:10.1128/aac.5.6.667. PMC 429032. PMID 15825423.
  4. ^ Phillips I, King BA, Shannon KP (March 1978). "The mechanisms of resistance to aminoglycosides in the genus Pseudomonas". Journal of Antimicrobial Chemotherapy. 4 (2): 121–9. doi:10.1093/jac/4.2.121. PMID 649532.
  5. ^ Keating MJ, Bodey GP, Valdivieso M, Rodriguez V (March 1979). "A randomized comparative trial of three aminoglycosides--comparison of continuous infusions of gentamicin, amikacin and sisomicin combined with carbenicillin in the treatment of infections in neutropenic patients with malignancies". Medicine. 58 (2): 159–70. doi:10.1097/00005792-197903000-00004. PMID 431401. S2CID 1035277.
  6. ^ Maki DG, Craig WA, Agger WA (Jun 1979). "A comparative clinical trial of sisomicin and gentamicin in major gram-negative infections". Infection. 7: S298–S300. doi:10.1007/bf01646260. S2CID 46971853.

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Sisomicin

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Sisomicin (bactoCeaze, ensamycin, and initially antibiotic 6640 and rickamicin), is an aminoglycoside antibiotic, isolated from the fermentation broth...

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Micromonospora

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end with -micin, such as gentamicin, mutamicin, netilmicin, retymicin, sisomicin, verdamicin, calicheamicin, and the recently found turbinmicin. Potent...

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Schedule H

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HYDROCHLORIDE 453. SILDENAFIL CITRATE 454. SIMVASTATIN 455. SIROLIMUS 456. SISOMICIN SULPHATE 457. S-NEOMINOPHAGEN 458. SODIUM PICOSULPHATE 459. SODIUM CROMOGLYCATE...

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Netilmicin

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(1-N-ethylsisomicin) is a semisynthetic aminoglycoside antibiotic, and a derivative of sisomicin, produced by Micromonospora inyoensis. Aminoglycoside antibiotics have...

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Aminoglycoside

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aminoglycoside. Kanamycin A Amikacin Tobramycin Dibekacin Gentamicin Sisomicin Netilmicin Neomycins B, C Neomycin E (paromomycin) Streptomycin Plazomicin...

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Gentamicin

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other related antibiotics produced by this genus (verdamicin, mutamicin, sisomicin, netilmicin, and retymicin) have their spellings ending in ~micin and...

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ATC code J01

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Kanamycin J01GB05 Neomycin J01GB06 Amikacin J01GB07 Netilmicin J01GB08 Sisomicin J01GB09 Dibekacin J01GB10 Ribostamycin J01GB11 Isepamicin J01GB12 Arbekacin...

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Eravacycline

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Plazomicin

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later. A generic version is manufactured by Cipla USA. It is derived from sisomicin by appending a hydroxy-aminobutyric acid substituent at position 1 and...

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Dihydrostreptomycin

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Apramycin Nourseothricin -micin (Micromonospora) Gentamicin# Netilmicin Sisomicin Micronomicin Plazomicin# Isepamicin Verdamicin Astromicin other Butirosin...

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