Basic information
- CAS
55779-06-1- Standard SMILES
CO[C@H]1[C@@H](O)[C@H](N)[C@@H](O[C@H]2O[C@H]([C@H](C)N)CC[C@H]2N)[C@H](O)[C@@H]1N(C)C(=O)CN- InChIKey
BIDUPMYXGFNAEJ-APGVDKLISA-N- Molecular formula
- C17H35N5O6
- Average molar mass
- 405.5 g/mol
- Monoisotopic mass
- 405.25873384
Overview
Astromicin is an amino cyclitol glycoside that is L-chiro-inositol in which the hydroxy groups at positions 1, 4, and 6 are replaced by aminoacetyl)methylamino, amino, and methoxy groups, respectively, and in which the hydroxy group at position 3 is converted to the corresponding 2,6-diamino-2,3,4,6,7-pentadeoxy-beta-L-lyxo-heptopyranoside. The major component of fortimicin, obtained from Micromonospora olivasterospora. It is administered (as the sulfate salt) by intramuscular injection or intravenous infusion for the treatment of severe systemic infections due to sensitive Gram-negative organisms. It has a role as a metabolite and an antibacterial agent. It is an amino cyclitol glycoside, an aminoglycoside antibiotic, a diol, a monocarboxylic acid amide and a primary amino compound.
Names & identifiers
- Preferred name
- Astromicin
- IUPAC
- 2-amino-N-[(1S,2R,3R,4S,5S,6R)-4-amino-3-[(2R,3R,6S)-3-amino-6-[(1S)-1-aminoethyl]oxan-2-yl]oxy-2,5-dihydroxy-6-methoxycyclohexyl]-N-methylacetamide
- English name
- FORTIMICIN
- Molecular formula
- C17H35N5O6
- Molecular weight
- 405.49
Names & synonyms
Show more names
Database identifiers
- CAS
55779-06-1- PubChem CID
- 5284517
- DTXSID
DTXSID2022624- ChEMBL
CHEMBL3084803- ChEBI
CHEBI:37923- UNII
- 7JHD84H15J
- Nikkaji
- J34.182G
Properties
Computed structural properties
- XLogP
- -4.4
- Topological polar surface area
- 193 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 6
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 528
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 200 ° · >200° (dec)
- alpha
- 25 · D25 +87.5° (c = 0.1 in water)
- Boiling point
- 526.82 °C · 526.82°C (rough estimate)
- Density
- 1.0897 · 1.0897 (rough estimate)
- refractive index
- 1.76 · 1.7600 (estimate)
- pka
- 13.16 · 13.16±0.70(Predicted)
- FDA UNII
- 7 JHD84H15J · 7JHD84H15J
- Toxicity
- 50 · LD50 (of the sulfate salt) in mice (mg/kg): 380 i.v.; 400 s.c. (Nara, 1977)
Safety & regulation
Safety data
- Toxicity
- LD50 (of the sulfate salt) in mice (mg/kg): 380 i.v.; 400 s.c. (Nara, 1977)
Chemistry & industry
Applications
UsesFORTIMICIN is aminoglycoside antibiotics and broad-spectrum antibiotics with good antibacterial activity against Gram-negative bacilli, such as Proteus, Serratia, Escherichia coli, Staphylococcus aureus, and Klebsiella pneumoniae, and they do not exhibit cross-resistance with other aminoglycoside antibiotics. They are used for bronchitis, pneumonia, pyelonephritis, peritonitis, cystitis, and other conditions caused by susceptible bacteria.
Upstream & downstream products
Upstream raw materials
Suppliers9 total
Additional notes
DefinitionChEBI: An amino cyclitol glycoside that is L-chiro-inositol in which the hydroxy groups at positions 1, 4, and 6 are replaced by aminoacetyl)methylamino, amino, and methoxy groups, respectively, and in which the hydroxy group at posi ion 3 is converted to the corresponding 2,6-diamino-2,3,4,6,7-pentadeoxy-beta-L-lyxo-heptopyranoside. The major component of fortimicin, obtained from Micromonospora olivasterospora. It is adm nistered (as the sulfate salt) by intramuscular injection or intravenous infusion for the treatment of severe systemic infections due to sensitive Gram-negative organisms.
Related reactions
No reaction records under the current filter.
Compound notes
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