Astromicin

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Astromicin
Astromicin.png
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
IV
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 2-amino-N-[(1S,2R,3R,4S,5S,6R)-4-amino-3-[(2R,3R,6S)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy-2,5-dihydroxy-6-methoxycyclohexyl]-N-methylacetamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H35N5O6
Molar mass 405.496 g·mol−1
3D model (JSmol)
  • O=C(N(C)[C@@H]2[C@@H](OC)[C@@H](O)[C@H](N)[C@@H](O[C@H]1O[C@H]([C@@H](N)C)CC[C@H]1N)[C@@H]2O)CN
  • InChI=1S/C17H35N5O6/c1-7(19)9-5-4-8(20)17(27-9)28-15-11(21)13(24)16(26-3)12(14(15)25)22(2)10(23)6-18/h7-9,11-17,24-25H,4-6,18-21H2,1-3H3/t7-,8+,9-,11-,12-,13-,14+,15+,16+,17+/m0/s1 Yes check.svgY
  • Key:BIDUPMYXGFNAEJ-APGVDKLISA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Astromicin (INN)(also frequently referenced in scientific journal articles as compounds Fortimicin A/B ) is an aminoglycoside antibiotic. Synthesized from Micromonospora olivasterospora(also named with additional o in olivoasterospora). [1] [2]

Related Research Articles

<i>Micromonospora</i> Genus of bacteria

Micromonospora is a genus of bacteria of the family Micromonosporaceae. They are gram-positive, spore-forming, generally aerobic, and form a branched mycelium; they occur as saprotrophic forms in soil and water. Various species are sources of aminoglycoside antibiotics with spellings that end with -micin, such as gentamicin, mutamicin, netilmicin, retymicin, sisomicin, verdamicin and the recently found turbinmicin. Potent new antifungal discovered in the microbiome of marine animals, unlike most other aminoglycoside names that end with -mycin.

Novobiocin

Novobiocin, also known as albamycin or cathomycin, is an aminocoumarin antibiotic that is produced by the actinomycete Streptomyces niveus, which has recently been identified as a subjective synonym for S. spheroides a member of the order Actinobacteria. Other aminocoumarin antibiotics include clorobiocin and coumermycin A1. Novobiocin was first reported in the mid-1950s.

Calicheamicin Chemical compound

The calicheamicins are a class of enediyne antitumor antibiotics derived from the bacterium Micromonospora echinospora, with calicheamicin γ1 being the most notable. It was isolated originally in the mid-1980s from the chalky soil, or "caliche pits", located in Kerrville, Texas. The sample was collected by a scientist working for Lederle Labs. It is extremely toxic to all cells and, in 2000, a CD33 antigen-targeted immunoconjugate N-acetyl dimethyl hydrazide calicheamicin was developed and marketed as targeted therapy against the non-solid tumor cancer acute myeloid leukemia (AML). A second calicheamicin-linked monoclonal antibody, inotuzumab ozogamicin an anti-CD22-directed antibody-drug conjugate, was approved by the U.S. Food and Drug Administration on August 17, 2017, for use in the treatment of adults with relapsed or refractory B-cell precursor acute lymphoblastic leukemia. Calicheamicin γ1 and the related enediyne esperamicin are the two of the most potent antitumor agents known.

Rhizoxin Chemical compound

Rhizoxin is an antimitotic agent with anti-tumor activity. It is isolated from a pathogenic plant fungus which causes rice seedling blight.

Thienamycin Chemical compound

Thienamycin is one of the most potent naturally produced antibiotics known thus far, discovered in Streptomyces cattleya in 1976. Thienamycin has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes. Thienamycin is a zwitterion at pH 7.

Ribostamycin Aminoglycoside antibiotic

Ribostamycin is an aminoglycoside-aminocyclitol antibiotic isolated from a streptomycete, Streptomyces ribosidificus, originally identified in a soil sample from Tsu City of Mie Prefecture in Japan. It is made up of 3 ring subunits: 2-deoxystreptamine (DOS), neosamine C, and ribose. Ribostamycin, along with other aminoglycosides with the DOS subunit, is an important broad-spectrum antibiotic with important use against human immunodeficiency virus and is considered a critically important antimicrobial by the World Health Organization., Resistance against aminoglycoside antibiotics, such as ribostamycin, is a growing concern. The resistant bacteria contain enzymes that modify the structure through phosphorylation, adenylation, and acetylation and prevent the antibiotic from being able to interact with the bacterial ribosomal RNAs.

Micronomicin

Micronomicin (INN) is an aminoglycoside antibiotic for use on the eye.

Enediyne

Enediynes are organic compounds containing two triple bonds and one double bond.

The aminocyclitols are compounds related to cyclitols. They possess features of relative and absolute configuration that are characteristic of their class and have been extensively studied; but these features are not clearly displayed by general methods of stereochemical nomenclature, so that special methods of specifying their configuration are justified and have long been used. In other than stereochemical respects, their nomenclature should follow the general rules of organic chemistry.

Dynemicin A Anti-cancer drug

Dynemicin A is an anti-cancer enediyne drug. It displays properties which illustrate promise for cancer treatments, but still requires further research.

Pikromycin Chemical compound

Pikromycin was studied by Brokmann and Hekel in 1951 and was the first antibiotic macrolide to be isolated. Pikromycin is synthesized through a type I polyketide synthase system in Streptomyces venezuelae, a species of Gram-positive bacterium in the genus Streptomyces. Pikromycin is derived from narbonolide, a 14-membered ring macrolide. Along with the narbonolide backbone, pikromycin includes a desosamine sugar and a hydroxyl group. Although Pikromycin is not a clinically useful antibiotic, it can be used as a raw material to synthesize antibiotic ketolide compounds such as ertythromycins and new epothilones.

2-deoxy-scyllo-inosose synthase is an enzyme with systematic name D-glucose-6-phosphate phosphate-lyase (2-deoxy-scyllo-inosose-forming). This enzyme catalyses the following chemical reaction

Terpentedienyl-diphosphate synthase is an enzyme with systematic name terpentedienyl-diphosphate lyase (decyclizing). This enzyme catalyses the following chemical reaction

Naphthomycins are a group of closely related antimicrobial chemical compounds isolated from Streptomyces. They are considered a subclass of ansamycins.

Actaplanin Chemical compound

Actaplanin is a complex of broad-spectrum antibiotics made by Actinoplanes bacteria. Research carried out by a group in Eli Lilly and Co. in 1984 identified several actaplanins using high-performance liquid chromatography. Actaplanins A, B1, B2, B3, C1 and G were shown to be composed of the same peptide core, an amino sugar, and varying amounts of glucose, mannose, and rhamnose.

Micromonospora citrea is an endophytic actinomycete, with type strain DSM 43903T. It produces citreamicins, several types of antibacterial antibiotics.

Micromonospora sagamiensis is an endophytic actinomycete, with type strain DSM 43912T. It produces sagamicin, an aminoglycoside antibiotic, as well as several mutational variants. Its cell wall contains only D-alanine.

Streptomyces griseoflavus is a bacterium species from the genus of Streptomyces which has been isolated from garden soil. Streptomyces griseoflavus produces bicozamycin, colabomycins A, colabomycins C, germacradienol and hormaomycin.

Streptomyces kasugaensis is a bacterium species from the genus of Streptomyces which has been isolated from soil from the city Nara in Japan. Streptomyces kasugaensis produces kasugamycin and thiolutin.

C-1027

C-1027 or Lidamycin is an antitumor antibiotic consisting of a complex of an enediyne chromophore and an apoprotein. It shows antibiotic activity against most Gram-positive bacteria. It is one of the most potent cytotoxic molecules known, due to its induction of a higher ratio of DNA double-strand breaks than single-strand breaks.

References

  1. Itoh S, Odakura Y, Kase H, Satoh S, Takahashi K, Iida T, Shirahata K, Nakayama K (December 1984). "Biosynthesis of astromicin and related antibiotics. I. Biosynthetic studies by bioconversion experiments". The Journal of Antibiotics. 37 (12): 1664–9. doi: 10.7164/antibiotics.37.1664 . PMID   6526734.
  2. Odakura Y, Kase H, Itoh S, Satoh S, Takasawa S, Takahashi K, Shirahata K, Nakayama K (December 1984). "Biosynthesis of astromicin and related antibiotics. II. Biosynthetic studies with blocked mutants of Micromonospora olivasterospora". The Journal of Antibiotics. 37 (12): 1670–80. doi: 10.7164/antibiotics.37.1670 . PMID   6526735.