Althiomycin

Last updated
Althiomycin
Althiomycin.svg
Names
IUPAC name
N-[2-Hydroxy-1-[4-(3-methoxy-5-oxo-2H-pyrrole-1-carbonyl)-4,5-dihydro-1,3-thiazol-2-yl]ethyl]-2-(nitrosomethylidene)-3H-1,3-thiazole-4-carboxamide
Other names
Altiomycin; Matamycin
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C16H17N5O6S2/c1-27-8-2-13(23)21(4-8)16(25)11-7-29-15(20-11)9(5-22)19-14(24)10-6-28-12(18-10)3-17-26/h2-3,6,9,11,18,22H,4-5,7H2,1H3,(H,19,24)
    Key: NZGOIHZOTAJJCD-UHFFFAOYSA-N
  • COC1=CC(=O)N(C1)C(=O)[C@H]1CSC(=N1)[C@H](CO)NC(=O)C1=CSC(\C=N\O)=N1
Properties
C16H17N5O6S2
Molar mass 439.46 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Althiomycin (matamycin) is a thiazole antibiotic, effective against Gram-positive and Gram-negative bacteria. The name matamycin is from "Mata Hari" [1] and the suffix -mycin .

Isolated from Streptomyces matensis , the compound was first described by Margalith et al. in 1959. [2] It acts a protein synthesis inhibitor and its site of action is the 50S subunit of the bacterial ribosome. [2]

Related Research Articles

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<span class="mw-page-title-main">Macrolide</span> Class of natural products

The Macrolides are a class of natural products that consist of a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. Macrolides belong to the polyketide class of natural products. Some macrolides have antibiotic or antifungal activity and are used as pharmaceutical drugs. Rapamycin is also a macrolide and was originally developed as an antifungal, but is now used as an immunosuppressant drug and is being investigated as a potential longevity therapeutic.

<span class="mw-page-title-main">Penicillin</span> Group of antibiotics derived from Penicillium fungi

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<span class="mw-page-title-main">Upper respiratory tract infection</span> Medical condition

An upper respiratory tract infection (URTI) is an illness caused by an acute infection, which involves the upper respiratory tract, including the nose, sinuses, pharynx, larynx or trachea. This commonly includes nasal obstruction, sore throat, tonsillitis, pharyngitis, laryngitis, sinusitis, otitis media, and the common cold. Most infections are viral in nature, and in other instances, the cause is bacterial. URTIs can also be fungal or helminthic in origin, but these are less common.

<span class="mw-page-title-main">Cephalosporin</span> Class of pharmaceutical drugs

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<span class="mw-page-title-main">Trivial name</span> Nonsystematic name for a chemical substance

In chemistry, a trivial name is a nonsystematic name for a chemical substance. That is, the name is not recognized according to the rules of any formal system of chemical nomenclature such as IUPAC inorganic or IUPAC organic nomenclature. A trivial name is not a formal name and is usually a common name.

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<span class="mw-page-title-main">Cinoxacin</span> Chemical compound

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<span class="mw-page-title-main">Phenoxymethylpenicillin</span> Chemical compound

Phenoxymethylpenicillin, also known as penicillin V (PcV) and penicillin VK, is an antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for the treatment of strep throat, otitis media, and cellulitis. It is also used to prevent rheumatic fever and to prevent infections following removal of the spleen. It is given by mouth.

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Streptomyces griseorubens is a bacterium species from the genus of Streptomyces which has been isolated from soil. Streptomyces griseorubens produces althiomycin. Streptomyces griseorubens produces matamycin and althiomycin.

Streptomyces hawaiiensis is a bacterium species from the genus of Streptomyces which has been isolated from soil in Hawaii in the United States. Streptomyces hawaiiensis produces bryamycin and acyldepsipeptides.

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.

Streptomyces rochei is a bacterium species from the genus of Streptomyces which has been isolated from soil in Russia. Streptomyces rochei produces borrelidin, butyrolactol A, butyrolactol B, uricase and streptothricin. Streptomyces rochei has antifungal activity against Fusarium oxysporum f.sp. lycopersici and Aspergillus fumigatus. Streptomyces rochei produces moenomycin and bambermycin. Streptomyces rochei produces amicetin A, amicetin B, amicetin C and streptolin. Streptomyces rochei produces endo-β-N-acetylglucosaminidase mithramycin, amicetin, bamicetin, and plicacetin.

Streptomyces tateyamensis is a bacterium species from the genus of Streptomyces which has been isolated from the sponge Haliclona from the pacific coastline of the city Tateyama in the Chiba prefecture in Japan. Streptomyces tateyamensis produces the antibiotic thiopeptin B.

<span class="mw-page-title-main">Gougerotin</span> Chemical compound

Gougerotin is a water-soluble pyrimidine-based antibiotic which is produced by the bacteria Streptomyces graminearus and Streptomyces gougerotii. Gougerotin is named after the dermatologist Henri-Eugène Gougerot. Gougerotin has activity against Gram-positive and Gram-negative bacteria as well as against viruses.

References

  1. Aronson J (October 1999). "That's show business". BMJ (Clinical Research Ed.). 319 (7215): 972. doi:10.1136/bmj.319.7215.972. PMC   1116803 . PMID   10514162.
  2. 1 2 Pestka S (1975). "Althiomycin". In Corcoran JW, Hahn FE, Snell JF, Arora KL (eds.). Mechanism of Action of Antimicrobial and Antitumor Agents. Antibiotics. Berlin Heidelberg: Springer-Verlag. pp. 323–6. doi:10.1007/978-3-642-46304-4_21. ISBN   978-3-642-46304-4.