Midecamycin

Last updated
Midecamycin
Midecamycin.png
Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
  • (2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-4-(dimethylamino)-5-hydroxy-6-{[(4R,6S,7R,9R,10R,11E,13E,16R)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-4-(propanoyloxy)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl propanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.047.784 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C41H67NO15
Molar mass 813.979 g·mol−1
3D model (JSmol)
Melting point 155 to 156 °C (311 to 313 °F)
Solubility in water Soluble in acidic/low pH water; Very soluble in methanol, chloroform, ethyl acetate, benzene, ethyl ether; Almost completely in ethanol(>95.5) mg/mL (20 °C)
  • O=CC[C@H]3C[C@@H](C)[C@@H](O)/C=C/C=C/C[C@H](OC(=O)C[C@@H](OC(=O)CC)[C@H](OC)[C@H]3O[C@@H]2O[C@@H]([C@@H](O[C@@H]1O[C@H]([C@H](OC(=O)CC)[C@](O)(C1)C)C)[C@H](N(C)C)[C@H]2O)C)C
  • InChI=1S/C41H67NO15/c1-11-30(45)54-29-21-32(47)51-24(4)16-14-13-15-17-28(44)23(3)20-27(18-19-43)37(38(29)50-10)57-40-35(48)34(42(8)9)36(25(5)53-40)56-33-22-41(7,49)39(26(6)52-33)55-31(46)12-2/h13-15,17,19,23-29,33-40,44,48-49H,11-12,16,18,20-22H2,1-10H3/b14-13+,17-15+/t23-,24-,25-,26+,27+,28+,29-,33+,34-,35-,36-,37+,38+,39+,40+,41-/m1/s1 Yes check.svgY
  • Key:DMUAPQTXSSNEDD-QALJCMCCSA-N Yes check.svgY
   (verify)

Midecamycin is a macrolide antibiotic [1] that is synthesized from Streptomyces mycarofaciens. [2]

Physical Properties

Its melting point may vary depending on the compound type and the source consulted. For example, the Merck Index gives a melting point of 155-156 Celsius for the A1 type while the Japanese Pharmacopoeia reports 153-158 Celsius. The Merck Index also gives a melting point of 122-125 Celsius for the A3 type.[ citation needed ]

Related Research Articles

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

Macrolides are a class of mostly natural products with 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">Aminoglycoside</span> Antibacterial drug

Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside (sugar). The term can also refer more generally to any organic molecule that contains amino sugar substructures. Aminoglycoside antibiotics display bactericidal activity against Gram-negative aerobes and some anaerobic bacilli where resistance has not yet arisen but generally not against Gram-positive and anaerobic Gram-negative bacteria.

Polyene antimycotics, sometimes referred to as polyene antibiotics, are a class of antimicrobial polyene compounds that target fungi. These polyene antimycotics are typically obtained from some species of Streptomyces bacteria. Previously, polyenes were thought to bind to ergosterol in the fungal cell membrane and thus weakening it and causing leakage of K+ and Na+ ions, which could contribute to fungal cell death. However, more detailed studies of polyene molecular properties have challenged this model suggesting that polyenes instead bind and extract ergosterol directly from the cellular membrane thus disrupting the many cellular functions ergosterols perform. Amphotericin B, nystatin, and natamycin are examples of polyene antimycotics. They are a subgroup of macrolides.

<span class="mw-page-title-main">Lincosamides</span> Group of antibiotics

Lincosamides are a class of antibiotics, which include lincomycin, clindamycin, and pirlimycin.

<span class="mw-page-title-main">Pristinamycin</span> Group of chemical compounds

Pristinamycin (INN), also spelled pristinamycine, is an antibiotic used primarily in the treatment of staphylococcal infections, and to a lesser extent streptococcal infections. It is a streptogramin group antibiotic, similar to virginiamycin, derived from the bacterium Streptomyces pristinaespiralis. It is marketed in Europe by Sanofi-Aventis under the trade name Pyostacine.

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

Platensimycin, a metabolite of Streptomyces platensis, is an antibiotic, which act by blocking enzymes.

<span class="mw-page-title-main">Rokitamycin</span> Type of antibiotic chemical

Rokitamycin is a macrolide antibiotic synthesized from strains of Streptomyces kitasatoensis.

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

Josamycin is a macrolide antibiotic. It was isolated by Hamao Umezawa and his colleagues from strains of Streptomyces narbonensis var. josamyceticus var. nova in 1964.

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

Oleandomycin is a macrolide antibiotic. It is synthesized from strains of Streptomyces antibioticus. It is weaker than erythromycin.

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

Hachimycin, also known as trichomycin, is a polyene macrolide antibiotic, antiprotozoal, and antifungal derived from streptomyces. It was first described in 1950, and in most research cases have been used for gynecological infections.

<i>Saccharopolyspora erythraea</i> Species of bacterium

Saccharopolyspora erythraea is a species of actinomycete bacteria within the genus Saccharopolyspora.

<span class="mw-page-title-main">Pikromycin</span> 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.

Streptomyces peucetius is a bacterium species in the genus Streptomyces.

Streptomyces albofaciens is a bacterium species from the genus of Streptomyces which produces oxytetracycline, spiramycin, albopeptin A, albopeptin B and alpomycin.

Streptomyces ambofaciens is a bacterium species from the genus Streptomyces which has been isolated from soil from France. Streptomyces ambofaciens produces ambobactin, foromacidin A, foromacidin B, foromacidin C, 18-deoxospiramicin I, 17-methylenespiramycin I and congocidin.

Streptomyces cirratus is a bacterium species from the genus of Streptomyces. Streptomyces cirratus produces phegomycin, phegomycin D, phegomycin DGPT, cirratiomycin A, cirramycin A and cirramycin B.

Streptomyces flavotricini is a bacterium species from the genus of Streptomyces which has been isolated from mountain forest soil. Streptomyces flavotricini produces bafilomycin K and aminoacylase.

Streptomyces phytohabitans is a bacterium species from the genus of Streptomyces which has been isolated from the plant Curcuma phaeocaulis from the Sichuan Province in China. Streptomyces phytohabitans produces the macrolides novonestmycin A and novonestmycin B.

Streptomyces lasiicapitis is a bacterium species from the genus of Streptomyces which has been isolated from the head of the ant Lasius fuliginosus. Streptomyces lasiicapitis produces the antibiotic kanchanamycin.

Cytochrome P450 family 107 subfamily G member 1 is an actinobacterial Cytochrome P450 enzyme originally from Streptomyces rapamycinicus, which catalyzes the oxidation reaction of C27 of pre-rapamycin in the biosynthesis pathway of the macrolide antibiotic rapamycin.

References

  1. Salhi A, Vindel JA, Brunaud M, Berceaux G, Marin A, Wuatelet C (1977). "Properties of midecamycin, a new macrolide antibiotic". Giornale Italiano di Chemioterapia. 24 (1–2): 67–76. PMID   308022.
  2. Wang YG, Hutchinson CR (1989). "Cloning of midecamycin biosynthetic genes from Streptomyces mycarofaciens 1748". Chinese Journal of Biotechnology. 5 (4): 191–201. PMID   2491329.