Hamycin

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Chemical structure of hamycin A Hamycin A.svg
Chemical structure of hamycin A

Hamycin is a pair polyene antimycotic organic compounds described in India. [1] It is a heptaene antifungal compound rather similar in chemical structure to amphotericin B except that it has an additional aromatic group bonded to the molecule. When pure, hamycin is a yellow, powdered solid. There are two versions of hamycin with very similar chemical structures: hamycin A and hamycin B. [2]

Contents

Sources

Hamycin is obtained from a strain of streptomyces bacteria growing in soil i.e., Streptomyces pimprina. This compound is being produced in India by Hindustan Antibiotics Limited, located at Pimpri, Pune, Maharashtra, India. It is similar to nystatin and it is more water-soluble.[ citation needed ]

Uses

It is useful as an antifungal antibiotic drug for topical as well as systemic mycoses.[ citation needed ]

Related Research Articles

In organic chemistry, polyenes are poly-unsaturated, organic compounds that contain at least three alternating double and single carbon–carbon bonds. These carbon–carbon double bonds interact in a process known as conjugation, resulting in some unusual optical properties. Related to polyenes are dienes, where there are only two alternating double and single bonds.

<span class="mw-page-title-main">Antifungal</span> Pharmaceutical fungicide or fungistatic used to treat and prevent mycosis

An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryptococcal meningitis, and others. Such drugs are usually obtained by a doctor's prescription, but a few are available over the counter (OTC).

<span class="mw-page-title-main">Nystatin</span> Pharmaceutical drug

Nystatin, sold under the brandname Mycostatin among others, is an antifungal medication. It is used to treat Candida infections of the skin including diaper rash, thrush, esophageal candidiasis, and vaginal yeast infections. It may also be used to prevent candidiasis in those who are at high risk. Nystatin may be used by mouth, in the vagina, or applied to the skin.

<span class="mw-page-title-main">Amphotericin B</span> Antifungal and antiparasitaric Chemical compound

Amphotericin B is an antifungal medication used for serious fungal infections and leishmaniasis. The fungal infections it is used to treat include mucormycosis, aspergillosis, blastomycosis, candidiasis, coccidioidomycosis, and cryptococcosis. For certain infections it is given with flucytosine. It is typically given intravenously.

<i>Streptomyces</i> Genus of bacteria

Streptomyces is the largest genus of Actinomycetota and the type genus of the family Streptomycetaceae. Over 500 species of Streptomyces bacteria have been described. As with the other Actinomycetota, streptomycetes are gram-positive, and have genomes with high GC content. Found predominantly in soil and decaying vegetation, most streptomycetes produce spores, and are noted for their distinct "earthy" odor that results from production of a volatile metabolite, geosmin.

Polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone (or reduced forms of a ketone) and methylene groups: (-CO-CH2-). First studied in the early 20th century, discovery, biosynthesis, and application of polyketides has evolved. It is a large and diverse group of secondary metabolites caused by its complex biosynthesis which resembles that of fatty acid synthesis. Because of this diversity, polyketides can have various medicinal, agricultural, and industrial applications. Many polyketides are medicinal or exhibit acute toxicity. Biotechnology has enabled discovery of more naturally-occurring polyketides and evolution of new polyketides with novel or improved bioactivity.

<span class="mw-page-title-main">Natamycin</span> Antifungal

Natamycin, also known as pimaricin, is an antifungal medication used to treat fungal infections around the eye. This includes infections of the eyelids, conjunctiva, and cornea. It is used as eyedrops. Natamycin is also used in the food industry as a preservative.

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">Filipin</span> Chemical compound

Filipin is a mixture of chemical compounds first isolated by chemists at the Upjohn company in 1955 from the mycelium and culture filtrates of a previously unknown actinomycete, Streptomyces filipinensis. It was discovered in a soil sample collected in the Philippine Islands, hence the name filipin. The isolate possessed potent antifungal activity. It was identified as a polyene macrolide based on its characteristic UV-Vis and IR spectra.

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

Pentamycin, also called fungichromin, is a macrolide antimicrobial. Pentamycin is a polyene antifungal antibiotic obtained from Streptomyces pentaticus. It is used in the treatment of vaginal candidiasis, for the protozoal infection trichomoniasis, and mixed infections. A 3 mg vaginal pessary is inserted once or twice daily for 5-10 days. It is also used to treat pulmonary aspergillosis as a dry powder inhalation system.

<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.

<span class="mw-page-title-main">Clavam</span> Class of antibiotics

Clavams are a class of antibiotics. This antibiotic is derived from Streptomyces clavuligerus NRRL 3585. Clavam is produced to form a new β-lactam antibiotic. This class is divided into the clavulanic acid class and the 5S clavams class. Clavulanic acid is a broad-spectrum antibiotic and 5S clavams may have anti-fungal properties. They are similar to penams, but with an oxygen substituted for the sulfur. Thus, they are also known as oxapenams.

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

Perimycin, also known as aminomycin and fungimycin, is polyene antibiotic produced by Streptomyces coelicolor var. aminophilus. The compound exhibits antifungal properties.

Venturicidins are a group of antifungal compounds. The first member of this class was isolated from Streptomyces bacteria in 1961. Additional members of this class were subsequently isolated and characterized. An antifungal substance "aabomycin A" was isolated from Streptomyces in 1969. However, in 1990 it was reported that aabomycin A is actually a 3:1 mixture of two related components, which were then named aabomycin A1 and aabomycin A2. The structures of these were shown to be identical with those of the previously characterized compounds venturicidin A and venturicidin B, respectively. A new analog, venturicidin C, was recently reported from a Streptomyces isolated from thermal vents associated with the Ruth Mullins coal fire in Kentucky.

Streptomyces isolates have yielded the majority of human, animal, and agricultural antibiotics, as well as a number of fundamental chemotherapy medicines. Streptomyces is the largest antibiotic-producing genus of Actinomycetota, producing chemotherapy, antibacterial, antifungal, antiparasitic drugs, and immunosuppressants. Streptomyces isolates are typically initiated with the aerial hyphal formation from the mycelium.

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

The cyclothiazomycins are a group of natural products, classified as thiopeptides, which are produced by various Streptomyces species of bacteria.

Streptomyces albidoflavus is a bacterium species from the genus of Streptomyces which has been isolated from soil from Poland. Streptomyces albidoflavus produces dibutyl phthalate and streptothricins.

Streptomyces halstedii is a bacterium species from the genus of Streptomyces which has been isolated from deeper soil layers. Streptomyces halstedii produces magnamycin B, vicenistatin deltamycin A2, deltamycin A3, bafilomycin B1 and bafilomycin C1. Streptomyces halstedii also produces complex antifungal antibiotics like oligomycins and the antibiotics anisomycin and sinefungin.

Streptomyces netropsis is a bacterium species from the genus of Streptomyces. Streptomyces netropsis produces the antibiotics netropsin and distamycin A and the antifungal polyene mycoheptin.

Butyrolactol A is an organic chemical compound of interest for its potential use as an antifungal antibiotic.

References

  1. Aggregation behaviour of hamycin and its interaction with membrane sterols
  2. Kotler-Brajtburg, J; Medoff, G; Kobayashi, GS; Boggs, S; Schlessinger, D; Pandey, RC; Rinehart, KL Jr (1979). "Classification of polyene antibiotics according to chemical structure and biological effects". Antimicrob Agents Chemother. 15 (5): 716–22. doi:10.1128/aac.15.5.716. PMC   352743 . PMID   393163.