Candicidin

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Candicidin
Candicidin.png
Clinical data
ATC code
Identifiers
  • 33-[(3-Amino-3,6-dideoxy-D-mannopyranosyl)oxy]-17-[6-(4-aminophenyl)-4-hydroxy-1,3-dimethyl-6-oxohexyl]-1,3,5,7,37-pentahydroxy-18-methyl-9,13,15-trioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
ECHA InfoCard 100.014.330 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C59H84N2O18
Molar mass 1109.317 g·mol−1
3D model (JSmol)
  • Nc1ccc(cc1)C(=O)CC(O)C(C)CC(C)C3OC(=O)CC(=O)CCCC(=O)CC(O)CC(O)CC(O)CC4(O)CC(O)C(C(=O)O)C(CC(OC2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)C=CC=CC=CC=CC=CC=CC=CC3C)O4
  • InChI=1S/C59H84N2O18/c1-35-18-15-13-11-9-7-5-6-8-10-12-14-16-21-46(77-58-55(72)53(61)54(71)38(4)76-58)31-50-52(57(73)74)49(69)34-59(75,79-50)33-45(66)29-44(65)28-43(64)27-41(62)19-17-20-42(63)30-51(70)78-56(35)37(3)26-36(2)47(67)32-48(68)39-22-24-40(60)25-23-39/h5-16,18,21-25,35-38,43-47,49-50,52-56,58,64-67,69,71-72,75H,17,19-20,26-34,60-61H2,1-4H3,(H,73,74)/b6-5-,9-7-,10-8-,13-11-,14-12-,18-15-,21-16-/t35?,36?,37?,38-,43?,44?,45?,46?,47?,49?,50?,52?,53+,54-,55+,56?,58?,59?/m1/s1 Yes check.svgY
  • Key:YKSVGLFNJPQDJE-WDANKXQLSA-N Yes check.svgY
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Candicidin is an antifungal compound obtained from Streptomyces griseus . It is active against some fungi including Candida albicans . Candicidin is administered intravaginally in the treatment of vulvovaginal candidiasis. [1]

This bioactive compound was named candicidin, because of its high activity on Candida albicans. [2]

Related Research Articles

<span class="mw-page-title-main">Candidiasis</span> Fungal infection due to any type of Candida

Candidiasis is a fungal infection due to any type of Candida. When it affects the mouth, in some countries it is commonly called thrush. Signs and symptoms include white patches on the tongue or other areas of the mouth and throat. Other symptoms may include soreness and problems swallowing. When it affects the vagina, it may be referred to as a yeast infection or thrush. Signs and symptoms include genital itching, burning, and sometimes a white "cottage cheese-like" discharge from the vagina. Yeast infections of the penis are less common and typically present with an itchy rash. Very rarely, yeast infections may become invasive, spreading to other parts of the body. This may result in fevers along with other symptoms depending on the parts involved.

<i>Candida albicans</i> Species of fungus

Candida albicans is an opportunistic pathogenic yeast that is a common member of the human gut flora. It can also survive outside the human body. It is detected in the gastrointestinal tract and mouth in 40–60% of healthy adults. It is usually a commensal organism, but it can become pathogenic in immunocompromised individuals under a variety of conditions. It is one of the few species of the genus Candida that causes the human infection candidiasis, which results from an overgrowth of the fungus. Candidiasis is, for example, often observed in HIV-infected patients. C. albicans is the most common fungal species isolated from biofilms either formed on (permanent) implanted medical devices or on human tissue. C. albicans, C. tropicalis, C. parapsilosis, and C. glabrata are together responsible for 50–90% of all cases of candidiasis in humans. A mortality rate of 40% has been reported for patients with systemic candidiasis due to C. albicans. By one estimate, invasive candidiasis contracted in a hospital causes 2,800 to 11,200 deaths yearly in the US. Nevertheless, these numbers may not truly reflect the true extent of damage this organism causes, given new studies indicating that C. albicans can cross the blood–brain barrier in mice.

<i>Candida</i> (fungus) Genus of ascomycete fungi

Candida is a genus of yeasts and is the most common cause of fungal infections worldwide. Many species are harmless commensals or endosymbionts of hosts including humans; however, when mucosal barriers are disrupted or the immune system is compromised they can invade and cause disease, known as an opportunistic infection. Candida is located on most mucosal surfaces and mainly the gastrointestinal tract, along with the skin. Candida albicans is the most commonly isolated species and can cause infections in humans and other animals. In winemaking, some species of Candida can potentially spoil wines.

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

Fluconazole is an antifungal medication used for a number of fungal infections. This includes candidiasis, blastomycosis, coccidiodomycosis, cryptococcosis, histoplasmosis, dermatophytosis, and pityriasis versicolor. It is also used to prevent candidiasis in those who are at high risk such as following organ transplantation, low birth weight babies, and those with low blood neutrophil counts. It is given either by mouth or by injection into a vein.

<span class="mw-page-title-main">Oral candidiasis</span> Fungal infection

Oral candidiasis, also known as oral thrush among other names, is candidiasis that occurs in the mouth. That is, oral candidiasis is a mycosis of Candida species on the mucous membranes of the mouth.

<i>Pseudowintera</i> Genus of trees

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

Caspofungin (INN) is a lipopeptide antifungal drug from Merck & Co., Inc. discovered by James Balkovec, Regina Black and Frances A. Bouffard. It is a member of a new class of antifungals termed the echinocandins. It works by inhibiting the enzyme (1→3)-β-D-glucan synthase and thereby disturbing the integrity of the fungal cell wall. Caspofungin was the first inhibitor of fungal (1→3)-β-D-glucan synthesis to be approved by the United States Food and Drug Administration. Caspofungin is administered intravenously.

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

Terconazole is an antifungal drug used to treat vaginal yeast infection. It comes as a lotion or a suppository and disrupts the biosynthesis of fats in a yeast cell. It has a relatively broad spectrum compared to azole compounds but not triazole compounds. Testing shows that it is a suitable compound for prophylaxis for those that suffer from chronic vulvovaginal candidiasis.

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

Anidulafungin (INN) is a semisynthetic echinocandin used as an antifungal drug. It was previously known as LY303366. It may also have application in treating invasive Aspergillus infection when used in combination with voriconazole. It is a member of the class of antifungal drugs known as the echinocandins; its mechanism of action is by inhibition of (1→3)-β-D-glucan synthase, an enzyme important to the synthesis of the fungal cell wall.

<i>Candida glabrata</i> Species of fungus

Candida glabrata is a species of haploid yeast of the genus Candida, previously known as Torulopsis glabrata. Despite the fact that no sexual life cycle has been documented for this species, C. glabrata strains of both mating types are commonly found. C. glabrata is generally a commensal of human mucosal tissues, but in today's era of wider human immunodeficiency from various causes, C. glabrata is often the second or third most common cause of candidiasis as an opportunistic pathogen. Infections caused by C. glabrata can affect the urogenital tract or even cause systemic infections by entrance of the fungal cells in the bloodstream (Candidemia), especially prevalent in immunocompromised patients.

<i>Candida lusitaniae</i> Species of fungus

Candida lusitaniae is a species of yeast in the genus Candida.

Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the skin, but it is also a precursor in the manufacture of many pharmaceuticals, personal hygiene products, cosmetics, and perfumes. Salts and esters of undecylenic acid are known as undecylenates.

Histatins are histidine-rich (cationic) antimicrobial proteins found in saliva. Histatin's involvement in antimicrobial activities makes histatin part of the innate immune system.

<span class="mw-page-title-main">Vaginal yeast infection</span> Medical condition

Vaginal yeast infection, also known as candidal vulvovaginitis and vaginal thrush, is excessive growth of yeast in the vagina that results in irritation. The most common symptom is vaginal itching, which may be severe. Other symptoms include burning with urination, a thick, white vaginal discharge that typically does not smell bad, pain during sex, and redness around the vagina. Symptoms often worsen just before a woman's period.

Denture-related stomatitis is a common condition where mild inflammation and redness of the oral mucous membrane occurs beneath a denture. In about 90% of cases, Candida species are involved, which are normally a harmless component of the oral microbiota in many people. Denture-related stomatitis is the most common form of oral candidiasis. It is more common in elderly people, and in those who wear a complete upper denture. Denture-related stomatitis is more likely to develop when the denture is left constantly in the mouth, rather than removing it during sleep, and when the denture is not cleaned regularly.

<span class="mw-page-title-main">Neil A. R. Gow</span> Professor of Microbiology

Neil Andrew Robert Gow is a professor of Microbiology and deputy Vice Chancellor at the University of Exeter. Previously he served at the University of Aberdeen for 38 years and retains an honorary Chair there.

Invasive candidiasis is an infection (candidiasis) that can be caused by various species of Candida yeast. Unlike Candida infections of the mouth and throat or vagina, invasive candidiasis is a serious, progressive, and potentially fatal infection that can affect the blood (fungemia), heart, brain, eyes, bones, and other parts of the body.

Carol Kumamoto is an American microbiologist who is Professor of Molecular Biology & Microbiology at Tufts University. She investigates the filamentous growth of Candida albicans, a fungal pathogen that causes several diseases. She is also interested in how C. albicans interacts with its host during colonisation and invasive diseases. She is a Fellow of the American Association for the Advancement of Science and the American Academy of Microbiology.

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

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References

  1. "Product information Candicidin" (PDF). Toku-E. 2012-01-11. Archived from the original (PDF) on 2014-04-08. Retrieved 2012-06-11.
  2. Waksman SA, Lechevalier HA, Schaffner CP (1965). "Candicidin and other polyenic antifungal antibiotics". Bulletin of the World Health Organization. 33 (2): 219–26. PMC   2475843 . PMID   5320588.