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    Chemistry

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    Also known as: Nystatin, 34786-70-4, W1lx4t91wi, Nystatinum, Terrastatin, Nyotran
    Molecular Formula
    C47H75NO17
    Molecular Weight
    926.1  g/mol
    InChI Key
    VQOXZBDYSJBXMA-NQTDYLQESA-N
    FDA UNII
    W1LX4T91WI
    Nystatin
    Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.
    1 2D Structure

    Nystatin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,3R,4R,7R,9R,11R,15S,16R,17R,18S,19E,21E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic acid
    2.1.2 InChI
    InChI=1S/C47H75NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-36(53)35(52)20-19-31(49)21-32(50)22-33(51)23-39(55)62-29(3)28(2)42(27)56/h5-6,8,10-18,27-38,40-44,46,49-54,56-58,61H,7,9,19-26,48H2,1-4H3,(H,59,60)/b6-5+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33+,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1
    2.1.3 InChI Key
    VQOXZBDYSJBXMA-NQTDYLQESA-N
    2.1.4 Canonical SMILES
    CC1C=CC=CCCC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(C(CCC(CC(CC(CC(=O)OC(C(C1O)C)C)O)O)O)O)O)O)O)C(=O)O)OC3C(C(C(C(O3)C)O)N)O
    2.1.5 Isomeric SMILES
    C[C@H]1/C=C/C=C/CC/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H]([C@@H](CC[C@H](C[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)O)N)O
    2.2 Other Identifiers
    2.2.1 UNII
    W1LX4T91WI
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Fungicidin

    2. Mycostatin

    3. Nilstat

    4. Nystatin

    5. Nystatin A2

    6. Nystatin A3

    7. Nystatin G

    8. Stamicin

    9. Stamycin

    2.3.2 Depositor-Supplied Synonyms

    1. Nystatin

    2. 34786-70-4

    3. W1lx4t91wi

    4. Nystatinum

    5. Terrastatin

    6. Nyotran

    7. (1s,3r,4r,7r,9r,11r,15s,16r,17r,18s,19e,21e,25e,27e,29e,31e,33r,35s,36r,37s)-33-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic Acid

    8. Mikostatin

    9. L-nystatin

    10. Unii-w1lx4t91wi

    11. Nystatin A1 [mi]

    12. Chembl450895

    13. Schembl18633553

    14. Dtxsid80872323

    15. Chebi:473992

    16. Lmpk06000004

    17. Akos032963569

    18. Zinc253387941

    19. Q27292191

    20. (7r,10r)-8,9-dideoxy-28,29-dihydro-7,10-dihydroxyamphotericin B

    21. (1s,3r,4e,6e,8e,10e,14e,16e,18s,19r,20r,21s,25r,27r,29r,32r,33r,35s,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-19,25,27,29,32,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,14,16-hexaene-38-carboxylic Acid

    22. (1s,3r,4r,7r,9r,11r,15s,16r,17r,18s,19e,21e,25e,27e,29e,31e,33r,35s,36r,37s)-33-[(3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy]-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic Acid

    23. (1s,3r,4r,7r,9r,11r,15s,16r,17r,18s,19e,21z,25e,27e,29e,31e,33r,35s,36r,37s)-33-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic Acid

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 926.1 g/mol
    Molecular Formula C47H75NO17
    XLogP3-0.2
    Hydrogen Bond Donor Count12
    Hydrogen Bond Acceptor Count18
    Rotatable Bond Count3
    Exact Mass925.50349992 g/mol
    Monoisotopic Mass925.50349992 g/mol
    Topological Polar Surface Area320 Ų
    Heavy Atom Count65
    Formal Charge0
    Complexity1620
    Isotope Atom Count0
    Defined Atom Stereocenter Count19
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count6
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Antibiotics, Antifungal; Antibiotics, Macrolide; Ionophores

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    MEDICATION (VET):Antifungal; growth promotant

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1208

    MEDICATION (VET): /Used in treatment of/ intestinal mycosis due to Candida albicans in poultry; occasionally orally in cats and dogs in suspected Candida intestinal overgrowth following antibiotic therapy, and also topically ... as cream or ointment on skin lesions ...

    Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 397

    Nystatin vaginal tablets are used as lozenges to treat oropharyngeal candidiasis since their slow dissolution rate provides prolonged oral contact. /NOT included in US product labeling/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2226

    For more Therapeutic Uses (Complete) data for NYSTATIN (9 total), please visit the HSDB record page.

    4.2 Drug Warning

    Since it is not known whether nystatin is distributed into human milk, the drug should be used with caution in nursing women.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 543

    Adverse effects occur infrequently with oral nystatin therapy. Mild and transitory nausea, vomiting, GI distress, and diarrhea have occurred; high oral doses (e.g., greater than 5 million units daily) are most likely to produce these adverse GI effects. Hypersensitivity reactions have been reported very rarely.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 543

    Patients should be instructed to contact their physician if symptoms of irritation or sensitization occur during nystatin therapy. Patients should be warned against interrupting or discontinuing vaginal nystatin therapy during a prescribed regimen, even during menstruation or if symptomatic relief occurs after only a few days of therapy, unless otherwise instructed by their physician. Patients should be advised that adjunctive measures such as therapeutic douches are not necessary and may be inadvisable during vaginal nystatin therapy; however, cleansing douches may be used in nonpregnant women, if desired, for aesthetic effect.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3432

    Adverse reactions to topically applied nystatin are very infrequent, even during prolonged use. Irritation has occurred rarely. Hypersensitivity reactions to nystatin have been reported only rarely; however, preservatives (eg, ethylenediamine, parabens, thimerosal) in some of the formulations are associated with a high incidence of contact dermatitis. An acneiform eruption has occurred rarely following topical application of nystatin and triamcinolone acetonide.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3432

    For more Drug Warnings (Complete) data for NYSTATIN (9 total), please visit the HSDB record page.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    Antifungal Agents

    Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

    Ionophores

    Chemical agents that increase the permeability of biological or artificial lipid membranes to specific ions. Most ionophores are relatively small organic molecules that act as mobile carriers within membranes or coalesce to form ion permeable channels across membranes. Many are antibiotics, and many act as uncoupling agents by short-circuiting the proton gradient across mitochondrial membranes. (See all compounds classified as Ionophores.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Polyenes [CS]; Polyene Antifungal [EPC]
    5.3 ATC Code

    A - Alimentary tract and metabolism

    A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

    A07A - Intestinal antiinfectives

    A07AA - Antibiotics

    A07AA02 - Nystatin

    D - Dermatologicals

    D01 - Antifungals for dermatological use

    D01A - Antifungals for topical use

    D01AA - Antibiotics

    D01AA01 - Nystatin

    G - Genito urinary system and sex hormones

    G01 - Gynecological antiinfectives and antiseptics

    G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

    G01AA - Antibiotics

    G01AA01 - Nystatin

    5.4 Absorption, Distribution and Excretion

    Nystatin penetrates eye poorly.

    American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 969

    Nystatin is poorly absorbed from the GI tract, and detectable blood concentrations are not obtained after usual doses. Following oral administration, nystatin is excreted almost entirely in feces as unchanged drug.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 543

    In healthy individuals, mean salivary nystatin concentrations in excess of those required in vitro for growth inhibition of clinically important Candida persist for approximately 2 hours after the beginning of oral dissolution of two nystatin lozenges (400,000 units) administered simultaneously.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3432

    Not absorbed following topical application to intact skin or mucous membranes.

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2225

    For more Absorption, Distribution and Excretion (Complete) data for NYSTATIN (6 total), please visit the HSDB record page.

    5.5 Mechanism of Action

    Nystatin exerts its antifungal activity by binding to sterols in the fungal cell membrane. The drug is not active against organisms (e.g., bacteria) that do not contain sterols in their cell membrane. As a result of this binding, the membrane is no longer able to function as a selective barrier, and potassium and other cellular constituents are lost.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 543

    ... /Antimicrobial/ agents that act directly on the cell membrane of the microorganism, affecting permeability and leading to leakage of intracellular compounds; these include ... the polyene antifungal agents nystatin ... which bind to cell-wall sterols ...

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1143

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    Looking for 1400-61-9 / Nystatin API manufacturers, exporters & distributors?

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    PharmaCompass offers a list of Nystatin API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, and more, enabling you to easily find the right Nystatin manufacturer or Nystatin supplier for your needs.

    Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Nystatin manufacturer or Nystatin supplier.

    API | Excipient name

    Nystatin

    Synonyms

    34786-70-4, W1lx4t91wi, Nystatinum, Terrastatin, Nyotran, (1s,3r,4r,7r,9r,11r,15s,16r,17r,18s,19e,21e,25e,27e,29e,31e,33r,35s,36r,37s)-33-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic acid

    Cas Number

    1400-61-9

    Unique Ingredient Identifier (UNII)

    W1LX4T91WI

    About Nystatin

    Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.

    Nystatin Manufacturers

    A Nystatin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Nystatin, including repackagers and relabelers. The FDA regulates Nystatin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Nystatin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Nystatin manufacturers with USDMF, JDMF, KDMF, CEP, GMP, and COA related information on PhamaCompass.

    Nystatin Suppliers

    A Nystatin supplier is an individual or a company that provides Nystatin active pharmaceutical ingredient (API) or Nystatin finished formulations upon request. The Nystatin suppliers may include Nystatin API manufacturers, exporters, distributors and traders.

    click here to find a list of Nystatin suppliers with USDMF, JDMF, KDMF, CEP, GMP, and COA related information on PharmaCompass.

    Nystatin USDMF

    A Nystatin DMF (Drug Master File) is a document detailing the whole manufacturing process of Nystatin active pharmaceutical ingredient (API) in detail. Different forms of Nystatin DMFs exist exist since differing nations have different regulations, such as Nystatin USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Nystatin DMF submitted to regulatory agencies in the US is known as a USDMF. Nystatin USDMF includes data on Nystatin's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Nystatin USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of Nystatin suppliers with USDMF on PharmaCompass.

    Nystatin CEP

    A Nystatin CEP of the European Pharmacopoeia monograph is often referred to as a Nystatin Certificate of Suitability (COS). The purpose of a Nystatin CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Nystatin EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Nystatin to their clients by showing that a Nystatin CEP has been issued for it. The manufacturer submits a Nystatin CEP (COS) as part of the market authorization procedure, and it takes on the role of a Nystatin CEP holder for the record. Additionally, the data presented in the Nystatin CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Nystatin DMF.

    A Nystatin CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Nystatin CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

    click here to find a list of Nystatin suppliers with CEP (COS) on PharmaCompass.

    Nystatin WC

    A Nystatin written confirmation (Nystatin WC) is an official document issued by a regulatory agency to a Nystatin manufacturer, verifying that the manufacturing facility of a Nystatin active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Nystatin APIs or Nystatin finished pharmaceutical products to another nation, regulatory agencies frequently require a Nystatin WC (written confirmation) as part of the regulatory process.

    click here to find a list of Nystatin suppliers with Written Confirmation (WC) on PharmaCompass.

    Nystatin NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Nystatin as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Nystatin API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Nystatin as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Nystatin and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Nystatin NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Nystatin suppliers with NDC on PharmaCompass.

    Nystatin GMP

    Nystatin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Nystatin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, and more, enabling you to easily find the right Nystatin GMP manufacturer or Nystatin GMP API supplier for your needs.

    Nystatin CoA

    A Nystatin CoA (Certificate of Analysis) is a formal document that attests to Nystatin's compliance with Nystatin specifications and serves as a tool for batch-level quality control.

    Nystatin CoA mostly includes findings from lab analyses of a specific batch. For each Nystatin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Nystatin may be tested according to a variety of international standards, such as European Pharmacopoeia (Nystatin EP), Nystatin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Nystatin USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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