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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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19-Jan-2022
28-May-2025
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ABOUT THIS PAGE

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

Nystatin manufacturers, exporters & distributors 1

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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, Price,and more, enabling you to easily find the right Nystatin manufacturer or Nystatin supplier for your needs.

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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-TRIAMCINOLONE ACETONIDE Manufacturers

A NYSTATIN-TRIAMCINOLONE ACETONIDE manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of NYSTATIN-TRIAMCINOLONE ACETONIDE, including repackagers and relabelers. The FDA regulates NYSTATIN-TRIAMCINOLONE ACETONIDE manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. NYSTATIN-TRIAMCINOLONE ACETONIDE 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-TRIAMCINOLONE ACETONIDE manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

NYSTATIN-TRIAMCINOLONE ACETONIDE Suppliers

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

click here to find a list of NYSTATIN-TRIAMCINOLONE ACETONIDE suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

NYSTATIN-TRIAMCINOLONE ACETONIDE USDMF

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

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

click here to find a list of NYSTATIN-TRIAMCINOLONE ACETONIDE suppliers with USDMF on PharmaCompass.

NYSTATIN-TRIAMCINOLONE ACETONIDE CEP

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

A NYSTATIN-TRIAMCINOLONE ACETONIDE CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. NYSTATIN-TRIAMCINOLONE ACETONIDE 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-TRIAMCINOLONE ACETONIDE suppliers with CEP (COS) on PharmaCompass.

NYSTATIN-TRIAMCINOLONE ACETONIDE 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-TRIAMCINOLONE ACETONIDE as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for NYSTATIN-TRIAMCINOLONE ACETONIDE 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-TRIAMCINOLONE ACETONIDE 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-TRIAMCINOLONE ACETONIDE and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a NYSTATIN-TRIAMCINOLONE ACETONIDE NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of NYSTATIN-TRIAMCINOLONE ACETONIDE suppliers with NDC on PharmaCompass.

NYSTATIN-TRIAMCINOLONE ACETONIDE GMP

NYSTATIN-TRIAMCINOLONE ACETONIDE 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-TRIAMCINOLONE ACETONIDE GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right NYSTATIN-TRIAMCINOLONE ACETONIDE GMP manufacturer or NYSTATIN-TRIAMCINOLONE ACETONIDE GMP API supplier for your needs.

NYSTATIN-TRIAMCINOLONE ACETONIDE CoA

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

NYSTATIN-TRIAMCINOLONE ACETONIDE CoA mostly includes findings from lab analyses of a specific batch. For each NYSTATIN-TRIAMCINOLONE ACETONIDE 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-TRIAMCINOLONE ACETONIDE may be tested according to a variety of international standards, such as European Pharmacopoeia (NYSTATIN-TRIAMCINOLONE ACETONIDE EP), NYSTATIN-TRIAMCINOLONE ACETONIDE JP (Japanese Pharmacopeia) and the US Pharmacopoeia (NYSTATIN-TRIAMCINOLONE ACETONIDE 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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