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3 Ingredion Pharma Solutions
23 Kerry
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6 Lonza Capsugel
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1 Nanjing Bold Chemical
2 Nomisma Healthcare
2 Novo Excipients
3 Pharmatrans-Sanaq
4 Pluviaendo
3 Prachin Chemical
1 Qianhao Chemical (Hebei) Co., Ltd
1 Qualicaps
27 Roquette
18 Seppic
4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd
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1 Zhejiang Huakang Pharmaceutical

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Synopsis

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278 RELATED EXCIPIENT COMPANIES

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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

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 Formula	C₄₇H₇₅NO₁₇
Molecular Weight	926.1 g/mol
XLogP3	-0.2
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	3
Exact Mass	925.50349992 g/mol
Monoisotopic Mass	925.50349992 g/mol
Topological Polar Surface Area	320 Å²
Heavy Atom Count	65
Formal Charge	0
Complexity	1620
Isotope Atom Count	0
Defined Atom Stereocenter Count	19
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	6
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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Centrient Pharmaceuticals

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API Reference Price

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GUJARAT","supplier":"CENTRIENT PHARMACEUTICALS","supplierCountry":"ITALY","foreign_port":"SCHIPOL AIRPORT","customer":"TORRENT PHARMACEUTICALS LIMITED","customerCountry":"INDIA","quantity":"440.00","actualQuantity":"440.002","unit":"KGS","unitRateFc":"672.4","totalValueFC":"299749","currency":"USD","unitRateINR":"57089.1","date":"17-Sep-2024","totalValueINR":"25119333.95","totalValueInUsd":"299749","indian_port":"Bombay Air","hs_no":"29412090","bill_no":"5646333","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Micronized","supplierPort":"SCHIPOL AIRPORT","supplierAddress":"N\/A","customerAddress":"TORRENT HOUSE,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1727461800,"product":"(PHARMACEUTICAL RAW MATERIAL) NYSTATIN IP\/EP\/USP (606.60 BOU@41.00=24870.60 USD)","address":"LINCOLN HOUSE, B\/H SATYAM","city":"AHMEDABAD ,GUJARAT","supplier":"ANTIBIOTICE SA","supplierCountry":"ROMANIA","foreign_port":"BUCHAREST","customer":"LINCOLN PHARMACEUTICALS","customerCountry":"INDIA","quantity":"4.00","actualQuantity":"4","unit":"KGS","unitRateFc":"259.1","totalValueFC":"1046.2","currency":"USD","unitRateINR":"21917.2","date":"28-Sep-2024","totalValueINR":"87668.87","totalValueInUsd":"1046.2","indian_port":"Ahmedabad Air","hs_no":"29419090","bill_no":"5862624","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"ROMANIA","selfForZScoreResived":"Pharma Grade","supplierPort":"BUCHAREST","supplierAddress":"1 VALEA LUPULUI STREE, 707410-LASI, ROMANIA VAT NO.RO1973096 ROMANIA RO","customerAddress":"LINCOLN HOUSE, B\/H SATYAM"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1727461800,"product":"(PHARMACEUTICAL RAW MATERIAL) NYSTATIN IP\/EP\/USP (606.60 BOU@41.00=24870.60 USD)","address":"LINCOLN HOUSE, B\/H SATYAM","city":"AHMEDABAD ,GUJARAT","supplier":"ANTIBIOTICE SA","supplierCountry":"ROMANIA","foreign_port":"BUCHAREST","customer":"LINCOLN PHARMACEUTICALS","customerCountry":"INDIA","quantity":"80.00","actualQuantity":"80","unit":"KGS","unitRateFc":"259.1","totalValueFC":"20923.1","currency":"USD","unitRateINR":"21917.2","date":"28-Sep-2024","totalValueINR":"1753377.3","totalValueInUsd":"20923.1","indian_port":"Ahmedabad Air","hs_no":"29419090","bill_no":"5862624","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"ROMANIA","selfForZScoreResived":"Pharma Grade","supplierPort":"BUCHAREST","supplierAddress":"1 VALEA LUPULUI STREE, 707410-LASI, ROMANIA VAT NO.RO1973096 ROMANIA RO","customerAddress":"LINCOLN HOUSE, B\/H SATYAM"}]

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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ACTIVE PHARMA INGREDIENTS

17 API Suppliers

10 USDMF

4 CEP/COS

10 NDC API

2 VMF

9 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

2 Drugs in Development

FINISHED DOSAGE FORMULATIONS

207 FDF Dossiers

123 FDA Orange Book

25 Europe

14 Canada

8 Australia

14 South Africa

23 Listed Dossiers

RELATED EXCIPIENT COMPANIES

4 Rochem International Inc

12 SPI Pharma

2 Seqens

8 DKSH

1 Pharm-RX Chemical

3 Faran Shimi Pharmaceutical

1 Boai NKY Pharmaceuticals Ltd

12 Gangwal Healthcare

8 Nanjing Well Pharmaceutical

1 Pfanstiehl

1 ACG Worldwide

12 Actylis

2 Aeon Procare

6 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

33 BASF

1 Clariant

10 Corel Pharma Chem

4 DFE Pharma

3 Finar

13 Gangwal Chemicals

5 Ideal Cures Pvt Ltd

3 Ingredion Pharma Solutions

23 Kerry

4 Kima Chemical

6 Lonza Capsugel

15 Microlex e.U

1 Nanjing Bold Chemical

2 Nomisma Healthcare

2 Novo Excipients

3 Pharmatrans-Sanaq

4 Pluviaendo

3 Prachin Chemical

1 Qianhao Chemical (Hebei) Co., Ltd

1 Qualicaps

27 Roquette

18 Seppic

4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

1 Shijiazhuang Huaxu Pharmaceutical

10 Sigachi Industries

3 The Dow Chemical Company

1 Valens Pharmachem

3 Vasa Pharmachem

1 Zhejiang Huakang Pharmaceutical

EXCIPIENTS BY APPLICATIONS

58 Fillers, Diluents & Binders

52 Coating Systems & Additives

39 Topical

39 Thickeners and Stabilizers

36 Solubilizers

33 Direct Compression

28 Controlled & Modified Release

22 Film Formers & Plasticizers

22 Disintegrants & Superdisintegrants

19 Parenteral

19 Co-Processed Excipients

18 Granulation