Structure via PubChem · Public domain (PubChem)
nystatin
Sign in to saveNystatin, sold under the brand name 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.
OverviewAI-generated
Nystatin is a polyene antifungal compound with the chemical formula C₄₇H₇₅NO₁₇. It has a mass of 925.5035 and a PubChem weight of 926.1. The molecule possesses a charge of 0, an xlogp of -0.2, and a topological polar surface area of 320. It contains 12 hydrogen bond donors and 18 hydrogen bond acceptors.
In clinical applications, nystatin is classified under antibiotics and combinations of antibacterials. It is available in various dose forms, including vaginal inserts, oral capsules, oral suspensions, topical creams, and topical ointments. Brand names for the drug include Bio-Statin, Nystop, and Nyamyc. Upsher-Smith Laboratories, LLC manufactures a human prescription drug containing nystatin for topical use. The compound is also found in combination products with amoxicillin, hydrocortisone, triamcinolone, neomycin, and thiostrepton.
Research and development activity for nystatin is documented in 5895 PubMed entries and 22 ClinicalTrials.gov records. The subject is referenced by 250 other encyclopedia articles.
Synthesized by Vinony from 29 facts across 7 sources: Wikidata, PubMed, PubChem, ClinicalTrials.gov, Rxnorm, Openfda, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.IUPAC_name
- (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-β-L-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
- Drug.C
- 47
- Drug.H
- 75
- Drug.N
- 1
- Drug.O
- 17
- Drug.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
- Drug.StdInChI
- 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
- Drug.StdInChIKey
- VQOXZBDYSJBXMA-NQTDYLQESA-N
- Drug.melting_point
- 44-46
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 458776717
- Drug.image
- Nystatin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 300
- Drug.image2
- Nystatin ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Mycostatin, others
via Wikipedia infobox
Chemical data
- Formula
- C47H75NO17
- Molecular weight
- 926.1 g/mol
- IUPAC name
- (1S,3R,4R,7R,9R,11R,15S,16R,17R,18S,19E,21E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2S,3R,4R,5R,6S)-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
- 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
- InChIKey
- VQOXZBDYSJBXMA-VHFLTRTASA-N
- XLogP
- -0.2
- Polar surface area
- 320 Ų
- H-bond donors
- 12
- H-bond acceptors
- 18
- Formal charge
- 0
via PubChem
Medication
- Generic name
- Nystatin
- Brand names
- Nyamyc, Bio-Statin, Nystop
- Drug class
- Polyene Antifungal, Combinations of antibacterials, Antibiotics
- Active ingredients
- nystatin, amoxicillin / nystatin, hydrocortisone / nystatin, nystatin / triamcinolone, neomycin / nystatin / thiostrepton / triamcinolone, nystatin / tolnaftate
- Route
- Topical
- Dosage form
- Vaginal Insert, Oral Capsule, Oral Suspension, Topical Cream, Topical Ointment
- Type
- Human Prescription Drug
- Manufacturer
- Upsher-Smith Laboratories, LLC
Indications: INDICATIONS AND USAGE Nyamyc® (Nystatin Topical Powder, USP) is indicated in the treatment of cutaneous or mucocutaneous mycotic infections caused by Candida albicans and other susceptible Candida species. Nyamyc® (Nystatin Topical Powder, USP) is not indicated for systemic, oral, intravaginal or… (per FDA label)
Research
5,895 papers- Nystatin.The Medical clinics of North America · 1970
- Nystatin.Annals of the New York Academy of Sciences · 1960
- The Persistence of Nystatin Use for Dermatophyte Infections.Journal of drugs in dermatology : JDD · 2023
- Nystatin LF (Aronex/Abbott).Current opinion in investigational drugs (London, England : 2000) · 2001
- Efficacy of nystatin for the treatment of oral candidiasis: a systematic review and meta-analysis.Drug design, development and therapy · 2016
via PubMed
Clinical Trials
22 registered- PHASE4COMPLETEDAntifungal Prophylaxis in Intensive Care Unit (ICU) PatientsPoliclinico Hospital · NCT01495039
- PHASE3COMPLETEDMagic Mouthwash Plus Sucralfate Versus Benzydamine Hydrochloride for the Treatment of Radiation-induced MucositisJuravinski Cancer Centre Foundation · NCT00814359
- NACOMPLETEDComparative Randomized Study of the Efficacy, Safety, and Toleration of Fluconazole Oral Suspension or Nystatin Oral Suspension in the Treatment of Patients With Oropharyngeal Candidiasis in Association With the Acquired Immunodeficiency SyndromePfizer · NCT00002112
- NACOMPLETEDA Study of Nystatin in the Prevention of Fungal Infections of the Mouth in Patients With AIDS or AIDS-Related SyndromesBristol-Myers Squibb · NCT00002293
- PHASE3COMPLETEDA Study to Compare Efficacy and Safety of an Ovule Containing Terconazole, Clindamycin and Fluocinolone Versus an Ovule Containing Metronidazole, Nystatin and Fluocinolone in the Treatment of Secondary Vulvar/ or Vaginal Symptoms of Infectious Vaginitis/ and Infectious VaginosisJanssen-Cilag, S.A. · NCT01867164
- NACOMPLETEDNystatin Pastilles for the Prevention of Oral Candidiasis in Patients With AIDS or ARCBristol-Myers Squibb · NCT00002057
Wikidata facts
- Instance of
- mixture
- Mass
- 925.5035
Show 6 more facts
- chemical formula
- C₄₇H₇₅NO₁₇
- World Health Organisation international non-proprietary name
- nystatin
- 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
- NCI Thesaurus ID
- C710
- subject has role
- antifungal
- Commons category
- Nystatin
via Wikidata · CC0
~12 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Adverse effects
- Mechanism of action
- Biosynthesis
- History
- Other uses
- Formulations
- Brand names
- References
Nystatin, sold under the brand name 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.
Common side effects when applied to the skin include burning, itching, and a rash. Common side effects when taken by mouth include vomiting and diarrhea. During pregnancy use in the vagina is safe while other formulations have not been studied in this group. It works by disrupting the cell membrane of the fungal cells.
Excerpted from Wikipedia’s “nystatin” article, available under the CC BY-SA 4.0 licence.