(21E,23E,25E,27E,31E,33E)-20-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,8,11,12,16,18,36-octahydroxy-35,37,38-trimethyl-2,14-dioxo-1-oxacyclooctatriaconta-21,23,25,27,31,33-hexaene-17-carboxylic acid

• ChemBase ID: 528
• Molecular Formular: C47H75NO17
• Molecular Mass: 926.0949
• Monoisotopic Mass: 925.50349995
• SMILES: O1C(OC2CC(O)C(C(O)CC(=O)CC(O)C(O)CCC(O)CC(O)CC(O)CC(=O)OC(C(C(O)C(C)/C=C/C=C/CC/C=C/C=C/C=C/C=C/2)C)C)C(=O)O)[C@@H](O)[C@@H](N)[C@H](O)[C@H]1C
• Canonical SMILES: OC1CCC(O)C(O)CC(=O)CC(O)C(C(=O)O)C(O)CC(/C=C/C=C/C=C/C=C/CC/C=C/C=C/C(C(C(C(OC(=O)CC(CC(C1)O)O)C)C)O)C)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)N)O
• InChI: InChI=1S/C47H75NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-35(65-47-45(60)42(48)44(59)30(4)64-47)26-39(56)41(46(61)62)38(55)24-34(52)23-37(54)36(53)20-19-31(49)21-32(50)22-33(51)25-40(57)63-29(3)28(2)43(27)58/h5-6,8,10-18,27-33,35-39,41-45,47,49-51,53-56,58-60H,7,9,19-26,48H2,1-4H3,(H,61,62)/b6-5+,10-8+,13-11+,14-12+,17-15+,18-16+/t27?,28?,29?,30-,31?,32?,33?,35?,36?,37?,38?,39?,41?,42+,43?,44-,45+,47?/m1/s1
• InChIKey: ZDFDJJJGIRGMBE-AFARJNEBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (21E,23E,25E,27E,31E,33E)-20-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,8,11,12,16,18,36-octahydroxy-35,37,38-trimethyl-2,14-dioxo-1-oxacyclooctatriaconta-21,23,25,27,31,33-hexaene-17-carboxylic acid
• IUPAC Traditional name: nystatin
• Brand Name: Barstatin 100; Candex; Korostatin; Myco-Triacet Ii; Mycolog-Ii; Mycostatin; Mykacet; Mykinac; Mytrex F; Nadostine; Nilstat; Nyaderm; Nysert; Nystaform; Nystatin sodium; Nystatin, sodium salt; Nystatin-Triamcinolone Acetonide; Nystex; Nystop; PMS Nystatin; Pedi-Dri; Sodium nystatin; nystatin dihydrate
• Synonyms: Nystatin

Database IDs

• CAS Number: 1400-61-9
• PubChem SID: 160963991; 46504780
• PubChem CID: 11953884

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6208467
• H Acceptors: 17
• H Donor: 12
• LogD (pH = 5.5): -2.669163
• LogD (pH = 7.4): -2.6722584
• Log P: -2.6661546
• Molar Refractivity: 245.175 cm^3
• Polarizability: 95.01487 Å^3
• Polar Surface Area: 327.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.82
• LOG S: -4.15
• Solubility (Water): 6.60e-02 g/l

PROPERTIES

Physical Property

• Solubility: 360 mg/L
• Hydrophobicity(logP): 0.5

DETAILS

DrugBank - DB00646

• Drug Groups: approved
• Description: Nystatin is a polyene antifungal drug to which many molds and yeasts are sensitive, including Candida spp. Nystatin has some toxicity associated with it when given intravenously, but it is not absorbed across intact skin or mucous membranes. It is considered a relatively safe drug for treating oral or gastrointestinal fungal infections.
• Indication: For treatment of cutaneous or mucocutaneous mycotic infections caused by Candida species
• Pharmacology: Nystatin is an antibiotic which is both fungistatic and fungicidal in vitro against a wide variety of yeasts and yeast-like fungi, including Candida albicans, C. parapsilosis, C. tropicalis, C. guilliermondi, C. pseudotropicalis, C. krusei, Torulopsis glabrata, Tricophyton rubrum, T. mentagrophytes. Nystatin acts by binding to sterols in the cell membrane of susceptible species resulting in a change in membrane permeability and the subsequent leakage of intracellular components. On repeated subculturing with increasing levels of nystatin, Candida albicans does not develop resistance to nystatin. Generally, resistance to nystatin does not develop during therapy. However, other species of Candida (C. tropicalis, C. guilliermondi, C. krusei, and C. stellatoides) become quite resistant on treatment with nystatin and simultaneously become cross resistant to amphotericin as well. This resistance is lost when the antibiotic is removed. Nystatin exhibits no appreciable activity against bacteria, protozoa, or viruses.
• Affected Organisms: Fungi
• Absorption: Nystatin is not absorbed from intact skin or mucous membrane.
• References: Akaike N, Harata N: Nystatin perforated patch recording and its applications to analyses of intracellular mechanisms. Jpn J Physiol. 1994;44(5):433-73. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Akaike N, Harata N: Nystatin perforated patch recording and its applications to analyses of intracellular mechanisms. Jpn J Physiol. 1994;44(5):433-73. Pubmed