(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编号: 528
• 分子式: C47H75NO17
• 平均质量: 926.0949
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: nystatin
• 商标名: 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
• 别名: Nystatin

登记号

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

理论计算性质

JChem

• Acid pKa: 3.6208467
• 质子受体: 17
• 质子供体: 12
• LogD (pH = 5.5): -2.669163
• LogD (pH = 7.4): -2.6722584
• Log P: -2.6661546
• 摩尔折射率: 245.175 cm^3
• 极化性: 95.01487 Å^3
• 极化表面积: 327.45 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -2.82
• LOG S: -4.15
• 溶解度: 6.60e-02 g/l

分子性质

理化性质

• 溶解度: 360 mg/L
• 疏水性(logP): 0.5

详细说明

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

参考文献

• 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