基本情報
- CAS
1403-17-4- 標準SMILES
CC1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C(OC2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)CC(O)C(C(=O)O)C(O)CC(=O)CC(O)CC(O)CC(O)CC(=O)CCCC(=O)CC(=O)OC1C(C)CC(C)C(O)CC(=O)c1ccc(N)cc1- InChIKey
OPGSFDUODIJJGF-JBUZINEHSA-N- 分子式
- C59H84N2O18
- 平均分子量
- 1,109.3 g/mol
- 単同位体質量
- 1,108.57191383
概要
Candicidin D is a 38-membered ring lactone containing seven (E)-double bonds between positions 22 and 35 and substituted by hydroxy groups at positions 9, 11, 13, 17 and 19, oxo groups at positions 3, 7 and 15, a carboxy group at position 18, a 3-amino-3,6-dideoxymannopyranosyloxy group at position 21, a methyl group at position 36 and a 7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl group at position 37. It is the major component of candicidin, a mixture of antifungal heptaene macrolides obtained from a strain of Streptomyces griseus. It has a role as a bacterial metabolite and an antifungal drug. It is a macrolide antibiotic and a polyene antibiotic.
名称と識別子
- 優先名称
- Candicidin
- IUPAC
- (23E,25E,27E,29E,31E,33E,35E)-22-[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-38-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-10,12,14,18,20-pentahydroxy-37-methyl-2,4,8,16-tetraoxo-1-oxacyclooctatriaconta-23,25,27,29,31,33,35-heptaene-19-carboxylic acid
- 英語名
- Candicidin
- 分子式
- C21H36O5
- 分子量
- 368.51
名称と別名
CANDICIDINCandeptin1403-17-4CandizidinCandicidinaCandicidineCandicidinum48N2IYJ202DTXSID301014435RefChem:56983G01AA04CHEBI:354984
名称をさらに表示
カンジシジンCandicidin complexcandimonCARBOPRSTLevorinumNSC 94219Canitracin
DTXCID301437025NSC94219NSC-94219215-763-7NSC-759868VanobidCandicidin D1(23E,25E,27E,29E,31E,33E,35E)-22-[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-38-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-10,12,14,18,20-pentahydroxy-37-methyl-2,4,8,16-tetraoxo-1-oxacyclooctatriaconta-23,25,27,29,31,33,35-heptaene-19-carboxylic acid
データベース識別子
- CAS
1403-17-4- PubChem CID
- 10079874
- DTXSID
DTXSID301014435- ChEMBL
CHEMBL1200647- ChEBI
CHEBI:3349- EC Number
- 215-763-7
物性
構造計算による物性
- XLogP
- 1.8
- 極性表面積
- 364 Ų
- 水素結合供与体数
- 11
- 水素結合受容体数
- 20
- 回転可能結合数
- 10
- 重原子数
- 79
- 形式電荷
- 0
- 複雑度
- 2,130
実験および物理化学的性質
DrugsPharmaceuticals -> Antibiotics
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
物理化学的性質
- 沸点
- 878.79 °C · 878.79°C (rough estimate)
- 比重(密度)
- 1.11 · 1.1100 (rough estimate)
- 屈折率
- 1.62 · 1.6200 (estimate)
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- 4.9 · DMSO:4.9(Max Conc. mg/mL);10.08(Max Conc. mM)Ethanol:12.5(Max Conc. mg/mL);25.72(Max Conc. mM)
- 外見
- A solid
- 色
- Light yellow to light brown
- 由来生物
- Streptomyces griseus
- 水溶解度
- 13.47 g/L · 13.47g/L(21℃)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- wgk
- WGK 3
- 毒性
- LD50 i.p. in mice: 14 mg/kg (Vining)
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Pharmacodynamics
Candicidin is a polyene antifungal antibiotic produced by a strain of <i>Streptomyces griseus</i>. It is especially effective against <i>Candida albicans</i> (more effective than amphotericin B), and is administered intravaginally in the treatment of vulvovaginal candidiasis.
Mechanism of Action
Ergosterol, the principal sterol in the fungal cytoplasmic membrane, is the target site of action of Candicidin. Candicidin binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death. There is some evidence that the binding site in the cell wall may be to fatty acids or fatty acid esters and that this binding capacity must be satisfied before candicidin can bring about its lethal effect by binding to sterol in the cell membrane.
MeSH Pharmacological Classification
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.
Substances that inhibit the growth or reproduction of BACTERIA.
応用分野
使用Candicidin is a macrocyclic heptaene antifungal complex produced by Streptomyces griseus and isolated by Lechevalier and colleagues in 1953. The candicidin complex comprises analogues A, B, C and D, with candicidin D as the major component. Candicidin is active against fungi, in particular Candida albicans, and is used clinically to treat vaginal candidiasis. Like all polyene antifungal metabolites, candicidin acts by binding to ergosterol and disrupting the fungal membrane.
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