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126-07-8 分子结构
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(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

ChemBase编号:283
分子式:C17H17ClO6
平均质量:352.76628
单一同位素质量:352.07136594
SMILES和InChIs

SMILES:
Clc1c2O[C@]3([C@@H](CC(=O)C=C3OC)C)C(=O)c2c(OC)cc1OC
Canonical SMILES:
COC1=CC(=O)C[C@H]([C@@]21Oc1c(C2=O)c(OC)cc(c1Cl)OC)C
InChI:
InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1
InChIKey:
DDUHZTYCFQRHIY-RBHXEPJQSA-N

引用这个纪录

CBID:283 http://www.chembase.cn/molecule-283.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
IUPAC传统名
griseofulvin
(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
商标名
Amudane
Biogrisin-fp
Curling factor
Delmofulvina
Fulcin
Fulcine
Fulvican grisactin
Fulvicin
Fulvicin P/G
Fulvicin U/F
Fulvicin-P/G
Fulvicin-U/F
Fulvina
Fulvinil
Fulvistatin
Fungivin
Greosin
Gresfeed
Gricin
Grifulin
Grifulvin
Grifulvin V
Gris-PEG
Grisactin
Grisactin Ultra
Griscofulvin
Grisefuline
Griseo
Griseofulvin forte
Griseofulvin-forte
Griseomix
Grisetin
Grisofulvin
Grisovin
Grisovin FP
Grizeofulvin
Grysio
Guservin
Lamoryl
Likuden
Likunden
Murfulvin
Neo-Fulcin
Neocid
Poncyl
Spirofulvin
Sporostatin
Sporostatin xan
Xuanjing
别名
(2S)-反式-7-氯-2′,4,6-三甲氧基-6′-甲基螺(苯并呋喃-2[3H],1′-[2]环己烯)-3,4′-二酮
灰黄霉素
(+)-灰黄霉素
灰黄霉素
Griseofulvina [INN-Spanish]
Griseofulvine [INN-French]
Griseofulvinum [INN-Latin]
Griseofulvin
(1'S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione
(2S)-trans-7-Chloro-2′,4,6-trimethoxy-6′-methylspiro(benzofuran-2[3H],1′-[2]cyclohexene)-3,4′-dione
Griseofulvin
(+)-Griseofulvin
(1'S,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methyl-spiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione
Amudane
Fulcin
Grisovi
(+)-Griseofulvin
Spirofulvin
Sporostatin
Xuanjing
Grisovin
Fulvicin
Curling factor
Gricin
Grifulvin
Grisactin
Norofulvin
Likuden
Idifulvin
(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
Griseofulvin
CAS号
126-07-8
EC号
204-767-4
MDL号
MFCD00082343
Beilstein号
95226
默克索引号
144549
PubChem SID
24895099
46508437
24895185
160963746
24869893
PubChem CID
441140
CHEBI ID
27779
ATC码
D01BA01
D01AA08
CHEMBL
562
Chemspider ID
389934
DrugBank ID
DB00400
KEGG ID
D00209
美国药典/FDA物质标识码
32HRV3E3D5
维基百科标题
Griseofulvin
Medline Plus
a682295

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 17.688671  质子受体
质子供体 LogD (pH = 5.5) 2.1721375 
LogD (pH = 7.4) 2.1721375  Log P 2.1721375 
摩尔折射率 87.8459 cm3 极化性 33.75892 Å3
极化表面积 71.06 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 2.71  LOG S -3.84 
溶解度 5.04e-02 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
8.64 mg/L expand 查看数据来源
Acetone expand 查看数据来源
Benzene expand 查看数据来源
Ethanol expand 查看数据来源
Ethyl Acetate expand 查看数据来源
Methanol expand 查看数据来源
外观
Crystalline Solid expand 查看数据来源
熔点
216-220 °C expand 查看数据来源
218 - 220°C expand 查看数据来源
218-220 °C(lit.) expand 查看数据来源
218-220°C expand 查看数据来源
220°C expand 查看数据来源
比旋光度
[α]17/D +370°, c = 1 in chloroform expand 查看数据来源
[α]20/D +355±5°, c = 1% in DMF(lit.) expand 查看数据来源
疏水性(logP)
2 expand 查看数据来源
2.053 expand 查看数据来源
保存条件
-20°C Freezer expand 查看数据来源
RTECS编号
WG9800000 expand 查看数据来源
欧盟危险性物质标志
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
60-61-40-43 expand 查看数据来源
61-40-43 expand 查看数据来源
安全公开号
22-36/37/39-45 expand 查看数据来源
53-45 expand 查看数据来源
TSCA收录
expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H317-H351-H360 expand 查看数据来源
H360-H351-H317 expand 查看数据来源
GHS警示性声明
P201-P280-P308 + P313 expand 查看数据来源
P261-P280-P302+P352-P321-P405-P501A expand 查看数据来源
个人保护装置
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand 查看数据来源
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand 查看数据来源
保存温度
-20°C expand 查看数据来源
给药途径
Oral expand 查看数据来源
生物利用度
Highly variable (25 to 70%) expand 查看数据来源
半衰期
9-21 hours expand 查看数据来源
代谢
Hepatic demethylation and glucuronidation expand 查看数据来源
法定药品分级
POM (UK), ?-only (U.S.) expand 查看数据来源
妊娠期药物分类
B3 (Australia), C (United States) expand 查看数据来源
生物活性机理
Binds tightly to new keratin which becomes highly resistant to fungal invasions expand 查看数据来源
纯度
≥95% (HPLC) expand 查看数据来源
95% expand 查看数据来源
97% expand 查看数据来源
97.0-102.0% expand 查看数据来源
级别
VETRANAL™, analytical standard expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
适用性
meets USP testing specifications expand 查看数据来源
生物来源
from Penicillium griseofulvum expand 查看数据来源
Metab. of Penicillium griseofulvum expand 查看数据来源
应用领域
activity against: Trichophyton rubrum expand 查看数据来源
Antifungal agent against expand 查看数据来源
Epidermophyton floccosum. expand 查看数据来源
Microsporum audouini expand 查看数据来源
Microsporum canis expand 查看数据来源
Microsporum gypseum expand 查看数据来源
Trichophyton crateriform expand 查看数据来源
Trichophyton gallinae expand 查看数据来源
Trichophyton interdigitalis expand 查看数据来源
Trichophyton megnini expand 查看数据来源
Trichophyton mentagrophytes expand 查看数据来源
Trichophyton schoenleini expand 查看数据来源
Trichophyton sulphureum expand 查看数据来源
Trichophyton tonsurans expand 查看数据来源
Trichophyton verrucosum expand 查看数据来源
Empirical Formula (Hill Notation)
C17H17ClO6 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia TRC TRC
DrugBank -  DB00400 external link
Item Information
Drug Groups approved
Description An antifungal antibiotic. Griseofulvin may be given by mouth in the treatment of tinea infections. [PubChem]
Indication For the treatment of ringworm infections of the skin, hair, and nails, namely: tinea corporis, tinea pedis, tinea cruris, tinea barbae, cradle cap or other conditions caused by Trichophyton or Microsporum fungi.
Pharmacology Griseofulvin is a mycotoxic metabolic product of Penicillium spp. It was the first available oral agent for the treatment of dermatophytoses and has now been used for more than forty years. Griseofulvin is fungistatic with in vitro activity against various species of Microsporum Epidermophyton, and Trichophyton. It has no effect on bacteria or on other genera of fungi. Following oral administration, griseofulvin is deposited in the keratin precursor cells and has a greater affinity for diseased tissue. The drug is tightly bound to the new keratin which becomes highly resistant to fungal invasions. Once the keratin-Griseofulvin complex reaches the skin site of action, it binds to fungal microtubules (tubulin) thus altering fungal mitosis.
Toxicity Side effects are minor: headaches, gastrointestinal reactions and cutaneous eruptions
Affected Organisms
Yeast and other Trichophyton or Microsporum fungi
Biotransformation Primarily hepatic with major metabolites being 6-methyl-griseofulvin and its glucuronide conjugate.
Absorption Poorly absorbed from GI ranging from 25 to 70% of an oral dose. Absorption is significantly enhanced by administration with or after a fatty meal.
Half Life 9-21 hours
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich -  856444 external link
Features and Benefits
抗有丝分裂。
Sigma Aldrich -  G2664 external link
Biochem/physiol Actions
Griseofulvin disrupts microtubule assembly and mitotic spindle stucture possibly via tubulin aggregation.
Sigma Aldrich -  G4753 external link
Biochem/physiol Actions
Antifungal. Mode of action: Disrupts the mitotic spindle structure and inhibits nuclear division.1 Induces apoptosis in human tumor cell lines.2
包装
5, 25, 50 g in poly bottle
Sigma Aldrich -  46309 external link
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC
Toronto Research Chemicals -  G787500 external link
It is an antifungal drug. It is used both in animal and in humans, to treat rigworm infections of the skin and nails. It is derived from the mold Penicillium griseofulvum.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
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