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75520-89-7 分子结构
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N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide

ChemBase编号:1205
分子式:C22H25NO6
平均质量:399.437
单一同位素质量:399.16818753
SMILES和InChIs

SMILES:
O(c1c2c(CC[C@H](NC(=O)C)c3c2ccc(OC)c(=O)c3)cc(OC)c1OC)C
Canonical SMILES:
COc1c(OC)cc2c(c1OC)c1ccc(c(=O)cc1[C@H](CC2)NC(=O)C)OC
InChI:
InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1
InChIKey:
IAKHMKGGTNLKSZ-INIZCTEOSA-N

引用这个纪录

CBID:1205 http://www.chembase.cn/molecule-1205.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
N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide
N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2,4,6,11,14-hexaen-10-yl]acetamide
N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0^{2,7}]hexadeca-1(16),2,4,6,11,14-hexaen-10-yl]acetamide
N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0^{2,7}]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide
IUPAC传统名
colchicine
N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.02,7]hexadeca-1(16),2,4,6,11,14-hexaen-10-yl]acetamide
商标名
Colbenemid
Col-probenecid
Condylon
Proben-C
别名
秋水仙素
秋水仙碱
Colchicine
(S)-N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide
N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]ethanamide
Colchicin
Colchicina
Colchicinum
Colchicine
N-[(7S)-5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide
(-)-Colchicine
Colchineos
Colchisol
Colcin
Colsaloid
Condylon
NSC 757
(S)-Colchicine >95%
(R)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide
(+)-Colchicine
(R)-Colchicine
Colchiceine methyl ether
Artrichine
CAS号
75520-89-7
64-86-8
EC号
200-598-5
MDL号
MFCD00078484
Beilstein号
2228813
默克索引号
142471
PubChem SID
24892656
160964667
24278348
PubChem CID
6167
CHEBI ID
27882
ATC码
M04AC01
CHEMBL
107
Chemspider ID
5933
DrugBank ID
DB01394
IUPHAR配体索引
2367
KEGG ID
D00570
美国药典/FDA物质标识码
SML2Y3J35T
维基百科标题
Colchicine
Medline Plus
a682711

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 15.057998  质子受体
质子供体 LogD (pH = 5.5) 1.4619884 
LogD (pH = 7.4) 1.4619886  Log P 1.4619886 
摩尔折射率 111.3756 cm3 极化性 41.70993 Å3
极化表面积 83.09 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.59  LOG S -4.16 
溶解度 2.76e-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
45 mg/mL at 25 oC [SEIDELL,A (1941)] expand 查看数据来源
Chloroform expand 查看数据来源
DMSO expand 查看数据来源
ethanol: soluble50 mg/mL 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
Pale Yellow Solid expand 查看数据来源
white to yellow powder expand 查看数据来源
Yellow Solid expand 查看数据来源
熔点
106-132°C expand 查看数据来源
150-152°C expand 查看数据来源
150-160 °C (dec.)(lit.) expand 查看数据来源
155-157°C expand 查看数据来源
ca 150°C dec. expand 查看数据来源
比旋光度
[α]24/D -443°, c = 1.7 in H2O expand 查看数据来源
疏水性(logP)
1.30 [HANSCH,C ET AL. (1995)] expand 查看数据来源
保存条件
-20°C Freezer expand 查看数据来源
Room Temperature (15-30°C), Protect from light expand 查看数据来源
保存注意事项
Light Sensitive expand 查看数据来源
RTECS编号
GH0700000 expand 查看数据来源
欧盟危险性物质标志
剧毒(Highly toxic) 剧毒(Highly toxic) (T+) expand 查看数据来源
联合国危险货物编号
1544 expand 查看数据来源
UN1544 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
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
联合国危险货物等级
6.1 expand 查看数据来源
联合国危险货物包装类别(PG)
1 expand 查看数据来源
I expand 查看数据来源
澳大利亚Hazchem
2X expand 查看数据来源
危险公开号
46-28 expand 查看数据来源
R:26/28 expand 查看数据来源
安全公开号
53-16-26-28-36/37-45 expand 查看数据来源
53-45 expand 查看数据来源
S:13-45 expand 查看数据来源
欧盟危险货物分类
T2 expand 查看数据来源
欧盟危险识别号(EUHIN)
6.1B expand 查看数据来源
美国ERG指导号
151 expand 查看数据来源
TSCA收录
expand 查看数据来源
GHS危险品标识
GHS05 expand 查看数据来源
GHS06 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
H300 + H330-H318-H340 expand 查看数据来源
H300-H340 expand 查看数据来源
GHS警示性声明
P201-P260-P264-P280-P284-P301 + P310 expand 查看数据来源
P281-P301+P310-P321-P308+P313-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
RID/ADR
UN 1544 6.1/PG 1 expand 查看数据来源
给药途径
Oral tablets expand 查看数据来源
排泄
Primarily feces, urine 10-20% expand 查看数据来源
半衰期
9.3 - 10.6 hours expand 查看数据来源
法定药品分级
RX/POM expand 查看数据来源
妊娠期药物分类
X expand 查看数据来源
相关基因信息
human ... ABCB1(5243), CYP3A4(1576)mouse ... Abcb1a(18671), Abcb1b(18669) expand 查看数据来源
生物活性机理
Exact mechanism unknown expand 查看数据来源
Interferes with kinin formation expand 查看数据来源
Leukocyte migration inhibitor expand 查看数据来源
Phagocytosis inhibitor expand 查看数据来源
Reduces phagocytosis with inflammatory expand 查看数据来源
Response abatement expand 查看数据来源
纯度
≥95% (HPLC) expand 查看数据来源
≥96.0% (HPLC) expand 查看数据来源
95% expand 查看数据来源
95% (dry wt.) expand 查看数据来源
质检报告
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
适用性
plant cell culture tested expand 查看数据来源
杂质
≤10% ethyl acetate + H2O expand 查看数据来源
≤3% water expand 查看数据来源
10% ethyl acetate and chloroform expand 查看数据来源
生物来源
Chief alkaloid from Colchicum autumnale, many other Colchicum spp., several Merendera spp., Gloriosa superba and others (Liliaceae) expand 查看数据来源
应用领域
Antirheumatic expand 查看数据来源
Cytostatic expand 查看数据来源
Immunosuppressive expand 查看数据来源
Potential HIV inhibitor expand 查看数据来源
产品线
BioReagent expand 查看数据来源
Empirical Formula (Hill Notation)
C22H25NO6 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02101406 external link
Special Shipping Requirements: Hazardous Material. Contact Customer Service for details. $8.00 additional service charge per shipment.
MP Biomedicals -  05208170 external link
MP Biomedicals Rare Chemical collection
DrugBank -  DB01394 external link
Item Information
Drug Groups approved
Description A major alkaloid from Colchicum autumnale L. and found also in other Colchicum species. Its primary therapeutic use is in the treatment of gout, but it has been used also in the therapy of familial Mediterranean fever (periodic disease). [PubChem]
Indication For treatment and relief of pain in attacks of acute gouty arthritis.
Pharmacology Colchicine is a highly poisonous alkaloid, originally extracted from plants of the genus Colchicum (Autumn crocus, also known as the "Meadow saffron"). Originally used to treat rheumatic complaints and especially gout, it was also prescribed for its cathartic and emetic effects. Its present medicinal use is mainly in the treatment of gout; as well, it is being investigated for its potential use as an anti-cancer drug. It can also be used as initial treatment for pericarditis and preventing recurrences of the condition.
Toxicity The onset of toxic effects is usually delayed for several hours or more after the ingestion of an acute overdose. Nausea, vomiting, abdominal pain, and diarrhea occur first. The diarrhea may be bloody due to hemorrhagic gastroenteritis. Burning sensations of the throat, stomach, and skin may be prominent symptoms. Extensive vascular damage may result in shock. Kidney damage, evidenced by hematuria and oliguria, may occur. Muscular weakness may be marked, and ascending paralysis of the central nervous system may develop; the patient usually remains conscious. Delirium and convulsions may occur. Death due to respiratory arrest may result. Although death from the ingestion of as little as 7 mg has been reported, much larger doses have been survived .
Affected Organisms
Humans and other mammals
Biotransformation Probably hepatic. Although colchicine metabolites have not been identified in humans, metabolism by mammalian hepatic microsomes has been demonstrated in vitro.
Absorption Colchicine is rapidly absorbed after oral administration, probably from the jejunum and ileum. However, the rate and extent of absorption are variable, depending on the tablet dissolution rate; variability in gastric emptying, intestinal motility, and pH at the absorption site; and the extent to which colchicine is bound to microtubules in gastrointestinal mucosal cells.
Half Life Elimination half-life is approximately 1 hour in healthy subjects, although a study with an extended sampling time reported mean terminal elimination half-life values of approximately 9 to 10.5 hours. Other studies have reported half-life values of approximately 2 hours in patients with alcoholic cirrhosis and approximately 2.5 hours in patients with familial Mediterranean fever.
Protein Binding Low to moderate (30 to 50%).
Elimination In healthy volunteers (n=12) 40 – 65% of 1 mg orally administered colchicine was recovered unchanged in urine.
Enterohepatic recirculation and biliary excretion are also postulated to play a role in colchicine elimination.
Distribution * 5 to 8 L/kg [healthy young volunteers]
Clearance * 0.17 L/hr/kg [familial Mediterranean fever patients with end-stage renal disease]
* 0.73 L/hr/kg [familial Mediterranean fever patients with normal renal function]
External Links
Wikipedia
RxList
Drugs.com
DrugBank -  DB08117 external link
Drug information: experimental
Sigma Aldrich -  C9754 external link
包装
1, 5 g in poly bottle
100, 500 mg in poly bottle
Biochem/physiol Actions
Antimitotic agent that disrupts microtubules by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pathway.
Sigma Aldrich -  C3915 external link
Biochem/physiol Actions
Colchicine is an inhibitor of microtubule polymerization which blocks chromosome segregation during meiosis. Consequently, Colchicine is used to induce polyploidy (tetraploid) in plant cells.
Sigma Aldrich -  855774 external link
Application
有关该生物碱在新陈代谢和药代动力学方面的综述,请查看 Z. Gastroenterol.。1,2
Sigma Aldrich -  27650 external link
Other Notes
Binds specifically with tubulin thus interfering with microtubule organization.1
Toronto Research Chemicals -  C640001 external link
The R-enantiomer of Colchicine (C640000). An antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lin
Toronto Research Chemicals -  C640000 external link
An antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pa

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Lunduena, R.F., et al.: Curr. Opin. Cell Biol., 4, 53 (1992)
  • Ceccatelli, S., et al.: Neuroreport, 8, 3779 (1992)
  • Want, T.H., et al.: J. Biol. Chem., 273, 4928 (1992)
  • Andreu, J.M., et al.: Biochemistry, 37, 8356 (1992)
  • Jordan, A., et al.: Med. Res. Rev
  • Lunduena, R.F., et al.: Curr. Opin. Cell Biol., 4, 53 (1992)
  • Ceccatelli, S., et al.: Neuroreport, 8, 3779 (1992)
  • Want, T.H., et al.: J. Biol. Chem., 273, 4928 (1992)
  • Andreu, J.M., et al.: Biochemistry, 37, 8356 (1992)
  • Jordan, A., et al.: Med. Res. Rev
  • J.Am.Coll.Cardiol. (26, No. 6, 1549-57, 1995)
  • Local delivery of biodegradable microparticles containing colchicine or a colchicine analogue: effects on restenosis and implications for catheter-based drug delivery.
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专利

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