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4342-03-4 分子结构
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5-(dimethyltriaz-1-en-1-yl)-1H-imidazole-4-carboxamide

ChemBase编号:729
分子式:C6H10N6O
平均质量:182.1832
单一同位素质量:182.09160897
SMILES和InChIs

SMILES:
c1(c(nc[nH]1)C(=O)N)/N=N/N(C)C
Canonical SMILES:
CN(/N=N/c1[nH]cnc1C(=O)N)C
InChI:
InChI=1S/C6H10N6O/c1-12(2)11-10-6-4(5(7)13)8-3-9-6/h3H,1-2H3,(H2,7,13)(H,8,9)/b11-10+
InChIKey:
FDKXTQMXEQVLRF-ZHACJKMWSA-N

引用这个纪录

CBID:729 http://www.chembase.cn/molecule-729.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
5-(dimethyltriaz-1-en-1-yl)-1H-imidazole-4-carboxamide
5-[(1E)-dimethyltriaz-1-en-1-yl]-1H-imidazole-4-carboxamide
IUPAC传统名
dtic-dome (TN)
dacarbazine
商标名
Deticene
别名
NSC-45388
Dacatic
Deticene
5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide
Dacarbazine
5-[3,3-Dimethyl-1-triazenyl]imidazole-4-carboxamide
Dacarbazino [INN-Spanish]
Dacarbazinum [INN-Latin]
DIC
DTIC
Dtic-Dome
ICDMT
Imidazole Carboxamide
ICDT
DTIE
Biocarbazine R
Dacarbazine
CAS号
4342-03-4
EC号
224-396-1
MDL号
MFCD00057167
PubChem SID
24893683
160964192
PubChem CID
5353562

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 5.890213  质子受体
质子供体 LogD (pH = 5.5) -0.5566359 
LogD (pH = 7.4) -1.3159575  Log P -0.42588896 
摩尔折射率 49.7106 cm3 极化性 16.888016 Å3
极化表面积 99.73 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -0.32  LOG S -2.13 
溶解度 1.36e+00 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
4220 mg/L expand 查看数据来源
DMSO expand 查看数据来源
Methanol expand 查看数据来源
外观
Off-White to Light Yellow Solid expand 查看数据来源
熔点
>205°C (dec) expand 查看数据来源
202°C expand 查看数据来源
疏水性(logP)
-1.6 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer expand 查看数据来源
2-8°C, Protect from light expand 查看数据来源
RTECS编号
NI3950000 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
德国WGK号
3 expand 查看数据来源
危险公开号
45-46-20/21/22-36/37/38 expand 查看数据来源
R:45 expand 查看数据来源
安全公开号
53-36/37/39-45 expand 查看数据来源
S:28-36/37/39-45-53 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
H312-H315-H319-H332-H335-H350 expand 查看数据来源
GHS警示性声明
P201-P261-P280-P305 + P351 + P338-P308 + P313 expand 查看数据来源
个人保护装置
Eyeshields, 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
保存温度
2-8°C expand 查看数据来源
作用靶点
DNA/RNA synthesis expand 查看数据来源
成盐信息
Free Base 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

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02157519 external link
(5-[3,3-Dimethyl-1-triazenyl]imidazole-4-carboxamide; DTIC)
DrugBank -  DB00851 external link
Item Information
Drug Groups approved
Description An antineoplastic agent. It has significant activity against melanomas. (from Martindale, The Extra Pharmacopoeia, 31st ed, p564)
Indication For the treatment of metastatic malignant melanoma. In addition, dacarbazine is also indicated for Hodgkin's disease as a secondary-line therapy when used in combination with other antineoplastic agents.
Pharmacology Dacarbazine is a synthetic analog of naturally occurring purine precursor 5-amino-1H-imidazole-4-carboxamide (AIC). After intravenous administration of dacarbazine, the volume of distribution exceeds total body water content suggesting localization in some body tissue, probably the liver. Its disappearance from the plasma is biphasic with initial half-life of 19 minutes and a terminal half-life of 5 hours. 1 In a patient with renal and hepatic dysfunctions, the half-lives were lengthened to 55 minutes and 7.2 hours. 1 The average cumulative excretion of unchanged DTIC in the urine is 40% of the injected dose in 6 hours. 1 DTIC is subject to renal tubular secretion rather than glomerular filtration. At therapeutic concentrations dacarbazine is not appreciably bound to human plasma protein.
Toxicity LD50=350mg/kg (orally in mice)
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Erratic, slow and incomplete
Half Life 5 hours
Protein Binding Less than 5%
Elimination Dacarbazine is subject to renal tubular secretion rather than glomerular filtration. In man, dacarbazine is extensively degraded. Besides unchanged dacarbazine, 5-aminoimidazole -4 carboxamide (AIC) is a major metabolite of dacarbazine excreted in the urine.
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1221 external link
Research Area: Cancer
Biological Activity:
Dacarbazine(DTIC-Dome) is an antineoplastic chemotherapy drug used in the treatment of various cancers, among them malignant melanoma, Hodgkin lymphoma, sarcoma, and islet cell carcinoma of the pancreas. [1]Dacarbazine belongs to the family of chemicals known as alkylating agents. Dacarbazine alkylates and cross-links DNA during all phases of the cell cycle, resulting in disruption of DNA function, cell cycle arrest, and apoptosis. [2]Dacarbazine is normally administered by injection (a shot) or intravenous infusion (IV) under the immediate supervision of a doctor or nurse. [1]
Sigma Aldrich -  D2390 external link
Application
Dacarbazine is a triazine antineoplastic agent that is used for DNA methylation via formation of methyl adducts. It is used to treat metastatic malignant melanomas and Hodgkin′s when used in combination with other antineoplastic agents. It is used to induce apoptosis in human cells1. It has been used to induce hepatotoxicity in mice2.
Biochem/physiol Actions
Dacarbazine has significant activity against melanomas. It is a synthetic analog of naturally occurring purine precursor 5-amino-1H-imidazole-4-carboxamide (AIC). Dacarbazine appears to exert cytotoxic effects by acting as an alkylating agent, by inhibiting DNA synthesis as a purine analog, and by inducing apoptosis1. Dacarbazine is not cell cycle-phase specific.
Toronto Research Chemicals -  D101400 external link
Dacarbazine is used as an antineoplastic for treatment of malignant melanoma and sarcomas.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • http://www.cancer.gov/drugdictionary/?CdrID=39768
  • Shealy, et al.: Biochem. Pharmacol., 11, 674 (1962)
  • Carter, et al.: Eur. J. Cancer, 8, 85 (1962)
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专利

专利

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