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甲硫尿嘧啶

甲硫尿嘧啶用途

Methylthiouracil 是一种抗甲状腺剂。Methylthiouracil 抑制 TNF-α 和 IL-6 的产生以及 NF-κB 和 ERK1/2 的活化。

甲硫尿嘧啶名称

[ CAS 号 ]:
56-04-2

[ 中文名 ]:
甲基硫脲嘧啶

[ 英文名 ]:
Methylthiouracil

[中文别名 ]:

[英文别名 ]:

4-Hydroxy-2-mercapto-6-methylpyrimidine
6-Methyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone
Metiur
4(3H)-pyrimidinone, 2-mercapto-6-methyl-
2-Mercapto-4-methyl-6-hydroxypyrimidine
Methiure
2(1H)-pyrimidinethione, 4-hydroxy-6-methyl-
4(1H)-Pyrimidinone, 2,3-dihydro-6-methyl-2-thioxo-
6-Hydroxy-2-mercapto-4-methylpyrimidine
6-Methyl-2-sulfanylpyrimidin-4(3H)-one

甲硫尿嘧啶生物活性

[ 描述 ]:

Methylthiouracil 是一种抗甲状腺剂。Methylthiouracil 抑制 TNF-α 和 IL-6 的产生以及 NF-κB 和 ERK1/2 的活化。

[ 相关类别 ]:

信号通路 >> 免疫及炎症 >> 白细胞介素相关

信号通路 >> 细胞凋亡 >> TNF受体

研究领域 >> 炎症/免疫

[ 靶点 ]

NF-κB

TNF-α

IL-6

ERK1

ERK2

[体外研究]

在加入LPS(100ng/mL)4小时后,用各种浓度的MTU(0-20μM)处理HUVEC 6小时。 MTU抑制内皮细胞中LPS介导的高通透性,最佳效果发生在5μM以上。通过用F-肌动蛋白标记的荧光素鬼笔环肽对HUVEC单层进行免疫荧光染色,检测MTU对HUVEC肌动蛋白细胞骨架排列的影响。对照HUVEC在整个细胞中表现出F-肌动蛋白的随机分布,其中肌动蛋白丝束在细胞边界处有一些定位。 LPS(100 ng/mL)对屏障的破坏表现为HUVEC中细胞旁间隙的形成。此外,用MTU(10或20μM)进行后处理导致LPS诱导的细胞间隙的形成被抑制,形成致密的F-肌动蛋白环。为了测试MTU的细胞毒性,在用MTU处理24小时的HUVEC中进行细胞活力测定。在浓度高达20μM时,MTU不会影响细胞活力[1]。

[体内研究]

MTU处理导致LPS诱导的染料腹膜渗漏的显着抑制。小鼠的平均循环血量为72mL/kg。由于本研究中平均小鼠体重为27 g,平均血容量为2 mL,因此注射MTU(142或284μg/ kg)导致外周血中最大浓度为10或20μM[1]。

[细胞实验]

MTT用作细胞活力的指标。原代人脐静脉内皮细胞（HUVEC）以5×103细胞/孔的密度在96孔板中生长。 24小时后，用新鲜培养基洗涤细胞，并用MTU（0-20μM）处理。孵育48小时后，洗涤细胞，加入100μLMTT（1mg / mL），然后温育4小时。最后，加入DMSO（150μL）以溶解形成的甲salt盐，并通过使用酶标仪在540nm处测量OD来确定甲salt盐的量[1]。

[动物实验]

小鼠[1]在该研究中使用雄性C57BL / 6小鼠（6-7周龄;平均体重，27g）。给小鼠施用LPS（0.3mg /小鼠或15mg / kg，静脉内）。 4小时后，用MTU（142或284μg/ kg，6小时）静脉内处理小鼠，并在生理盐水中注射1％伊文思蓝染料溶液。 6小时后，处死小鼠并通过用5mL生理盐水洗涤腔并通过以200xg离心10分钟来收集腹膜渗出物。在650nm处读取上清液的吸光度。血管渗透率表示为渗透到腹膜腔中的μg染料/小鼠，并使用标准曲线确定。

[参考文献]

[1]. Ku SK, et al. Anti-inflammatory effects of methylthiouracil in vitro and in vivo. Toxicol Appl Pharmacol. 2015 Nov 1;288(3):374-86.

[相关活性小分子]

甲硫尿嘧啶物理化学性质

[ 密度 ]:
1.4±0.1 g/cm3

[ 沸点 ]:
342.3ºC at 760 mmHg

[ 熔点 ]:
~330 °C (dec.)(lit.)

[ 分子式 ]:
C₅H₆N₂OS

[ 分子量 ]:
142.179

[ 闪点 ]:
160.8ºC

[ 精确质量 ]:
142.020081

[ PSA ]:
80.74000

[ LogP ]:
0.31

[ 外观性状 ]:
白色粉末

[ 折射率 ]:
1.638

[ 储存条件 ]:
室温

[ 稳定性 ]:
Stability Incompatible with strong oxidizing agents, iodine, metals.

[ 水溶解性 ]:
INSOLUBLE

甲硫尿嘧啶MSDS

详细MSDS(安全技术说明书)

甲硫尿嘧啶毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YR0875000

CHEMICAL NAME :: Uracil, 6-methyl-2-thio-

CAS REGISTRY NUMBER :: 56-04-2

LAST UPDATED :: 199801

DATA ITEMS CITED :: 20

MOLECULAR FORMULA :: C5-H6-N2-O-S

MOLECULAR WEIGHT :: 142.19

WISWESSER LINE NOTATION :: T6MYMVJ BUS F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NATUAS Nature. (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736) V.1- 1869- Volume(issue)/page/year: 157,659,1946

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 920 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 13,882,1958

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: AD277-689

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85KYAH "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989 Volume(issue)/page/year: 11,963,1989 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5950 mg/kg/17W-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: NATUAS Nature. (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736) V.1- 1869- Volume(issue)/page/year: 157,659,1946 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9100 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Endocrine - thyroid tumors

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 19,870,1959

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 196 gm/kg/1Y-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors Endocrine - thyroid tumors

REFERENCE :: CANCAR Cancer (Philadelphia). (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1948- Volume(issue)/page/year: 40,2188,1977

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 53750 mg/kg/65W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Endocrine - thyroid tumors

REFERENCE :: BJCAAI British Journal of Cancer. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants. RG21 2XS, UK) V.1- 1947- Volume(issue)/page/year: 7,181,1953

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 27783 mg/kg/60W-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Endocrine - thyroid tumors

REFERENCE :: BJCAAI British Journal of Cancer. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants. RG21 2XS, UK) V.1- 1947- Volume(issue)/page/year: 4,223,1950 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 1344 mg/kg

SEX/DURATION :: female 19-42 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Effects on Newborn - other neonatal measures or effects

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,1281,1953

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 375 mg/kg

SEX/DURATION :: female 10-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Effects on Newborn - behavioral

REFERENCE :: ZYDXEN Zhongguo Yike Daxue Xuebao. Journal of China Medical University. (China International Book Trading Corp. POB 399, Beijing 100044, Peop. Rep. China) V.1- 19??-m/* Volume(issue)/page/year: 21,349,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 10 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: KAIZAN Kaibogaku Zasshi. Journal of Anatomy. (Nippon Kaibo Gakkai, c/o Tokyo Daigaku Igakubu, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113, Japan) V.1- 1928- Volume(issue)/page/year: 42,90,1967

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 900 mg/kg

SEX/DURATION :: female 1-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - endocrine system

REFERENCE :: OSDIAF Osaka Shiritsu Daigaku Igaku Zasshi. Journal of the Osaka City Medical Center. (Osaka, Japan) V.4-23, 1955-74. For publisher information, see OIGZDE. Volume(issue)/page/year: 8,1281,1959 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 7,53,1974 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 7,53,1974 IARC Cancer Review:Group 2B IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW AMSSAQ Acta Medica Scandinavica, Supplement. (Almqvist & Wiksell, POB 45150, S-10430 Stockholm, Sweden) No.1-730, 1921-88. Volume(issue)/page/year: 196,85,1947 TOXICOLOGY REVIEW MJAUAJ Medical Journal of Australia. (Australasian Medical Pub. Co. Ltd., 71-79 Arundel St., Glebe, N.S.W., Australia) V.1- 1914- Volume(issue)/page/year: 2,524,1948

甲硫尿嘧啶安全信息

[ 符号 ]:

GHS07, GHS08

[ 信号词 ]:
Warning

[ 危害声明 ]:
H302-H351

[ 警示性声明 ]:
P281

[ 个人防护装备 ]:
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

[ 危害码 (欧洲) ]:
Xn: Harmful;

[ 风险声明 (欧洲) ]:
R22;R40

[ 安全声明 (欧洲) ]:
S36/37-S45

[ 危险品运输编码 ]:
UN 3077 9/PG 3

[ WGK德国 ]:
3

[ RTECS号 ]:
YR0875000

[ 海关编码 ]:
29335995

甲硫尿嘧啶合成路线

详细合成路线

甲硫尿嘧啶上下游产品

甲硫尿嘧啶上游产品

甲硫尿嘧啶下游产品

甲硫尿嘧啶制备

由乙酰乙酸乙酯与硫脲反应而得。将硫脲溶解于氢氧化钠溶液中，滴加乙酰乙酸乙酯，控制温度在37℃以下。反应2h后，加水和活性炭，在70-80℃脱色0.5h。过滤，滤液用盐酸酸化至pH4-5，冷却至室温，过滤，洗涤。滤饼用水重结晶，得成品。收率66%。生产中，也可先将乙酰乙酸乙酯和硫脲混合，再滴加氧化钠溶液；还可用无水碳酸钠代替氢氧化钠，收率大致相同。

甲硫尿嘧啶海关

[ 海关编码 ]: 2933599090

[ 中文概述 ]:
2933599090. 其他结构上有嘧啶环的化合物(包括其他结构上有哌嗪环的化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

甲硫尿嘧啶文献

Identifying chelators for metalloprotein inhibitors using a fragment-based approach.

J. Med. Chem. 54 , 591-602, (2011)

Fragment-based lead design (FBLD) has been used to identify new metal-binding groups for metalloenzyme inhibitors. When screened at 1 mM, a chelator fragment library (CFL-1.1) of 96 compounds produced...

Hydration energies of protonated and sodiated thiouracils.

J. Am. Soc. Mass Spectrom. 25(12) , 2134-42, (2014)

Hydration reactions of protonated and sodiated thiouracils (2-thiouracil, 6-methyl-2-thiouracil, and 4-thiouracil) generated by electrospray ionization have been studied in a gas phase at 10 mbar usin...

Simultaneous determination of thyreostatic residues in animal tissues by matrix solid-phase dispersion and gas chromatography-mass spectrometry.

J. Chromatogr. A. 1074 , 1-7, (2005)

A method for determination of thyreostatic residues in animal tissues by matrix solid-phase dispersion (MSPD) and gas chromatography-mass spectrometry in selected ion detection mode was developed. Thy...

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