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CAS: 446-86-6
分子式: C9H7N7O2S
分子量: 277.29
沸点: 685.7ºC at 760 mmHg
熔点: 243-244 °C
中文名称: 
硫唑嘌呤
6-(1-甲基-4-硝基咪唑-5-硫基)嘌呤
依木兰
依米兰
英文名称: 
6-(1-Methyl-4-nitro-5-imidazolythio)-9H-pur-ine
Imura
6-((1-methyl-4-nitroimidazol-5-yl)thio)-purin
6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-1h-purin
6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-1h-purine
6-((1-methyl-4-nitroimidazol-5-yl)thio)purine
6-(1'-methyl-4'-nitro-5'-imidazolyl)-mercaptopurine
6-(1-methyl-4-nitroimidazol-5-ylthio)purin
6-(1-methyl-4-nitroimidazol-5-ylthio)purine
6-(1-methyl-p-nitro-5-imidazolyl)-thiopurine
6-(methyl-p-nitro-5-imidazolyl)-thiopurine
azamun
azanin
azathioprine
bw 57-322
imuran
imurek
imurel
methylnitroimidazolylmercaptopurine
muran
nci-c03474
nsc-39084
azathioprine usp
展开更多英文名
性质描述: 该品为淡黄色轻质结晶性粉末或针状结晶体,熔点243-244(分解)。易溶于碱性溶液,极微溶于乙醇,几乎不溶于水。无臭,味微苦。
生产方法: 以草酸二乙酯为原料,经胺化、环合、氯化、硝化、缩合而得。1.胺化将草酸二乙酯及甲醇投入反应锅中,冷却至20℃以下,通入干燥的甲胺气体到饱和后冷却到10℃以下,析出结晶,过滤烘干,得乙二酰二甲胺,熔点为210-212℃,收率95.8%。2.环合、氯化将过量的乙二酰二甲胺和五氯化磷分次投入反应锅中,在70-80℃下保温2h,放置过夜,减压蒸出氧氯化磷,温度不超过100℃,冷却,加入冰水,搅拌,用30-40%碱液调节pH为9-10,静置。分出油状物,母液冷却,析出无机盐后过滤,用氯仿洗涤,并用氯仿抽提母液。合并油层及氯仿层,回收氯仿,减压蒸馏,收集沸点110-115℃(4.0kPa)馏分,得1-甲基-5-氯咪唑。收率为52%。3.硝化将1-甲基-5-氯咪唑加入搪玻璃反应锅,然后冷却下加入硝酸。继续在冷却下滴加硫酸,加毕,在100℃反应2h,再冷却,加入冰水析出产品,经过滤干燥得-5氯-1-甲基-4-硝基咪唑。收率为86%。4.缩合将6-巯基嘌呤、氢氧化钠、水和5-氯-1-甲基-4-硝基咪唑一起煮沸4h,反应产物用乙酸调节pH至析出硫唑嘌呤。
用途: 用作免疫抑制药,抗肿瘤药。
推荐供应商
货号品牌产品名称规格包装、参考价格详情
A829528MACKLIN硫唑嘌呤98%172元/1g;   450元/5g;   1732元/25g;   展开
储存:室温
状态:淡黄色晶体粉末
折射率:1.923
A795161MACKLIN硫唑嘌呤10mM in DMSO430元/1ml;   展开
储存:-20°C
A2069TCIAzathioprine>98.0%(T)(HPLC)540元/5G;   1990元/25G;   展开

基本信息

纯度/分析方法>98.0%(T)(HPLC)
分子式/分子量C9H7N7O2S = 277.26
外观与形状(20℃)固体
储存温度<0℃
应避免的情况光,加热
Reaxys-RN1225351
PubChem物质ID87559964
Merck Index (14)902
MDL编号MFCD00069203

技术规格

AppearanceLight yellow to Yellow to Green powder to crystal
Purity(HPLC)min. 98.0 area%
Purity(Neutralization titration)min. 98.0 %

物性(参考值)

熔点244 ℃(dec.)
水溶性不溶
溶解性(易溶于)氯仿,乙醇

安全信息

图形或危害标志
信号词危险
危险性说明H302 : 吞咽有害。
H315 : 造成皮肤刺激。
H319 : 造成严重眼刺激。
H350 : 可能致癌。
防范说明P501 : 将内装物/容器送到批准的废物处理厂处理。
P270 : 使用本产品时不要进食、饮水或吸烟。
P202 : 在阅读并明了所有安全措施前切勿搬动。
P201 : 使用前取得专用说明。
P264 : 作业后彻底清洗皮肤。
P280 : 戴防护手套/穿防护服/戴防护眼罩/戴防护面具。
P302 + P352 : 如皮肤沾染:用水充分清洗。
P308 + P313 : 如接触到或有疑虑:求医/就诊。
P337 + P313 : 如仍觉眼刺激:求医/就诊。
P305 + P351 + P338 : 如进入眼睛:用水小心冲洗几分钟。如戴隐形眼镜并可方便地取出,取出隐形眼镜。继续冲洗。
P362+P364 : 脱掉沾污的衣服,清洗后方可重新使用。
P332 + P313 : 如发生皮肤刺激:求医/就诊。
P301 + P312 + P330 : 如误吞咽:如感觉不适,呼叫急救中心/医生。漱口。
P405 : 存放处须加锁。

相关法规

RTECS#UO8925000
190614J&KAzathioprine98%, 一种免疫抑制剂, 用于器官移植和自身免疫性疾病188元/1G;   751元/5G;   展开

基本信息

分子式C9H7N7O2S
分子量277.26
熔点244
MDL编码MFCD00069203
Beilstein1225351
Merck14,902
EINECS 编号207-175-4
存储条件Freezer -20℃

产品描述

Azathioprine 是一种抑制免疫系统的药物,抑制了嘌呤的合成以及GTP结合蛋白Rac1的激活,用于器官移植和自身免疫性疾病。

靶点(IC50 & Targe)

HGPRT

Rac1

体外研究

在原代人CD4+ T淋巴细胞中,Azathioprine抑制Rac1的靶基因如细胞分裂素活化蛋白激酶激酶(MEK)中的活化NF-κB,和bcl-X(L),从而导致细胞凋亡的线粒体途径。Azathioprine通过调制Rac1的活性从而将一个共刺激信号转换成细胞凋亡信号。[1]Azathioprine生成-6-硫代GTP,从而经由Vav活性对Rac蛋白防止有效的免疫应答的发展。[2] Azathioprine(1 mM)恢复ATP水平和阻止细胞损伤,而培养在葡萄糖富集培养基增强ATP水平和可改善细胞死亡。Azathioprine降低生存能力,在1天为5-34%,而4天为42-92%。[3] 在原代培养的大鼠肝细胞中,Azathioprine降低肝细胞的生存力和诱导下列事件:细胞内减少谷胱甘肽(GSH)耗竭,代谢活性降低,和乳酸脱氢酶的释放。在完整分离的大鼠肝线粒体中,Azathioprine对肝细胞的效果和膨胀和增加的氧消耗。 [4]

体内研究

在小鼠大鼠脑内移植体中,Azathioprine和cyclosporin A或prednisolone联用导致14/15的移植体(93%)的存活率,而对照组是11/14(79%)。[5]

参考文献

[1] Tiede I, et al. J Clin Invest, 2003, 111(8), 1133-1145.

[2] Poppe D, et al. J Immunol, 2006, 176(1), 640-651.

[3] Tapner MJ, et al. J Hepatol, 2004, 40(3), 454-463.

[4] Menor C, et al. J Pharmacol Exp Ther, 2004, 311(2), 668-676.

[5] Pedersen EB, et al. Exp Brain Res, 1995, 106(2), 181-186.

安全信息

图形或危害标志
提示语Danger
危险说明H302
H315
H319
H335
H350
防范说明P201
P261
P305+P351+P338
P308+P313
WGK3
RTECSUO8925000
A4638Sigma-AldrichAzathioprine≥98%1426.98元/1 G;   展开

产品说明

包装

1 g in glass bottle

生化/生理作用

在脱发性斑秃(自身免疫性脱发)的治疗中显示出希望,并在男女之间的疗效上无差异。

基本信息

经验(实验)分子式C9H7N7O2S
分子量277.26
EC 号207-175-4
MDL编号MFCD00069203
PubChem化学物质编号57653853
NACRESNA.77

产品性质

生物来源synthetic (organic)
质量水平100
测定≥98%
形式powder
溶解性1 M NH4OH: 20 mg/mL, clear to slightly hazy
储存温度−20℃
SMILES stringCn1cnc(c1Sc2ncnc3[nH]cnc23)[N+]([O-])=O
InChI1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
InChI keyLMEKQMALGUDUQG-UHFFFAOYSA-N
Gene Informationhuman ... PPAT(5471)

安全信息

象形图GHS07GHS08
警示用语:Danger
危险声明H302 - H315 - H319 - H335 - H350
预防措施声明P201 - P301 + P312 + P330 - P302 + P352 - P305 + P351 + P338 - P308 + P313
危险分类Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
靶器官Respiratory system
储存分类代码6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
WGKWGK 3
闪点(F)Not applicable
闪点(C)Not applicable
个人防护装备Eyeshields, Faceshields, Gloves, type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
PHR1282SupelcoAzathioprinePharmaceutical Secondary Standard; Certified Reference Material855.65元/1 G;   展开

产品说明

一般描述

Azathioprine is a potentially useful antileukaemic drug, with immunosuppressive action, which is administered orally or by I.V route. It is widely used to treat a variety of auto-immune disorders and also has a marked effect on T-lymphocytes and suppresses cell mediated immunity.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

应用

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
Azathioprine may be used as a pharmaceutical reference standard for the quantification of the analyte in pharmaceutical formulations using 1H NMR spectroscopy and spectrophotometric techniques.

分析说明

These secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available.

其他说明

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

附注

To see an example of a Certificate of Analysis for this material enter LRAA0017 in the slot below. This is an example certificate only and may not be the lot that you receive.

基本信息

经验(实验)分子式C9H7N7O2S
分子量277.26
EC 号207-175-4
MDL编号MFCD00069203
PubChem化学物质编号329823278
NACRESNA.24

产品性质

质量水平300
等级certified reference material
pharmaceutical secondary standard
CofAcurrent certificate can be downloaded
technique(s)HPLC: suitable
gas chromatography (GC): suitable
application(s)pharmaceutical (small molecule)
格式neat
药典可追溯性traceable to BP 26
traceable to PhEur A1500000
traceable to USP 1046001
储存温度2-30℃
SMILES stringCn1cnc(c1Sc2ncnc3[nH]cnc23)[N+]([O-])=O
InChI1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
InChI keyLMEKQMALGUDUQG-UHFFFAOYSA-N
Gene Informationhuman ... PPAT(5471)

安全信息

象形图GHS07GHS08
警示用语:Danger
危险声明H302 - H315 - H319 - H335 - H350
预防措施声明P201 - P301 + P312 + P330 - P302 + P352 - P305 + P351 + P338 - P308 + P313
危险分类Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
靶器官Respiratory system
储存分类代码6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
WGKWGK 3
闪点(F)Not applicable
闪点(C)Not applicable
A1500000AzathioprineEuropean Pharmacopoeia (EP) Reference Standard1277.32元/ ;   展开

产品说明

一般描述

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

包装

Unit quantity: 100 mg. Subject to change. The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

注意

Please find SDS provided by EDQM here..

其他说明

Sales restrictions may apply.

基本信息

经验(实验)分子式C9H7N7O2S
分子量277.26
MDL编号MFCD00069203
PubChem化学物质编号329770711
NACRESNA.24

产品性质

等级pharmaceutical primary standard
manufacturer/tradenameEDQM
application(s)pharmaceutical (small molecule)
格式neat
储存温度2-8℃
SMILES stringCn1cnc(c1Sc2ncnc3[nH]cnc23)[N+]([O-])=O
InChI1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
InChI keyLMEKQMALGUDUQG-UHFFFAOYSA-N
Gene Informationhuman ... PPAT(5471)

安全信息

象形图GHS07GHS08
警示用语:Danger
危险声明H302 - H315 - H319 - H335 - H350 - H361fd
预防措施声明P201 - P301 + P312 + P330 - P302 + P352 - P305 + P351 + P338 - P308 + P313
危险分类Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3
靶器官Respiratory system
储存分类代码6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGKWGK 3
1046001USPAzathioprineUnited States Pharmacopeia (USP) Reference Standard3231.47元/200 MG;   展开

产品说明

一般描述

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

分析说明

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

其他说明

USP issued SDS can be found here.
Sales restrictions may apply.

基本信息

经验(实验)分子式C9H7N7O2S
分子量277.26
MDL编号MFCD00069203
PubChem化学物质编号329749088
NACRESNA.24

产品性质

等级pharmaceutical primary standard
manufacturer/tradenameUSP
application(s)pharmaceutical (small molecule)
格式neat
储存温度2-8℃
SMILES stringCn1cnc(c1Sc2ncnc3[nH]cnc23)[N+]([O-])=O
InChI1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
InChI keyLMEKQMALGUDUQG-UHFFFAOYSA-N
Gene Informationhuman ... PPAT(5471)

安全信息

象形图GHS07GHS08
警示用语:Danger
危险声明H302 - H315 - H319 - H335 - H350
预防措施声明P201 - P280 - P301 + P312 + P330 - P305 + P351 + P338 - P308 + P313
危险分类Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
靶器官Respiratory system
储存分类代码6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
WGKWGK 3
闪点(F)Not applicable
闪点(C)Not applicable
BP026AzathioprineBritish Pharmacopoeia (BP) Reference Standard2144.18元/100 MG;   展开

产品说明

一般描述

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

包装

Unit quantity: 100 mg. Subject to change. The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity please visit British Pharmacopoeia

其他说明

Sales restrictions may apply.

基本信息

经验(实验)分子式C9H7N7O2S
分子量277.26
MDL编号MFCD00069203
NACRESNA.24

产品性质

等级pharmaceutical primary standard
manufacturer/tradenameBP
格式neat
储存温度−20℃
SMILES stringCn1cnc(c1Sc2ncnc3[nH]cnc23)[N+]([O-])=O
InChI1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
InChI keyLMEKQMALGUDUQG-UHFFFAOYSA-N
Gene Informationhuman ... PPAT(5471)

安全信息

象形图GHS07GHS08
警示用语:Danger
危险声明H302 - H315 - H319 - H335 - H350
预防措施声明P201 - P261 - P264 - P280 - P304 + P340 + P312 - P308 + P313
危险分类Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
靶器官Respiratory system
储存分类代码6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
WGKWGK 3
闪点(F)Not applicable
闪点(C)Not applicable
448203Fluorochem6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-9H-purine95%484元/250mg;   1078元/1g;   1716元/5g;   展开

基本信息

CAS Number446-86-6
MDL NumberMFCD00055974
Melting Point243-244℃

安全信息

图形或危害标志
危险性说明 H302: Harmful if swallowed.
H312: Harmful in contact with skin.
H315: Causes skin irritation.
H319: Causes serious eye irritation.
H332: Harmful if inhaled.
H335: May cause respiratory irritation.
H340: May cause genetic defects ..
H350: May cause cancer ..
H360: May damage fertility or the unborn child .
防范说明 P201: Obtain special instructions before use.
P202: Do not handle until all safety precautions have been read and understood.
P233: Keep container tightly closed.
P260: Do not breathe .
P261: Avoid breathing
P264: Wash hands thoroughly after handling.
P270: Do not eat, drink or smoke when using this product.
P271: Use only outdoors or in a well-ventilated area.
P280: Wear .
P281: Use personal protective equipment as required.
P301 + P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
P302 + P352: IF ON SKIN: Wash with plenty of soap and water.
P304: IF INHALED: .
P304 + P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P308 + P313: IF exposed or concerned: Get medical advice/ attention.
P312: Call a POISON CENTER or doctor/physician if you feel unwell.
P321: Specific treatment (see . on this label).
P322: Specific measures (see . on this label).
P330: Rinse mouth.
P332 + P313: If skin irritation occurs: Get medical advice/ attention.
P337 + P313: If eye irritation persists: Get medical advice/attention.
P340: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P362: Take off contaminated clothing and wash before reuse.
P363: Wash contaminated clothing before reuse.
P403: Store in a well-ventilated place.
P403 + P233: Store in a well-ventilated place. Keep container tightly closed.
P405: Store locked up.
P501: Dispose of contents/container to local regulations.
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