2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione 酞胺哌啶酮
CAS 50-35-1 MFCD00153873
化学结构图
SMILES: O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1
化学属性
| Mol. Formula | C13H10N2O4 |
|---|---|
| Mol. Weight | 258.23 |
| Melting Point | 266-270 |
| Solubility | Soluble in DMSO, not in water |
| TSCA | No |
| Appearance | Solid powder 白色粉末 |
别名和识别编码
| Chemical Name | 2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione |
|---|---|
| Synonym | (±)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione ()-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione (+/-)-2-(2,6-DIOXO-3-PIPERIDINYL)-1H-ISOINDOLE-1,3(2H)-DIONE (±)-2-(2,6-Dio 1H-Isoindole-1,3(2H)-dione, 2-(2,6-d 2,6-Dioxo-3-phthalimidopiperidine 2-(2,6-dioxo-3-piperidin 3-PHTHALIMIDOGLUTARIMIDE ALPHA-PHTHALIMIDOGLUTARIMIDE Asmaval Bonbrain Contergan Dist Enterosediv Imida-lab Imidene N-(2,6-DIOXO-3-PIPERIDINYL)PHTHALIMIDE N-Phthaloylglutamimide NeO Noctosediv Noxodyn Pangul Pantosediv Profarmil Psychotablets Quietoplex Sedoval Shinnibrol Talargan Thalidomide { |
| MDL Number | MFCD00153873 |
| CAS Number | 50-35-1 |
| PubChem Substance ID | 5426 |
| EC Number | 200-031-1 |
| Merck Number | 9255 |
| Chemical Name Translation | 酞胺哌啶酮 |
| Reaxys-RN | 30233 |
| Beilstein Registry Number | 22(5)13,224 |
| Wiswesser Line Notation | T56 BVNVJ C- DT6VMVTJ |
| LabNetwork Molecule ID | LN00243537 |
| InChI | InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17) |
| Formula | C13H10N2O4 |
| IUPAC Name | 2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione |
| InChIKey | UEJJHQNACJXSKW-UHFFFAOYSA-N |
| Canonical SMILES | O=C1N(C(CC2)C(NC2=O)=O)C(C3=C1C=CC=C3)=O |
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分类
- {SNA} Angiogenesis Inhibi
- {SNA} Angiogenesis Inhibitors,
- {SNA} Angiogenesis, Angiogenesis Inhibitors, Angiogenesis Regulators, Approved Therapeutics/Drug Candidates, Bioactive Small Molecules, Cancer Research, Celgene, Cell Biology, Cell Signaling and Neuroscience, Cytoskeleton and Extracellular Matrix, Extracellular Matrix, T
- {SNA} Angiogenesis, Angiogenesis Inhibitors, Angiogenesis Regulators, Approved Therapeutics/Drug Candidates, Bioactive Small Molecules, Celgene, Cell Signaling and Neuroscience, Cytoskeleton and Extracellular Matrix, Extracellular Matrix, T, 癌症研究, 细胞生物学
- {
产品应用
- Thalidomide is a synthetic derivative of glutamic acid (alpha-phthalimido-glutarimide) with teratogenic, immunomodulatory, anti-inflammatory and anti-angiogenic properties. Thalidomide acts primarily by inhibiting both the production of tumor necrosis factor alpha (TNF-alpha) in stimulated peripheral monocytes and the activities of interleukins and interferons. This agent also inhibits polymorphonuclear chemotaxis and monocyte phagocytosis. In addition, thalidomide inhibits pro-angiogenic factors such as vascular endothelial growth factor (VEGF) and basic fibroblast growth factor (bFGF), thereby inhibiting angiogenesis.
安全信息
GHS Symbol
- H301 Toxic if swallowed 吞食有毒
- H302 Harmful if swallowed 吞食有害
- H312 Harmful in contact with skin 皮肤接触有害
- H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
- H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
- P201 Obtain special instructions before use. 使用前获取专门指示。
- P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
- P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
- P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
- P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
- P281 Use personal protective equipment as required. 使用所需的个人防护装备。
- P301+P310
- P301+P310+P330
- P301+P312
- P302+P350
- P308+P313
- P330 Rinse mouth. 漱口
- P405 Store locked up. 上锁保管。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
- S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
- S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
- S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
- S22 Do not breathe dust 不要吸入粉尘；
- S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
- R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
- R22 Harmful if swallowed 吞咽有害
- R62 Possible risk of impaired fertility 有削弱生殖能力的危险
- R46 May cause inheritable genetic damage 可能引起遗传基因损害
- R25 Toxic if swallowed 吞咽有毒
- R21 Harmful in contact with skin 与皮肤接触有害
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 34 gm/kg/57W-I TOXIC EFFECTS : Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application Lungs, Thorax, or Respiration - tumors REFERENCE : NATUAS Nature. (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736) V.1- 1869- Volume(issue)/page/year: 200,1016,1963
{hazard_comTYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Administration onto the skin SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 1550 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 14,515,1969
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >6 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 194,39,1971
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 2 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : LIFSAK Life Sciences. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1-8, 1962-69; V.14- 1974- Volume(issue)/page/year: 3,721,1964
TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : >1538 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951-
TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Human Lymphocyte DOSE/DURATION : 1 mg/L REFERENCE : AMSVAZ Acta Medica Scandinavica. (Almqvist & Wiksell, POB 45150, S-10430 Stockholm, Sweden) V.52-224, 1919-88. Volume(issue)/page/year: 177,783,1965
TYPE OF TEST : Cytogenetic analysis ROUTE OF EXPOSURE : Oral TEST SYSTEM : Rodent - rat DOSE/DURATION : 7600 mg/kg/30D (Continuous) REFERENCE : NATUAS Nature. (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736) V.1- 1869- Volume(issue)/page/year: 202,1080,1964
TYPE OF TEST : Unscheduled DNA synthesis ROUTE OF EXPOSURE : Intraperitoneal TEST SYSTEM : Rodent - rat DOSE/DURATION : 80 mg/kg REFERENCE : JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 171,109,1970
TYPE OF TEST : Mutation test systems - not otherwise specified ROUTE OF EXPOSURE : Intraperitoneal TEST SYSTEM : Rodent - rat DOSE/DURATION : 80 mg/kg REFERENCE : JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 171,109,1970
TYPE OF TEST : Mutation in microorganisms TEST SYSTEM : Microorganism - not otherwise specified DOSE/DURATION : 10 gm/L REFERENCE : BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 118,563,1979
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE : 17500 ug/kg SEX/DURATION : female 1-5 week(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system REFERENCE : BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 1,123,1963
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rabbit DOSE : 150 mg/kg SEX/DURATION : female 7 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) REFERENCE : JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 160,189,1968
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported SPECIES OBSERVED : Rodent - rat DOSE : 1700 mg/kg SEX/DURATION : female 6-22 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 20,283,1964
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE : 750 mg/kg SEX/DURATION : female 2-7 day(s) after conception TOXIC EFFECTS :
其他信息
- MSDS 信息:2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione(50-35-1).msds
- Sigma Aldrich:50-35-1(sigmaaldrich)
- 治疗风湿病:国外学者报道，用反应停(沙利度胺)治疗7例多种抗炎药和免疫抑制无效的类风湿性病患者，结果多数在数周内缓解，剂量在400～600mg/d，所有病人的血沉和类风湿因子滴度都正常化或明显下降，其中1例的类风湿结节在12周时消失。有人用反应停和甲氨蝶呤联合治疗7例难治性类风湿病人，5例坚持治疗者中，4例在3～9个月关节压痛改善和关节肿胀减轻。 沙利度胺能治疗的风湿病如下： 1，白塞氏病。 2，系统性红斑狼疮。 3，类风湿关节炎。 4，结节性红斑、克罗恩病。 5，硬皮病：在治疗开始后12周内，可明显改善胃食管反流症状、十二指溃疡愈合和色素减退。 6，成人Still病。 7，难治性强直性脊柱炎、多发性骨髓瘤（MM)。 临床上治疗风湿病从小剂量开始使用，每晚25--50mg/天，逐渐加量至100--200mg/天，最大剂量不超过400mg/天。
- (±)-Thalidomide
- MOL 文件:50-35-1.mol
- 谷氨酸衍生物:沙利度胺 (Thalidomide)是一种合成的谷氨酸衍生物,俗称反应停、沙立度胺、酞胺哌酮、酞胺哌啶酮、酞谷酰亚胺、酞咪哌啶酮，室温下为白色结晶性粉末，无臭，无味，微溶于水、甲醇、乙醇或丙酮，易溶于二甲基甲酰胺或吡啶，不溶于乙醚、氯仿或苯。 20世纪50年代，由德国开发此药物主要是用于治疗癫痫，但由于缺乏有效性，随后被作为一种睡眠辅助用药，同时在怀孕期间广泛用于孕妇止吐。 20世纪60年代初，反应停事件---出现大量的沙利度胺导致的婴儿畸形报道（如：短肢畸形、长骨缺损、耳廓缺失、唇裂、心脏和胃肠道畸形等），从而被很多国家禁止使用，并撤出医药市场，然而科学家并未全盘否定沙利度胺，继续对它进行深入研究，特别是在免疫、抗炎、抗血管生成的药理和一些疑难病症上的临床治疗研究中取得了令人欣喜和鼓舞的结果，从而使人们对沙利度胺又有了新的认识。 20世纪70年代起，随着对麻风、风湿病和多种类型恶性肿瘤的研究进展陆续出现，以色列皮肤病学沙利度胺作为镇静药给麻风性结节红斑病人使用，症状迅速改善。以后许多例麻风性结节红斑病人使用反应均获得很好的治疗效果，1998年美国FDA批准沙利度胺用于治疗麻风结节性红斑。 2004年美国血液学学会年会上，美国梅奥医院RaJkumar报告了沙利度胺及其类似物(lenalidomide)一线治疗多发性骨髓瘤的2项研究结果，沙利度胺及其类似物lenalidomide均可有效治疗多发性骨髓瘤，lenalidomide疗效好于沙利度胺。 2006年5月美国FDA批准用于治疗多发性骨髓瘤。
- Thalidomide作为一种镇静药，免疫调节剂，用于治疗许多癌症的症状。Thalidomide抑制E3泛素连接酶（一种CRBN-DDB1-Cul4A复合物）。
- 用途一:镇静剂，对于各型麻风病反应如发热、结节红斑、神经痛、关节痛、淋巴结肿大等有一定疗效，对麻风无治疗作用
- 不良反应:沙利度胺治疗过程中出现的不良反应主要有：困倦、头晕、嗜睡、头痛、便秘、恶心、呕吐、口干、皮肤干燥、红斑性和丘疹水疱性短暂皮疹等，但都不严重，终止给药后都会消失。 应该注意的不良反应是多发性神经炎，主要症状是表面或深部感觉消失和肌肉虚弱，症状的出现与剂量和疗程都不成比例，症状开始出现的时间差别也很大，对于不终止治疗的病例，这种症状是不可逆的。此外，还有白细胞降低、肝功能异常以及众所周知的致畸形作用。其他少见的副作用包括心动过缓、水肿、血凝异常、肾功能衰竭、肺炎、感觉异常、甲状腺功能低下。
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