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50-35-1 (Thalidomide)

1

Identification

Thalidomide Thalidomide
Name Thalidomide
Formula C13H10N2O4
MW 258.23
CAS No. 50-35-1
EINECS 200-031-1
Smiles O=C(C1=C2C=CC=C1)N(C2=O)C(CCC3=O)C(N3)=O
Synonyms 2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione; 2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
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)
2

Introduction

Thalidomide can directly inhibit angiogenesis induced by bFGF or VEGF in vivo. IC50 value: Target: Thalidomide was commonly used therapeutically in the late 1950's; however, it was withdrawn from the market when it was discovered to cause birth defects.

Background Information

Thalidomide is an immunomodulatory compound and the prototype of the thalidomide class of drugs. Thalidomide inhibits TNFα production by stimulated human monocytes and induces monocyte apoptosis. Thalidomide costimulates primary human T lymphocytes and inhibits angiogenesis. ......by AbMole BioScience
Thalidomide can directly inhibit angiogenesis induced by bFGF or VEGF in vivo. ......by AdooQ BioScience, LLC
Thalidomide was introduced as a sedative drug, immunomodulatory agent and also is investigated for treating symptoms of many cancers. Thalidomide inhibits an E3 ubiquitin ligase, which is a CRBN-DDB1-Cul4A complex. ......by BOC Sciences
Cell-permeable. A teratogen and sedative-hypnotic with inherent anti-inflammatory properties. A selective inhibitor of tumor necrosis factor α (TNF-α) synthesis. Thalidomide initiates its teratogenic effects by binding to cereblon (CRBN), a thalidomide-binding protein, and inhibiting the associated ubiquitin ligase activity. ......by BioVision, Inc.,
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. ......by MedKoo Biosciences, Inc.
Thalidomide was introduced as a sedative drug, immunomodulatory agent and also is investigated for treating symptoms of many cancers. Thalidomide inhibits an E3 ubiquitin ligase, which is a CRBN-DDB1-Cul4A complex. ......by Selleck Chemicals LLC
A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppressive and anti-angiogenic activity. It inhibits release of TUMOR NECROSIS FACTOR-ALPHA from monocytes, and modulates other cytokine action. ......by Target Molecule Corp.
Selective inhibitor of tumor necrosis factor α (TNF-α) synthesis. Also binds cereblon, inhibiting ubiquitin ligase activity. Teratogen, sedative-hypnotic with inherent anti-inflammatory properties. ......by Tocris Bioscience Inc.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000023065

Storage condition

Solubility

DMSO >20 mg/mL by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 52 mg/mL (201.37 mM); Ethanol2 mg/mL (7.74 mM); Water<1 mg/mL (<1 mM); In vivo 30% PEG400+0.5% Tween80+5% Propylene glycol5 mg/mL by Selleck Chemicals LLC
5

Mechanism and Indication

Signaling Pathways Others
Target Others
Research Area Cancer
Indications Multiple myeloma Multiple myeloma Uveitis Multiple myeloma Multiple myeloma
6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Thalidomide Second Military Medical University PLA Multiple myeloma 2010/6/30 2014/6/30 Phase 4 Clinical
Thalidomide PETHEMA Foundation Multiple myeloma 2007/1/31 2010/6/30 Phase 4 Clinical
Thalidomide University of Cincinnati Uveitis 2004/1/31 2006/8/31 Phase 4 Clinical
Thalidomide Millennium Pharmaceuticals Inc Multiple myeloma 2007/6/30 2013/5/31 Phase 3 Clinical
Thalidomide University of Arkansas Multiple myeloma 2006/11/30 2013/4/30 Phase 3 Clinical
Thalidomide - Launched
7

Safety Data of Thalidomide

Hazard Symbols : T
Risk Statements : R46;R61;R21;R25;R62
Safety Statements : S53;S22;S26;S36/37/39;S45
Transport Information : UN 2811
RTECS : TI4375000
WGKGermany : 3
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
A.G. Scientific, Inc. USA
AbMole BioScience USA
Abcam 100mg/USD55() USA
AdooQ BioScience, LLC USA
Apexbio Technology LLC USA
Ark Pharm, Inc. USA
Astatech, Inc. USA
BOC Sciences
BioVision, Inc., 10mg/USD70() USA
Biochempartner Co., Ltd China
CHEMSCENE, LLC 200mg/USD80();500mg/USD150() USA
Cayman Chemical Company 100mg/USD39() USA
Changzhou Hangyu Pharmaceutical Technology Co., Ltd. China
Changzhou Kangzheng Pharmachem Technology Co., Ltd. China
Changzhou Sanling Chemical Co., Ltd. China
Datang (Hangzhou) Pharmachem Co., Ltd. China
EMD Millipore 100mg/USD119() USA
LKT Laboratories Inc. USA
MedChemexpress Co., Ltd. 200mg/USD80();500mg/USD150() USA
MedKoo Biosciences, Inc. 100mg/USD35() USA
Microbiologica Quimica e Farmaceutica Ltda. Brazil
Quzhou Rundong Chemical Co., Ltd. China
Santa Cruz Biotechnology, Inc. 100mg/USD86() USA
Selleck Chemicals LLC 200mg/USD147(In stock);10mM/1mLIn DMSO/USD190(In stock) USA
Shanghai Haoyuan Chemexpress Co., Ltd. 200mg/USD80();500mg/USD150() China
Sigma-Aldrich, Inc. 100mg/USD63() USA
Target Molecule Corp. 2mg/USD36();10mg/USD98();50mg/USD197();200mg/USD286() USA
Tocris Bioscience Inc. 100mg/USD79() USA
Tokyo Chemical Industry Co., Ltd. 1g/USD108() Japan
Toronto Research Chemicals Inc. 100mg/USD50() Canada
VDM BIOCHEMICALS,Inc. 100mg/USD70() USA
Xiangyang Jinsheng Pharmaceutical Co., Ltd. China
10

Related Products

Other Forms of 50-35-1

Name CAS No Formula MW
(S)-Thalidomide 841-67-8 C13H10N2O4 258.2295
(R)-Thalidomide 2614-06-4 C13H10N2O4 258.2295
Thalidomide (D4) 1219177-18-0 C13H6D4N2O4 262.25

Recommended Compounds in Others

Name CAS No Formula MW
(R)-(+)-Etomoxir (sodium salt) 828934-41-4 C15H18ClNaO4 320.74
Dictamine 484-29-7 C12H9NO2 199.21
3,3',5-Triiodo-L-thyronine (sodium) 55-06-1 C15H11I3NNaO4 672.9553
Fabomotizole (hydrochloride) 173352-39-1 C15H22ClN3O2S 343.8721
FPH2 957485-64-2 C14H16ClN5O2S 353.83
α-Tocopherol (phosphate) 38976-17-9 C29H51O5P 510.69
BAMB-4 891025-25-5 C15H12N2O2 252.27
LDN-27219 312946-37-5 C20H16N4O2S2 408.5
ISO-1 478336-92-4 C12H13NO4 235.24
Aurothioglucose 12192-57-3 C6H11AuO5S 392.18
Oxybenzone 131-57-7 C14H12O3 228.24
ITX3 347323-96-0 C22H17N3OS 371.45
Cardiogreen 3599-32-4 C43H47N2NaO6S2 774.96
Skp2 Inhibitor C1 432001-69-9 C18H13BrN2O4S2 465.34
INH1 313553-47-8 C18H16N2OS 308.4
PF6-AM 1268491-69-5 C33H31BO12 630.4
XEN445 1515856-92-4 C18H17F3N2O3 366.33
Disperse Blue 148 52239-04-0 C19H19N5O4S 413.45026
Solvent Blue 35 17354-14-2 C22H26N2O2 350.454
CID-797718 370586-05-3 C12H11NO3 217.2206

Recommended Compounds in Same Indication

Name CAS No Formula MW
Quisinostat 875320-29-9 C21H26N6O2 394.4702
AT9283 896466-04-9 C19H23N7O2 381.43
MLN9708 1239908-20-3 C20H23BCl2N2O9 517.12
Panobinostat 404950-80-7 C21H23N3O2 349.43
Carfilzomib 868540-17-4 C40H57N5O7 719.91
ARRY-520 (R enantiomer) 885060-08-2 C20H22F2N4O2S 420.48
ARRY-520 885060-09-3 C20H22F2N4O2S 420.48
Delanzomib 847499-27-8 C21H28BN3O5 413.28
RO4929097 847925-91-1 C22H20F5N3O3 469.4
Erastin 571203-78-6 C30H31ClN4O4 547.04
AT7519 844442-38-2 C16H17Cl2N5O2 382.24
Danusertib 827318-97-8 C26H30N6O3 474.55
Masitinib 790299-79-5 C28H30N6OS 498.64
Pomalidomide 19171-19-8 C13H11N3O4 273.24
Lenalidomide 191732-72-6 C13H13N3O3 259.26
PHA-680632 398493-79-3 C28H35N7O2 501.62
INK-128 1224844-38-5
Lenalidomide (hydrochloride) 1243329-97-6 C13H14ClN3O3 295.72
AVN-944 297730-17-7 C25H27N5O5 477.51
Vorinostat 149647-78-9 C14H20N2O3 264.32
11

Route of Synthesis

12

References

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More Information

Thalidomide

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