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Thalidomide

Thalidomide structure

CAS No:
50-35-1
Formula:
C13H10N2O4
Chemical Name:
Thalidomide
Synonyms:
1H-Isoindole-1,3(2H)-dione,2-(2,6-dioxo-3-piperidinyl)-;Phthalimide,N-(2,6-dioxo-3-piperidyl)-;2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione;K 17;Contergan;N-(2,6-Dioxo-3-piperidyl)phthalimide;Distaval;Kevadon;α-Phthalimidoglutarimide;α-(N-Phthalimido)glutarimide;3-Phthalimidoglutarimide;N-Phthaloylglutamimide;α-N-Phthalylglutaramide;Softenon;Thalidomide;Sedoval;Softenil;Quetimid;Talimol;(±)-Thalidomide;1,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline;Thalomid;Celgene;Suaramide;Talinol;Neurosedyn;NSC 66847;Sedalis;Pantosediv;NSC 527179;Myrin;Sauramide;Pharmion;Thaled;Synovir;N-(2,6-Dioxo-3-piperidinyl)phthalimide;Immunoprin;2-(2,6-Dioxopiperidin-3-yl)isoindoline-1,3-dione;2-(2,6-Dioxopiperidin-3-yl)isoindole-1,3-dione;2-(2,6-Dioxo-piperidin-3-yl)-isoindole-1,3-dione;2-(2,6-Dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione;731-40-8;14088-68-7
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

Thalidomide is initially promoted as a sedative, inhibits ereblon (CRBN), a part of the cullin-4 E3 ubiquitin ligase complex CUL4-RBX1-DDB1, with a Kd of ∼250 nM, and has immunomodulatory, anti-inflammatory and anti-angiogenic cancer properties.

Thalidomide Basic Attributes

Molecular Weight：

258.23

Exact Mass：

258.23

EC Number：

200-031-1

HScode：

2925190090

Characteristics

PSA：

83.6

XLogP3：

0.3

Appearance：

white

Density：

1.5±0.1 g/cm3

Melting Point：

270 °C

Boiling Point：

509.7°C at 760 mmHg

Flash Point：

262.1±28.2 °C

Refractive Index：

1.646

Water Solubility：

H2O: <0.1 g/100 mL at 22 ºC;45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.6 mg/mL

Storage Conditions：

Store at RT

Vapor Pressure：

2.05X10-14 mm Hg at 25 deg C (est)

Toxicity：

LD50 oral in mouse: 2gm/kg

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

46-61-21-25-62-22

safety instructions：

53-22-26-36/37/39-45

RTECS Number：

TI4375000

Marks：

Stability/Shelf Life：

Stable. Combustible. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P201-P280-P301 + P312 + P330-P308 + P313

Hazard Statements：

H302-H360D

Thalidomide Use and Manufacturing

Thalidomide was prescribed as an anti-nausea agent to help pregnant women with morning sickness in the late 1950s. It was found to be a potent teratogen, causing many different forms of birth defects and was withdrawn from the market. Thalidomide and synthetic analogs have recently been proven effective in treating inflammation associated with diseases such as leprosy, arthritis and Crohn’s disease, and in cancers such as multiple myeloma. The direct target for the teratogenicity of thalidomide was not discovered until 2010, when it was found that it interacts directly with the protein cereblon (CRBN; IC50 = 8.5 nM), a ubiquitously-expressed E3 ligase. Binding of thalidomide analogs to CRBN-DNA damage binding protein-1 complexes account for the immunomodulatory and antiproliferative effects of these compounds.[Cayman Chemical]

Computed Properties

Molecular Weight:258.23
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:258.06405680
Monoisotopic Mass:258.06405680
Topological Polar Surface Area:83.6
Heavy Atom Count:19
Complexity:449
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Unspecified

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

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Registered Holders

SHILPA PHARMA LIFESCIENCES LTD

United States
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