Basic information
- CAS
841-67-8- Standard SMILES
O=C1CC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1- InChIKey
UEJJHQNACJXSKW-VIFPVBQESA-N- Molecular formula
- C13H10N2O4
- Average molar mass
- 258.23 g/mol
- Monoisotopic mass
- 258.0640568
Overview
(S)-thalidomide is a 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione that has S-configuration at the chiral centre. It has a role as a teratogenic agent. It is an enantiomer of a (R)-thalidomide.
Names & identifiers
- Preferred name
- (S)-Thalidomide
- IUPAC
- 2-[(3S)-2,6-dioxopiperidin-3-yl]isoindole-1,3-dione
- English name
- (-)-THALIDOMIDE
- Molecular formula
- C13H10N2O4
- Molecular weight
- 258.23
Names & synonyms
(S)-Thalidomide841-67-8(-)-ThalidomideS-(-)-ThalidomideThalidomide, L-NSC 917302-[(3S)-2,6-dioxopiperidin-3-yl]-1H-isoindole-1,3(2H)-dionePhthalimide, N-(2,6-dioxo-3-piperidyl)-, (-)-Phthalimide, N-(2,6-dioxo-3-piperidyl)-, L-(-)-DTXSID1046972CHEBI:619181H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-, (S)-
Show more names
(–)-ThalidomideThalidomide (S)-Isomer(S)Thalidomide,(S) Thalidomide6-dioxo-3-piperidyl)-n-(l-(-)-phthalimidN-[(S)-2,6-Dioxopiperidine-3-yl]phthalimide(-)-THALIDOMIDE >98% INHIBITOR OF ANGIOG EN(-)-N-[(S)-2,6-Dioxo-3-piperidinyl]phthalimide
2-((3S)-2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dioneRefChem:408251DTXCID9026972635-910-2(S)-(-)-thalidomidel-ThalidomideS-Thalidomide(S)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
Database identifiers
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 83.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 449
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 269 · 269-271°C
- Boiling point
- 401.48 °C · 401.48°C (rough estimate)
- Density
- 1.2944 · 1.2944 (rough estimate)
- refractive index
- 1.53 · 1.5300 (estimate)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO: soluble
- form
- solid
- pka
- 10.7 · 10.70±0.40(Predicted)
- color
- white
- optical activity
- 23 · [α]23/D 62.6°, c = 2 in DMF(lit.)
- 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)/t9-/m0/s1
- InChIKey
- UEJJHQNACJXSKW-VIFPVBQESA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- TI4925050
- ridadr
- UN 2811 6.1/PG 2
- risk_code
- 61-22
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- T
- safety_code
- 53-36/37/39-45
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H302-H360
- Hazard Classifications
- Acute Tox. 4 OralRepr. 1B
- Precautionary statements
- P201-P301+P312+P330-P308+P313
Chemistry & industry
Pharmacology
Metabolism/Metabolites(-)-thalidomide has known human metabolites that include (-)-thalidomide arene oxide, 5'-Hydroxythalidomide, and 5-hydroxy-thalidomide.
Applications
UsesOptically active isomer of Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative
UsesThalidomide has been used to study its teratogenic effects in chicken embryos and human embryonic cells. This study reported that thalidomide causes limb defects by stabilizing PTEN, inhibiting the expression of Akt and activating caspase-dependent apoptosis. Thalidomide has also been used for studying glutathione mediated teratogenic resistance in mouse embryos.
General DescriptionThalidomide is a stereoisomer, which exists in two enantiomeric states. The S enantiomer is teratogenic. Thalidomide consists of two linked rings, a phthalimide and glutarimide ring.
Upstream & downstream products
Downstream products
Suppliers44 total
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
武汉誉祥医药科技有限公司13971275651 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
烟台盛凯伦生物制品有限公司13356901049 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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