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Substance Name: Thalidomide [USAN:USP:INN:BAN:JAN]
RN: 50-35-1
UNII: 4Z8R6ORS6L
InChIKey: UEJJHQNACJXSKW-UHFFFAOYSA-N
Note
- A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects.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.
Molecular Formula
- C13-H10-N2-O4
Molecular Weight
- 258.232
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Classification Codes
- Angiogenesis Inhibitors
- Angiogenesis Modulating Agents
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antineoplastic Agents
- Antiviral (COVID-19)
- Drug / Therapeutic Agent
- Growth Inhibitors
- Growth Substances
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- Immunologic Factors
- Immunosuppressive Agents
- Leprostatic Agents
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- Noxae
- Reproductive Effect
- Sedative-Hypnotic
- Teratogens
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Names and Synonyms
Name of Substance
- Thalidomide
- Thalidomide [USAN:USP:INN:BAN:JAN]
MeSH Heading
- Thalidomide
Synonyms
- (+-)-N-(2,6-Dioxo-3-piperidyl)phthalimide
- (+-)-Thalidomide
- 1,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline
- 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-
- 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-, (+-)-
- 2,6-Dioxo-3-phthalimidopiperidine
- 3-Phthalimidoglutarimide
- 5-22-13-00224 (Beilstein Handbook Reference)
- Actimid
- AI3-50606
- Algosediv
- alpha-(N-Phthalimido)glutarimide
- alpha-N-Phthalylglutaramide
- alpha-Phthalimidoglutarimide
- Asidon 3
- Asmadion
- Asmaval
- Bonbrain
- BRN 0030233
- Calmore
- Calmorex
- CCRIS 8148
- Contergan
- Corronarobetin
- Distaval
- E-217
- Ectiluran
- EINECS 200-031-1
- ENMD 0995
- Enterosediv
- Gastrinide
- Glupan
- Glutanon
- Glutarimide, 2-phthalimido-
- Grippex
- Hippuzon
- HSDB 3586
- Imida-lab
- Imidan (peyta)
- Imidene
- Isomin
- K 17
- K-17
- Kevadon
- N-(2,6-Dioxo-3-piperidyl)phthalimide
- N-Phthaloylglutamimide
- N-Phthalyl-glutaminsaeure-imid
- N-Phthalyl-glutaminsaeure-imid [German]
- N-Phthalylglutamic acid imide
- Neaufatin
- Neosedyn
- Neosydyn
- Nerosedyn
- Neufatin
- Neurodyn
- Neurosedin
- Neurosedym
- Nevrodyn
- Nibrol
- Noctosediv
- Noxodyn
- NSC 527179
- NSC-66847
- Pangul
- Pantosediv
- Phthalimide, N-(2,6-dioxo-3-piperidyl)-
- Poly-giron
- Polygripan
- Predni-sediv
- Pro-Bam M
- Pro-ban M
- Profarmil
- Psycholiquid
- Psychotablets
- Quetimid
- Quietoplex
- Sandormin
- Sedalis sedi-lab
- Sedimide
- Sedin
- Sedisperil
- Sedoval
- Shin-naito S
- Shinnibrol
- Sleepan
- Slipro
- Softenil
- Softenon
- Talargan
- Talidomida
- Talidomida [INN-Spanish]
- Talidomide
- Talidomide [DCIT]
- Talimol
- Talismol
- Telagan
- Telargean
- Tensival
- Thalidomide
- Thalidomide Celgene
- Thalidomidum
- Thalidomidum [INN-Latin]
- Thalin
- Thalinette
- Thalomid
- Thalomide
- Theophilcholine
- Ulcerfen
- UNII-4Z8R6ORS6L
- Valgis
- Valgraine
- Yodomin
Systematic Names
- 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-
- Phthalimide, N-(2,6-dioxo-3-piperidyl)-
- Thalidomide
Superlist Name
- Thalidomide
Registry Numbers
CAS Registry Number
- 50-35-1
FDA UNII
- 4Z8R6ORS6L
Other Registry Numbers
- 14088-68-7
- 731-40-8
System Generated Number
- 0000050351
Structure Descriptors
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)InChIKey
UEJJHQNACJXSKW-UHFFFAOYSA-NSmiles
O=C1CCC(N2C(=O)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | oral | > 1538mg/kg (1538mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 6, Pg. 426, 1956. | |
mouse | LD50 | oral | 2gm/kg (2000mg/kg) | Life Sciences. Vol. 3, Pg. 721, 1964. | |
mouse | LD50 | oral | > 10gm/kg (10000mg/kg) | Nature. Vol. 215, Pg. 296, 1967. | |
mouse | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 6, Pg. 426, 1956. | |
mouse | LDLo | intraperitoneal | 800mg/kg (800mg/kg) | Toxicology and Applied Pharmacology. Vol. 23, Pg. 288, 1972. | |
rat | LD50 | intraperitoneal | > 6gm/kg (6000mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 194, Pg. 39, 1971. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 270 | deg C | EXP | |
log P (octanol-water) | 0.33 | (none) | EXP | |
Water Solubility | 545 | mg/L | 25 | EXP |
Vapor Pressure | 2.08E-14 | mm Hg | 25 | EST |
Henry's Law Constant | 1.29E-16 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 4.37E-11 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.