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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  • A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects.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
 

Classification Codes

  • Angiogenesis Inhibitors
  • Angiogenesis Modulating Agents
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Growth Inhibitors
  • Growth Substances
  • Human Data
  • Immunologic Factors
  • Immunosuppressive Agents
  • Leprostatic Agents
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Sedative-Hypnotic
  • Teratogens
  • Tumor Data

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

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-N

Smiles

N1(C2C(=O)NC(=O)CC2)C(=O)c2c(C1=O)cccc2

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.