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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB01041
rdf:type
n3:Drug
n3:description
A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects.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 immunosuppresive and anti-angiogenic activity. It inhibits release of tumor necrosis factor-alpha from monocytes, and modulates other cytokine action. [PubChem]
n3:dosage
n5:271B5873-363D-11E5-9242-09173F13E4C5 n5:271B5874-363D-11E5-9242-09173F13E4C5 n5:271B5875-363D-11E5-9242-09173F13E4C5 n5:271B5876-363D-11E5-9242-09173F13E4C5
n3:group
withdrawn approved investigational
n3:halfLife
The mean half-life of elimination ranges from approximately 5 to 7 hours following a single dose and is not altered upon multiple dosing.
n3:indication
For the acute treatment of the cutaneous manifestations of moderate to severe erythema nodosum leprosum (ENL). Also for use as maintenance therapy for prevention and suppression of the cutaneous manifestations of ENL recurrence.
owl:sameAs
n23:DB01041 n24:DB01041
dcterms:title
Thalidomide
adms:identifier
n7:Thalidomide n9:5426 n12:46505665 n15:5233 n16:DB01041 n17:50070114 n18:59572-205-14 n19:PA451644 n20:C07910 n21:D00754
n3:mechanismOfAction
In patients with erythema nodosum leprosum (ENL) the mechanism of action is not fully understood. Available data from in vitro studies and preliminary clinical trials suggest that the immunologic effects of this compound can vary substantially under different conditions, but may be related to suppression of excessive tumor necrosis factor-alpha (TNF-a) production and down-modulation of selected cell surface adhesion molecules involved in leukocyte migration. For example, administration of thalidomide has been reported to decrease circulating levels of TNF-a in patients with ENL, however, it has also been shown to increase plasma TNF-a levels in HIV-seropositive patients. As a cancer treatment, the drug may act as a VEGF inhibitor.
n3:packager
n27:271B586D-363D-11E5-9242-09173F13E4C5 n27:271B586B-363D-11E5-9242-09173F13E4C5 n27:271B586C-363D-11E5-9242-09173F13E4C5
n3:patent
n14:6235756 n14:2157288 n14:7230012 n14:2505964
n3:routeOfElimination
Thalidomide itself has less than 0.7% of the dose excreted in the urine as unchanged drug.
n3:synonym
N-Phthalylglutamic acid imide (+-)-Thalidomide α-phthalimidoglutarimide Distaval Thalidomidum 3-Phthalimidoglutarimide Talidomida 2,6-dioxo-3-phthalimidopiperidine alpha-(N-Phthalimido)glutarimide Pro-ban M α-(N-phthalimido)glutarimide N-(2,6-dioxo-3-piperidyl)phthalimide Thalidomide (±)-N-(2,6-dioxo-3-piperidyl)phthalimide Softenon (±)-thalidomide N-Phthalyl-glutaminsaeure-imid alpha-Phthalimidoglutarimide Sedalis K-17 alpha-N-Phthalylglutaramide N-Phthaloylglutamimide α-N-phthalylglutaramide 1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline Talimol (+-)-N-(2,6-dioxo-3-Piperidyl)phthalimide
n3:toxicity
The R-configuration and the S-configuration are more toxic individually than the racemic mixture. The LD<sub>50</sub> could not be established in mice for racemic thalidomide, whereas LD<sub>50</sub> values for the R and S configurations are reported to be 0.4 to 0.7 g/kg and 0.5 to 1.5 g/kg, respectively.
n3:proteinBinding
55% and 66% for the (+)R and (&minus;)S enantiomers, respectively.
n3:synthesisReference
Jamshed Shah, "Synthesis and anti-tumor activity of nitrogen substituted thalidomide analogs." U.S. Patent US20030139451, issued July 24, 2003.
n10:hasConcept
n11:M0021267
foaf:page
n26:thalidom.htm n28:thalidomide.html
n3:IUPAC-Name
n4:271B587B-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5881-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5880-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B587D-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B587E-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B587F-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5891-363D-11E5-9242-09173F13E4C5 n4:271B5879-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5893-363D-11E5-9242-09173F13E4C5 n4:271B587A-363D-11E5-9242-09173F13E4C5 n4:271B5877-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5878-363D-11E5-9242-09173F13E4C5
n29:hasATCCode
n30:L04AX02
n3:H-Bond-Acceptor-Count
n4:271B5887-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5888-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5882-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5883-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5885-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5884-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5886-363D-11E5-9242-09173F13E4C5
n3:absorption
The absolute bioavailability has not yet been characterized in human subjects due to its poor aqueous solubility. In studies of both healthy volunteers and subjects with Hansen&rsquo;s disease, the mean time to peak plasma concentrations (Tmax) ranged from 2.9 to 5.7 hours indicating that thalidomide is slowly absorbed from the gastrointestinal tract.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
50-35-1
n3:category
n3:containedIn
n8:271B5872-363D-11E5-9242-09173F13E4C5 n8:271B5870-363D-11E5-9242-09173F13E4C5 n8:271B5871-363D-11E5-9242-09173F13E4C5 n8:271B586E-363D-11E5-9242-09173F13E4C5 n8:271B586F-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B588D-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B588F-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5890-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5892-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B588C-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B588B-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B588E-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B587C-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5889-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B588A-363D-11E5-9242-09173F13E4C5