File:Thalidomide_enantiomers.svg · Wikimedia Commons · See Wikimedia Commons
thalidomide
Sign in to saveAlso known as K-17, 1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline, N-(2,6-dioxo-3-piperidyl)phthalimide, (±)-thalidomide, 3-Phthalimidoglutarimide, N-Phthalyl-glutaminsaeure-imid, Talidomida, Thalidomidum
Thalidomide, sold under the brand names Contergan, Distaval and Thalomid among others, is an oral administered medication used to treat a number of cancers (e.g., multiple myeloma), graft-versus-host disease, and many skin disorders (e.g., complications of leprosy such as skin lesions). Thalidomide has been used to treat conditions associated with HIV: aphthous ulcers, HIV-associated wasting syndrome, diarrhea, and Kaposi's sarcoma, but increases in HIV viral load have been reported.
Thalidomide is a medication taken by mouth that is used today to treat various cancers, graft-versus-host disease, skin conditions, and certain HIV-related problems. It matters because it is an effective treatment option for several serious medical conditions, though it has been associated with some complications in certain uses, such as increases in HIV viral load in some patients.
AI-generated from the Wikipedia summary — may contain errors.
Key facts
- Drug.Watchedfields
- changed
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 420478187
- Drug.image
- Thalidomide enantiomers.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.chirality
- Racemic mixture
- Drug.tradename
- Contergan, Thalomid, others
- Drug.MedlinePlus
- a699032
- Drug.licence_EU
- yes
- Drug.DailyMedID
- Thalidomide
- Drug.licence_US
- Thalidomide
- Drug.pregnancy_AU
- X
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- L04
- Drug.ATC_suffix
- AX02
- Drug.legal_AU
- S4
- Drug.legal_BR
- C3
via Wikipedia infobox
Chemical data
- Formula
- C13H10N2O4
- Molecular weight
- 258.23 g/mol
- IUPAC name
- 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione
- SMILES
- C1CC(=O)NC(=O)C1N2C(=O)C3=CC=CC=C3C2=O
- InChIKey
- UEJJHQNACJXSKW-UHFFFAOYSA-N
- XLogP
- 0.3
- Polar surface area
- 83.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 258.064057
Show 7 more facts
- Commons category
- Thalidomide
- chemical formula
- C₁₃H₁₀N₂O₄
- World Health Organisation international non-proprietary name
- thalidomide
- canonical SMILES
- C1CC(=O)NC(=O)C1N2C(=O)C3=CC=CC=C3C2=O
- defined daily dose
- 0.1
- MCN code
- 2925.19.10
- native label
- Thalidomide
Sources (12)
via Wikidata · CC0
~28 min read
Article
24 sectionsContents
- Medical uses
- Contraindications
- Adverse effects
- Interactions
- Overdose
- Pharmacology
- Chirality and biological activity
- Chemistry
- History
- Leprosy treatment
- Cancer treatment
- Society and culture
- Birth defect crisis
- Notable cases
- Change in drug regulations
- Impact on research involving women
- Quality of life
- Brand names
- Research
- Thalidomide analogs
- Clinical research
- References
- Further reading
- External links
Thalidomide, sold under the brand names Contergan, Distaval and Thalomid among others, is an oral administered medication used to treat a number of cancers (e.g., multiple myeloma), graft-versus-host disease, and many skin disorders (e.g., complications of leprosy such as skin lesions). Thalidomide has been used to treat conditions associated with HIV: aphthous ulcers, HIV-associated wasting syndrome, diarrhea, and Kaposi's sarcoma, but increases in HIV viral load have been reported.
Common side effects include sleepiness, rash, and dizziness. Severe side effects include tumor lysis syndrome, blood clots, and peripheral neuropathy. Thalidomide is a known human teratogen and carries an extremely high risk of severe, life-threatening birth defects if administered or taken during pregnancy. It causes skeletal deformities such as amelia (absence of legs and/or arms), absence of bones, and phocomelia (malformation of the limbs). A single dose of thalidomide, regardless of dosage, is enough to cause teratogenic effects.