Thalidomide

This article is about the drug. For the thalidomide scandal and birth defect crisis, see Thalidomide scandal.

Thalidomide
Clinical data
Pronunciation/θəˈlɪdəmaɪd/[1]
Trade namesContergan, Thalomid, others
Other namesα-Phthalimidoglutarimide
AHFS/Drugs.comMonograph
MedlinePlusa699032
License data
Pregnancy
category
  • AU: X (High risk)
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability90%
Protein binding55% and 66% for the (R)-(+)- and (S)-(−)-enantiomers, respectively[5]
MetabolismLiver (minimally via CYP2C19-mediated 5-hydroxylation; mostly via non-enzymatic hydrolysis at the four amide sites)[5]
Elimination half-life5–7.5 hours (dose-dependent)[5]
ExcretionUrine, feces and semen[5]
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.029
Chemical and physical data
FormulaC13H10N2O4
Molar mass258.233 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • O=C1c2ccccc2C(=O)N1C3CCC(=O)NC3=O
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) Y
  • Key:UEJJHQNACJXSKW-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Thalidomide, sold under the brand names Contergan 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).[6][7] 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.[6]

Common side effects include sleepiness, rash, and dizziness.[6] Severe side effects include tumor lysis syndrome, blood clots, and peripheral neuropathy.[8] Thalidomide is a known human teratogen and carries an extremely high risk of severe, life-threatening birth defects if administered or taken during pregnancy.[6] 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.[6]

Thalidomide was first marketed in 1957 in West Germany, where it was available as an over-the-counter drug.[9][10] When first released, thalidomide was promoted for anxiety, trouble sleeping, "tension", and morning sickness.[10][11] While it was initially thought to be safe in pregnancy, thalidomide was found to cause birth defects, resulting in its removal from the market in Europe in 1961.[9][10] The total number of infants severely harmed by thalidomide use during pregnancy is estimated at over 10,000, possibly 20,000, of whom about 40% died around the time of birth.[6][10] Those who survived had limb, eye, urinary tract, and heart problems.[9] Its initial entry into the US market was prevented by Frances Kelsey, a reviewer at the FDA.[11] The birth defects caused by thalidomide led to the development of greater drug regulation and monitoring in many countries.[9][11]

It was approved in the United States in 1998 for use as a treatment for cancer.[6] It is on the World Health Organization's List of Essential Medicines.[12] It is available as a generic medication.[8][13]

  1. ^ "Thalidomide". Oxford English Dictionary (Online ed.). Oxford University Press. (Subscription or participating institution membership required.)
  2. ^ "Thalomid- thalidomide capsule". DailyMed. 11 March 2021. Archived from the original on 21 October 2022. Retrieved 21 October 2022.
  3. ^ "Thalidomide BMS EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 21 October 2022. Retrieved 21 October 2022.
  4. ^ "Thalidomide Lipomed EPAR". European Medicines Agency. 18 July 2022. Archived from the original on 21 October 2022. Retrieved 21 October 2022.
  5. ^ a b c d Teo SK, Colburn WA, Tracewell WG, Kook KA, Stirling DI, Jaworsky MS, et al. (2004). "Clinical pharmacokinetics of thalidomide". Clinical Pharmacokinetics. 43 (5): 311–27. doi:10.2165/00003088-200443050-00004. PMID 15080764. S2CID 37728304.
  6. ^ a b c d e f g "Thalidomide Monograph for Professionals". Drugs.com. 7 April 2023. Updated as required.
  7. ^ "Thalidomide | C13H10N2O4". PubChem. National Center for Biotechnology Information, National Library of Medicine. CID 5426. Archived from the original on 13 February 2023. Retrieved 13 February 2023.
  8. ^ a b British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 936. ISBN 9780857113382.
  9. ^ a b c d Cuthbert A (2003). The Oxford Companion to the Body. Oxford University Press. p. 682. doi:10.1093/acref/9780198524038.001.0001. ISBN 9780198524038.
  10. ^ a b c d Miller MT (1991). "Thalidomide embryopathy: a model for the study of congenital incomitant horizontal strabismus". Transactions of the American Ophthalmological Society. 89: 623–74. PMC 1298636. PMID 1808819.
  11. ^ a b c Loue S, Sajatovic M (2004). Encyclopedia of Women's Health. Springer Science & Business Media. p. 644. ISBN 9780306480737. Archived from the original on 15 November 2021. Retrieved 25 August 2020.
  12. ^ Organization WH (2021). Model list of essential medicines: 22nd list. Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  13. ^ "First Generic Drug Approvals". U.S. Food and Drug Administration. 30 May 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.
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