Thalidomide
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| Pronunciation | /θəˈlɪdəmaɪd/ |
| Trade names | Contergan, Thalomid, others |
| Other names | α-Phthalimidoglutarimide |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a699032 |
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| Routes of administration | By mouth |
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| Pharmacokinetic data | |
| Bioavailability | 90% |
| Protein binding | 55% and 66% for the (R)-(+)- and (S)-(−)-enantiomers, respectively |
| Metabolism | Liver (minimally via CYP2C19-mediated 5-hydroxylation; mostly via non-enzymatic hydrolysis at the four amide sites) |
| Elimination half-life | 5–7.5 hours (dose-dependent) |
| Excretion | Urine, feces and semen |
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| ECHA InfoCard | 100.000.029 |
| Chemical and physical data | |
| Formula | C13H10N2O4 |
| Molar mass | 258.233 g·mol−1 |
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| Chirality | Racemic mixture |
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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). 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.
Thalidomide was first marketed in 1957 in West Germany, where it was available as an over-the-counter drug. When first released, thalidomide was promoted for anxiety, trouble sleeping, "tension", and morning sickness. 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. 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. Those who survived had limb, eye, urinary tract, and heart problems. Its initial entry into the US market was prevented by Frances Kelsey, a reviewer at the FDA. The birth defects caused by thalidomide led to the development of greater drug regulation and monitoring in many countries.
It was approved in the United States in 1998 for use as a treatment for cancer. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.