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Pronunciation | /θəˈlɪdəmaɪd/[1] |
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[5] |
Metabolism | Liver (minimally via CYP2C19-mediated 5-hydroxylation; mostly via non-enzymatic hydrolysis at the four amide sites)[5] |
Elimination half-life | 5–7.5 hours (dose-dependent)[5] |
Excretion | Urine, feces and semen[5] |
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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 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][8] 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.[9] Thalidomide is a known human teratogen and carries an extremely high risk of severe, life-threatening birth defects if administered 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.[6]
Thalidomide was first marketed in 1957 in West Germany, where it was available over the counter.[10][11] When first released, thalidomide was promoted for anxiety, trouble sleeping, "tension", and morning sickness.[11][12] While it was initially thought to be safe in pregnancy, concerns regarding birth defects arose, resulting in its removal from the market in Europe in 1961.[10][11] 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][11] Those who survived had limb, eye, urinary tract, and heart problems.[10] Its initial entry into the US market was prevented by Frances Kelsey, a reviewer at the FDA.[12] The birth defects caused by thalidomide led to the development of greater drug regulation and monitoring in many countries.[10][12]
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.[13][14] It is available as a generic medication.[9][15]
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