Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H10N2O4 |
Molecular Weight | 258.2295 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1N(C2CCC(=O)NC2=O)C(=O)C3=CC=CC=C13
InChI
InChIKey=UEJJHQNACJXSKW-UHFFFAOYSA-N
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)
DescriptionSources: http://www.drugbank.ca/drugs/DB01041Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020785s051lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB01041
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020785s051lbl.pdf
Thalidomide is an immunomodulatory agent with a spectrum of activity that is not fully characterized. Thalidomide is racemic — it contains both left and right-handed isomers in equal amounts: one enantiomer is effective against morning sickness, and the other is teratogenic. The enantiomers are converted to each other in vivo. That is, if a human is given D-thalidomide or L-thalidomide, both isomers can be found in the serum. Hence, administering only one enantiomer will not prevent the teratogenic effect in humans. 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. Thalidomide is used 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. Thalidomide is sold under the brand name Immunoprin, among others.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22650377
Curator's Comment: Thalidomide, an inhibitor of TNF-α protein synthesis is readily capable of crossing the blood-brain barrier
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q96SW2 Gene ID: 51185.0 Gene Symbol: CRBN Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB01041 |
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Target ID: CHEMBL1825 Sources: http://www.drugbank.ca/drugs/DB01041 |
200.0 µM [IC50] | ||
Target ID: CHEMBL3251 Sources: http://www.drugbank.ca/drugs/DB01041 |
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Target ID: CHEMBL4142 Sources: http://www.drugbank.ca/drugs/DB01041 |
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Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11909713 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | THALOMID Approved UseTHALOMID in combination with dexamethasone is indicated for the treatment of patients with newly diagnosed multiple myeloma (MM).
THALOMID is indicated for the acute treatment of the cutaneous manifestations of moderate to severe erythema nodosum leprosum (ENL).
THALOMID is not indicated as monotherapy for such ENL treatment in the presence of moderate to severe neuritis.
THALOMID is also indicated as maintenance therapy for prevention and suppression of the cutaneous manifestations of ENL recurrence. Launch Date9.0046077E11 |
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Primary | THALOMID Approved UseTHALOMID in combination with dexamethasone is indicated for the treatment of patients with newly diagnosed multiple myeloma (MM).
THALOMID is indicated for the acute treatment of the cutaneous manifestations of moderate to severe erythema nodosum leprosum (ENL).
THALOMID is not indicated as monotherapy for such ENL treatment in the presence of moderate to severe neuritis.
THALOMID is also indicated as maintenance therapy for prevention and suppression of the cutaneous manifestations of ENL recurrence. Launch Date9.0046077E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 mg/L |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
THALIDOMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
19.8 mg × h/L |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
THALIDOMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.17 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
THALIDOMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
45% |
THALIDOMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
400 mg/m2 1 times / day multiple, oral MTD Dose: 400 mg/m2, 1 times / day Route: oral Route: multiple Dose: 400 mg/m2, 1 times / day Co-administed with:: Carboplatin, i.v(1/21 days) Sources: Page: p.4397 |
unhealthy, 11 n = 10 Health Status: unhealthy Condition: Cancer Age Group: 11 Sex: M+F Population Size: 10 Sources: Page: p.4397 |
DLT: Somnolence... Dose limiting toxicities: Somnolence (20%) Sources: Page: p.4397 |
400 mg/m2 1 times / day multiple, oral MTD Dose: 400 mg/m2, 1 times / day Route: oral Route: multiple Dose: 400 mg/m2, 1 times / day Co-administed with:: Carboplatin, i.v(1/21 days) Sources: Page: p.4397 |
unhealthy, 11 n = 6 Health Status: unhealthy Condition: Cancer Age Group: 11 Sex: M+F Population Size: 6 Sources: Page: p.4397 |
DLT: Ataxia... Dose limiting toxicities: Ataxia (16.7%) Sources: Page: p.4397 |
150 mg 2 times / day multiple, oral MTD Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: Page: p.658 |
unhealthy, 57 n = 7 Health Status: unhealthy Condition: Hepatocellular carcinoma Age Group: 57 Sex: M+F Population Size: 7 Sources: Page: p.658 |
|
200 mg 2 times / day multiple, oral Studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: Page: p.658 |
unhealthy, 57 n = 2 Health Status: unhealthy Condition: Hepatocellular carcinoma Age Group: 57 Sex: M+F Population Size: 2 Sources: Page: p.658 |
DLT: Dyspnea... |
400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Erythema nodosum leprosum Sources: Page: p.1 |
Disc. AE: Fetal damage, Deep vein thrombosis... AEs leading to discontinuation/dose reduction: Fetal damage Sources: Page: p.1Deep vein thrombosis Pulmonary embolism |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Somnolence | 20% DLT |
400 mg/m2 1 times / day multiple, oral MTD Dose: 400 mg/m2, 1 times / day Route: oral Route: multiple Dose: 400 mg/m2, 1 times / day Co-administed with:: Carboplatin, i.v(1/21 days) Sources: Page: p.4397 |
unhealthy, 11 n = 10 Health Status: unhealthy Condition: Cancer Age Group: 11 Sex: M+F Population Size: 10 Sources: Page: p.4397 |
Ataxia | 16.7% DLT |
400 mg/m2 1 times / day multiple, oral MTD Dose: 400 mg/m2, 1 times / day Route: oral Route: multiple Dose: 400 mg/m2, 1 times / day Co-administed with:: Carboplatin, i.v(1/21 days) Sources: Page: p.4397 |
unhealthy, 11 n = 6 Health Status: unhealthy Condition: Cancer Age Group: 11 Sex: M+F Population Size: 6 Sources: Page: p.4397 |
Dyspnea | 50% DLT |
200 mg 2 times / day multiple, oral Studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: Page: p.658 |
unhealthy, 57 n = 2 Health Status: unhealthy Condition: Hepatocellular carcinoma Age Group: 57 Sex: M+F Population Size: 2 Sources: Page: p.658 |
Deep vein thrombosis | Disc. AE | 400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Erythema nodosum leprosum Sources: Page: p.1 |
Fetal damage | Disc. AE | 400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Erythema nodosum leprosum Sources: Page: p.1 |
Pulmonary embolism | Disc. AE | 400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Erythema nodosum leprosum Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
---|---|---|
Lack of in vitro antimicrosporidian activity of thalidomide. | 1999 Sep |
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Thalidomide neuropathy: role of F-wave monitoring. | 2000 Aug |
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Thalidomide for treatment of patients with chronic graft-versus-host disease. | 2000 Dec 1 |
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Thalidomide in gastrointestinal disorders. | 2001 |
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A cybernetic theory of morality and moral autonomy. | 2001 Apr |
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Low-dose thalidomide plus dexamethasone is an effective salvage therapy for advanced myeloma. | 2001 Apr |
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Treatment of Behçet's disease--an update. | 2001 Apr |
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Pharmacotherapeutic options in inflammatory bowel disease: an update. | 2001 Feb |
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Thalidomide. | 2001 Feb |
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[Suppression of synthesis of tumor necrosis factor]. | 2001 Jan |
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Safety profile of thalidomide after 53 weeks of oral administration in beagle dogs. | 2001 Jan |
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Treatment strategies for recurrent oral aphthous ulcers. | 2001 Jan 1 |
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Clinical aspects and management of AIDS-related Kaposi's sarcoma. | 2001 Jul |
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Thalidomide and immunomodulatory derivatives augment natural killer cell cytotoxicity in multiple myeloma. | 2001 Jul 1 |
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Extended survival in advanced and refractory multiple myeloma after single-agent thalidomide: identification of prognostic factors in a phase 2 study of 169 patients. | 2001 Jul 15 |
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Thalidomide and prednisolone inhibit growth factor-induced human retinal pigment epithelium cell proliferation in vitro. | 2001 Jul-Aug |
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Thalidomide dose proportionality assessment following single doses to healthy subjects. | 2001 Jun |
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Color Doppler ultrasonography of the superior mesenteric artery for prenatal ultrasonographic diagnosis of a left-sided congenital diaphragmatic hernia. | 2001 Jun |
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Effectors of inflammation in actinic prurigo. | 2001 Jun |
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Deep venous thrombosis and thalidomide therapy for multiple myeloma. | 2001 Jun 21 |
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[Thalidomide and thrombosis: three observations]. | 2001 Jun 9 |
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Prognostic factors and current practice in treatment of myelofibrosis with myeloid metaplasia: an update anno 2000. | 2001 Mar |
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Cutaneous lupus erythematosus. | 2001 Mar |
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Anti-tumor necrosis factor monoclonal antibody therapy for gastrointestinal Behçet's disease: a case report. | 2001 Mar |
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Embryonic mouse submandibular salivary gland morphogenesis and the TNF/TNF-R1 signal transduction pathway. | 2001 Mar 1 |
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Thalidomide in multiple myeloma: lack of response of soft-tissue plasmacytomas. | 2001 May |
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Approach to corticosteroid-dependent and corticosteroid-refractory Crohn's disease. | 2001 May |
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Thalidomide and its dermatologic uses. | 2001 May |
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Pilot study using the combination of methotrexate and thalidomide in the treatment of rheumatoid arthritis. | 2001 May-Jun |
Sample Use Guides
MM: 200 mg orally once daily. The recommended dose of
dexamethasone is 40 mg/day on days 1-4, 9-12, and 17-20
every 28 days.
• ENL: 100 to 300 mg/day for an episode of cutaneous ENL.
Up to 400 mg/day for severe cutaneous ENL.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22011961
The minimum dose of thalidomide used (1 uM) inhibited TNF-α production in HTLV-1-infected subjects in vitro.
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
43890
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FDA ORPHAN DRUG |
80194
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FDA ORPHAN DRUG |
30788
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WHO-ATC |
L04AX02
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FDA ORPHAN DRUG |
115598
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FDA ORPHAN DRUG |
43790
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NDF-RT |
N0000008663
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WHO-VATC |
QL04AX02
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FDA ORPHAN DRUG |
90795
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EU-Orphan Drug |
EU/3/01/067
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NDF-RT |
N0000008663
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FDA ORPHAN DRUG |
585417
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FDA ORPHAN DRUG |
110197
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FDA ORPHAN DRUG |
72092
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NCI_THESAURUS |
C129820
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FDA ORPHAN DRUG |
114998
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NCI_THESAURUS |
C1742
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FDA ORPHAN DRUG |
121898
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FDA ORPHAN DRUG |
187204
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FDA ORPHAN DRUG |
94995
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NCI_THESAURUS |
C574
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FDA ORPHAN DRUG |
32188
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EMA ASSESSMENT REPORTS |
THALIDOMIDE CELGENE (AUTHORIZED: MUTIPLE MYELOMA)
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NCI_THESAURUS |
C54677
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FDA ORPHAN DRUG |
82594
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LIVERTOX |
NBK548371
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Code System | Code | Type | Description | ||
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50-35-1
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527179
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10432
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4Z8R6ORS6L
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DTXSID9022524
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100000089194
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1652500
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4Z8R6ORS6L
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74947
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D013792
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5426
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66847
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DB01041
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7327
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CHEMBL468
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THALIDOMIDE
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SUB10958MIG
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9513
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C870
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200-031-1
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762
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2616
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m10673
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3586
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ACTIVE MOIETY
METABOLITE (PARENT)
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METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
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