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Thalidomide
Identification
- Name
- Thalidomide
- Accession Number
- DB01041
- Description
A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppresive and anti-angiogenic activity. It inhibits release of tumor necrosis factor-alpha from monocytes, and modulates other cytokine action. [PubChem]
- Type
- Small Molecule
- Groups
- Approved, Investigational, Withdrawn
- Structure
Structure for Thalidomide (DB01041)
- Weight
- Average: 258.2295
Monoisotopic: 258.064056818 - Chemical Formula
- C13H10N2O4
- Synonyms
- (+-)-N-(2,6-dioxo-3-Piperidyl)phthalimide
- (+-)-Thalidomide
- (±)-N-(2,6-dioxo-3-piperidyl)phthalimide
- (±)-thalidomide
- 1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline
- 2,6-dioxo-3-phthalimidopiperidine
- 3-Phthalimidoglutarimide
- alpha-(N-Phthalimido)glutarimide
- alpha-N-Phthalylglutaramide
- N-(2,6-dioxo-3-piperidyl)phthalimide
- N-Phthaloylglutamimide
- N-Phthalyl-glutaminsaeure-imid
- N-Phthalylglutamic acid imide
- Talidomida
- Thalidomide
- Thalidomidum
- α-(N-phthalimido)glutarimide
- α-N-phthalylglutaramide
- α-phthalimidoglutarimide
- External IDs
- NSC-527179
- NSC-66847
Pharmacology
- Indication
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.
- Associated Conditions
- Chronic Graft Versus Host Disease
- Multiple Myeloma (MM)
- Stomatitis, Aphthous
- Uremic Pruritus
- Waldenström's Macroglobulinemia (WM)
- Advanced Systemic light chain amyloidosis
- Moderate Erythema nodosum leprosum
- Refractory Graft versus host disease
- Severe Erythema nodosum leprosum
- Treatment naive multiple myeloma
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
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.
- Mechanism of action
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.
Target Actions Organism AProtein cereblon inhibitorHumans ATumor necrosis factor inhibitorHumans ANuclear factor NF-kappa-B p105 subunit antagonistHumans ADNA intercalationHumans AFibroblast growth factor receptor 2 antagonistHumans UProstaglandin G/H synthase 2 antagonistHumans Ualpha1-acid glycoprotein binderHumans - Absorption
The absolute bioavailability has not yet been characterized in human subjects due to its poor aqueous solubility. In studies of both healthy volunteers and subjects with Hansen’s disease, the mean time to peak plasma concentrations (Tmax) ranged from 2.9 to 5.7 hours indicating that thalidomide is slowly absorbed from the gastrointestinal tract.
- Volume of distribution
- Not Available
- Protein binding
55% and 66% for the (+)R and (−)S enantiomers, respectively.
- Metabolism
Thalidomide itself does not appear to be hepatically metabolized to any large extent, but appears to undergo non-enzymatic hydrolysis in plasma to multiple metabolites. Thalidomide may be metabolized hepatically by enzymes of the cytochrome P450 enzyme system. The end product of metabolism, phthalic acid, is excreted as a glycine conjugate.
Hover over products below to view reaction partners
- Route of elimination
Thalidomide itself has less than 0.7% of the dose excreted in the urine as unchanged drug.
- Half-life
The mean half-life of elimination ranges from approximately 5 to 7 hours following a single dose and is not altered upon multiple dosing.
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
The R-configuration and the S-configuration are more toxic individually than the racemic mixture. The LD50 could not be established in mice for racemic thalidomide, whereas LD50 values for the R and S configurations are reported to be 0.4 to 0.7 g/kg and 0.5 to 1.5 g/kg, respectively.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbatacept The metabolism of Thalidomide can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Thalidomide. Abiraterone The metabolism of Thalidomide can be decreased when combined with Abiraterone. Acebutolol The risk or severity of adverse effects can be increased when Thalidomide is combined with Acebutolol. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Thalidomide. Acetazolamide Acetazolamide may increase the central nervous system depressant (CNS depressant) activities of Thalidomide. Acetohexamide The metabolism of Thalidomide can be decreased when combined with Acetohexamide. Acetophenazine Acetophenazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide. Acetyl sulfisoxazole The metabolism of Thalidomide can be decreased when combined with Acetyl sulfisoxazole. Acetyldigitoxin Acetyldigitoxin may decrease the cardiotoxic activities of Thalidomide. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid alcohol. Ingesting alcohol may increase the drowsiness caused by thalidomide.
- Take after a meal. Wait at least 1 hour after eating before taking thalidomide.
Products
- International/Other Brands
- Contergan / Distaval / K-17 / Pro-ban M / Sedalis / Softenon / Talimol / Thaled
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataThalidomide Celgene Capsule 50 mg Oral Celgene Europe Bv 2008-04-16 Not applicable EU 
Thalomid Capsule 50 mg/1 Oral Celgene Corporation 2003-06-20 Not applicable US 
Thalomid Capsule 150 mg/1 Oral Celgene Corporation 2007-03-20 Not applicable US Thalomid Capsule 50 mg Oral Celgene 2010-11-01 Not applicable Canada 
Thalomid Capsule 100 mg Oral Celgene 2011-02-17 Not applicable Canada Thalomid Capsule 150 mg Oral Celgene Not applicable Not applicable Canada Thalomid Capsule 100 mg/1 Oral Celgene Corporation 2003-06-20 Not applicable US Thalomid Capsule 200 mg/1 Oral Celgene Corporation 2003-06-20 Not applicable US Thalomid Capsule 200 mg Oral Celgene 2011-02-17 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- L04AX02 — Thalidomide
- Drug Categories
- Acids, Carbocyclic
- Angiogenesis Inhibitors
- Angiogenesis Modulating Agents
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Cardiotoxic antineoplastic agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A5 Inducers
- Cytochrome P-450 CYP3A5 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Decreased Immunologically Active Molecule Activity
- Drugs causing inadvertant photosensitivity
- Growth Inhibitors
- Growth Substances
- Heterocyclic Compounds, Fused-Ring
- Hypotensive Agents
- Imides
- Immunologic Factors
- Immunomodulatory Agents
- Immunosuppressive Agents
- Isoindoles
- Leprostatic Agents
- Myelosuppressive Agents
- Noxae
- Photosensitizing Agents
- Phthalic Acids
- Phthalimides
- Piperidines
- Piperidones
- Teratogens
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Isoindoles and derivatives
- Sub Class
- Isoindolines
- Direct Parent
- Phthalimides
- Alternative Parents
- Alpha amino acids and derivatives / Isoindoles / Piperidinediones / Delta lactams / N-substituted carboxylic acid imides / Benzenoids / N-unsubstituted carboxylic acid imides / Dicarboximides / Azacyclic compounds / Organopnictogen compounds show 4 more
- Substituents
- Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid imide / Carboxylic acid imide, n-substituted / Carboxylic acid imide, n-unsubstituted / Delta-lactam show 14 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- piperidones, phthalimides (CHEBI:74947)
Chemical Identifiers
- UNII
- 4Z8R6ORS6L
- CAS number
- 50-35-1
- InChI Key
- UEJJHQNACJXSKW-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione
- SMILES
- O=C1N(C2CCC(=O)NC2=O)C(=O)C2=CC=CC=C12
References
- Synthesis Reference
Jamshed Shah, "Synthesis and anti-tumor activity of nitrogen substituted thalidomide analogs." U.S. Patent US20030139451, issued July 24, 2003.
US20030139451- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015175
- KEGG Drug
- D00754
- KEGG Compound
- C07910
- PubChem Compound
- 5426
- PubChem Substance
- 46505665
- ChemSpider
- 5233
- BindingDB
- 50070114
- 10432
- ChEBI
- 74947
- ChEMBL
- CHEMBL468
- Therapeutic Targets Database
- DAP000865
- PharmGKB
- PA451644
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Thalidomide
- AHFS Codes
- 92:20.00 — Immunomodulatory Agents
- FDA label
- Download (180 KB)
- MSDS
- Download (58.6 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Multiple Myeloma (MM) 1 4 Completed Treatment Multiple Myeloma (MM) 1 4 Not Yet Recruiting Treatment Cancer, Therapy-Related 1 4 Not Yet Recruiting Treatment Coronary Artery Disease (CAD) 1 4 Recruiting Treatment Cutaneous Lupus / Juvenile SLE / Systemic Lupus Erythematosus (SLE) 1 4 Recruiting Treatment Malignant Neoplasm of Stomach 1 4 Recruiting Treatment Mantle Cell Lymphoma (MCL) 1 4 Recruiting Treatment Non-Small Cell Lung Carcinoma (NSCLC) 1 4 Recruiting Treatment Waldenström's Macroglobulinemia (WM) 1 4 Terminated Treatment Uveitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Celgene
- IDT Australia Ltd.
- Penn Pharmaceutical Services Ltd.
- Dosage Forms
Form Route Strength Capsule Oral Capsule Oral 50 mg Capsule 50 mg Capsule Oral 100 mg Capsule Oral 100 mg/1 Capsule Oral 150 mg Capsule Oral 150 mg/1 Capsule Oral 200 mg/1 Capsule Oral 200 mg Capsule Oral 50 mg/1 - Prices
Unit description Cost Unit Thalomid 28 50 mg capsule Disp Pack 4372.47USD disp Thalomid 200 mg capsule 277.5USD capsule Thalomid 150 mg capsule 260.61USD capsule Thalomid 100 mg capsule 243.73USD capsule Thalomid 50 mg capsule 150.15USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS6235756 No 2001-05-22 2013-03-01 US CA2505964 No 2009-07-28 2023-11-13 Canada CA2157288 No 2005-11-08 2014-02-24 Canada US6045501 No 2000-04-04 2018-08-28 US US6315720 No 2001-11-13 2020-10-23 US US6561976 No 2003-05-13 2018-08-28 US US6561977 No 2003-05-13 2020-10-23 US US6755784 No 2004-06-29 2020-10-23 US US6869399 No 2005-03-22 2020-10-23 US US6908432 No 2005-06-21 2018-08-28 US US7141018 No 2006-11-28 2020-10-23 US US7435745 No 2008-10-14 2017-11-03 US US7874984 No 2011-01-25 2018-08-28 US US7959566 No 2011-06-14 2020-10-23 US US8204763 No 2012-06-19 2018-08-28 US US8315886 No 2012-11-20 2020-10-23 US US8626531 No 2014-01-07 2020-10-23 US US8589188 No 2013-11-19 2018-08-28 US US7230012 No 2007-06-12 2023-12-09 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 270 °C PhysProp water solubility 545 mg/L (at 25 °C) BUDAVARI,S ET AL. (1996) logP 0.33 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 2.55 mg/mL ALOGPS logP 0.42 ALOGPS logP 0.016 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 11.59 ChemAxon pKa (Strongest Basic) -6.4 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 83.55 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 64.32 m3·mol-1 ChemAxon Polarizability 24.42 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9775 Blood Brain Barrier + 0.9382 Caco-2 permeable - 0.5651 P-glycoprotein substrate Substrate 0.5301 P-glycoprotein inhibitor I Non-inhibitor 0.5115 P-glycoprotein inhibitor II Non-inhibitor 0.8951 Renal organic cation transporter Non-inhibitor 0.8179 CYP450 2C9 substrate Non-substrate 0.7904 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.5309 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.9378 Biodegradation Not ready biodegradable 0.8838 Rat acute toxicity 3.3039 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9769 hERG inhibition (predictor II) Non-inhibitor 0.8735
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Substrate recognition component of a DCX (DDB1-CUL4-X-box) E3 protein ligase complex that mediates the ubiquitination and subsequent proteasomal degradation of target proteins, such as MEIS2. Norma...
- Gene Name
- CRBN
- Uniprot ID
- Q96SW2
- Uniprot Name
- Protein cereblon
- Molecular Weight
- 50545.375 Da
References
- Zhu YX, Kortuem KM, Stewart AK: Molecular mechanism of action of immune-modulatory drugs thalidomide, lenalidomide and pomalidomide in multiple myeloma. Leuk Lymphoma. 2013 Apr;54(4):683-7. doi: 10.3109/10428194.2012.728597. Epub 2012 Sep 28. [PubMed:22966948]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Tumor necrosis factor receptor binding
- Specific Function
- Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...
- Gene Name
- TNF
- Uniprot ID
- P01375
- Uniprot Name
- Tumor necrosis factor
- Molecular Weight
- 25644.15 Da
References
- Richardson P, Hideshima T, Anderson K: Thalidomide in multiple myeloma. Biomed Pharmacother. 2002 May;56(3):115-28. [PubMed:12046682]
- Fu LM, Fu-Liu CS: Thalidomide and tuberculosis. Int J Tuberc Lung Dis. 2002 Jul;6(7):569-72. [PubMed:12102294]
- Enomoto N, Takei Y, Hirose M, Ikejima K, Miwa H, Kitamura T, Sato N: Thalidomide prevents alcoholic liver injury in rats through suppression of Kupffer cell sensitization and TNF-alpha production. Gastroenterology. 2002 Jul;123(1):291-300. [PubMed:12105857]
- Rajkumar SV: Thalidomide in the treatment of multiple myeloma. Expert Rev Anticancer Ther. 2001 Jun;1(1):20-8. [PubMed:12113124]
- Vescovo G, Ravara B, Angelini A, Sandri M, Carraro U, Ceconi C, Dalla Libera L: Effect of thalidomide on the skeletal muscle in experimental heart failure. Eur J Heart Fail. 2002 Aug;4(4):455-60. [PubMed:12167383]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Turk BE, Jiang H, Liu JO: Binding of thalidomide to alpha1-acid glycoprotein may be involved in its inhibition of tumor necrosis factor alpha production. Proc Natl Acad Sci U S A. 1996 Jul 23;93(15):7552-6. [PubMed:8755512]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Transcriptional repressor activity, rna polymerase ii transcription regulatory region sequence-specific binding
- Specific Function
- NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
- Gene Name
- NFKB1
- Uniprot ID
- P19838
- Uniprot Name
- Nuclear factor NF-kappa-B p105 subunit
- Molecular Weight
- 105355.175 Da
References
- Yasui K, Kobayashi N, Yamazaki T, Agematsu K: Thalidomide as an immunotherapeutic agent: the effects on neutrophil-mediated inflammation. Curr Pharm Des. 2005;11(3):395-401. [PubMed:15723633]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Yes
Intercalation
References
- Stephens TD, Bunde CJ, Fillmore BJ: Mechanism of action in thalidomide teratogenesis. Biochem Pharmacol. 2000 Jun 15;59(12):1489-99. [PubMed:10799645]
- Shoji A, Kuwahara M, Ozaki H, Sawai H: Modified DNA aptamer that binds the (R)-isomer of a thalidomide derivative with high enantioselectivity. J Am Chem Soc. 2007 Feb 7;129(5):1456-64. [PubMed:17263432]
- Stephens TD, Fillmore BJ: Hypothesis: thalidomide embryopathy-proposed mechanism of action. Teratology. 2000 Mar;61(3):189-95. [PubMed:10661908]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein tyrosine kinase activity
- Specific Function
- Tyrosine-protein kinase that acts as cell-surface receptor for fibroblast growth factors and plays an essential role in the regulation of cell proliferation, differentiation, migration and apoptosi...
- Gene Name
- FGFR2
- Uniprot ID
- P21802
- Uniprot Name
- Fibroblast growth factor receptor 2
- Molecular Weight
- 92024.29 Da
References
- Eichholz A, Merchant S, Gaya AM: Anti-angiogenesis therapies: their potential in cancer management. Onco Targets Ther. 2010 Jun 24;3:69-82. [PubMed:20616958]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Horrobin DF: A low toxicity maintenance regime, using eicosapentaenoic acid and readily available drugs, for mantle cell lymphoma and other malignancies with excess cyclin D1 levels. Med Hypotheses. 2003 May;60(5):615-23. [PubMed:12710892]
- Hada M, Mizutari K: [A case report of metastatic pancreatic cancer that responded remarkably to the combination of thalidomide, celecoxib and irinotecan]. Gan To Kagaku Ryoho. 2004 Sep;31(9):1407-10. [PubMed:15446566]
- Payvandi F, Wu L, Haley M, Schafer PH, Zhang LH, Chen RS, Muller GW, Stirling DI: Immunomodulatory drugs inhibit expression of cyclooxygenase-2 from TNF-alpha, IL-1beta, and LPS-stimulated human PBMC in a partially IL-10-dependent manner. Cell Immunol. 2004 Aug;230(2):81-8. [PubMed:15598423]
- Wiedmann MW, Caca K: Molecularly targeted therapy for gastrointestinal cancer. Curr Cancer Drug Targets. 2005 May;5(3):171-93. [PubMed:15892618]
- Du GJ, Lin HH, Xu QT, Wang MW: Thalidomide inhibits growth of tumors through COX-2 degradation independent of antiangiogenesis. Vascul Pharmacol. 2005 Aug;43(2):112-9. [PubMed:15982930]
- Kim JH, Scialli AR: Thalidomide: the tragedy of birth defects and the effective treatment of disease. Toxicol Sci. 2011 Jul;122(1):1-6. doi: 10.1093/toxsci/kfr088. Epub 2011 Apr 19. [PubMed:21507989]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Components:
References
- Turk BE, Jiang H, Liu JO: Binding of thalidomide to alpha1-acid glycoprotein may be involved in its inhibition of tumor necrosis factor alpha production. Proc Natl Acad Sci U S A. 1996 Jul 23;93(15):7552-6. [PubMed:8755512]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Okada Y, Murayama N, Yanagida C, Shimizu M, Guengerich FP, Yamazaki H: Drug interactions of thalidomide with midazolam and cyclosporine A: heterotropic cooperativity of human cytochrome P450 3A5. Drug Metab Dispos. 2009 Jan;37(1):18-23. doi: 10.1124/dmd.108.024679. Epub 2008 Oct 23. [PubMed:18948377]
- Ando Y, Fuse E, Figg WD: Thalidomide metabolism by the CYP2C subfamily. Clin Cancer Res. 2002 Jun;8(6):1964-73. [PubMed:12060642]
- Li Y, Jiang Z, Xiao Y, Li L, Gao Y: Metabolism of thalidomide by human liver microsome cytochrome CYP2C19 is required for its antimyeloma and antiangiogenic activities in vitro. Hematol Oncol. 2012 Mar;30(1):13-21. doi: 10.1002/hon.992. Epub 2011 Jun 3. [PubMed:21638302]
- Ando Y, Price DK, Dahut WL, Cox MC, Reed E, Figg WD: Pharmacogenetic associations of CYP2C19 genotype with in vivo metabolisms and pharmacological effects of thalidomide. Cancer Biol Ther. 2002 Nov-Dec;1(6):669-73. doi: 10.4161/cbt.318. [PubMed:12642692]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Ando Y, Fuse E, Figg WD: Thalidomide metabolism by the CYP2C subfamily. Clin Cancer Res. 2002 Jun;8(6):1964-73. [PubMed:12060642]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inducer
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Drug created on June 13, 2005 07:24 / Updated on September 25, 2020 15:13
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