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Identification
NameThalidomide
Accession NumberDB01041  (APRD01251)
TypeSmall Molecule
GroupsApproved, Investigational, Withdrawn
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A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects.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]

Structure
Thumb
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
alpha-Phthalimidoglutarimide
Distaval
K-17
N-(2,6-dioxo-3-piperidyl)phthalimide
N-Phthaloylglutamimide
N-Phthalyl-glutaminsaeure-imid
N-Phthalylglutamic acid imide
Pro-ban M
Sedalis
Softenon
Talidomida
Talimol
Thalidomide
Thalidomidum
α-(N-phthalimido)glutarimide
α-N-phthalylglutaramide
α-phthalimidoglutarimide
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Thalomidcapsule50 mg/1oralCelgene Corporation2003-06-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thalomidcapsule50 mgoralCelgene Inc2010-11-01Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thalomidcapsule150 mgoralCelgene IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thalomidcapsule200 mgoralCelgene Inc2011-02-17Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thalomidcapsule100 mgoralCelgene Inc2011-02-17Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thalomidcapsule200 mg/1oralCelgene Corporation2003-06-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thalomidcapsule150 mg/1oralCelgene Corporation2007-03-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thalomidcapsule100 mg/1oralCelgene Corporation2003-06-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
ConterganNot Available
DistavalNot Available
K-17Not Available
SedalisNot Available
SoftenonNot Available
TalimolNot Available
ThaledNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number50-35-1
WeightAverage: 258.2295
Monoisotopic: 258.064056818
Chemical FormulaC13H10N2O4
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoindoles and derivatives
Sub ClassIsoindolines
Direct ParentIsoindolones
Alternative Parents
Substituents
  • Isoindolone
  • Isoindole
  • Piperidinedione
  • Piperidinone
  • Dicarboximide
  • Delta-lactam
  • 3-aminopiperidine
  • Benzenoid
  • Piperidine
  • Carboxylic acid imide, n-unsubstituted
  • Carboxylic acid imide
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor 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.
PharmacodynamicsThalidomide 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 actionIn 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.
AbsorptionThe 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 distributionNot Available
Protein binding55% 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.

SubstrateEnzymesProduct
Thalidomide
cis, trans-5'-HydroxythalidomideDetails
Thalidomide
5-HydroxythalidomideDetails
Thalidomide
Thalidomide arene oxideDetails
Thalidomide arene oxide
Not Available
5-HydroxythalidomideDetails
5-Hydroxythalidomide
5,6-dihydroxythalidomideDetails
Thalidomide
Not Available
4-phthalimidoglutaramic acidDetails
Thalidomide
Not Available
2-phthalimidoglutaramic acidDetails
2-phthalimidoglutaramic acid
Not Available
2-phthalimidoglutaric acidDetails
4-phthalimidoglutaramic acid
Not Available
2-phthalimidoglutaric acidDetails
Thalidomide
Not Available
alpha-(o-carboxybenzamido)glutarimideDetails
4-phthalimidoglutaramic acid
Not Available
4-(o-carboxybenzamido)glutaramic acidDetails
2-phthalimidoglutaramic acid
Not Available
2-(o-carboxybenzamido)glutaramic acidDetails
alpha-(o-carboxybenzamido)glutarimide
Not Available
2-(o-carboxybenzamido)glutaramic acidDetails
4-(o-carboxybenzamido)glutaramic acid
Not Available
2-(o-carboxybenzamido)glutaric acidDetails
4-(o-carboxybenzamido)glutaramic acid
Not Available
2-(o-carboxybenzamido)glutaric acidDetails
2-(o-carboxybenzamido)glutaramic acid
Not Available
2-(o-carboxybenzamido)glutaric acidDetails
Route of eliminationThalidomide itself has less than 0.7% of the dose excreted in the urine as unchanged drug.
Half lifeThe mean half-life of elimination ranges from approximately 5 to 7 hours following a single dose and is not altered upon multiple dosing.
ClearanceNot Available
ToxicityThe 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9775
Blood Brain Barrier+0.9382
Caco-2 permeable-0.5651
P-glycoprotein substrateSubstrate0.5301
P-glycoprotein inhibitor INon-inhibitor0.5115
P-glycoprotein inhibitor IINon-inhibitor0.8951
Renal organic cation transporterNon-inhibitor0.8179
CYP450 2C9 substrateNon-substrate0.7904
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5309
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9378
BiodegradationNot ready biodegradable0.8838
Rat acute toxicity3.3039 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9769
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Capsuleoral100 mg/1
Capsuleoral100 mg
Capsuleoral150 mg
Capsuleoral150 mg/1
Capsuleoral200 mg/1
Capsuleoral200 mg
Capsuleoral50 mg/1
Capsuleoral50 mg
Prices
Unit descriptionCostUnit
Thalomid 28 50 mg capsule Disp Pack4372.47USD disp
Thalomid 200 mg capsule277.5USD capsule
Thalomid 150 mg capsule260.61USD capsule
Thalomid 100 mg capsule243.73USD capsule
Thalomid 50 mg capsule150.15USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
Canada21572882005-11-082014-02-24
Canada25059642009-07-282023-11-13
United States62357561993-03-012013-03-01
United States72300122003-12-092023-12-09
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point270 °CPhysProp
water solubility545 mg/L (at 25 °C)BUDAVARI,S ET AL. (1996)
logP0.33HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.55 mg/mLALOGPS
logP0.42ALOGPS
logP0.016ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)11.59ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.32 m3·mol-1ChemAxon
Polarizability24.42 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-hz30000000-77362eaf27267f59650dView in MoNA
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 ReferencesNot Available
External Links
ATC CodesL04AX02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (180 KB)
MSDSDownload (58.6 KB)
Interactions
Drug Interactions
Drug
AbataceptThe risk or severity of adverse effects can be increased when Thalidomide is combined with Abatacept.
AlfentanilAlfentanil may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
AlprazolamAlprazolam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
AmitriptylineAmitriptyline may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
AmobarbitalAmobarbital may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
AmoxapineAmoxapine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
AnakinraThe risk or severity of adverse effects can be increased when Thalidomide is combined with Anakinra.
AripiprazoleAripiprazole may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
AsenapineAsenapine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
AzelastineAzelastine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
BaclofenBaclofen may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
BrexpiprazoleBrexpiprazole may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
BromazepamBromazepam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
BrompheniramineBrompheniramine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
BuprenorphineBuprenorphine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
BuspironeBuspirone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ButabarbitalButabarbital may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ButorphanolButorphanol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
CanakinumabThe risk or severity of adverse effects can be increased when Thalidomide is combined with Canakinumab.
CarbamazepineCarbamazepine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
CarbinoxamineCarbinoxamine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
CarisoprodolCarisoprodol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Certolizumab pegolThalidomide may increase the immunosuppressive activities of Certolizumab pegol.
CetirizineCetirizine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ChlordiazepoxideChlordiazepoxide may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ChlorotrianiseneChlorotrianisene may increase the thrombogenic activities of Thalidomide.
ChlorphenamineChlorphenamine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ChlorpromazineChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ChlorzoxazoneChlorzoxazone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ClemastineClemastine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ClobazamClobazam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ClomipramineClomipramine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ClonazepamClonazepam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ClonidineClonidine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ClorazepateClorazepate may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ClozapineClozapine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
CyclizineCyclizine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
CyclobenzaprineCyclobenzaprine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
CyproheptadineCyproheptadine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
DantroleneDantrolene may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Darbepoetin alfaDarbepoetin alfa may increase the thrombogenic activities of Thalidomide.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Thalidomide.
DesfluraneDesflurane may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
DesipramineDesipramine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
DesloratadineDesloratadine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
DexamethasoneDexamethasone may increase the dermatologic adverse activities of Thalidomide.
Dexchlorpheniramine maleateDexchlorpheniramine maleate may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
DiazepamDiazepam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
DienogestDienogest may increase the thrombogenic activities of Thalidomide.
DimenhydrinateDimenhydrinate may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
DiphenhydramineDiphenhydramine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
DoxepinDoxepin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
EfavirenzEfavirenz may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
EntacaponeEntacapone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Epoetin alfaEpoetin alfa may increase the thrombogenic activities of Thalidomide.
EstazolamEstazolam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
EstradiolEstradiol may increase the thrombogenic activities of Thalidomide.
EstropipateEstropipate may increase the thrombogenic activities of Thalidomide.
EszopicloneEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
EthanolThalidomide may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
EthosuximideEthosuximide may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
EthotoinEthotoin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
EtonogestrelEtonogestrel may increase the thrombogenic activities of Thalidomide.
EzogabineEzogabine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
FelbamateFelbamate may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
FentanylFentanyl may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
FexofenadineFexofenadine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
FlibanserinFlibanserin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
FlunarizineFlunarizine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
FlupentixolFlupentixol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
FluphenazineFluphenazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
FlurazepamFlurazepam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
FosphenytoinFosphenytoin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
GabapentinGabapentin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
gabapentin enacarbilgabapentin enacarbil may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Gamma Hydroxybutyric AcidGamma Hydroxybutyric Acid may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
GuanfacineGuanfacine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
HaloperidolHaloperidol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
HydrocodoneHydrocodone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
HydromorphoneHydromorphone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
IloperidoneIloperidone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ImipramineImipramine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
IsofluraneIsoflurane may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
KetamineKetamine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
LamotrigineLamotrigine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
LeflunomideThe risk or severity of adverse effects can be increased when Thalidomide is combined with Leflunomide.
LevetiracetamLevetiracetam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
LevocabastineLevocabastine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
LevocetirizineLevocetirizine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
LevonorgestrelLevonorgestrel may increase the thrombogenic activities of Thalidomide.
LevorphanolLevorphanol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
LoratadineLoratadine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
LorazepamLorazepam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
LoxapineLoxapine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
LurasidoneLurasidone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
MaprotilineMaprotiline may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
MeclizineMeclizine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Medroxyprogesterone AcetateMedroxyprogesterone Acetate may increase the thrombogenic activities of Thalidomide.
MeprobamateMeprobamate may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Thalidomide.
MetaxaloneMetaxalone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
MethadoneMethadone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
MethocarbamolMethocarbamol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
MethohexitalMethohexital may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
MethotrimeprazineMethotrimeprazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Methoxy polyethylene glycol-epoetin betaMethoxy polyethylene glycol-epoetin beta may increase the thrombogenic activities of Thalidomide.
MethsuximideMethsuximide may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
MetyrosineThalidomide may increase the sedative activities of Metyrosine.
MidazolamMidazolam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
MirtazapineMirtazapine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
MorphineMorphine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
NalbuphineNalbuphine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
NatalizumabThe risk or severity of adverse effects can be increased when Thalidomide is combined with Natalizumab.
NitrazepamNitrazepam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Nitrous oxideNitrous oxide may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
NorethindroneNorethindrone may increase the thrombogenic activities of Thalidomide.
NortriptylineNortriptyline may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
OlanzapineOlanzapine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
OlopatadineOlopatadine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
OrphenadrineThalidomide may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
OxazepamOxazepam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
OxycodoneOxycodone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
OxymorphoneOxymorphone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PaliperidonePaliperidone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PamidronateThalidomide may increase the nephrotoxic activities of Pamidronate.
ParaldehydeThalidomide may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Thalidomide is combined with Paroxetine.
PentazocinePentazocine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PentobarbitalPentobarbital may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PerphenazinePerphenazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PethidinePethidine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PhenobarbitalPhenobarbital may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PhenytoinPhenytoin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Thalidomide.
PimozidePimozide may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PipotiazinePipotiazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PizotifenPizotifen may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PomalidomidePomalidomide may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PramipexoleThalidomide may increase the sedative activities of Pramipexole.
PregabalinPregabalin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PrimidonePrimidone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ProchlorperazineProchlorperazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PromazinePromazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PromethazinePromethazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
PropofolPropofol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ProtriptylineProtriptyline may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
QuazepamQuazepam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
QuetiapineQuetiapine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
RamelteonRamelteon may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
RemifentanilRemifentanil may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ReserpineReserpine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
RilonaceptThe risk or severity of adverse effects can be increased when Thalidomide is combined with Rilonacept.
RisperidoneRisperidone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
RoflumilastRoflumilast may increase the immunosuppressive activities of Thalidomide.
RopiniroleThalidomide may increase the sedative activities of Ropinirole.
RotigotineThalidomide may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Thalidomide.
ScopolamineScopolamine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Scopolamine butylbromideScopolamine butylbromide may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
SecobarbitalSecobarbital may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
SevofluraneSevoflurane may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Thalidomide.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
StiripentolStiripentol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
SufentanilSufentanil may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
SuvorexantSuvorexant may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Thalidomide.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TasimelteonTasimelteon may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TemazepamTemazepam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TetrabenazineTetrabenazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ThioridazineThioridazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ThiothixeneThiothixene may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TiagabineTiagabine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TizanidineTizanidine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TocilizumabTocilizumab may increase the immunosuppressive activities of Thalidomide.
TofacitinibThe risk or severity of adverse effects can be increased when Thalidomide is combined with Tofacitinib.
TolcaponeTolcapone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TopiramateTopiramate may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TramadolTramadol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TrastuzumabTrastuzumab may increase the neutropenic activities of Thalidomide.
TriazolamTriazolam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TrifluoperazineTrifluoperazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TrimipramineTrimipramine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TriprolidineTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
VedolizumabThe risk or severity of adverse effects can be increased when Thalidomide is combined with Vedolizumab.
VigabatrinVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ZaleplonZaleplon may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ZiconotideZiconotide may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ZiprasidoneZiprasidone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ZoledronateThe risk or severity of adverse effects can be increased when Thalidomide is combined with Zoledronate.
ZolpidemZolpidem may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ZonisamideZonisamide may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ZopicloneZopiclone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ZuclopenthixolZuclopenthixol may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Food InteractionsNot Available

Targets

1. Protein cereblon

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Protein cereblon Q96SW2 Details

References:

  1. 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

2. Tumor necrosis factor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Tumor necrosis factor P01375 Details

References:

  1. Richardson P, Hideshima T, Anderson K: Thalidomide in multiple myeloma. Biomed Pharmacother. 2002 May;56(3):115-28. Pubmed
  2. Fu LM, Fu-Liu CS: Thalidomide and tuberculosis. Int J Tuberc Lung Dis. 2002 Jul;6(7):569-72. Pubmed
  3. 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
  4. Rajkumar SV: Thalidomide in the treatment of multiple myeloma. Expert Rev Anticancer Ther. 2001 Jun;1(1):20-8. Pubmed
  5. 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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  7. 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

3. Nuclear factor NF-kappa-B p105 subunit

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Nuclear factor NF-kappa-B p105 subunit P19838 Details

References:

  1. 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
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

4. DNA

Kind: Nucleotide

Organism: Human

Pharmacological action: yes

Actions: intercalation

Components

Name UniProt ID Details

References:

  1. Stephens TD, Bunde CJ, Fillmore BJ: Mechanism of action in thalidomide teratogenesis. Biochem Pharmacol. 2000 Jun 15;59(12):1489-99. Pubmed
  2. Shoji A, Kuwahara M, Ozaki H, Sawai H: Modified DNA aptamer that binds the®-isomer of a thalidomide derivative with high enantioselectivity. J Am Chem Soc. 2007 Feb 7;129(5):1456-64. Pubmed
  3. Stephens TD, Fillmore BJ: Hypothesis: thalidomide embryopathy-proposed mechanism of action. Teratology. 2000 Mar;61(3):189-95. Pubmed

5. Fibroblast growth factor receptor 2

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Fibroblast growth factor receptor 2 P21802 Details

References:

  1. Eichholz A, Merchant S, Gaya AM: Anti-angiogenesis therapies: their potential in cancer management. Onco Targets Ther. 2010 Jun 24;3:69-82. Pubmed

6. Prostaglandin G/H synthase 2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

References:

  1. 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
  2. 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
  3. 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
  4. Wiedmann MW, Caca K: Molecularly targeted therapy for gastrointestinal cancer. Curr Cancer Drug Targets. 2005 May;5(3):171-93. Pubmed
  5. 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
  6. 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

7. Nuclear factor kappa-light-chain-enhancer of activated B cells

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details

References:

  1. 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

8. alpha1-acid glycoprotein

Kind: Protein group

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Alpha-1-acid glycoprotein 1 P02763 Details
Alpha-1-acid glycoprotein 2 P19652 Details

References:

  1. 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

Enzymes

1. Cytochrome P450 2C19

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. 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
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. Pubmed
  2. 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

3. Cytochrome P450 1A1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. 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

4. Cytochrome P450 2E1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. 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

5. Cytochrome P450 2C9

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. 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

6. Prostaglandin G/H synthase 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

References:

  1. 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

7. Prostaglandin G/H synthase 2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

References:

  1. 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

8. Cytochrome P450 3A5

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. 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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13