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Identification
NameAlitretinoin
Accession NumberDB00523  (APRD00017)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionAn important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth; and embryonic development. An excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute). [PubChem]
Structure
Thumb
Synonyms
(2e,4e,6Z,8e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
(7e,9Z,11e,13e)-Retinoic acid
9-cis-Retinoic acid
9-cis-Tretinoin
9(Z)-Retinoic acid
Alitretinoin
Alitretinoína
Alitrétinoïne
Alitretinoinum
Panretin
Panretyn
External Identifiers
  • BAL4079
  • CCRIS 7098
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PanretinGel60 mg/60gTopicalEisai Inc.1999-02-03Not applicableUs
PanretinGel0.1 %CutaneousEisai Ltd2000-10-11Not applicableEu
PanretinGel0.1 %TopicalLigand Pharmaceuticals Inc.Not applicableNot applicableCanada
ToctinoCapsule10 mgOralGlaxosmithkline Inc2011-01-11Not applicableCanada
ToctinoCapsule30 mgOralGlaxosmithkline Inc2010-11-19Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII1UA8E65KDZ
CAS number5300-03-8
WeightAverage: 300.4351
Monoisotopic: 300.20893014
Chemical FormulaC20H28O2
InChI KeySHGAZHPCJJPHSC-ZVCIMWCZSA-N
InChI
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
IUPAC Name
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
SMILES
C\C(\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C(\C)=C\C(O)=O
Pharmacology
IndicationFor topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma.
Structured Indications
PharmacodynamicsAlitretinoin (9-cis-retinoic acid) is a naturally-occurring endogenous retinoid indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma. Alitretinoin inhibits the growth of Kaposi's sarcoma (KS) cells in vitro.
Mechanism of actionAlitretinoin binds to and activates all known intracellular retinoid receptor subtypes (RARa, RARb, RARg, RXRa, RXRb and RXRg). Once activated these receptors function as transcription factors that regulate the expression of genes that control the process of cellular differentiation and proliferation in both normal and neoplastic cells.
TargetKindPharmacological actionActionsOrganismUniProt ID
Retinoic acid receptor alphaProteinyes
agonist
HumanP10276 details
Retinoic acid receptor RXR-alphaProteinyes
agonist
HumanP19793 details
Retinoic acid receptor betaProteinyes
agonist
HumanP10826 details
Retinoic acid receptor RXR-betaProteinyes
agonist
HumanP28702 details
Retinoic acid receptor gammaProteinyes
agonist
HumanP13631 details
Retinoic acid receptor RXR-gammaProteinyes
agonist
HumanP48443 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Retinol MetabolismMetabolicSMP00074
Vitamin A DeficiencyDiseaseSMP00336
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetaminophenThe serum concentration of Alitretinoin can be increased when it is combined with Acetaminophen.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Alitretinoin.Approved
AfatinibThe serum concentration of Alitretinoin can be increased when it is combined with Afatinib.Approved
AlbendazoleThe serum concentration of Alitretinoin can be increased when it is combined with Albendazole.Approved, Vet Approved
AldosteroneThe serum concentration of Alitretinoin can be decreased when it is combined with Aldosterone.Experimental
AlectinibThe serum concentration of Alitretinoin can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Alitretinoin can be increased when it is combined with Alfentanil.Approved, Illicit
AmantadineThe serum concentration of Alitretinoin can be increased when it is combined with Amantadine.Approved
Aminohippuric acidThe serum concentration of Alitretinoin can be increased when it is combined with Aminohippuric acid.Approved
AmiodaroneThe serum concentration of Alitretinoin can be decreased when it is combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Alitretinoin can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Alitretinoin can be increased when it is combined with Amlodipine.Approved
AmprenavirThe serum concentration of Alitretinoin can be decreased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Alitretinoin can be increased when it is combined with Amsacrine.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Alitretinoin.Investigational
AstemizoleThe serum concentration of Alitretinoin can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe serum concentration of Alitretinoin can be increased when it is combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Alitretinoin can be increased when it is combined with Atenolol.Approved
AtorvastatinThe serum concentration of Alitretinoin can be increased when it is combined with Atorvastatin.Approved
AzelastineThe serum concentration of Alitretinoin can be increased when it is combined with Azelastine.Approved
AzithromycinThe serum concentration of Alitretinoin can be increased when it is combined with Azithromycin.Approved
BenzocaineThe serum concentration of Alitretinoin can be increased when it is combined with Benzocaine.Approved
BepridilThe serum concentration of Alitretinoin can be increased when it is combined with Bepridil.Approved, Withdrawn
BevacizumabBevacizumab may increase the cardiotoxic activities of Alitretinoin.Approved, Investigational
BiperidenThe serum concentration of Alitretinoin can be increased when it is combined with Biperiden.Approved
BosutinibThe serum concentration of Alitretinoin can be increased when it is combined with Bosutinib.Approved
BromocriptineThe serum concentration of Alitretinoin can be increased when it is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe serum concentration of Alitretinoin can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe serum concentration of Alitretinoin can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Alitretinoin.Approved
CaffeineThe serum concentration of Alitretinoin can be increased when it is combined with Caffeine.Approved
CanagliflozinThe serum concentration of Alitretinoin can be increased when it is combined with Canagliflozin.Approved
CandesartanThe serum concentration of Alitretinoin can be increased when it is combined with Candesartan.Approved
CaptoprilThe serum concentration of Alitretinoin can be increased when it is combined with Captopril.Approved
CarbamazepineThe serum concentration of Alitretinoin can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarvedilolThe serum concentration of Alitretinoin can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Alitretinoin can be increased when it is combined with Caspofungin.Approved
ChloroquineThe serum concentration of Alitretinoin can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorotrianiseneThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Alitretinoin.Withdrawn
ChlorpromazineThe serum concentration of Alitretinoin can be increased when it is combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe serum concentration of Alitretinoin can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Alitretinoin can be increased when it is combined with Chlorprothixene.Approved, Withdrawn
ChlortetracyclineThe risk or severity of adverse effects can be increased when Chlortetracycline is combined with Alitretinoin.Approved, Vet Approved
CholesterolThe serum concentration of Alitretinoin can be increased when it is combined with Cholesterol.Experimental
Cholic AcidThe serum concentration of Alitretinoin can be decreased when it is combined with Cholic Acid.Approved
CilazaprilThe serum concentration of Alitretinoin can be increased when it is combined with Cilazapril.Approved
CimetidineThe serum concentration of Alitretinoin can be decreased when it is combined with Cimetidine.Approved
CiprofloxacinThe serum concentration of Alitretinoin can be increased when it is combined with Ciprofloxacin.Approved, Investigational
CitalopramThe serum concentration of Alitretinoin can be increased when it is combined with Citalopram.Approved
ClarithromycinThe serum concentration of Alitretinoin can be increased when it is combined with Clarithromycin.Approved
ClofazimineThe serum concentration of Alitretinoin can be increased when it is combined with Clofazimine.Approved, Investigational
ClomipramineThe serum concentration of Alitretinoin can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe serum concentration of Alitretinoin can be decreased when it is combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Alitretinoin can be increased when it is combined with Cobicistat.Approved
ColchicineThe serum concentration of Alitretinoin can be increased when it is combined with Colchicine.Approved
ColforsinThe serum concentration of Alitretinoin can be increased when it is combined with Colforsin.Experimental
Conjugated Equine EstrogensThe therapeutic efficacy of Conjugated Equine Estrogens can be decreased when used in combination with Alitretinoin.Approved
CrizotinibThe serum concentration of Alitretinoin can be increased when it is combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Alitretinoin.Approved, Investigational
CyclosporineThe serum concentration of Alitretinoin can be decreased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
DaclatasvirThe serum concentration of Alitretinoin can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Alitretinoin can be increased when it is combined with Dactinomycin.Approved
DasatinibThe serum concentration of Alitretinoin can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Alitretinoin can be decreased when it is combined with Daunorubicin.Approved
DemeclocyclineThe risk or severity of adverse effects can be increased when Demeclocycline is combined with Alitretinoin.Approved
DesipramineThe serum concentration of Alitretinoin can be increased when it is combined with Desipramine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Alitretinoin.Approved
DesloratadineThe serum concentration of Alitretinoin can be increased when it is combined with Desloratadine.Approved, Investigational
DesogestrelThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Alitretinoin.Approved
DexamethasoneThe serum concentration of Alitretinoin can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe serum concentration of Alitretinoin can be increased when it is combined with Dextromethorphan.Approved
DiclofenacThe serum concentration of Alitretinoin can be increased when it is combined with Diclofenac.Approved, Vet Approved
DienestrolThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Alitretinoin.Approved
DienogestThe therapeutic efficacy of Dienogest can be decreased when used in combination with Alitretinoin.Approved
DiethylstilbestrolThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Alitretinoin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Alitretinoin.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Alitretinoin.Approved
DihydroergotamineThe serum concentration of Alitretinoin can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Alitretinoin can be increased when it is combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Alitretinoin can be increased when it is combined with Dipyridamole.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Alitretinoin.Approved, Investigational
DoxazosinThe serum concentration of Alitretinoin can be increased when it is combined with Doxazosin.Approved
DoxepinThe serum concentration of Alitretinoin can be increased when it is combined with Doxepin.Approved
DoxorubicinThe serum concentration of Alitretinoin can be decreased when it is combined with Doxorubicin.Approved, Investigational
DoxycyclineThe risk or severity of adverse effects can be increased when Doxycycline is combined with Alitretinoin.Approved, Investigational, Vet Approved
DronabinolThe serum concentration of Alitretinoin can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneThe serum concentration of Alitretinoin can be increased when it is combined with Dronedarone.Approved
DrospirenoneThe therapeutic efficacy of Drospirenone can be decreased when used in combination with Alitretinoin.Approved
ElbasvirThe serum concentration of Alitretinoin can be increased when it is combined with Elbasvir.Approved
EnalaprilThe serum concentration of Alitretinoin can be increased when it is combined with Enalapril.Approved, Vet Approved
EnzalutamideThe serum concentration of Alitretinoin can be increased when it is combined with Enzalutamide.Approved
ErgonovineThe serum concentration of Alitretinoin can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Alitretinoin can be increased when it is combined with Ergotamine.Approved
ErythromycinThe serum concentration of Alitretinoin can be decreased when it is combined with Erythromycin.Approved, Vet Approved
EstradiolThe therapeutic efficacy of Estradiol can be decreased when used in combination with Alitretinoin.Approved, Investigational, Vet Approved
EstramustineThe serum concentration of Alitretinoin can be increased when it is combined with Estramustine.Approved
EstriolThe serum concentration of Alitretinoin can be decreased when it is combined with Estriol.Approved, Vet Approved
Estrogens, esterifiedThe therapeutic efficacy of Estrogens, esterified can be decreased when used in combination with Alitretinoin.Approved
EstroneThe serum concentration of Alitretinoin can be decreased when it is combined with Estrone.Approved
Estrone sulfateThe therapeutic efficacy of Estrone sulfate can be decreased when used in combination with Alitretinoin.Approved
Ethinyl EstradiolThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Alitretinoin.Approved
Ethynodiol diacetateThe therapeutic efficacy of Ethynodiol diacetate can be decreased when used in combination with Alitretinoin.Approved
EtonogestrelThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Alitretinoin.Approved, Investigational
EtoposideThe serum concentration of Alitretinoin can be increased when it is combined with Etoposide.Approved
EtravirineThe serum concentration of Alitretinoin can be increased when it is combined with Etravirine.Approved
FelodipineThe serum concentration of Alitretinoin can be increased when it is combined with Felodipine.Approved, Investigational
FentanylThe serum concentration of Alitretinoin can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe serum concentration of Alitretinoin can be increased when it is combined with Fexofenadine.Approved
FidaxomicinThe serum concentration of Alitretinoin can be increased when it is combined with Fidaxomicin.Approved
FluconazoleThe serum concentration of Alitretinoin can be increased when it is combined with Fluconazole.Approved
FluoxetineThe serum concentration of Alitretinoin can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe serum concentration of Alitretinoin can be increased when it is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Alitretinoin can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Alitretinoin can be increased when it is combined with Flurazepam.Approved, Illicit
FluvoxamineThe serum concentration of Alitretinoin can be increased when it is combined with Fluvoxamine.Approved, Investigational
GefitinibThe serum concentration of Alitretinoin can be increased when it is combined with Gefitinib.Approved, Investigational
GenisteinThe serum concentration of Alitretinoin can be increased when it is combined with Genistein.Investigational
GestodeneThe therapeutic efficacy of Gestodene can be decreased when used in combination with Alitretinoin.Approved
GlyburideThe serum concentration of Alitretinoin can be increased when it is combined with Glyburide.Approved
GlycerolThe serum concentration of Alitretinoin can be increased when it is combined with Glycerol.Experimental
Gramicidin DThe serum concentration of Alitretinoin can be increased when it is combined with Gramicidin D.Approved
GrepafloxacinThe serum concentration of Alitretinoin can be increased when it is combined with Grepafloxacin.Withdrawn
HaloperidolThe serum concentration of Alitretinoin can be increased when it is combined with Haloperidol.Approved
HexestrolThe therapeutic efficacy of Hexestrol can be decreased when used in combination with Alitretinoin.Withdrawn
HydrocortisoneThe serum concentration of Alitretinoin can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
IdelalisibThe serum concentration of Alitretinoin can be increased when it is combined with Idelalisib.Approved
ImatinibThe serum concentration of Alitretinoin can be increased when it is combined with Imatinib.Approved
ImipramineThe serum concentration of Alitretinoin can be increased when it is combined with Imipramine.Approved
IndinavirThe serum concentration of Alitretinoin can be decreased when it is combined with Indinavir.Approved
IndomethacinThe serum concentration of Alitretinoin can be increased when it is combined with Indomethacin.Approved, Investigational
IsavuconazoniumThe serum concentration of Alitretinoin can be increased when it is combined with Isavuconazonium.Approved, Investigational
ItraconazoleThe serum concentration of Alitretinoin can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Alitretinoin can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Alitretinoin can be increased when it is combined with Ivermectin.Approved, Vet Approved
KetamineThe serum concentration of Alitretinoin can be increased when it is combined with Ketamine.Approved, Vet Approved
KetoconazoleThe serum concentration of Alitretinoin can be increased when it is combined with Ketoconazole.Approved, Investigational
LansoprazoleThe serum concentration of Alitretinoin can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Alitretinoin can be increased when it is combined with Lapatinib.Approved, Investigational
LevofloxacinThe serum concentration of Alitretinoin can be increased when it is combined with Levofloxacin.Approved, Investigational
LevonorgestrelThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Alitretinoin.Approved, Investigational
LevothyroxineThe serum concentration of Alitretinoin can be decreased when it is combined with Levothyroxine.Approved
LidocaineThe serum concentration of Alitretinoin can be increased when it is combined with Lidocaine.Approved, Vet Approved
LiothyronineThe serum concentration of Alitretinoin can be decreased when it is combined with Liothyronine.Approved, Vet Approved
LiotrixThe serum concentration of Alitretinoin can be decreased when it is combined with Liotrix.Approved
LisinoprilThe serum concentration of Alitretinoin can be increased when it is combined with Lisinopril.Approved, Investigational
LomitapideThe serum concentration of Alitretinoin can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Alitretinoin can be increased when it is combined with Loperamide.Approved
LopinavirThe serum concentration of Alitretinoin can be increased when it is combined with Lopinavir.Approved
LoratadineThe serum concentration of Alitretinoin can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Alitretinoin can be increased when it is combined with Losartan.Approved
LovastatinThe serum concentration of Alitretinoin can be increased when it is combined with Lovastatin.Approved, Investigational
LumacaftorThe serum concentration of Alitretinoin can be decreased when it is combined with Lumacaftor.Approved
LynestrenolThe therapeutic efficacy of Lynestrenol can be decreased when used in combination with Alitretinoin.Investigational
MaprotilineThe serum concentration of Alitretinoin can be increased when it is combined with Maprotiline.Approved
MebendazoleThe serum concentration of Alitretinoin can be increased when it is combined with Mebendazole.Approved, Vet Approved
Medroxyprogesterone acetateThe therapeutic efficacy of Medroxyprogesterone acetate can be decreased when used in combination with Alitretinoin.Approved, Investigational
MefloquineThe serum concentration of Alitretinoin can be increased when it is combined with Mefloquine.Approved
Megestrol acetateThe serum concentration of Alitretinoin can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MeprobamateThe serum concentration of Alitretinoin can be increased when it is combined with Meprobamate.Approved, Illicit
MestranolThe therapeutic efficacy of Mestranol can be decreased when used in combination with Alitretinoin.Approved
MethadoneThe serum concentration of Alitretinoin can be increased when it is combined with Methadone.Approved
MethallenestrilThe therapeutic efficacy of Methallenestril can be decreased when used in combination with Alitretinoin.Experimental
MethotrexateAlitretinoin may increase the hepatotoxic activities of Methotrexate.Approved
MetoprololThe serum concentration of Alitretinoin can be increased when it is combined with Metoprolol.Approved, Investigational
MibefradilThe serum concentration of Alitretinoin can be increased when it is combined with Mibefradil.Withdrawn
MiconazoleThe serum concentration of Alitretinoin can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Alitretinoin can be decreased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Alitretinoin can be decreased when it is combined with Mifepristone.Approved, Investigational
MinocyclineThe risk or severity of adverse effects can be increased when Minocycline is combined with Alitretinoin.Approved, Investigational
MitomycinThe serum concentration of Alitretinoin can be increased when it is combined with Mitomycin.Approved
MitoxantroneThe serum concentration of Alitretinoin can be decreased when it is combined with Mitoxantrone.Approved, Investigational
MorphineThe serum concentration of Alitretinoin can be increased when it is combined with Morphine.Approved, Investigational
NaltrexoneThe serum concentration of Alitretinoin can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaringeninThe serum concentration of Alitretinoin can be increased when it is combined with Naringenin.Experimental
NefazodoneThe serum concentration of Alitretinoin can be decreased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Alitretinoin can be decreased when it is combined with Nelfinavir.Approved
NeostigmineThe serum concentration of Alitretinoin can be increased when it is combined with Neostigmine.Approved, Vet Approved
NicardipineThe serum concentration of Alitretinoin can be increased when it is combined with Nicardipine.Approved
NifedipineThe serum concentration of Alitretinoin can be decreased when it is combined with Nifedipine.Approved
NilotinibThe serum concentration of Alitretinoin can be increased when it is combined with Nilotinib.Approved, Investigational
NisoldipineThe serum concentration of Alitretinoin can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Alitretinoin can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Alitretinoin can be increased when it is combined with Nitrendipine.Approved
NorelgestrominThe therapeutic efficacy of Norelgestromin can be decreased when used in combination with Alitretinoin.Approved
NorethisteroneThe serum concentration of Alitretinoin can be decreased when it is combined with Norethisterone.Approved
NorgestimateThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Alitretinoin.Approved
NorgestrelThe therapeutic efficacy of Norgestrel can be decreased when used in combination with Alitretinoin.Approved
OmeprazoleThe serum concentration of Alitretinoin can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OuabainOuabain may decrease the cardiotoxic activities of Alitretinoin.Approved
OxytetracyclineThe risk or severity of adverse effects can be increased when Oxytetracycline is combined with Alitretinoin.Approved, Vet Approved
P-NitrophenolThe serum concentration of Alitretinoin can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Alitretinoin.Approved, Vet Approved
Palmitic AcidThe serum concentration of Alitretinoin can be increased when it is combined with Palmitic Acid.Experimental
PantoprazoleThe serum concentration of Alitretinoin can be increased when it is combined with Pantoprazole.Approved
ParoxetineThe serum concentration of Alitretinoin can be increased when it is combined with Paroxetine.Approved, Investigational
PerindoprilThe serum concentration of Alitretinoin can be increased when it is combined with Perindopril.Approved
PhenobarbitalThe serum concentration of Alitretinoin can be decreased when it is combined with Phenobarbital.Approved
PimozideThe serum concentration of Alitretinoin can be increased when it is combined with Pimozide.Approved
Platelet Activating FactorThe serum concentration of Alitretinoin can be decreased when it is combined with Platelet Activating Factor.Experimental
PonatinibThe serum concentration of Alitretinoin can be increased when it is combined with Ponatinib.Approved
PosaconazoleThe serum concentration of Alitretinoin can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Alitretinoin can be increased when it is combined with Pravastatin.Approved
PrazosinThe serum concentration of Alitretinoin can be increased when it is combined with Prazosin.Approved
PrednisoneThe serum concentration of Alitretinoin can be increased when it is combined with Prednisone.Approved, Vet Approved
ProbenecidThe serum concentration of Alitretinoin can be increased when it is combined with Probenecid.Approved
ProgesteroneThe serum concentration of Alitretinoin can be decreased when it is combined with Progesterone.Approved, Vet Approved
PromethazineThe serum concentration of Alitretinoin can be increased when it is combined with Promethazine.Approved
PropafenoneThe serum concentration of Alitretinoin can be increased when it is combined with Propafenone.Approved
PropranololThe serum concentration of Alitretinoin can be increased when it is combined with Propranolol.Approved, Investigational
ProtriptylineThe serum concentration of Alitretinoin can be increased when it is combined with Protriptyline.Approved
QuercetinThe serum concentration of Alitretinoin can be increased when it is combined with Quercetin.Experimental
QuinacrineThe serum concentration of Alitretinoin can be increased when it is combined with Quinacrine.Approved
QuinidineThe serum concentration of Alitretinoin can be increased when it is combined with Quinidine.Approved
QuinineThe serum concentration of Alitretinoin can be increased when it is combined with Quinine.Approved
RanitidineThe serum concentration of Alitretinoin can be increased when it is combined with Ranitidine.Approved
RanolazineThe serum concentration of Alitretinoin can be increased when it is combined with Ranolazine.Approved, Investigational
ReboxetineThe serum concentration of Alitretinoin can be increased when it is combined with Reboxetine.Approved, Investigational
RegorafenibThe serum concentration of Alitretinoin can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Alitretinoin can be decreased when it is combined with Reserpine.Approved
RifampicinThe serum concentration of Alitretinoin can be decreased when it is combined with Rifampicin.Approved
RilpivirineThe serum concentration of Alitretinoin can be increased when it is combined with Rilpivirine.Approved
RitonavirThe serum concentration of Alitretinoin can be decreased when it is combined with Ritonavir.Approved, Investigational
RolapitantThe serum concentration of Alitretinoin can be increased when it is combined with Rolapitant.Approved
SaquinavirThe serum concentration of Alitretinoin can be decreased when it is combined with Saquinavir.Approved, Investigational
ScopolamineThe serum concentration of Alitretinoin can be increased when it is combined with Scopolamine.Approved
SelegilineThe serum concentration of Alitretinoin can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineThe serum concentration of Alitretinoin can be increased when it is combined with Sertraline.Approved
SimeprevirThe serum concentration of Alitretinoin can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Alitretinoin can be increased when it is combined with Simvastatin.Approved
SirolimusThe serum concentration of Alitretinoin can be decreased when it is combined with Sirolimus.Approved, Investigational
SorafenibThe serum concentration of Alitretinoin can be increased when it is combined with Sorafenib.Approved, Investigational
SpironolactoneThe serum concentration of Alitretinoin can be increased when it is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Alitretinoin can be decreased when it is combined with St. John's Wort.Nutraceutical
StaurosporineThe serum concentration of Alitretinoin can be increased when it is combined with Staurosporine.Experimental
StreptozocinThe serum concentration of Alitretinoin can be decreased when it is combined with Streptozocin.Approved
SulfinpyrazoneThe serum concentration of Alitretinoin can be increased when it is combined with Sulfinpyrazone.Approved
SumatriptanThe serum concentration of Alitretinoin can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibThe serum concentration of Alitretinoin can be increased when it is combined with Sunitinib.Approved, Investigational
Synthetic Conjugated Estrogens, AThe therapeutic efficacy of Synthetic Conjugated Estrogens, A can be decreased when used in combination with Alitretinoin.Approved
TacrineThe serum concentration of Alitretinoin can be increased when it is combined with Tacrine.Withdrawn
TacrolimusThe serum concentration of Alitretinoin can be decreased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenThe serum concentration of Alitretinoin can be decreased when it is combined with Tamoxifen.Approved
Taurocholic AcidThe serum concentration of Alitretinoin can be increased when it is combined with Taurocholic Acid.Experimental
TelmisartanThe serum concentration of Alitretinoin can be increased when it is combined with Telmisartan.Approved, Investigational
TemsirolimusThe serum concentration of Alitretinoin can be increased when it is combined with Temsirolimus.Approved
TerazosinThe serum concentration of Alitretinoin can be increased when it is combined with Terazosin.Approved
TerfenadineThe serum concentration of Alitretinoin can be increased when it is combined with Terfenadine.Withdrawn
TesmilifeneThe serum concentration of Alitretinoin can be decreased when it is combined with Tesmilifene.Investigational
TestosteroneThe serum concentration of Alitretinoin can be increased when it is combined with Testosterone.Approved, Investigational
TetracyclineThe risk or severity of adverse effects can be increased when Tetracycline is combined with Alitretinoin.Approved, Vet Approved
TicagrelorThe serum concentration of Alitretinoin can be increased when it is combined with Ticagrelor.Approved
TolvaptanThe serum concentration of Alitretinoin can be increased when it is combined with Tolvaptan.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Alitretinoin.Approved, Investigational
TrazodoneThe serum concentration of Alitretinoin can be decreased when it is combined with Trazodone.Approved, Investigational
TrifluoperazineThe serum concentration of Alitretinoin can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Alitretinoin can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimThe serum concentration of Alitretinoin can be decreased when it is combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe serum concentration of Alitretinoin can be increased when it is combined with Trimipramine.Approved
TroleandomycinThe serum concentration of Alitretinoin can be increased when it is combined with Troleandomycin.Approved
VenlafaxineThe serum concentration of Alitretinoin can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Alitretinoin can be decreased when it is combined with Verapamil.Approved
VinblastineThe serum concentration of Alitretinoin can be decreased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Alitretinoin can be decreased when it is combined with Vincristine.Approved, Investigational
VinorelbineThe serum concentration of Alitretinoin can be increased when it is combined with Vinorelbine.Approved, Investigational
Vitamin AThe risk or severity of adverse effects can be increased when Vitamin A is combined with Alitretinoin.Approved, Nutraceutical, Vet Approved
ZimelidineThe serum concentration of Alitretinoin can be increased when it is combined with Zimelidine.Withdrawn
Food InteractionsNot Available
References
Synthesis Reference

Hector F. DeLuca, Praveen K. Tadikonda, “Method of synthesis of retinoic acid.” U.S. Patent US5808120, issued December, 1975.

US5808120
General ReferencesNot Available
External Links
ATC CodesD11AH04L01XX22
AHFS Codes
  • 84:16.00
  • 92:00.00
PDB EntriesNot Available
FDA labelDownload (21.8 KB)
MSDSDownload (37.3 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9925
Blood Brain Barrier+0.9311
Caco-2 permeable+0.7603
P-glycoprotein substrateNon-substrate0.6144
P-glycoprotein inhibitor INon-inhibitor0.8912
P-glycoprotein inhibitor IINon-inhibitor0.8088
Renal organic cation transporterNon-inhibitor0.8639
CYP450 2C9 substrateNon-substrate0.8221
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.6025
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.8831
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9301
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9252
Ames testNon AMES toxic0.8944
CarcinogenicityNon-carcinogens0.7081
BiodegradationReady biodegradable0.5554
Rat acute toxicity2.1455 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9562
hERG inhibition (predictor II)Non-inhibitor0.9538
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Eisai inc
Packagers
Dosage forms
FormRouteStrength
GelCutaneous0.1 %
GelTopical0.1 %
GelTopical60 mg/60g
CapsuleOral10 mg
CapsuleOral30 mg
Prices
Unit descriptionCostUnit
Retin-A Micro Pump 0.04% Gel 50 gm Bottle246.73USD bottle
Retin-A Micro Pump 0.1% Gel 50 gm Bottle246.73USD bottle
Retin-A Micro 0.04% Gel 45 gm Tube212.3USD tube
Retin-A Micro 0.1% Gel 45 gm Tube212.3USD tube
Retin-A 0.1% Cream 45 gm Tube211.1USD tube
Retin-A 0.05% Cream 45 gm Tube181.16USD tube
Retin-A 0.025% Cream 45 gm Tube163.07USD tube
Retin-A 0.025% Gel 45 gm Tube162.79USD tube
Retin-A 0.01% Gel 45 gm Tube161.48USD tube
Retin-A Micro 0.04% Gel 20 gm Tube123.7USD tube
Retin-A Micro 0.1% Gel 20 gm Tube117.51USD tube
Retin-A 0.1% Cream 20 gm Tube112.51USD tube
Retin-A 0.05% Cream 20 gm Tube97.85USD tube
Retin-A 0.025% Cream 20 gm Tube85.59USD tube
Retin-A 0.01% Gel 15 gm Tube75.83USD tube
Retin-A 0.025% Gel 15 gm Tube69.01USD tube
Panretin 0.1% gel41.0USD g
Vesanoid 10 mg capsule31.54USD capsule
Retin-a micro 0.04% gel5.65USD g
Retin-a micro 0.1% gel5.65USD g
Retin-a micro pump 0.04% gel4.74USD g
Retin-a micro pump 0.1% gel4.74USD g
Retin-a 0.05% cream4.64USD g
Retin-a 0.1% cream4.51USD g
Renova 0.02% cream4.46USD g
Renova pump 0.02% cream4.28USD g
Retin-a 0.025% cream4.14USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2301907 No2009-02-102018-08-18Canada
US5932622 No1996-08-032016-08-03Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point189-190 °CNot Available
water solubility0.6 mg/LNot Available
logP4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00477 mg/mLALOGPS
logP5.66ALOGPS
logP5.01ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.79 m3·mol-1ChemAxon
Polarizability35.95 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoid skeleton
  • Diterpenoid
  • Carbocyclic fatty acid
  • Medium-chain fatty acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RX...
Gene Name:
RARA
Uniprot ID:
P10276
Molecular Weight:
50770.805 Da
References
  1. Baumann L, Vujevich J, Halem M, Martin LK, Kerdel F, Lazarus M, Pacheco H, Black L, Bryde J: Open-label pilot study of alitretinoin gel 0.1% in the treatment of photoaging. Cutis. 2005 Jul;76(1):69-73. [PubMed:16144296 ]
  2. Milliano MT, Luxon BA: Rat hepatic stellate cells become retinoid unresponsive during activation. Hepatol Res. 2005 Nov;33(3):225-33. Epub 2005 Oct 25. [PubMed:16253547 ]
  3. Rasooly R, Schuster GU, Gregg JP, Xiao JH, Chandraratna RA, Stephensen CB: Retinoid x receptor agonists increase bcl2a1 expression and decrease apoptosis of naive T lymphocytes. J Immunol. 2005 Dec 15;175(12):7916-29. [PubMed:16339527 ]
  4. Schrage K, Koopmans G, Joosten EA, Mey J: Macrophages and neurons are targets of retinoic acid signaling after spinal cord contusion injury. Eur J Neurosci. 2006 Jan;23(2):285-95. [PubMed:16420438 ]
  5. Ritter M, Kattmann D, Teichler S, Hartmann O, Samuelsson MK, Burchert A, Bach JP, Kim TD, Berwanger B, Thiede C, Jager R, Ehninger G, Schafer H, Ueki N, Hayman MJ, Eilers M, Neubauer A: Inhibition of retinoic acid receptor signaling by Ski in acute myeloid leukemia. Leukemia. 2006 Mar;20(3):437-43. [PubMed:16424870 ]
  6. Cheng C, Michaels J, Scheinfeld N: Alitretinoin: a comprehensive review. Expert Opin Investig Drugs. 2008 Mar;17(3):437-43. doi: 10.1517/13543784.17.3.437 . [PubMed:18321241 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXR...
Gene Name:
RXRA
Uniprot ID:
P19793
Molecular Weight:
50810.835 Da
References
  1. Bartholin L, Powers SE, Melhuish TA, Lasse S, Weinstein M, Wotton D: TGIF inhibits retinoid signaling. Mol Cell Biol. 2006 Feb;26(3):990-1001. [PubMed:16428452 ]
  2. Calleja C, Messaddeq N, Chapellier B, Yang H, Krezel W, Li M, Metzger D, Mascrez B, Ohta K, Kagechika H, Endo Y, Mark M, Ghyselinck NB, Chambon P: Genetic and pharmacological evidence that a retinoic acid cannot be the RXR-activating ligand in mouse epidermis keratinocytes. Genes Dev. 2006 Jun 1;20(11):1525-38. [PubMed:16751185 ]
  3. Zhelyaznik N, Mey J: Regulation of retinoic acid receptors alpha, beta and retinoid X receptor alpha after sciatic nerve injury. Neuroscience. 2006 Sep 15;141(4):1761-74. Epub 2006 Jun 19. [PubMed:16782282 ]
  4. Fukasawa H, Kagechika H, Shudo K: [Retinoid therapy for autoimmune diseases]. Nihon Rinsho Meneki Gakkai Kaishi. 2006 Jun;29(3):114-26. [PubMed:16819260 ]
  5. Mizuguchi Y, Wada A, Nakagawa K, Ito M, Okano T: Antitumoral activity of 13-demethyl or 13-substituted analogues of all-trans retinoic acid and 9-cis retinoic acid in the human myeloid leukemia cell line HL-60. Biol Pharm Bull. 2006 Sep;29(9):1803-9. [PubMed:16946489 ]
  6. Cheng C, Michaels J, Scheinfeld N: Alitretinoin: a comprehensive review. Expert Opin Investig Drugs. 2008 Mar;17(3):437-43. doi: 10.1517/13543784.17.3.437 . [PubMed:18321241 ]
  7. Garnock-Jones KP, Perry CM: Alitretinoin: in severe chronic hand eczema. Drugs. 2009 Aug 20;69(12):1625-34. doi: 10.2165/11202200-000000000-00000. [PubMed:19678713 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence or presence of ho...
Gene Name:
RARB
Uniprot ID:
P10826
Molecular Weight:
50488.63 Da
References
  1. Mizuiri H, Yoshida K, Toge T, Oue N, Aung PP, Noguchi T, Yasui W: DNA methylation of genes linked to retinoid signaling in squamous cell carcinoma of the esophagus: DNA methylation of CRBP1 and TIG1 is associated with tumor stage. Cancer Sci. 2005 Sep;96(9):571-7. [PubMed:16128742 ]
  2. Milliano MT, Luxon BA: Rat hepatic stellate cells become retinoid unresponsive during activation. Hepatol Res. 2005 Nov;33(3):225-33. Epub 2005 Oct 25. [PubMed:16253547 ]
  3. Liu Z, Zhang L, Ding F, Li J, Guo M, Li W, Wang Y, Yu Z, Zhan Q, Wu M, Liu Z: 5-Aza-2'-deoxycytidine induces retinoic acid receptor-beta(2) demethylation and growth inhibition in esophageal squamous carcinoma cells. Cancer Lett. 2005 Dec 18;230(2):271-83. [PubMed:16297713 ]
  4. Nalbandian A, Pang AL, Rennert OM, Chan WY, Ravindranath N, Djakiew D: A novel function of differentiation revealed by cDNA microarray profiling of p75NTR-regulated gene expression. Differentiation. 2005 Oct;73(8):385-96. [PubMed:16316409 ]
  5. Husson M, Enderlin V, Delacourte A, Ghenimi N, Alfos S, Pallet V, Higueret P: Retinoic acid normalizes nuclear receptor mediated hypo-expression of proteins involved in beta-amyloid deposits in the cerebral cortex of vitamin A deprived rats. Neurobiol Dis. 2006 Jul;23(1):1-10. Epub 2006 Mar 10. [PubMed:16531051 ]
  6. Garnock-Jones KP, Perry CM: Alitretinoin: in severe chronic hand eczema. Drugs. 2009 Aug 20;69(12):1625-34. doi: 10.2165/11202200-000000000-00000. [PubMed:19678713 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5 (By similarity). Specifically bin...
Gene Name:
RXRB
Uniprot ID:
P28702
Molecular Weight:
56921.38 Da
References
  1. Brtko J: Role of retinoids and their cognate nuclear receptors in breast cancer chemoprevention. Cent Eur J Public Health. 2007 Mar;15(1):3-6. [PubMed:17491551 ]
  2. Germain P, Chambon P, Eichele G, Evans RM, Lazar MA, Leid M, De Lera AR, Lotan R, Mangelsdorf DJ, Gronemeyer H: International Union of Pharmacology. LXIII. Retinoid X receptors. Pharmacol Rev. 2006 Dec;58(4):760-72. [PubMed:17132853 ]
  3. Bergheim I, Wolfgarten E, Bollschweiler E, Holscher AH, Bode CH, Parlesak A: Role of retinoic acid receptors in squamous-cell carcinoma in human esophagus. J Carcinog. 2005 Nov 8;4:20. [PubMed:16277658 ]
  4. Schrage K, Koopmans G, Joosten EA, Mey J: Macrophages and neurons are targets of retinoic acid signaling after spinal cord contusion injury. Eur J Neurosci. 2006 Jan;23(2):285-95. [PubMed:16420438 ]
  5. Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [PubMed:16109390 ]
  6. Cheng C, Michaels J, Scheinfeld N: Alitretinoin: a comprehensive review. Expert Opin Investig Drugs. 2008 Mar;17(3):437-43. doi: 10.1517/13543784.17.3.437 . [PubMed:18321241 ]
  7. Garnock-Jones KP, Perry CM: Alitretinoin: in severe chronic hand eczema. Drugs. 2009 Aug 20;69(12):1625-34. doi: 10.2165/11202200-000000000-00000. [PubMed:19678713 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, acts m...
Gene Name:
RARG
Uniprot ID:
P13631
Molecular Weight:
50341.405 Da
References
  1. Dzhagalov I, Chambon P, He YW: Regulation of CD8+ T lymphocyte effector function and macrophage inflammatory cytokine production by retinoic acid receptor gamma. J Immunol. 2007 Feb 15;178(4):2113-21. [PubMed:17277115 ]
  2. Parrella E, Gianni M, Fratelli M, Barzago MM, Raska I Jr, Diomede L, Kurosaki M, Pisano C, Carminati P, Merlini L, Dallavalle S, Tavecchio M, Rochette-Egly C, Terao M, Garattini E: Antitumor activity of the retinoid-related molecules (E)-3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid (ST1926) and 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid (CD437) in F9 teratocarcinoma: Role of retinoic acid receptor gamma and retinoid-independent pathways. Mol Pharmacol. 2006 Sep;70(3):909-24. Epub 2006 Jun 20. [PubMed:16788091 ]
  3. Li M, Hener P, Zhang Z, Kato S, Metzger D, Chambon P: Topical vitamin D3 and low-calcemic analogs induce thymic stromal lymphopoietin in mouse keratinocytes and trigger an atopic dermatitis. Proc Natl Acad Sci U S A. 2006 Aug 1;103(31):11736-41. Epub 2006 Jul 31. [PubMed:16880407 ]
  4. Garnock-Jones KP, Perry CM: Alitretinoin: in severe chronic hand eczema. Drugs. 2009 Aug 20;69(12):1625-34. doi: 10.2165/11202200-000000000-00000. [PubMed:19678713 ]
  5. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXR...
Gene Name:
RXRG
Uniprot ID:
P48443
Molecular Weight:
50870.72 Da
References
  1. Adamczewski Z, Makarewicz J, Mikosinski S, Knapska-Kucharska M, Gunerska-Szadkowska A, Oszukowska L, Karwowska A, Lewinski A: [Application of 13-cis-retinoic acid in patients with 131I scintigraphically-negative metastases of differentiated thyroid carcinoma]. Endokrynol Pol. 2006 Jul-Aug;57(4):403-6. [PubMed:17006844 ]
  2. Brtko J: Role of retinoids and their cognate nuclear receptors in breast cancer chemoprevention. Cent Eur J Public Health. 2007 Mar;15(1):3-6. [PubMed:17491551 ]
  3. Germain P, Chambon P, Eichele G, Evans RM, Lazar MA, Leid M, De Lera AR, Lotan R, Mangelsdorf DJ, Gronemeyer H: International Union of Pharmacology. LXIII. Retinoid X receptors. Pharmacol Rev. 2006 Dec;58(4):760-72. [PubMed:17132853 ]
  4. He JC, Lu TC, Fleet M, Sunamoto M, Husain M, Fang W, Neves S, Chen Y, Shankland S, Iyengar R, Klotman PE: Retinoic acid inhibits HIV-1-induced podocyte proliferation through the cAMP pathway. J Am Soc Nephrol. 2007 Jan;18(1):93-102. Epub 2006 Dec 20. [PubMed:17182884 ]
  5. Day RM, Lee YH, Park AM, Suzuki YJ: Retinoic acid inhibits airway smooth muscle cell migration. Am J Respir Cell Mol Biol. 2006 Jun;34(6):695-703. Epub 2006 Feb 2. [PubMed:16456186 ]
  6. Garnock-Jones KP, Perry CM: Alitretinoin: in severe chronic hand eczema. Drugs. 2009 Aug 20;69(12):1625-34. doi: 10.2165/11202200-000000000-00000. [PubMed:19678713 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Transporter activity
Specific Function:
Transports retinoic acid to the nucleus. Regulates the access of retinoic acid to the nuclear retinoic acid receptors.
Gene Name:
CRABP2
Uniprot ID:
P29373
Molecular Weight:
15692.925 Da
References
  1. Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [PubMed:16109390 ]
  2. Donato LJ, Noy N: Suppression of mammary carcinoma growth by retinoic acid: proapoptotic genes are targets for retinoic acid receptor and cellular retinoic acid-binding protein II signaling. Cancer Res. 2005 Sep 15;65(18):8193-9. [PubMed:16166294 ]
  3. Bry K, Lappalainen U: Pathogenesis of bronchopulmonary dysplasia: the role of interleukin 1beta in the regulation of inflammation-mediated pulmonary retinoic acid pathways in transgenic mice. Semin Perinatol. 2006 Jun;30(3):121-8. [PubMed:16813970 ]
  4. Wei T, Geiser AG, Qian HR, Su C, Helvering LM, Kulkarini NH, Shou J, N'Cho M, Bryant HU, Onyia JE: DNA microarray data integration by ortholog gene analysis reveals potential molecular mechanisms of estrogen-dependent growth of human uterine fibroids. BMC Womens Health. 2007 Apr 2;7:5. [PubMed:17407572 ]
  5. Boorjian SA, Milowsky MI, Kaplan J, Albert M, Cobham MV, Coll DM, Mongan NP, Shelton G, Petrylak D, Gudas LJ, Nanus DM: Phase 1/2 clinical trial of interferon alpha2b and weekly liposome-encapsulated all-trans retinoic acid in patients with advanced renal cell carcinoma. J Immunother. 2007 Sep;30(6):655-62. [PubMed:17667529 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Transporter activity
Specific Function:
Cytosolic CRABPs may regulate the access of retinoic acid to the nuclear retinoic acid receptors.
Gene Name:
CRABP1
Uniprot ID:
P29762
Molecular Weight:
15565.45 Da
References
  1. Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [PubMed:16109390 ]
  2. Goelden U, Pfoertner S, Hansen W, Toepfer T, von Knobloch R, Hofmann R, Buer J, Schrader AJ: Expression and functional influence of cellular retinoic acid-binding protein II in renal cell carcinoma. Urol Int. 2005;75(3):269-76. [PubMed:16215318 ]
  3. Levadoux-Martin M, Li Y, Blackburn A, Chabanon H, Hesketh JE: Perinuclear localisation of cellular retinoic acid binding protein I mRNA. Biochem Biophys Res Commun. 2006 Feb 3;340(1):326-31. [PubMed:16376305 ]
  4. Jetten AM: Multi-stage program of differentiation in human epidermal keratinocytes: regulation by retinoids. J Invest Dermatol. 1990 Nov;95(5 Suppl):44S-46S. [PubMed:16788631 ]
  5. Bry K, Lappalainen U: Pathogenesis of bronchopulmonary dysplasia: the role of interleukin 1beta in the regulation of inflammation-mediated pulmonary retinoic acid pathways in transgenic mice. Semin Perinatol. 2006 Jun;30(3):121-8. [PubMed:16813970 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Schuetz EG, Yasuda K, Arimori K, Schuetz JD: Human MDR1 and mouse mdr1a P-glycoprotein alter the cellular retention and disposition of erythromycin, but not of retinoic acid or benzo(a)pyrene. Arch Biochem Biophys. 1998 Feb 15;350(2):340-7. [PubMed:9473310 ]
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Drug created on June 13, 2005 07:24 / Updated on December 04, 2016 02:42