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Identification
NamePrasterone
Accession NumberDB01708  (EXPT00519, DB06593)
TypeSmall Molecule
GroupsApproved, Nutraceutical
DescriptionPrasterone, also known as dehydroepiandrosterone (DHEA) is a major C19 steroid produced by the adrenal cortex. It is also produced in small quantities in the testis and the ovary. Dehydroepiandrosterone (DHEA) can be converted to testosterone; androstenedione; estradiol; and estrone. Most of DHEA is sulfated (dehydroepiandrosterone sulfate) before secretion. In the United States, DHEA or DHEAS have been advertised with claims that they may be beneficial for a wide variety of ailments. DHEA and DHEAS are readily available in the United States, where they are marketed as over-the-counter dietary supplements. In November 2016, DHEA was approved (as Intrarosa) to treat women experiencing moderate to severe pain during sexual intercourse (dyspareunia), a symptom of vulvar and vaginal atrophy (VVA), due to menopause. In Canada, a prescription is required to buy DHEA.
Structure
Thumb
Synonyms
3-beta-Hydroxy-5-androsten-17-one
3beta-hydroxyandrost-5-en-17-one
3β-hydroxyandrost-5-en-17-one
5-dehydroepiandrosterone
5-DHEA
Dehydroandrosterone
Dehydroepiandrosterone
Dehydroisoandrosterone
DHEA
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BiolaifNot Available
FidelinPaladin
OVIGYN-DAlembic Pharmaceuicals Ltd
Brand mixtures
NameLabellerIngredients
PrasteraHealth Science Funding, Llc
SaltsNot Available
Categories
UNII459AG36T1B
CAS number53-43-0
WeightAverage: 288.4244
Monoisotopic: 288.20893014
Chemical FormulaC19H28O2
InChI KeyFMGSKLZLMKYGDP-USOAJAOKSA-N
InChI
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1
IUPAC Name
(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@]([H])(O)CC[C@]12C
Pharmacology
IndicationDHEA is taken as a supplement for a variety of unsubstantiated indications. The following indications have shown promise and are backed up by some scientific evidence: schizophrenia (DHEA may be more effective in women than men); improving the appearance of older people’s skin (taking DHEA by mouth seems to increase skin thickness and moisture, and decrease facial “age spots” in elderly men and women); improving ability to achieve an erection in men with sexual dysfunction. Additionally, DHEA has shown promise in improving symptoms of lupus (SLE). Taking DHEA by mouth along with conventional treatment may help reduce the number of times symptoms flare up and may allow a reduction in the dose of prescription drugs needed. DHEA may also help SLE symptoms such as muscle ache and mouth ulcers. DHEA also seems to strengthen bones in SLE patients being treated with high-dose steroids (corticosteroids). DHEA also shows promise in the treatment of osteoporosis. Taking DHEA by mouth daily seems to improve bone mineral density (BMD) in older women and men with osteoporosis or osteopenia (pre-osteoporosis). DHEA may also increase BMD in young women with the eating disorder called anorexia nervosa. DHEA is often prescribed in India for the induction of ovulation to improve chances of pregnancy.
Structured Indications Not Available
PharmacodynamicsDHEA is naturally produced from cholesterol through two cytochrome P450 enzymes. Cholesterol is converted to pregnenolone by the enzyme P450 scc (side chain cleavage); then another enzyme, CYP17A1, converts pregnenolone to 17α-Hydroxypregnenolone and then to DHEA. Regular exercise is known to increase DHEA production in the body. Calorie restriction has also been shown to increase DHEA in primates. Some theorize that the increase in endogenous DHEA brought about by calorie restriction is partially responsible for the longer life expectancy known to be associated with calorie restriction.
Mechanism of actionDHEA can be understood as a prohormone for the sex steroids. DHEAS may be viewed as buffer and reservoir. As most DHEA is produced by the zona reticularis of the adrenal cortex, it is argued that there is a role in the immune and stress response. As almost all DHEA is derived from the adrenal glands, blood measurements of DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have elevated levels of DHEAS.
TargetKindPharmacological actionActionsOrganismUniProt ID
Estrogen receptorProteinunknown
binder
HumanP03372 details
Estrogen receptor betaProteinunknown
activator
HumanQ92731 details
GABA-A receptor (anion channel)Protein groupunknown
antagonist
Humannot applicabledetails
NMDA receptorProtein groupunknown
agonist
Humannot applicabledetails
Androgen receptorProteinunknown
agonist
HumanP10275 details
Estradiol 17-beta-dehydrogenase 1ProteinunknownNot AvailableHumanP14061 details
Bile salt sulfotransferaseProteinunknownNot AvailableHumanQ06520 details
Sulfotransferase family cytosolic 2B member 1ProteinunknownNot AvailableHumanO00204 details
Peroxisome proliferator-activated receptor alphaProteinunknown
activator
HumanQ07869 details
Sigma non-opioid intracellular receptor 1Proteinunknown
agonist
HumanQ99720 details
Nuclear receptor subfamily 1 group I member 2Proteinunknown
activator
HumanO75469 details
Nuclear receptor subfamily 1 group I member 3Proteinunknown
activator
HumanQ14994 details
Steroid Delta-isomeraseProteinunknownNot AvailablePseudomonas putidaP07445 details
Cholesterol oxidaseProteinunknownNot AvailableBrevibacterium sterolicumP22637 details
Related Articles
AbsorptionFollowing a 50-mg DHEA PO dose in cynomolgus monkeys, systemic availability was only 3.1 +/- 0.4%. [PMID: 12970301]
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic. As shown by their high conversion ratios (in a study involving cynomolgus monkeys), the major circulating metabolites of DHEA are DHEA-S, androsterone glucuronide, and androstane-3 alpha,17 beta-diol-glucuronide. [PMID: 12970301]

SubstrateEnzymesProduct
Prasterone
Not Available
Dehydroepiandrosterone sulfateDetails
Prasterone
Not Available
Dehydroepiandrosterone 3-glucuronideDetails
Route of eliminationNot Available
Half life12 hours
ClearanceNot Available
ToxicityAcute oral toxicity (LD50): >10000 mg/kg [Rat]. Lowest Published Toxic Dose (TDL) [Man] - Route: Oral; Dose: 10 mg/kg/2W intermittent.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Prasterone is combined with 1,10-Phenanthroline.Experimental
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Prasterone.Approved
AcetovanilloneThe risk or severity of adverse effects can be increased when Acetovanillone is combined with Prasterone.Investigational
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Prasterone.Approved, Vet Approved
AdapaleneThe risk or severity of adverse effects can be increased when Adapalene is combined with Prasterone.Approved
AldesleukinPrasterone may decrease the antineoplastic activities of Aldesleukin.Approved
ALT-110The risk or severity of adverse effects can be increased when Prasterone is combined with ALT-110.Investigational
Aluminum hydroxideThe bioavailability of Prasterone can be decreased when combined with Aluminum hydroxide.Approved
Aluminum phosphateThe bioavailability of Prasterone can be decreased when combined with Aluminum phosphate.Approved
AmbenoniumThe risk or severity of adverse effects can be increased when Prasterone is combined with Ambenonium.Approved
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Prasterone.Approved
AmiodaroneThe metabolism of Prasterone can be decreased when combined with Amiodarone.Approved, Investigational
Amphotericin BPrasterone may increase the hypokalemic activities of Amphotericin B.Approved, Investigational
AnisodamineThe risk or severity of adverse effects can be increased when Anisodamine is combined with Prasterone.Investigational
AntipyrineThe risk or severity of adverse effects can be increased when Antipyrine is combined with Prasterone.Approved
ApremilastThe risk or severity of adverse effects can be increased when Apremilast is combined with Prasterone.Approved, Investigational
AprepitantThe serum concentration of Prasterone can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Prasterone can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Prasterone can be decreased when combined with Atomoxetine.Approved
Atracurium besylateAtracurium besylate may increase the adverse neuromuscular activities of Prasterone.Approved
AzapropazoneThe risk or severity of adverse effects can be increased when Azapropazone is combined with Prasterone.Withdrawn
AzelastineThe risk or severity of adverse effects can be increased when Azelastine is combined with Prasterone.Approved
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Prasterone.Approved, Investigational
BazedoxifeneThe risk or severity of adverse effects can be increased when Prasterone is combined with Bazedoxifene.Approved, Investigational
BendroflumethiazidePrasterone may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenoxaprofenThe risk or severity of adverse effects can be increased when Benoxaprofen is combined with Prasterone.Withdrawn
Benzoic AcidThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Prasterone.Approved
Betulinic AcidThe risk or severity of adverse effects can be increased when Betulinic Acid is combined with Prasterone.Investigational
BexaroteneThe serum concentration of Prasterone can be decreased when it is combined with Bexarotene.Approved, Investigational
Bismuth SubcitrateThe bioavailability of Prasterone can be decreased when combined with Bismuth Subcitrate.Approved
BoceprevirThe metabolism of Prasterone can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Prasterone can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Prasterone can be decreased when it is combined with Bosentan.Approved, Investigational
BromfenacThe risk or severity of adverse effects can be increased when Bromfenac is combined with Prasterone.Approved
BucillamineThe risk or severity of adverse effects can be increased when Bucillamine is combined with Prasterone.Investigational
BumetanidePrasterone may increase the hypokalemic activities of Bumetanide.Approved
CalcitriolThe therapeutic efficacy of Calcitriol can be decreased when used in combination with Prasterone.Approved, Nutraceutical
Calcium carbonateThe bioavailability of Prasterone can be decreased when combined with Calcium carbonate.Approved
CarbamazepineThe metabolism of Prasterone can be increased when combined with Carbamazepine.Approved, Investigational
CarprofenThe risk or severity of adverse effects can be increased when Carprofen is combined with Prasterone.Approved, Vet Approved, Withdrawn
CastanospermineThe risk or severity of adverse effects can be increased when Castanospermine is combined with Prasterone.Experimental
CDX-110The risk or severity of adverse effects can be increased when Prasterone is combined with CDX-110.Investigational
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with Prasterone.Approved, Investigational
CeritinibThe serum concentration of Prasterone can be increased when it is combined with Ceritinib.Approved
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with Prasterone.Approved, Vet Approved
ChlorothiazidePrasterone may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorotrianiseneThe risk or severity of adverse effects can be increased when Prasterone is combined with Chlorotrianisene.Withdrawn
ChlorthalidonePrasterone may increase the hypokalemic activities of Chlorthalidone.Approved
CholestyramineCholestyramine can cause a decrease in the absorption of Prasterone resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CinoxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Cinoxacin.Approved, Withdrawn
CiprofloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Ciprofloxacin.Approved, Investigational
ClarithromycinThe metabolism of Prasterone can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Prasterone can be decreased when combined with Clemastine.Approved
ClonixinThe risk or severity of adverse effects can be increased when Clonixin is combined with Prasterone.Approved
ClotrimazoleThe metabolism of Prasterone can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Prasterone can be decreased when combined with Cobicistat.Approved
ColesevelamColesevelam can cause a decrease in the absorption of Prasterone resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of Prasterone resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ConivaptanThe serum concentration of Prasterone can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated Equine EstrogensThe risk or severity of adverse effects can be increased when Prasterone is combined with Conjugated Equine Estrogens.Approved
Corticorelin ovine triflutateThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Prasterone.Approved
CoumaphosThe risk or severity of adverse effects can be increased when Prasterone is combined with Coumaphos.Vet Approved
CrizotinibThe metabolism of Prasterone can be decreased when combined with Crizotinib.Approved
CurcuminThe risk or severity of adverse effects can be increased when Curcumin is combined with Prasterone.Investigational
CyclosporineThe metabolism of Prasterone can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
D-LimoneneThe risk or severity of adverse effects can be increased when D-Limonene is combined with Prasterone.Investigational
DabrafenibThe serum concentration of Prasterone can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Prasterone can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Prasterone can be increased when it is combined with Dasatinib.Approved, Investigational
DecamethoniumThe risk or severity of adverse effects can be increased when Prasterone is combined with Decamethonium.Approved
DeferasiroxThe serum concentration of Prasterone can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Prasterone can be decreased when combined with Delavirdine.Approved
DemecariumThe risk or severity of adverse effects can be increased when Prasterone is combined with Demecarium.Approved
dersalazineThe risk or severity of adverse effects can be increased when dersalazine is combined with Prasterone.Investigational
DexamethasoneThe serum concentration of Prasterone can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DichlorvosThe risk or severity of adverse effects can be increased when Prasterone is combined with Dichlorvos.Vet Approved
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Prasterone.Approved, Vet Approved
DienestrolThe risk or severity of adverse effects can be increased when Prasterone is combined with Dienestrol.Approved
DiethylstilbestrolThe risk or severity of adverse effects can be increased when Prasterone is combined with Diethylstilbestrol.Approved
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Prasterone.Approved
DihydroergotamineThe metabolism of Prasterone can be decreased when combined with Dihydroergotamine.Approved
DihydrotestosteronePrasterone may increase the fluid retaining activities of Dihydrotestosterone.Illicit
DiltiazemThe metabolism of Prasterone can be decreased when combined with Diltiazem.Approved
DonepezilThe risk or severity of adverse effects can be increased when Prasterone is combined with Donepezil.Approved
DoxycyclineThe metabolism of Prasterone can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Prasterone can be decreased when combined with Dronedarone.Approved
DroxicamThe risk or severity of adverse effects can be increased when Droxicam is combined with Prasterone.Approved
DuvelisibThe risk or severity of adverse effects can be increased when Duvelisib is combined with Prasterone.Investigational
E6201The risk or severity of adverse effects can be increased when E6201 is combined with Prasterone.Investigational
EbselenThe risk or severity of adverse effects can be increased when Ebselen is combined with Prasterone.Investigational
EchothiophateThe risk or severity of adverse effects can be increased when Prasterone is combined with Echothiophate.Approved
EdrophoniumThe risk or severity of adverse effects can be increased when Prasterone is combined with Edrophonium.Approved
EfavirenzThe serum concentration of Prasterone can be decreased when it is combined with Efavirenz.Approved, Investigational
EnoxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Enoxacin.Approved
EnzalutamideThe serum concentration of Prasterone can be decreased when it is combined with Enzalutamide.Approved
EpirizoleThe risk or severity of adverse effects can be increased when Epirizole is combined with Prasterone.Approved
ErythromycinThe metabolism of Prasterone can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Prasterone can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstradiolThe risk or severity of adverse effects can be increased when Prasterone is combined with Estradiol.Approved, Investigational, Vet Approved
EstriolThe risk or severity of adverse effects can be increased when Prasterone is combined with Estriol.Approved, Vet Approved
EstroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Estrone.Approved
Etacrynic acidPrasterone may increase the hypokalemic activities of Etacrynic acid.Approved
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with Prasterone.Approved, Investigational
Ethinyl EstradiolThe risk or severity of adverse effects can be increased when Prasterone is combined with Ethinyl Estradiol.Approved
EtodolacThe risk or severity of adverse effects can be increased when Etodolac is combined with Prasterone.Approved, Investigational, Vet Approved
EtofenamateThe risk or severity of adverse effects can be increased when Etofenamate is combined with Prasterone.Approved
EtoricoxibThe risk or severity of adverse effects can be increased when Etoricoxib is combined with Prasterone.Approved, Investigational
EtravirineThe serum concentration of Prasterone can be decreased when it is combined with Etravirine.Approved
Evening primrose oilThe risk or severity of adverse effects can be increased when Evening primrose oil is combined with Prasterone.Approved
exisulindThe risk or severity of adverse effects can be increased when exisulind is combined with Prasterone.Investigational
FenbufenThe risk or severity of adverse effects can be increased when Fenbufen is combined with Prasterone.Approved
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Prasterone.Approved
FenthionThe risk or severity of adverse effects can be increased when Prasterone is combined with Fenthion.Vet Approved
FleroxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Fleroxacin.Approved
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Prasterone.Approved, Withdrawn
FluconazoleThe metabolism of Prasterone can be decreased when combined with Fluconazole.Approved
FlumequineThe risk or severity of adverse effects can be increased when Prasterone is combined with Flumequine.Withdrawn
FlunixinThe risk or severity of adverse effects can be increased when Flunixin is combined with Prasterone.Vet Approved
FluoxymesteronePrasterone may increase the fluid retaining activities of Fluoxymesterone.Approved, Illicit
FlurbiprofenThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Prasterone.Approved, Investigational
FluvoxamineThe metabolism of Prasterone can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Prasterone can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Prasterone can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Prasterone can be increased when combined with Fosphenytoin.Approved
FurosemidePrasterone may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
Fusidic AcidThe serum concentration of Prasterone can be increased when it is combined with Fusidic Acid.Approved
G17DTThe risk or severity of adverse effects can be increased when Prasterone is combined with G17DT.Investigational
GalantamineThe risk or severity of adverse effects can be increased when Prasterone is combined with Galantamine.Approved
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Prasterone is combined with Gallamine Triethiodide.Approved
GarenoxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Garenoxacin.Investigational
GatifloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Gatifloxacin.Approved, Investigational
GemifloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Gemifloxacin.Approved, Investigational
GenisteinThe risk or severity of adverse effects can be increased when Prasterone is combined with Genistein.Investigational
GI-5005The risk or severity of adverse effects can be increased when Prasterone is combined with GI-5005.Investigational
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Prasterone is combined with Ginkgo biloba.Approved, Nutraceutical
Glycerol PhenylbutyrateThe therapeutic efficacy of Glycerol Phenylbutyrate can be decreased when used in combination with Prasterone.Approved
GrepafloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Grepafloxacin.Withdrawn
HexestrolThe risk or severity of adverse effects can be increased when Prasterone is combined with Hexestrol.Withdrawn
HigenamineThe risk or severity of adverse effects can be increased when Higenamine is combined with Prasterone.Investigational
HMPL-004The risk or severity of adverse effects can be increased when HMPL-004 is combined with Prasterone.Investigational
Huperzine AThe risk or severity of adverse effects can be increased when Prasterone is combined with Huperzine A.Investigational
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Prasterone.Approved, Investigational
HydrochlorothiazidePrasterone may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazidePrasterone may increase the hypokalemic activities of Hydroflumethiazide.Approved
IbuprofenThe risk or severity of adverse effects can be increased when Ibuprofen is combined with Prasterone.Approved
IbuproxamThe risk or severity of adverse effects can be increased when Ibuproxam is combined with Prasterone.Withdrawn
IcatibantThe risk or severity of adverse effects can be increased when Icatibant is combined with Prasterone.Approved
IdelalisibThe serum concentration of Prasterone can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Prasterone can be decreased when combined with Imatinib.Approved
IndacaterolIndacaterol may increase the hypokalemic activities of Prasterone.Approved
IndapamidePrasterone may increase the hypokalemic activities of Indapamide.Approved
IndinavirThe metabolism of Prasterone can be decreased when combined with Indinavir.Approved
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with Prasterone.Approved, Investigational
IndoprofenThe risk or severity of adverse effects can be increased when Indoprofen is combined with Prasterone.Withdrawn
INGN 201The risk or severity of adverse effects can be increased when Prasterone is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Prasterone is combined with INGN 225.Investigational
IsavuconazoniumThe metabolism of Prasterone can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoflurophateThe risk or severity of adverse effects can be increased when Prasterone is combined with Isoflurophate.Approved, Withdrawn
IsoniazidThe serum concentration of Isoniazid can be decreased when it is combined with Prasterone.Approved
IsoxicamThe risk or severity of adverse effects can be increased when Isoxicam is combined with Prasterone.Withdrawn
IsradipineThe metabolism of Prasterone can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Prasterone can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Prasterone can be increased when it is combined with Ivacaftor.Approved
KebuzoneThe risk or severity of adverse effects can be increased when Kebuzone is combined with Prasterone.Experimental
KetoconazoleThe metabolism of Prasterone can be decreased when combined with Ketoconazole.Approved, Investigational
KetoprofenThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Prasterone.Approved, Vet Approved
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Prasterone.Approved
LeflunomideThe risk or severity of adverse effects can be increased when Leflunomide is combined with Prasterone.Approved, Investigational
LevofloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Levofloxacin.Approved, Investigational
LisofyllineThe risk or severity of adverse effects can be increased when Lisofylline is combined with Prasterone.Investigational
LomefloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Lomefloxacin.Approved
LopinavirThe metabolism of Prasterone can be decreased when combined with Lopinavir.Approved
LornoxicamThe risk or severity of adverse effects can be increased when Lornoxicam is combined with Prasterone.Approved
LovastatinThe metabolism of Prasterone can be decreased when combined with Lovastatin.Approved, Investigational
LoxoprofenThe risk or severity of adverse effects can be increased when Loxoprofen is combined with Prasterone.Approved
LuliconazoleThe serum concentration of Prasterone can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Prasterone can be increased when combined with Lumacaftor.Approved
LumiracoxibThe risk or severity of adverse effects can be increased when Lumiracoxib is combined with Prasterone.Approved, Investigational
MagaldrateThe bioavailability of Prasterone can be decreased when combined with Magaldrate.Withdrawn
Magnesium carbonateThe bioavailability of Prasterone can be decreased when combined with Magnesium carbonate.Approved
Magnesium hydroxideThe bioavailability of Prasterone can be decreased when combined with Magnesium hydroxide.Approved
Magnesium oxideThe bioavailability of Prasterone can be decreased when combined with Magnesium oxide.Approved
Magnesium salicylateThe risk or severity of adverse effects can be increased when Magnesium salicylate is combined with Prasterone.Approved
Magnesium TrisilicateThe bioavailability of Prasterone can be decreased when combined with Magnesium Trisilicate.Approved
MalathionThe risk or severity of adverse effects can be increased when Prasterone is combined with Malathion.Approved, Investigational
MasoprocolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Prasterone.Approved
Meclofenamic acidThe risk or severity of adverse effects can be increased when Meclofenamic acid is combined with Prasterone.Approved, Vet Approved
Mefenamic acidThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with Prasterone.Approved
MefloquineThe risk or severity of adverse effects can be increased when Prasterone is combined with Mefloquine.Approved
MeloxicamThe risk or severity of adverse effects can be increased when Meloxicam is combined with Prasterone.Approved, Vet Approved
MemantineThe risk or severity of adverse effects can be increased when Prasterone is combined with Memantine.Approved, Investigational
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Prasterone.Approved
MestranolThe risk or severity of adverse effects can be increased when Prasterone is combined with Mestranol.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Prasterone.Withdrawn
MethallenestrilThe risk or severity of adverse effects can be increased when Prasterone is combined with Methallenestril.Experimental
Methanesulfonyl FluorideThe risk or severity of adverse effects can be increased when Prasterone is combined with Methanesulfonyl Fluoride.Investigational
MethyclothiazidePrasterone may increase the hypokalemic activities of Methyclothiazide.Approved
MethyltestosteronePrasterone may increase the fluid retaining activities of Methyltestosterone.Approved
MetolazonePrasterone may increase the hypokalemic activities of Metolazone.Approved
MifepristoneThe therapeutic efficacy of Prasterone can be decreased when used in combination with Mifepristone.Approved, Investigational
MinaprineThe risk or severity of adverse effects can be increased when Prasterone is combined with Minaprine.Approved
MitotaneThe serum concentration of Prasterone can be decreased when it is combined with Mitotane.Approved
MivacuriumMivacurium may increase the adverse neuromuscular activities of Prasterone.Approved
MizoribineThe risk or severity of adverse effects can be increased when Mizoribine is combined with Prasterone.Investigational
ModafinilThe serum concentration of Prasterone can be decreased when it is combined with Modafinil.Approved, Investigational
MoxifloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Moxifloxacin.Approved, Investigational
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Prasterone.Approved, Investigational
Mycophenolic acidThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with Prasterone.Approved
NabumetoneThe risk or severity of adverse effects can be increased when Nabumetone is combined with Prasterone.Approved
NafamostatThe risk or severity of adverse effects can be increased when Nafamostat is combined with Prasterone.Investigational
NafcillinThe serum concentration of Prasterone can be decreased when it is combined with Nafcillin.Approved
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Prasterone.Approved
Nalidixic AcidThe risk or severity of adverse effects can be increased when Prasterone is combined with Nalidixic Acid.Approved
NaproxenThe risk or severity of adverse effects can be increased when Naproxen is combined with Prasterone.Approved, Vet Approved
NCX 4016The risk or severity of adverse effects can be increased when NCX 4016 is combined with Prasterone.Investigational
NefazodoneThe metabolism of Prasterone can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Prasterone can be decreased when combined with Nelfinavir.Approved
NemonoxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Nemonoxacin.Investigational
NeostigmineThe risk or severity of adverse effects can be increased when Prasterone is combined with Neostigmine.Approved, Vet Approved
NepafenacThe risk or severity of adverse effects can be increased when Nepafenac is combined with Prasterone.Approved
NetupitantThe serum concentration of Prasterone can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Prasterone can be increased when combined with Nevirapine.Approved
NicorandilThe risk or severity of adverse effects can be increased when Prasterone is combined with Nicorandil.Approved
Niflumic AcidThe risk or severity of adverse effects can be increased when Niflumic Acid is combined with Prasterone.Approved
NilotinibThe metabolism of Prasterone can be decreased when combined with Nilotinib.Approved, Investigational
NimesulideThe risk or severity of adverse effects can be increased when Nimesulide is combined with Prasterone.Approved, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with Prasterone.Investigational
NorfloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Norfloxacin.Approved
OfloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Ofloxacin.Approved
OlaparibThe metabolism of Prasterone can be decreased when combined with Olaparib.Approved
OlopatadineThe risk or severity of adverse effects can be increased when Olopatadine is combined with Prasterone.Approved
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Prasterone.Approved
OrgoteinThe risk or severity of adverse effects can be increased when Orgotein is combined with Prasterone.Vet Approved
OsimertinibThe serum concentration of Prasterone can be increased when it is combined with Osimertinib.Approved
OxandrolonePrasterone may increase the fluid retaining activities of Oxandrolone.Approved, Investigational
OxaprozinThe risk or severity of adverse effects can be increased when Oxaprozin is combined with Prasterone.Approved
OxymetholonePrasterone may increase the fluid retaining activities of Oxymetholone.Approved, Illicit
OxyphenbutazoneThe risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with Prasterone.Withdrawn
PalbociclibThe serum concentration of Prasterone can be increased when it is combined with Palbociclib.Approved
ParecoxibThe risk or severity of adverse effects can be increased when Parecoxib is combined with Prasterone.Approved
PazufloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Pazufloxacin.Investigational
PefloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Pefloxacin.Approved
PentobarbitalThe metabolism of Prasterone can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Prasterone can be increased when combined with Phenobarbital.Approved
Phenylacetic acidThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Prasterone.Approved
PhenylbutazoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Prasterone.Approved, Vet Approved
PhenytoinThe metabolism of Prasterone can be increased when combined with Phenytoin.Approved, Vet Approved
PhysostigmineThe risk or severity of adverse effects can be increased when Prasterone is combined with Physostigmine.Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Prasterone.Approved, Investigational
PiretanidePrasterone may increase the hypokalemic activities of Piretanide.Experimental
PirfenidoneThe risk or severity of adverse effects can be increased when Pirfenidone is combined with Prasterone.Investigational
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with Prasterone.Approved, Investigational
Polyestradiol phosphateThe risk or severity of adverse effects can be increased when Prasterone is combined with Polyestradiol phosphate.Approved
PolythiazidePrasterone may increase the hypokalemic activities of Polythiazide.Approved
PosaconazoleThe metabolism of Prasterone can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Prasterone can be increased when combined with Primidone.Approved, Vet Approved
PromestrieneThe risk or severity of adverse effects can be increased when Prasterone is combined with Promestriene.Investigational
PropacetamolThe risk or severity of adverse effects can be increased when Propacetamol is combined with Prasterone.Approved
PrulifloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Prulifloxacin.Investigational
PTC299The risk or severity of adverse effects can be increased when PTC299 is combined with Prasterone.Investigational
PyridostigmineThe risk or severity of adverse effects can be increased when Prasterone is combined with Pyridostigmine.Approved
QuinestrolThe risk or severity of adverse effects can be increased when Prasterone is combined with Quinestrol.Approved
QuinethazonePrasterone may increase the hypokalemic activities of Quinethazone.Approved
Rabies vaccineThe risk or severity of adverse effects can be increased when Prasterone is combined with Rabies vaccine.Approved
RanolazineThe metabolism of Prasterone can be decreased when combined with Ranolazine.Approved, Investigational
RapacuroniumRapacuronium may increase the adverse neuromuscular activities of Prasterone.Withdrawn
ResveratrolThe risk or severity of adverse effects can be increased when Resveratrol is combined with Prasterone.Experimental, Investigational
RifabutinThe metabolism of Prasterone can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Prasterone can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Prasterone can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Prasterone can be decreased when combined with Ritonavir.Approved, Investigational
RivastigmineThe risk or severity of adverse effects can be increased when Prasterone is combined with Rivastigmine.Approved, Investigational
RofecoxibThe risk or severity of adverse effects can be increased when Rofecoxib is combined with Prasterone.Investigational, Withdrawn
RosoxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Rosoxacin.Approved
S EquolThe risk or severity of adverse effects can be increased when Prasterone is combined with S Equol.Investigational
SalicylamideThe risk or severity of adverse effects can be increased when Salicylamide is combined with Prasterone.Approved
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Prasterone.Approved, Vet Approved
SalsalateThe risk or severity of adverse effects can be increased when Salsalate is combined with Prasterone.Approved
SaquinavirThe metabolism of Prasterone can be decreased when combined with Saquinavir.Approved, Investigational
SecoisolariciresinolThe risk or severity of adverse effects can be increased when Prasterone is combined with Secoisolariciresinol.Investigational
SeratrodastThe risk or severity of adverse effects can be increased when Seratrodast is combined with Prasterone.Approved, Investigational
SildenafilThe metabolism of Prasterone can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Prasterone can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Prasterone can be increased when it is combined with Simeprevir.Approved
Sodium phenylbutyrateThe therapeutic efficacy of Sodium phenylbutyrate can be decreased when used in combination with Prasterone.Approved
SparfloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Sparfloxacin.Approved
SRP 299The risk or severity of adverse effects can be increased when Prasterone is combined with SRP 299.Investigational
SRT501The risk or severity of adverse effects can be increased when SRT501 is combined with Prasterone.Investigational
St. John's WortThe serum concentration of Prasterone can be decreased when it is combined with St. John's Wort.Nutraceutical
StanozololPrasterone may increase the fluid retaining activities of Stanozolol.Approved, Vet Approved
StiripentolThe serum concentration of Prasterone can be increased when it is combined with Stiripentol.Approved
SulfasalazineThe risk or severity of adverse effects can be increased when Sulfasalazine is combined with Prasterone.Approved
SulfisoxazoleThe metabolism of Prasterone can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with Prasterone.Approved
SuprofenThe risk or severity of adverse effects can be increased when Suprofen is combined with Prasterone.Approved, Withdrawn
Synthetic Conjugated Estrogens, AThe risk or severity of adverse effects can be increased when Prasterone is combined with Synthetic Conjugated Estrogens, A.Approved
Synthetic Conjugated Estrogens, BThe risk or severity of adverse effects can be increased when Prasterone is combined with Synthetic Conjugated Estrogens, B.Approved
TacrineThe risk or severity of adverse effects can be increased when Prasterone is combined with Tacrine.Withdrawn
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Prasterone.Approved
TelithromycinThe metabolism of Prasterone can be decreased when combined with Telithromycin.Approved
TemafloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Temafloxacin.Withdrawn
TenoxicamThe risk or severity of adverse effects can be increased when Tenoxicam is combined with Prasterone.Approved
TepoxalinThe risk or severity of adverse effects can be increased when Tepoxalin is combined with Prasterone.Vet Approved
TeriflunomideThe risk or severity of adverse effects can be increased when Teriflunomide is combined with Prasterone.Approved
TestosteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Testosterone.Approved, Investigational
TG4010The risk or severity of adverse effects can be increased when Prasterone is combined with TG4010.Investigational
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Prasterone.Approved
TiboloneThe risk or severity of adverse effects can be increased when Prasterone is combined with Tibolone.Approved
TiclopidineThe metabolism of Prasterone can be decreased when combined with Ticlopidine.Approved
TinoridineThe risk or severity of adverse effects can be increased when Tinoridine is combined with Prasterone.Investigational
TocilizumabThe serum concentration of Prasterone can be decreased when it is combined with Tocilizumab.Approved
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Tolfenamic Acid is combined with Prasterone.Approved
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with Prasterone.Approved
TorasemidePrasterone may increase the hypokalemic activities of Torasemide.Approved
TranilastThe risk or severity of adverse effects can be increased when Tranilast is combined with Prasterone.Approved, Investigational
TrichlorfonThe risk or severity of adverse effects can be increased when Prasterone is combined with Trichlorfon.Vet Approved
TrichlormethiazidePrasterone may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
Trisalicylate-cholineThe risk or severity of adverse effects can be increased when Trisalicylate-choline is combined with Prasterone.Approved
TrovafloxacinThe risk or severity of adverse effects can be increased when Prasterone is combined with Trovafloxacin.Approved, Withdrawn
TubocurarineThe risk or severity of adverse effects can be increased when Prasterone is combined with Tubocurarine.Approved
ValdecoxibThe risk or severity of adverse effects can be increased when Valdecoxib is combined with Prasterone.Investigational, Withdrawn
VenlafaxineThe metabolism of Prasterone can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Prasterone can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Prasterone can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinPrasterone may increase the anticoagulant activities of Warfarin.Approved
ZaltoprofenThe risk or severity of adverse effects can be increased when Zaltoprofen is combined with Prasterone.Approved
ZeranolThe risk or severity of adverse effects can be increased when Prasterone is combined with Zeranol.Vet Approved
ZileutonThe risk or severity of adverse effects can be increased when Zileuton is combined with Prasterone.Approved, Investigational, Withdrawn
ZiprasidoneThe metabolism of Prasterone can be decreased when combined with Ziprasidone.Approved
ZomepiracThe risk or severity of adverse effects can be increased when Zomepirac is combined with Prasterone.Withdrawn
Food InteractionsNot Available
References
Synthesis Reference

Isao Sugimoto, Yoko Sawase, “Stable preparation of water-soluble salts of dehydroepiandrosterone sulfate for parenteral administration.” U.S. Patent US4061744, issued January, 1977.

US4061744
General References
  1. Baker WL, Karan S, Kenny AM: Effect of dehydroepiandrosterone on muscle strength and physical function in older adults: a systematic review. J Am Geriatr Soc. 2011 Jun;59(6):997-1002. doi: 10.1111/j.1532-5415.2011.03410.x. Epub 2011 Jun 7. [PubMed:21649617 ]
  2. Alkatib AA, Cosma M, Elamin MB, Erickson D, Swiglo BA, Erwin PJ, Montori VM: A systematic review and meta-analysis of randomized placebo-controlled trials of DHEA treatment effects on quality of life in women with adrenal insufficiency. J Clin Endocrinol Metab. 2009 Oct;94(10):3676-81. doi: 10.1210/jc.2009-0672. Epub 2009 Sep 22. [PubMed:19773400 ]
  3. Arlt W: Dehydroepiandrosterone and ageing. Best Pract Res Clin Endocrinol Metab. 2004 Sep;18(3):363-80. [PubMed:15261843 ]
  4. Wallace MB, Lim J, Cutler A, Bucci L: Effects of dehydroepiandrosterone vs androstenedione supplementation in men. Med Sci Sports Exerc. 1999 Dec;31(12):1788-92. [PubMed:10613429 ]
  5. Grimley Evans J, Malouf R, Huppert F, van Niekerk JK: Dehydroepiandrosterone (DHEA) supplementation for cognitive function in healthy elderly people. Cochrane Database Syst Rev. 2006 Oct 18;(4):CD006221. [PubMed:17054283 ]
  6. Fuller SJ, Tan RS, Martins RN: Androgens in the etiology of Alzheimer's disease in aging men and possible therapeutic interventions. J Alzheimers Dis. 2007 Sep;12(2):129-42. [PubMed:17917157 ]
  7. Thijs L, Fagard R, Forette F, Nawrot T, Staessen JA: Are low dehydroepiandrosterone sulphate levels predictive for cardiovascular diseases? A review of prospective and retrospective studies. Acta Cardiol. 2003 Oct;58(5):403-10. [PubMed:14609305 ]
  8. Barrett-Connor E, Khaw KT, Yen SS: A prospective study of dehydroepiandrosterone sulfate, mortality, and cardiovascular disease. N Engl J Med. 1986 Dec 11;315(24):1519-24. [PubMed:2946952 ]
  9. Arnlov J, Pencina MJ, Amin S, Nam BH, Benjamin EJ, Murabito JM, Wang TJ, Knapp PE, D'Agostino RB Sr, Bhasin S, Vasan RS: Endogenous sex hormones and cardiovascular disease incidence in men. Ann Intern Med. 2006 Aug 1;145(3):176-84. [PubMed:16880459 ]
  10. Crosbie D, Black C, McIntyre L, Royle PL, Thomas S: Dehydroepiandrosterone for systemic lupus erythematosus. Cochrane Database Syst Rev. 2007 Oct 17;(4):CD005114. [PubMed:17943841 ]
  11. Mattison JA, Lane MA, Roth GS, Ingram DK: Calorie restriction in rhesus monkeys. Exp Gerontol. 2003 Jan-Feb;38(1-2):35-46. [PubMed:12543259 ]
  12. Roberts E: The importance of being dehydroepiandrosterone sulfate (in the blood of primates): a longer and healthier life? Biochem Pharmacol. 1999 Feb 15;57(4):329-46. [PubMed:9933021 ]
  13. Leblanc M, Labrie C, Belanger A, Candas B, Labrie F: Bioavailability and pharmacokinetics of dehydroepiandrosterone in the cynomolgus monkey. J Clin Endocrinol Metab. 2003 Sep;88(9):4293-302. [PubMed:12970301 ]
  14. Casson PR, Lindsay MS, Pisarska MD, Carson SA, Buster JE: Dehydroepiandrosterone supplementation augments ovarian stimulation in poor responders: a case series. Hum Reprod. 2000 Oct;15(10):2129-32. [PubMed:11006185 ]
  15. Chang DM, Lan JL, Lin HY, Luo SF: Dehydroepiandrosterone treatment of women with mild-to-moderate systemic lupus erythematosus: a multicenter randomized, double-blind, placebo-controlled trial. Arthritis Rheum. 2002 Nov;46(11):2924-7. [PubMed:12428233 ]
  16. The NIH National Library of Medicine [Link]
External Links
ATC CodesA14AA07G03EA03
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (19.8 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9611
Caco-2 permeable+0.8816
P-glycoprotein substrateSubstrate0.6176
P-glycoprotein inhibitor IInhibitor0.6272
P-glycoprotein inhibitor IINon-inhibitor0.9014
Renal organic cation transporterNon-inhibitor0.7596
CYP450 2C9 substrateNon-substrate0.8415
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7404
CYP450 1A2 substrateNon-inhibitor0.9313
CYP450 2C9 inhibitorNon-inhibitor0.9672
CYP450 2D6 inhibitorNon-inhibitor0.9476
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8399
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9013
Ames testNon AMES toxic0.9382
CarcinogenicityNon-carcinogens0.947
BiodegradationNot ready biodegradable0.8998
Rat acute toxicity1.5214 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8861
hERG inhibition (predictor II)Non-inhibitor0.7176
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
KitOral
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point140-141 °CPhysProp
water solubility63.5 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.23HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0438 mg/mLALOGPS
logP3.53ALOGPS
logP3.36ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.66 m3·mol-1ChemAxon
Polarizability34.09 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-004i-4920000000-9dc14963a290268534b8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-3910000000-2bbc760dbeb7f9f1ebfcView in MoNA
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, 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
MSMass Spectrum (Electron Ionization)splash10-0a4l-6940000000-948ad487c238d48aa9beView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Chen F, Knecht K, Birzin E, Fisher J, Wilkinson H, Mojena M, Moreno CT, Schmidt A, Harada S, Freedman LP, Reszka AA: Direct agonist/antagonist functions of dehydroepiandrosterone. Endocrinology. 2005 Nov;146(11):4568-76. Epub 2005 Jun 30. [PubMed:15994348 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by...
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Chen F, Knecht K, Birzin E, Fisher J, Wilkinson H, Mojena M, Moreno CT, Schmidt A, Harada S, Freedman LP, Reszka AA: Direct agonist/antagonist functions of dehydroepiandrosterone. Endocrinology. 2005 Nov;146(11):4568-76. Epub 2005 Jun 30. [PubMed:15994348 ]
Kind
Protein group
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Components:
NameUniProt IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1P14867 Details
Gamma-aminobutyric acid receptor subunit alpha-2P47869 Details
Gamma-aminobutyric acid receptor subunit alpha-3P34903 Details
Gamma-aminobutyric acid receptor subunit alpha-4P48169 Details
Gamma-aminobutyric acid receptor subunit alpha-5P31644 Details
Gamma-aminobutyric acid receptor subunit alpha-6Q16445 Details
Gamma-aminobutyric acid receptor subunit beta-1P18505 Details
Gamma-aminobutyric acid receptor subunit beta-2P47870 Details
Gamma-aminobutyric acid receptor subunit beta-3P28472 Details
Gamma-aminobutyric acid receptor subunit deltaO14764 Details
Gamma-aminobutyric acid receptor subunit epsilonP78334 Details
Gamma-aminobutyric acid receptor subunit gamma-1Q8N1C3 Details
Gamma-aminobutyric acid receptor subunit gamma-2P18507 Details
Gamma-aminobutyric acid receptor subunit gamma-3Q99928 Details
Gamma-aminobutyric acid receptor subunit piO00591 Details
Gamma-aminobutyric acid receptor subunit thetaQ9UN88 Details
References
  1. Sousa A, Ticku MK: Interactions of the neurosteroid dehydroepiandrosterone sulfate with the GABA(A) receptor complex reveals that it may act via the picrotoxin site. J Pharmacol Exp Ther. 1997 Aug;282(2):827-33. [PubMed:9262347 ]
Kind
Protein group
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Voltage-gated cation channel activity
Specific Function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic plasticity, synaptogenesis, excitotoxicity, memory acquisition and learning. It mediates neuronal functions in glutamate neurotransmission. Is involved in the cell surface targeting of NMDA receptors (By similarity).
Components:
NameUniProt IDDetails
Glutamate receptor ionotropic, NMDA 1Q05586 Details
Glutamate receptor ionotropic, NMDA 2AQ12879 Details
Glutamate receptor ionotropic, NMDA 2BQ13224 Details
Glutamate receptor ionotropic, NMDA 2CQ14957 Details
Glutamate receptor ionotropic, NMDA 2DO15399 Details
Glutamate receptor ionotropic, NMDA 3AQ8TCU5 Details
Glutamate receptor ionotropic, NMDA 3BO60391 Details
References
  1. Compagnone NA, Mellon SH: Dehydroepiandrosterone: a potential signalling molecule for neocortical organization during development. Proc Natl Acad Sci U S A. 1998 Apr 14;95(8):4678-83. [PubMed:9539798 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Chen F, Knecht K, Birzin E, Fisher J, Wilkinson H, Mojena M, Moreno CT, Schmidt A, Harada S, Freedman LP, Reszka AA: Direct agonist/antagonist functions of dehydroepiandrosterone. Endocrinology. 2005 Nov;146(11):4568-76. Epub 2005 Jun 30. [PubMed:15994348 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Testosterone dehydrogenase (nad+) activity
Specific Function:
Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name:
HSD17B1
Uniprot ID:
P14061
Molecular Weight:
34949.715 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. 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
unknown
General Function:
Sulfotransferase activity
Specific Function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name:
SULT2A1
Uniprot ID:
Q06520
Molecular Weight:
33779.57 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. 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
unknown
General Function:
Steroid sulfotransferase activity
Specific Function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. I...
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular Weight:
41307.32 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. 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
unknown
Actions
activator
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fa...
Gene Name:
PPARA
Uniprot ID:
Q07869
Molecular Weight:
52224.595 Da
References
  1. Kohalmy K, Tamasi V, Kobori L, Sarvary E, Pascussi JM, Porrogi P, Rozman D, Prough RA, Meyer UA, Monostory K: Dehydroepiandrosterone induces human CYP2B6 through the constitutive androstane receptor. Drug Metab Dispos. 2007 Sep;35(9):1495-501. Epub 2007 Jun 25. [PubMed:17591676 ]
  2. Tamasi V, Miller KK, Ripp SL, Vila E, Geoghagen TE, Prough RA: Modulation of receptor phosphorylation contributes to activation of peroxisome proliferator activated receptor alpha by dehydroepiandrosterone and other peroxisome proliferators. Mol Pharmacol. 2008 Mar;73(3):968-76. Epub 2007 Dec 13. [PubMed:18079279 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Opioid receptor activity
Specific Function:
Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma membrane. Involved in the regulation of different receptors it plays a role in BDNF signaling and EGF signaling. Also regulates ion channels like the potassium channel and could modulate neurotransmitt...
Gene Name:
SIGMAR1
Uniprot ID:
Q99720
Molecular Weight:
25127.52 Da
References
  1. Waterhouse RN, Chang RC, Atuehene N, Collier TL: In vitro and in vivo binding of neuroactive steroids to the sigma-1 receptor as measured with the positron emission tomography radioligand [18F]FPS. Synapse. 2007 Jul;61(7):540-6. [PubMed:17447254 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and is...
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
References
  1. Kohalmy K, Tamasi V, Kobori L, Sarvary E, Pascussi JM, Porrogi P, Rozman D, Prough RA, Meyer UA, Monostory K: Dehydroepiandrosterone induces human CYP2B6 through the constitutive androstane receptor. Drug Metab Dispos. 2007 Sep;35(9):1495-501. Epub 2007 Jun 25. [PubMed:17591676 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
Zinc ion binding
Specific Function:
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element.
Gene Name:
NR1I3
Uniprot ID:
Q14994
Molecular Weight:
39942.145 Da
References
  1. Kohalmy K, Tamasi V, Kobori L, Sarvary E, Pascussi JM, Porrogi P, Rozman D, Prough RA, Meyer UA, Monostory K: Dehydroepiandrosterone induces human CYP2B6 through the constitutive androstane receptor. Drug Metab Dispos. 2007 Sep;35(9):1495-501. Epub 2007 Jun 25. [PubMed:17591676 ]
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
unknown
General Function:
Steroid delta-isomerase activity
Specific Function:
Not Available
Gene Name:
ksi
Uniprot ID:
P07445
Molecular Weight:
14535.48 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. 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
Brevibacterium sterolicum
Pharmacological action
unknown
General Function:
Steroid delta-isomerase activity
Specific Function:
Catalyzes the oxidation and isomerization of cholesterol to cholestenone (4-cholesten-3-one), which is an initial step in the cholesterol degradation process.
Gene Name:
choB
Uniprot ID:
P22637
Molecular Weight:
59357.765 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. 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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 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 ]
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Drug created on June 13, 2005 07:24 / Updated on November 18, 2016 11:04