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Identification
Name4-Androstenedione
Accession NumberDB01536  (EXPT00569, DB07386)
TypeSmall Molecule
GroupsExperimental, Illicit
DescriptionA delta-4 C19 steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. [PubChem]
Structure
Thumb
Synonyms
4-Androstene-3,17-dione
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 BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII409J2J96VR
CAS number63-05-8
WeightAverage: 286.4085
Monoisotopic: 286.193280076
Chemical FormulaC19H26O2
InChI KeyAEMFNILZOJDQLW-QAGGRKNESA-N
InChI
InChI=1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
IUPAC Name
(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action4-androstenedione is a 19-carbon steroid hormone produced in the adrenal glands and the gonads as an intermediate step in the biochemical pathway that produces the androgen testosterone and the estrogens estrone and estradiol.
TargetKindPharmacological actionActionsOrganismUniProt ID
Estradiol 17-beta-dehydrogenase 1Proteinyes
inducer
HumanP14061 details
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1Proteinyes
positive allosteric modulator
HumanP14060 details
6-deoxyerythronolide B hydroxylaseProteinunknown
inducer
Saccharopolyspora erythraea (strain NRRL 23338)Q00441 details
Aldo-keto reductase family 1 member C3Proteinunknown
inducer
HumanP42330 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 organismsNot Available
Pathways
PathwayCategorySMPDB ID
Aromatase deficiencyDiseaseSMP00565
17-Beta Hydroxysteroid Dehydrogenase III DeficiencyDiseaseSMP00356
Androgen and Estrogen MetabolismMetabolicSMP00068
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 4-Androstenedione is combined with 1,10-Phenanthroline.Experimental
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with 4-Androstenedione.Approved
AcetovanilloneThe risk or severity of adverse effects can be increased when Acetovanillone is combined with 4-Androstenedione.Investigational
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with 4-Androstenedione.Approved, Vet Approved
AdapaleneThe risk or severity of adverse effects can be increased when Adapalene is combined with 4-Androstenedione.Approved
Aldesleukin4-Androstenedione may decrease the antineoplastic activities of Aldesleukin.Approved
ALT-110The risk or severity of adverse effects can be increased when 4-Androstenedione is combined with ALT-110.Investigational
Aluminum hydroxideThe bioavailability of 4-Androstenedione can be decreased when combined with Aluminum hydroxide.Approved
Aluminum phosphateThe bioavailability of 4-Androstenedione can be decreased when combined with Aluminum phosphate.Approved
AmbenoniumThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Ambenonium.Approved
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with 4-Androstenedione.Approved
AmiodaroneThe serum concentration of 4-Androstenedione can be increased when it is combined with Amiodarone.Approved, Investigational
Amphotericin B4-Androstenedione 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 4-Androstenedione.Investigational
AntipyrineThe risk or severity of adverse effects can be increased when Antipyrine is combined with 4-Androstenedione.Approved
ApremilastThe risk or severity of adverse effects can be increased when Apremilast is combined with 4-Androstenedione.Approved, Investigational
AprepitantThe serum concentration of 4-Androstenedione can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe serum concentration of 4-Androstenedione can be increased when it is combined with Atazanavir.Approved, Investigational
Atracurium besylateAtracurium besylate may increase the adverse neuromuscular activities of 4-Androstenedione.Approved
AzapropazoneThe risk or severity of adverse effects can be increased when Azapropazone is combined with 4-Androstenedione.Withdrawn
AzelastineThe risk or severity of adverse effects can be increased when Azelastine is combined with 4-Androstenedione.Approved
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with 4-Androstenedione.Approved, Investigational
BazedoxifeneThe serum concentration of 4-Androstenedione can be increased when it is combined with Bazedoxifene.Approved, Investigational
Bendroflumethiazide4-Androstenedione may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenoxaprofenThe risk or severity of adverse effects can be increased when Benoxaprofen is combined with 4-Androstenedione.Withdrawn
Benzoic AcidThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with 4-Androstenedione.Approved
Betulinic AcidThe risk or severity of adverse effects can be increased when Betulinic Acid is combined with 4-Androstenedione.Investigational
Bismuth SubcitrateThe bioavailability of 4-Androstenedione can be decreased when combined with Bismuth Subcitrate.Approved
BoceprevirThe serum concentration of 4-Androstenedione can be increased when it is combined with Boceprevir.Approved
BromfenacThe risk or severity of adverse effects can be increased when Bromfenac is combined with 4-Androstenedione.Approved
BucillamineThe risk or severity of adverse effects can be increased when Bucillamine is combined with 4-Androstenedione.Investigational
Bumetanide4-Androstenedione may increase the hypokalemic activities of Bumetanide.Approved
CalcitriolThe therapeutic efficacy of Calcitriol can be decreased when used in combination with 4-Androstenedione.Approved, Nutraceutical
Calcium carbonateThe bioavailability of 4-Androstenedione can be decreased when combined with Calcium carbonate.Approved
CarbamazepineThe serum concentration of 4-Androstenedione can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarprofenThe risk or severity of adverse effects can be increased when Carprofen is combined with 4-Androstenedione.Approved, Vet Approved, Withdrawn
CastanospermineThe risk or severity of adverse effects can be increased when Castanospermine is combined with 4-Androstenedione.Experimental
CDX-110The risk or severity of adverse effects can be increased when 4-Androstenedione is combined with CDX-110.Investigational
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with 4-Androstenedione.Approved, Investigational
Ceritinib4-Androstenedione may increase the hyperglycemic activities of Ceritinib.Approved
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with 4-Androstenedione.Approved, Vet Approved
Chlorothiazide4-Androstenedione may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorotrianiseneThe serum concentration of 4-Androstenedione can be increased when it is combined with Chlorotrianisene.Withdrawn
Chlorthalidone4-Androstenedione may increase the hypokalemic activities of Chlorthalidone.Approved
CholestyramineCholestyramine can cause a decrease in the absorption of 4-Androstenedione resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CinoxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Cinoxacin.Approved, Withdrawn
CiprofloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Ciprofloxacin.Approved, Investigational
ClarithromycinThe serum concentration of 4-Androstenedione can be increased when it is combined with Clarithromycin.Approved
ClonixinThe risk or severity of adverse effects can be increased when Clonixin is combined with 4-Androstenedione.Approved
CobicistatThe serum concentration of 4-Androstenedione can be increased when it is combined with Cobicistat.Approved
ColesevelamColesevelam can cause a decrease in the absorption of 4-Androstenedione resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of 4-Androstenedione resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Conjugated Equine EstrogensThe serum concentration of 4-Androstenedione can be increased when it is combined with Conjugated Equine Estrogens.Approved
Corticorelin ovine triflutateThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with 4-Androstenedione.Approved
CoumaphosThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Coumaphos.Vet Approved
CurcuminThe risk or severity of adverse effects can be increased when Curcumin is combined with 4-Androstenedione.Investigational
D-LimoneneThe risk or severity of adverse effects can be increased when D-Limonene is combined with 4-Androstenedione.Investigational
DarunavirThe serum concentration of 4-Androstenedione can be increased when it is combined with Darunavir.Approved
DecamethoniumThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Decamethonium.Approved
DeferasiroxThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Deferasirox.Approved, Investigational
DemecariumThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Demecarium.Approved
dersalazineThe risk or severity of adverse effects can be increased when dersalazine is combined with 4-Androstenedione.Investigational
DichlorvosThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Dichlorvos.Vet Approved
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with 4-Androstenedione.Approved, Vet Approved
DienestrolThe serum concentration of 4-Androstenedione can be increased when it is combined with Dienestrol.Approved
DiethylstilbestrolThe serum concentration of 4-Androstenedione can be increased when it is combined with Diethylstilbestrol.Approved
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with 4-Androstenedione.Approved
Dihydrotestosterone4-Androstenedione may increase the fluid retaining activities of Dihydrotestosterone.Illicit
DonepezilThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Donepezil.Approved
DroxicamThe risk or severity of adverse effects can be increased when Droxicam is combined with 4-Androstenedione.Approved
DuvelisibThe risk or severity of adverse effects can be increased when Duvelisib is combined with 4-Androstenedione.Investigational
E6201The risk or severity of adverse effects can be increased when E6201 is combined with 4-Androstenedione.Investigational
EbselenThe risk or severity of adverse effects can be increased when Ebselen is combined with 4-Androstenedione.Investigational
EchothiophateThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Echothiophate.Approved
EdrophoniumThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Edrophonium.Approved
EnoxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Enoxacin.Approved
EnzalutamideThe serum concentration of 4-Androstenedione 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 4-Androstenedione.Approved
EstradiolThe serum concentration of 4-Androstenedione can be increased when it is combined with Estradiol.Approved, Investigational, Vet Approved
EstriolThe serum concentration of 4-Androstenedione can be increased when it is combined with Estriol.Approved, Vet Approved
EstroneThe serum concentration of 4-Androstenedione can be increased when it is combined with Estrone.Approved
Etacrynic acid4-Androstenedione may increase the hypokalemic activities of Etacrynic acid.Approved
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with 4-Androstenedione.Approved, Investigational
Ethinyl EstradiolThe serum concentration of 4-Androstenedione can be increased when it is combined with Ethinyl Estradiol.Approved
EtodolacThe risk or severity of adverse effects can be increased when Etodolac is combined with 4-Androstenedione.Approved, Investigational, Vet Approved
EtofenamateThe risk or severity of adverse effects can be increased when Etofenamate is combined with 4-Androstenedione.Approved
EtoricoxibThe risk or severity of adverse effects can be increased when Etoricoxib is combined with 4-Androstenedione.Approved, Investigational
Evening primrose oilThe risk or severity of adverse effects can be increased when Evening primrose oil is combined with 4-Androstenedione.Approved
exisulindThe risk or severity of adverse effects can be increased when exisulind is combined with 4-Androstenedione.Investigational
FenbufenThe risk or severity of adverse effects can be increased when Fenbufen is combined with 4-Androstenedione.Approved
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with 4-Androstenedione.Approved
FenthionThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Fenthion.Vet Approved
FleroxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Fleroxacin.Approved
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with 4-Androstenedione.Approved, Withdrawn
FlumequineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Flumequine.Withdrawn
FlunixinThe risk or severity of adverse effects can be increased when Flunixin is combined with 4-Androstenedione.Vet Approved
Fluoxymesterone4-Androstenedione 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 4-Androstenedione.Approved, Investigational
FosaprepitantThe serum concentration of 4-Androstenedione can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of 4-Androstenedione can be decreased when it is combined with Fosphenytoin.Approved
Furosemide4-Androstenedione may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
G17DTThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with G17DT.Investigational
GalantamineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Galantamine.Approved
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Gallamine Triethiodide.Approved
GarenoxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Garenoxacin.Investigational
GatifloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Gatifloxacin.Approved, Investigational
GemifloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Gemifloxacin.Approved, Investigational
GenisteinThe serum concentration of 4-Androstenedione can be increased when it is combined with Genistein.Investigational
GI-5005The risk or severity of adverse effects can be increased when 4-Androstenedione is combined with GI-5005.Investigational
Ginkgo bilobaThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Ginkgo biloba.Approved, Nutraceutical
Glycerol PhenylbutyrateThe therapeutic efficacy of Glycerol Phenylbutyrate can be decreased when used in combination with 4-Androstenedione.Approved
GrepafloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Grepafloxacin.Withdrawn
HexestrolThe serum concentration of 4-Androstenedione can be increased when it is combined with Hexestrol.Withdrawn
HigenamineThe risk or severity of adverse effects can be increased when Higenamine is combined with 4-Androstenedione.Investigational
HMPL-004The risk or severity of adverse effects can be increased when HMPL-004 is combined with 4-Androstenedione.Investigational
Huperzine AThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Huperzine A.Investigational
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with 4-Androstenedione.Approved, Investigational
Hydrochlorothiazide4-Androstenedione may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
Hydroflumethiazide4-Androstenedione may increase the hypokalemic activities of Hydroflumethiazide.Approved
IbuprofenThe risk or severity of adverse effects can be increased when Ibuprofen is combined with 4-Androstenedione.Approved
IbuproxamThe risk or severity of adverse effects can be increased when Ibuproxam is combined with 4-Androstenedione.Withdrawn
IcatibantThe risk or severity of adverse effects can be increased when Icatibant is combined with 4-Androstenedione.Approved
IdelalisibThe serum concentration of 4-Androstenedione can be increased when it is combined with Idelalisib.Approved
IndacaterolIndacaterol may increase the hypokalemic activities of 4-Androstenedione.Approved
Indapamide4-Androstenedione may increase the hypokalemic activities of Indapamide.Approved
IndinavirThe serum concentration of 4-Androstenedione can be increased when it is combined with Indinavir.Approved
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with 4-Androstenedione.Approved, Investigational
IndoprofenThe risk or severity of adverse effects can be increased when Indoprofen is combined with 4-Androstenedione.Withdrawn
INGN 201The risk or severity of adverse effects can be increased when 4-Androstenedione is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when 4-Androstenedione is combined with INGN 225.Investigational
IsoflurophateThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Isoflurophate.Approved, Withdrawn
IsoniazidThe serum concentration of Isoniazid can be decreased when it is combined with 4-Androstenedione.Approved
IsoxicamThe risk or severity of adverse effects can be increased when Isoxicam is combined with 4-Androstenedione.Withdrawn
ItraconazoleThe serum concentration of 4-Androstenedione can be increased when it is combined with Itraconazole.Approved, Investigational
KebuzoneThe risk or severity of adverse effects can be increased when Kebuzone is combined with 4-Androstenedione.Experimental
KetoconazoleThe serum concentration of 4-Androstenedione can be increased when it is combined with Ketoconazole.Approved, Investigational
KetoprofenThe risk or severity of adverse effects can be increased when Ketoprofen is combined with 4-Androstenedione.Approved, Vet Approved
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with 4-Androstenedione.Approved
LeflunomideThe risk or severity of adverse effects can be increased when Leflunomide is combined with 4-Androstenedione.Approved, Investigational
LevofloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Levofloxacin.Approved, Investigational
LisofyllineThe risk or severity of adverse effects can be increased when Lisofylline is combined with 4-Androstenedione.Investigational
LomefloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Lomefloxacin.Approved
LopinavirThe serum concentration of 4-Androstenedione can be increased when it is combined with Lopinavir.Approved
LornoxicamThe risk or severity of adverse effects can be increased when Lornoxicam is combined with 4-Androstenedione.Approved
LoxoprofenThe risk or severity of adverse effects can be increased when Loxoprofen is combined with 4-Androstenedione.Approved
LumacaftorThe serum concentration of 4-Androstenedione can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibThe risk or severity of adverse effects can be increased when Lumiracoxib is combined with 4-Androstenedione.Approved, Investigational
MagaldrateThe bioavailability of 4-Androstenedione can be decreased when combined with Magaldrate.Withdrawn
Magnesium carbonateThe bioavailability of 4-Androstenedione can be decreased when combined with Magnesium carbonate.Approved
Magnesium hydroxideThe bioavailability of 4-Androstenedione can be decreased when combined with Magnesium hydroxide.Approved
Magnesium oxideThe bioavailability of 4-Androstenedione 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 4-Androstenedione.Approved
Magnesium TrisilicateThe bioavailability of 4-Androstenedione can be decreased when combined with Magnesium Trisilicate.Approved
MalathionThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Malathion.Approved, Investigational
MasoprocolThe risk or severity of adverse effects can be increased when Masoprocol is combined with 4-Androstenedione.Approved
Meclofenamic acidThe risk or severity of adverse effects can be increased when Meclofenamic acid is combined with 4-Androstenedione.Approved, Vet Approved
Mefenamic acidThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with 4-Androstenedione.Approved
MefloquineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Mefloquine.Approved
MeloxicamThe risk or severity of adverse effects can be increased when Meloxicam is combined with 4-Androstenedione.Approved, Vet Approved
MemantineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Memantine.Approved, Investigational
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with 4-Androstenedione.Approved
MestranolThe serum concentration of 4-Androstenedione can be increased when it is combined with Mestranol.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with 4-Androstenedione.Withdrawn
MethallenestrilThe serum concentration of 4-Androstenedione can be increased when it is combined with Methallenestril.Experimental
Methanesulfonyl FluorideThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Methanesulfonyl Fluoride.Investigational
Methyclothiazide4-Androstenedione may increase the hypokalemic activities of Methyclothiazide.Approved
Methyltestosterone4-Androstenedione may increase the fluid retaining activities of Methyltestosterone.Approved
Metolazone4-Androstenedione may increase the hypokalemic activities of Metolazone.Approved
MifepristoneThe therapeutic efficacy of 4-Androstenedione can be decreased when used in combination with Mifepristone.Approved, Investigational
MinaprineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Minaprine.Approved
MitotaneThe serum concentration of 4-Androstenedione can be decreased when it is combined with Mitotane.Approved
MivacuriumMivacurium may increase the adverse neuromuscular activities of 4-Androstenedione.Approved
MizoribineThe risk or severity of adverse effects can be increased when Mizoribine is combined with 4-Androstenedione.Investigational
MoxifloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Moxifloxacin.Approved, Investigational
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with 4-Androstenedione.Approved, Investigational
Mycophenolic acidThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with 4-Androstenedione.Approved
NabumetoneThe risk or severity of adverse effects can be increased when Nabumetone is combined with 4-Androstenedione.Approved
NafamostatThe risk or severity of adverse effects can be increased when Nafamostat is combined with 4-Androstenedione.Investigational
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with 4-Androstenedione.Approved
Nalidixic AcidThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Nalidixic Acid.Approved
NaproxenThe risk or severity of adverse effects can be increased when Naproxen is combined with 4-Androstenedione.Approved, Vet Approved
NCX 4016The risk or severity of adverse effects can be increased when NCX 4016 is combined with 4-Androstenedione.Investigational
NefazodoneThe serum concentration of 4-Androstenedione can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of 4-Androstenedione can be increased when it is combined with Nelfinavir.Approved
NemonoxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Nemonoxacin.Investigational
NeostigmineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Neostigmine.Approved, Vet Approved
NepafenacThe risk or severity of adverse effects can be increased when Nepafenac is combined with 4-Androstenedione.Approved
NevirapineThe serum concentration of 4-Androstenedione can be decreased when it is combined with Nevirapine.Approved
NicorandilThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Nicorandil.Approved
Niflumic AcidThe risk or severity of adverse effects can be increased when Niflumic Acid is combined with 4-Androstenedione.Approved
NimesulideThe risk or severity of adverse effects can be increased when Nimesulide is combined with 4-Androstenedione.Approved, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with 4-Androstenedione.Investigational
NorfloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Norfloxacin.Approved
OfloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Ofloxacin.Approved
OlopatadineThe risk or severity of adverse effects can be increased when Olopatadine is combined with 4-Androstenedione.Approved
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with 4-Androstenedione.Approved
OrgoteinThe risk or severity of adverse effects can be increased when Orgotein is combined with 4-Androstenedione.Vet Approved
Oxandrolone4-Androstenedione 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 4-Androstenedione.Approved
Oxymetholone4-Androstenedione 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 4-Androstenedione.Withdrawn
ParecoxibThe risk or severity of adverse effects can be increased when Parecoxib is combined with 4-Androstenedione.Approved
PazufloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Pazufloxacin.Investigational
PefloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Pefloxacin.Approved
PentobarbitalThe serum concentration of 4-Androstenedione can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe serum concentration of 4-Androstenedione can be decreased when it is combined with Phenobarbital.Approved
Phenylacetic acidThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with 4-Androstenedione.Approved
PhenylbutazoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with 4-Androstenedione.Approved, Vet Approved
PhenytoinThe serum concentration of 4-Androstenedione can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PhysostigmineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Physostigmine.Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with 4-Androstenedione.Approved, Investigational
Piretanide4-Androstenedione may increase the hypokalemic activities of Piretanide.Experimental
PirfenidoneThe risk or severity of adverse effects can be increased when Pirfenidone is combined with 4-Androstenedione.Investigational
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with 4-Androstenedione.Approved, Investigational
Polyestradiol phosphateThe serum concentration of 4-Androstenedione can be increased when it is combined with Polyestradiol phosphate.Approved
Polythiazide4-Androstenedione may increase the hypokalemic activities of Polythiazide.Approved
PosaconazoleThe serum concentration of 4-Androstenedione can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe serum concentration of 4-Androstenedione can be decreased when it is combined with Primidone.Approved, Vet Approved
PromestrieneThe serum concentration of 4-Androstenedione can be increased when it is combined with Promestriene.Investigational
PropacetamolThe risk or severity of adverse effects can be increased when Propacetamol is combined with 4-Androstenedione.Approved
PrulifloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Prulifloxacin.Investigational
PTC299The risk or severity of adverse effects can be increased when PTC299 is combined with 4-Androstenedione.Investigational
PyridostigmineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Pyridostigmine.Approved
QuinestrolThe serum concentration of 4-Androstenedione can be increased when it is combined with Quinestrol.Approved
Quinethazone4-Androstenedione may increase the hypokalemic activities of Quinethazone.Approved
Rabies vaccineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Rabies vaccine.Approved
RapacuroniumRapacuronium may increase the adverse neuromuscular activities of 4-Androstenedione.Withdrawn
ResveratrolThe risk or severity of adverse effects can be increased when Resveratrol is combined with 4-Androstenedione.Experimental, Investigational
RifabutinThe serum concentration of 4-Androstenedione can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of 4-Androstenedione can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of 4-Androstenedione can be decreased when it is combined with Rifapentine.Approved
RitonavirThe serum concentration of 4-Androstenedione can be increased when it is combined with Ritonavir.Approved, Investigational
RivastigmineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Rivastigmine.Approved, Investigational
RofecoxibThe risk or severity of adverse effects can be increased when Rofecoxib is combined with 4-Androstenedione.Investigational, Withdrawn
RosoxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Rosoxacin.Approved
S EquolThe serum concentration of 4-Androstenedione can be increased when it is combined with S Equol.Investigational
SalicylamideThe risk or severity of adverse effects can be increased when Salicylamide is combined with 4-Androstenedione.Approved
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with 4-Androstenedione.Approved, Vet Approved
SalsalateThe risk or severity of adverse effects can be increased when Salsalate is combined with 4-Androstenedione.Approved
SaquinavirThe serum concentration of 4-Androstenedione can be increased when it is combined with Saquinavir.Approved, Investigational
SecoisolariciresinolThe serum concentration of 4-Androstenedione can be increased when it is combined with Secoisolariciresinol.Investigational
SeratrodastThe risk or severity of adverse effects can be increased when Seratrodast is combined with 4-Androstenedione.Approved, Investigational
Sodium phenylbutyrateThe therapeutic efficacy of Sodium phenylbutyrate can be decreased when used in combination with 4-Androstenedione.Approved
SparfloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Sparfloxacin.Approved
SRP 299The risk or severity of adverse effects can be increased when 4-Androstenedione is combined with SRP 299.Investigational
SRT501The risk or severity of adverse effects can be increased when SRT501 is combined with 4-Androstenedione.Investigational
St. John's WortThe serum concentration of 4-Androstenedione can be decreased when it is combined with St. John's Wort.Nutraceutical
Stanozolol4-Androstenedione may increase the fluid retaining activities of Stanozolol.Approved, Vet Approved
SulfasalazineThe risk or severity of adverse effects can be increased when Sulfasalazine is combined with 4-Androstenedione.Approved
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with 4-Androstenedione.Approved
SuprofenThe risk or severity of adverse effects can be increased when Suprofen is combined with 4-Androstenedione.Approved, Withdrawn
Synthetic Conjugated Estrogens, AThe serum concentration of 4-Androstenedione can be increased when it is combined with Synthetic Conjugated Estrogens, A.Approved
Synthetic Conjugated Estrogens, BThe serum concentration of 4-Androstenedione can be increased when it is combined with Synthetic Conjugated Estrogens, B.Approved
TacrineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Tacrine.Withdrawn
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with 4-Androstenedione.Approved
TelithromycinThe serum concentration of 4-Androstenedione can be increased when it is combined with Telithromycin.Approved
TemafloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Temafloxacin.Withdrawn
TenoxicamThe risk or severity of adverse effects can be increased when Tenoxicam is combined with 4-Androstenedione.Approved
TepoxalinThe risk or severity of adverse effects can be increased when Tepoxalin is combined with 4-Androstenedione.Vet Approved
TeriflunomideThe risk or severity of adverse effects can be increased when Teriflunomide is combined with 4-Androstenedione.Approved
Testosterone4-Androstenedione may increase the fluid retaining activities of Testosterone.Approved, Investigational
TG4010The risk or severity of adverse effects can be increased when 4-Androstenedione is combined with TG4010.Investigational
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with 4-Androstenedione.Approved
TiboloneThe serum concentration of 4-Androstenedione can be increased when it is combined with Tibolone.Approved
TinoridineThe risk or severity of adverse effects can be increased when Tinoridine is combined with 4-Androstenedione.Investigational
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Tolfenamic Acid is combined with 4-Androstenedione.Approved
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with 4-Androstenedione.Approved
Torasemide4-Androstenedione may increase the hypokalemic activities of Torasemide.Approved
TranilastThe risk or severity of adverse effects can be increased when Tranilast is combined with 4-Androstenedione.Approved, Investigational
TrichlorfonThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Trichlorfon.Vet Approved
Trichlormethiazide4-Androstenedione 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 4-Androstenedione.Approved
TrovafloxacinThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Trovafloxacin.Approved, Withdrawn
TubocurarineThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Tubocurarine.Approved
ValdecoxibThe risk or severity of adverse effects can be increased when Valdecoxib is combined with 4-Androstenedione.Investigational, Withdrawn
VoriconazoleThe serum concentration of 4-Androstenedione can be increased when it is combined with Voriconazole.Approved, Investigational
Warfarin4-Androstenedione may increase the anticoagulant activities of Warfarin.Approved
ZaltoprofenThe risk or severity of adverse effects can be increased when Zaltoprofen is combined with 4-Androstenedione.Approved
ZeranolThe serum concentration of 4-Androstenedione can be increased when it is combined with Zeranol.Vet Approved
ZileutonThe risk or severity of adverse effects can be increased when Zileuton is combined with 4-Androstenedione.Approved, Investigational, Withdrawn
ZomepiracThe risk or severity of adverse effects can be increased when Zomepirac is combined with 4-Androstenedione.Withdrawn
Food InteractionsNot Available
References
Synthesis Reference

Angela M. H. Brodie, Harry J. Brodie, David A. Marsh, “Ester derivatives of 4-hydroxy-4-androstene-3,17-dione and a method for inhibiting estrogen biosynthesis.” U.S. Patent US4235893, issued October, 1962.

US4235893
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9793
Caco-2 permeable+0.8011
P-glycoprotein substrateSubstrate0.5526
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IINon-inhibitor0.6615
Renal organic cation transporterNon-inhibitor0.6632
CYP450 2C9 substrateNon-substrate0.8548
CYP450 2D6 substrateNon-substrate0.9131
CYP450 3A4 substrateSubstrate0.7193
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9387
CYP450 2D6 inhibitorNon-inhibitor0.9386
CYP450 2C19 inhibitorNon-inhibitor0.8138
CYP450 3A4 inhibitorNon-inhibitor0.8483
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8067
Ames testNon AMES toxic0.9508
CarcinogenicityNon-carcinogens0.9313
BiodegradationNot ready biodegradable0.9343
Rat acute toxicity1.5360 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7599
hERG inhibition (predictor II)Non-inhibitor0.7469
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point158 °CPhysProp
water solubility57.8 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.75HANSCH,C ET AL. (1995)
logS-3.69ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.027 mg/mLALOGPS
logP2.93ALOGPS
logP3.93ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)19.03ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.61 m3·mol-1ChemAxon
Polarizability33.2 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (11.2 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-004l-5910000000-518e1ad38bcc73325b53View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-004l-5910000000-5172e05f9889ee2bfaf4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-36e848ba16b141eef47bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-9600000000-712954fc35a84c8217deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9300000000-f8e9aa16b4b208b69f7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-000f-8940000000-e12025ea2b7808c64b9cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-059m-3940000000-9cb32ac21e46afb2829aView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D 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
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inducer
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
positive allosteric modulator
General Function:
Steroid delta-isomerase activity
Specific Function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxypr...
Gene Name:
HSD3B1
Uniprot ID:
P14060
Molecular Weight:
42251.25 Da
References
  1. Ishii-Ohba H, Inano H, Tamaoki B: Purification and properties of testicular 3 beta-hydroxy-5-ene-steroid dehydrogenase and 5-ene-4-ene isomerase. J Steroid Biochem. 1986 Oct;25(4):555-60. [PubMed:2945972 ]
Kind
Protein
Organism
Saccharopolyspora erythraea (strain NRRL 23338)
Pharmacological action
unknown
Actions
inducer
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific Function:
Catalyzes the NADPH-dependent conversion of 6-deoxyerythronolide B (6-DEB) to erythronolide B (EB) by the insertion of an oxygen at the 6S position of 6-DEB. Requires the participation of a ferredoxin and a ferredoxin reductase for the transfer of electrons from NADPH to the monooxygenase.
Gene Name:
eryF
Uniprot ID:
Q00441
Molecular Weight:
45098.685 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms andro...
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular Weight:
36852.89 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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23