Identification

Name
Equilin
Accession Number
DB02187  (EXPT01355)
Type
Small Molecule
Groups
Approved
Description

An estrogenic steroid produced by horses. It has a total of four double bonds in the A- and B-ring. High concentration of euilin is found in the urine of pregnant mares. [PubChem]

Equilin is one of the estrogens present in the mixture of estrogens isolated from horse urine and marketed as Premarin. Premarin became the most commonly used form of estrogen for hormone replacement therapy in the United States of America. Estrone is the major estrogen in Premarin (about 50%) and equilin is present as about 25% of the total. Estrone is a major estrogen that is normally found in women. Equilin is not normally present in women, so there has been interest in the effects of equilin on the human body. [Wikipedia]

The estrogens in Premarin are present mainly as "conjugates", modified chemical forms in which the active estrogen is coupled to another chemical group such as sulfate. Estrone sulfate is usually the major form of estrogen in women. After being taken into a woman's body, the conjugated estrogens of Premarin are converted to the active unconjugated estrogens or excreted from the woman's body. Estrone can be converted to estradiol, which is thought to be the major active estrogen in women. [Wikipedia]

Structure
Thumb
Synonyms
  • 1,3,5,7-Estratetraen-3-ol-17-one
  • 7-Dehydroestrone
  • Dihydroequilenin
  • Equilin
Categories
UNII
08O86EX0J4
CAS number
474-86-2
Weight
Average: 268.3502
Monoisotopic: 268.146329884
Chemical Formula
C18H20O2
InChI Key
WKRLQDKEXYKHJB-HFTRVMKXSA-N
InChI
InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3-5,10,14,16,19H,2,6-9H2,1H3/t14-,16+,18+/m1/s1
IUPAC Name
(1S,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5,9-tetraen-14-one
SMILES
[H][[email protected]@]12CCC(=O)[[email protected]@]1(C)CC[[email protected]]1([H])C3=C(CC=C21)C=C(O)C=C3

Pharmacology

Indication

For the treatment of moderate to severe vasomotor symptoms associated with the menopause, atrophic vaginitis, osteoporosis, hypoestrogenism due to hypogonadism, castration, primary ovarian failure, breast cancer (for palliation only), and Advanced androgen-dependent carcinoma of the prostate (for palliation only)

Structured Indications
Not Available
Pharmacodynamics

Equilin is a component of Premarin (conjugated estrogens), a mixture of the water soluble salts of sulfate esters from estrone, equilin, 17 alpha-dihydroequilin, and other related steroids, may be derived from pregnant equine urine or yam and soy plants. Estrogens are important in the development and maintenance of the female reproductive system and secondary sex characteristics. They promote growth and development of the vagina, uterus, and fallopian tubes, and enlargement of the breasts. Indirectly, they contribute to the shaping of the skeleton, maintenance of tone and elasticity of urogenital structures, changes in the epiphyses of the long bones that allow for the pubertal growth spurt and its termination, growth of axillary and pubic hair, and pigmentation of the nipples and genitals. Decline of estrogenic activity at the end of the menstrual cycle can bring on menstruation, although the cessation of progesterone secretion is the most important factor in the mature ovulatory cycle. However, in the preovulatory or nonovulatory cycle, estrogen is the primary determinant in the onset of menstruation. Estrogens also affect the release of pituitary gonadotropins. The pharmacologic effects of conjugated estrogens are similar to those of endogenous estrogens.

Mechanism of action

Estrogens enter the cells of responsive tissues (e.g., female organs, breasts, hypothalamus, pituitary) where they interact with a protein receptor, subsequently increasing the rate of synthesis of DNA, RNA, and some proteins. Estrogens decrease the secretion of gonadotropin-releasing hormone by the hypothalamus, reducing the secretion of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the pituitary.

TargetActionsOrganism
UEstradiol 17-beta-dehydrogenase 1Not AvailableHuman
UEstrogen receptor alphaNot AvailableHuman
Absorption

Well absorbed.

Volume of distribution
Not Available
Protein binding

90% bound to plasma proteins

Metabolism

Hepatic

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Equilin is combined with 1,10-Phenanthroline.Experimental
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Equilin.Approved
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Equilin.Approved
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Equilin.Approved, Vet Approved
AdapaleneThe risk or severity of adverse effects can be increased when Adapalene is combined with Equilin.Approved
AlclofenacThe risk or severity of adverse effects can be increased when Alclofenac is combined with Equilin.Approved, Withdrawn
AldesleukinEquilin may decrease the antineoplastic activities of Aldesleukin.Approved
AlgeldrateThe bioavailability of Equilin can be decreased when combined with Algeldrate.Experimental
AlmagateThe bioavailability of Equilin can be decreased when combined with Almagate.Experimental
AlmasilateThe bioavailability of Equilin can be decreased when combined with Almasilate.Experimental
AlminoprofenThe risk or severity of adverse effects can be increased when Alminoprofen is combined with Equilin.Experimental
AloglutamolThe bioavailability of Equilin can be decreased when combined with Aloglutamol.Experimental
AloxiprinThe risk or severity of adverse effects can be increased when Aloxiprin is combined with Equilin.Experimental
AluminiumThe bioavailability of Equilin can be decreased when combined with Aluminium.Approved
Aluminium acetoacetateThe bioavailability of Equilin can be decreased when combined with Aluminium acetoacetate.Experimental
Aluminium glycinateThe bioavailability of Equilin can be decreased when combined with Aluminium glycinate.Experimental
Aluminum hydroxideThe bioavailability of Equilin can be decreased when combined with Aluminum hydroxide.Approved
AmbenoniumThe risk or severity of adverse effects can be increased when Equilin is combined with Ambenonium.Approved
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Equilin.Approved
AmiodaroneThe serum concentration of Equilin can be increased when it is combined with Amiodarone.Approved, Investigational
Amphotericin BEquilin may increase the hypokalemic activities of Amphotericin B.Approved, Investigational
AndrographolideThe risk or severity of adverse effects can be increased when Andrographolide is combined with Equilin.Investigational
AnisodamineThe risk or severity of adverse effects can be increased when Anisodamine is combined with Equilin.Investigational
AntipyrineThe risk or severity of adverse effects can be increased when Antipyrine is combined with Equilin.Approved
ApocyninThe risk or severity of adverse effects can be increased when Apocynin is combined with Equilin.Investigational
ApremilastThe risk or severity of adverse effects can be increased when Apremilast is combined with Equilin.Approved, Investigational
AprepitantThe serum concentration of Equilin can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe serum concentration of Equilin can be increased when it is combined with Atazanavir.Approved, Investigational
Atracurium besylateAtracurium besylate may increase the adverse neuromuscular activities of Equilin.Approved
AzapropazoneThe risk or severity of adverse effects can be increased when Azapropazone is combined with Equilin.Withdrawn
AzelastineThe risk or severity of adverse effects can be increased when Azelastine is combined with Equilin.Approved
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Equilin.Approved, Investigational
BCG vaccineThe risk or severity of adverse effects can be increased when Equilin is combined with BCG vaccine.Investigational
BendazacThe risk or severity of adverse effects can be increased when Bendazac is combined with Equilin.Experimental
BendroflumethiazideEquilin may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenorilateThe risk or severity of adverse effects can be increased when Benorilate is combined with Equilin.Experimental
BenoxaprofenThe risk or severity of adverse effects can be increased when Benoxaprofen is combined with Equilin.Withdrawn
Benzoic AcidThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Equilin.Approved
BevoniumThe risk or severity of adverse effects can be increased when Bevonium is combined with Equilin.Experimental
Bismuth SubcitrateThe bioavailability of Equilin can be decreased when combined with Bismuth Subcitrate.Approved
Bismuth subnitrateThe bioavailability of Equilin can be decreased when combined with Bismuth subnitrate.Experimental
BoceprevirThe serum concentration of Equilin can be increased when it is combined with Boceprevir.Withdrawn
BromfenacThe risk or severity of adverse effects can be increased when Bromfenac is combined with Equilin.Approved
BucillamineThe risk or severity of adverse effects can be increased when Bucillamine is combined with Equilin.Investigational
BufexamacThe risk or severity of adverse effects can be increased when Bufexamac is combined with Equilin.Experimental
BumadizoneThe risk or severity of adverse effects can be increased when Bumadizone is combined with Equilin.Experimental
BumetanideEquilin may increase the hypokalemic activities of Bumetanide.Approved
CalcitriolThe therapeutic efficacy of Calcitriol can be decreased when used in combination with Equilin.Approved, Nutraceutical
Calcium CarbonateThe bioavailability of Equilin can be decreased when combined with Calcium Carbonate.Approved
Calcium silicateThe bioavailability of Equilin can be decreased when combined with Calcium silicate.Experimental
Capromab pendetideEquilin may decrease effectiveness of Capromab pendetide as a diagnostic agent.Approved
CarbamazepineThe serum concentration of Equilin can be decreased when it is combined with Carbamazepine.Approved, Investigational
Carbaspirin calciumThe risk or severity of adverse effects can be increased when Carbaspirin calcium is combined with Equilin.Experimental
CarprofenThe risk or severity of adverse effects can be increased when Carprofen is combined with Equilin.Approved, Vet Approved, Withdrawn
CastanospermineThe risk or severity of adverse effects can be increased when Castanospermine is combined with Equilin.Experimental
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with Equilin.Approved, Investigational
CeritinibEquilin may increase the hyperglycemic activities of Ceritinib.Approved
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with Equilin.Approved, Vet Approved
ChlorothiazideEquilin may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorotrianiseneThe serum concentration of Equilin can be increased when it is combined with Chlorotrianisene.Withdrawn
ChlorthalidoneEquilin may increase the hypokalemic activities of Chlorthalidone.Approved
CholestyramineCholestyramine can cause a decrease in the absorption of Equilin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Choline magnesium trisalicylateThe risk or severity of adverse effects can be increased when Choline magnesium trisalicylate is combined with Equilin.Approved
CinoxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Cinoxacin.Approved, Withdrawn
ClarithromycinThe serum concentration of Equilin 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 Equilin.Approved
Clostridium tetani toxoid antigen (formaldehyde inactivated)The risk or severity of adverse effects can be increased when Equilin is combined with Clostridium tetani toxoid antigen (formaldehyde inactivated).Approved
CobicistatThe serum concentration of Equilin can be increased when it is combined with Cobicistat.Approved
ColesevelamColesevelam can cause a decrease in the absorption of Equilin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of Equilin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Conjugated estrogensThe serum concentration of Equilin can be increased when it is combined with Conjugated estrogens.Approved
Corticorelin ovine triflutateThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Equilin.Approved
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The risk or severity of adverse effects can be increased when Equilin is combined with Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated).Approved
CoumaphosThe risk or severity of adverse effects can be increased when Equilin is combined with Coumaphos.Vet Approved
CurcuminThe risk or severity of adverse effects can be increased when Curcumin is combined with Equilin.Investigational
CyclopenthiazideEquilin may increase the hypokalemic activities of Cyclopenthiazide.Experimental
D-LimoneneThe risk or severity of adverse effects can be increased when D-Limonene is combined with Equilin.Investigational
DaidzeinThe serum concentration of Equilin can be increased when it is combined with Daidzein.Experimental
DarunavirThe serum concentration of Equilin can be increased when it is combined with Darunavir.Approved
DecamethoniumThe risk or severity of adverse effects can be increased when Equilin is combined with Decamethonium.Approved
DeferasiroxThe risk or severity of adverse effects can be increased when Equilin is combined with Deferasirox.Approved, Investigational
DemecariumThe risk or severity of adverse effects can be increased when Equilin is combined with Demecarium.Approved
dersalazineThe risk or severity of adverse effects can be increased when dersalazine is combined with Equilin.Investigational
DichlorvosThe risk or severity of adverse effects can be increased when Equilin is combined with Dichlorvos.Vet Approved
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Equilin.Approved, Vet Approved
DienestrolThe serum concentration of Equilin can be increased when it is combined with Dienestrol.Approved
DiethylstilbestrolThe serum concentration of Equilin can be increased when it is combined with Diethylstilbestrol.Approved
DifenpiramideThe risk or severity of adverse effects can be increased when Difenpiramide is combined with Equilin.Experimental
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Equilin.Approved
DihydrotestosteroneEquilin may increase the fluid retaining activities of Dihydrotestosterone.Illicit
DistigmineThe risk or severity of adverse effects can be increased when Equilin is combined with Distigmine.Experimental
DonepezilThe risk or severity of adverse effects can be increased when Equilin is combined with Donepezil.Approved
DroxicamThe risk or severity of adverse effects can be increased when Droxicam is combined with Equilin.Approved
DuvelisibThe risk or severity of adverse effects can be increased when Duvelisib is combined with Equilin.Investigational
E-6201The risk or severity of adverse effects can be increased when E-6201 is combined with Equilin.Investigational
EchothiophateThe risk or severity of adverse effects can be increased when Equilin is combined with Echothiophate.Approved
EdrophoniumThe risk or severity of adverse effects can be increased when Equilin is combined with Edrophonium.Approved
EnoxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Enoxacin.Approved
EnzalutamideThe serum concentration of Equilin can be decreased when it is combined with Enzalutamide.Approved
EpimestrolThe serum concentration of Equilin can be increased when it is combined with Epimestrol.Experimental
EpirizoleThe risk or severity of adverse effects can be increased when Epirizole is combined with Equilin.Approved
EquolThe serum concentration of Equilin can be increased when it is combined with Equol.Investigational
EstradiolThe serum concentration of Equilin can be increased when it is combined with Estradiol.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Equilin can be increased when it is combined with Estriol.Approved, Vet Approved
EstroneThe serum concentration of Equilin can be increased when it is combined with Estrone.Approved
Etacrynic acidEquilin may increase the hypokalemic activities of Etacrynic acid.Approved
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with Equilin.Approved, Investigational
EthenzamideThe risk or severity of adverse effects can be increased when Ethenzamide is combined with Equilin.Experimental
Ethinyl EstradiolThe serum concentration of Equilin 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 Equilin.Approved, Investigational, Vet Approved
EtofenamateThe risk or severity of adverse effects can be increased when Etofenamate is combined with Equilin.Approved
EtoricoxibThe risk or severity of adverse effects can be increased when Etoricoxib is combined with Equilin.Approved, Investigational
Evening primrose oilThe risk or severity of adverse effects can be increased when Evening primrose oil is combined with Equilin.Approved
exisulindThe risk or severity of adverse effects can be increased when exisulind is combined with Equilin.Investigational
FelbinacThe risk or severity of adverse effects can be increased when Felbinac is combined with Equilin.Experimental
FenbufenThe risk or severity of adverse effects can be increased when Fenbufen is combined with Equilin.Approved
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Equilin.Approved
FenthionThe risk or severity of adverse effects can be increased when Equilin is combined with Fenthion.Vet Approved
FentiazacThe risk or severity of adverse effects can be increased when Fentiazac is combined with Equilin.Experimental
FeprazoneThe risk or severity of adverse effects can be increased when Feprazone is combined with Equilin.Experimental
Ferulic acidThe risk or severity of adverse effects can be increased when Ferulic acid is combined with Equilin.Experimental
FleroxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Fleroxacin.Approved
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Equilin.Approved, Withdrawn
FlumequineThe risk or severity of adverse effects can be increased when Equilin is combined with Flumequine.Withdrawn
FlunixinThe risk or severity of adverse effects can be increased when Flunixin is combined with Equilin.Vet Approved
FlunoxaprofenThe risk or severity of adverse effects can be increased when Flunoxaprofen is combined with Equilin.Experimental
FluoxymesteroneEquilin 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 Equilin.Approved, Investigational
FosaprepitantThe serum concentration of Equilin can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Equilin can be decreased when it is combined with Fosphenytoin.Approved
FurosemideEquilin may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
G17DTThe risk or severity of adverse effects can be increased when Equilin is combined with G17DT.Investigational
GalantamineThe risk or severity of adverse effects can be increased when Equilin is combined with Galantamine.Approved
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Equilin is combined with Gallamine Triethiodide.Approved
GarenoxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Garenoxacin.Investigational
GatifloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Gatifloxacin.Approved, Investigational
GemifloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Gemifloxacin.Approved, Investigational
GenisteinThe serum concentration of Equilin can be increased when it is combined with Genistein.Investigational
GI-5005The risk or severity of adverse effects can be increased when Equilin is combined with GI-5005.Investigational
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Equilin is combined with Ginkgo biloba.Approved, Nutraceutical
GLPG-0492Equilin may increase the fluid retaining activities of GLPG-0492.Investigational
Glycerol PhenylbutyrateThe therapeutic efficacy of Glycerol Phenylbutyrate can be decreased when used in combination with Equilin.Approved
GrepafloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Grepafloxacin.Withdrawn
GuacetisalThe risk or severity of adverse effects can be increased when Guacetisal is combined with Equilin.Experimental
Hemoglobin crosfumarilThe risk or severity of adverse effects can be increased when Hemoglobin crosfumaril is combined with Equilin.Experimental
HexestrolThe serum concentration of Equilin 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 Equilin.Investigational
Huperzine AThe risk or severity of adverse effects can be increased when Equilin is combined with Huperzine A.Investigational
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Equilin.Approved, Investigational
HydrochlorothiazideEquilin may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideEquilin may increase the hypokalemic activities of Hydroflumethiazide.Approved
HydrotalciteThe bioavailability of Equilin can be decreased when combined with Hydrotalcite.Experimental
IbuprofenThe risk or severity of adverse effects can be increased when Ibuprofen is combined with Equilin.Approved
IbuproxamThe risk or severity of adverse effects can be increased when Ibuproxam is combined with Equilin.Withdrawn
IcatibantThe risk or severity of adverse effects can be increased when Icatibant is combined with Equilin.Approved
IdelalisibThe serum concentration of Equilin can be increased when it is combined with Idelalisib.Approved
Imidazole salicylateThe risk or severity of adverse effects can be increased when Imidazole salicylate is combined with Equilin.Experimental
IndacaterolIndacaterol may increase the hypokalemic activities of Equilin.Approved
IndapamideEquilin may increase the hypokalemic activities of Indapamide.Approved
IndinavirThe serum concentration of Equilin can be increased when it is combined with Indinavir.Approved
IndobufenThe risk or severity of adverse effects can be increased when Indobufen is combined with Equilin.Investigational
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with Equilin.Approved, Investigational
IndoprofenThe risk or severity of adverse effects can be increased when Indoprofen is combined with Equilin.Withdrawn
INGN 201The risk or severity of adverse effects can be increased when Equilin is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Equilin is combined with INGN 225.Investigational
IpidacrineThe risk or severity of adverse effects can be increased when Equilin is combined with Ipidacrine.Experimental
IsoflurophateThe risk or severity of adverse effects can be increased when Equilin is combined with Isoflurophate.Approved, Withdrawn
IsoniazidThe serum concentration of Isoniazid can be decreased when it is combined with Equilin.Approved
IsoxicamThe risk or severity of adverse effects can be increased when Isoxicam is combined with Equilin.Withdrawn
ItraconazoleThe serum concentration of Equilin 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 Equilin.Experimental
KetoconazoleThe serum concentration of Equilin 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 Equilin.Approved, Vet Approved
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Equilin.Approved
LeflunomideThe risk or severity of adverse effects can be increased when Leflunomide is combined with Equilin.Approved, Investigational
LevofloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Levofloxacin.Approved, Investigational
LisofyllineThe risk or severity of adverse effects can be increased when Lisofylline is combined with Equilin.Investigational
LonazolacThe risk or severity of adverse effects can be increased when Lonazolac is combined with Equilin.Experimental
LopinavirThe serum concentration of Equilin 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 Equilin.Approved
LoxoprofenThe risk or severity of adverse effects can be increased when Loxoprofen is combined with Equilin.Approved
LumacaftorThe serum concentration of Equilin 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 Equilin.Approved, Investigational
MagaldrateThe bioavailability of Equilin can be decreased when combined with Magaldrate.Withdrawn
Magnesium HydroxideThe bioavailability of Equilin can be decreased when combined with Magnesium Hydroxide.Approved
Magnesium oxideThe bioavailability of Equilin can be decreased when combined with Magnesium oxide.Approved
Magnesium peroxideThe bioavailability of Equilin can be decreased when combined with Magnesium peroxide.Experimental
Magnesium salicylateThe risk or severity of adverse effects can be increased when Magnesium salicylate is combined with Equilin.Approved
Magnesium silicateThe bioavailability of Equilin can be decreased when combined with Magnesium silicate.Experimental
Magnesium TrisilicateThe bioavailability of Equilin can be decreased when combined with Magnesium Trisilicate.Approved
MalathionThe risk or severity of adverse effects can be increased when Equilin is combined with Malathion.Approved, Investigational
MasoprocolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Equilin.Approved
Meclofenamic acidThe risk or severity of adverse effects can be increased when Meclofenamic acid is combined with Equilin.Approved, Vet Approved
Mefenamic acidThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with Equilin.Approved
MefloquineThe risk or severity of adverse effects can be increased when Equilin is combined with Mefloquine.Approved
MeloxicamThe risk or severity of adverse effects can be increased when Meloxicam is combined with Equilin.Approved, Vet Approved
MemantineThe risk or severity of adverse effects can be increased when Equilin is combined with Memantine.Approved, Investigational
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Equilin.Approved
MesteroloneEquilin may increase the fluid retaining activities of Mesterolone.Experimental
MestranolThe serum concentration of Equilin 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 Equilin.Withdrawn
MethallenestrilThe serum concentration of Equilin can be increased when it is combined with Methallenestril.Experimental
Methanesulfonyl FluorideThe risk or severity of adverse effects can be increased when Equilin is combined with Methanesulfonyl Fluoride.Investigational
MethyclothiazideEquilin may increase the hypokalemic activities of Methyclothiazide.Approved
Methyl salicylateThe risk or severity of adverse effects can be increased when Equilin is combined with Methyl salicylate.Approved, Vet Approved
MethyltestosteroneEquilin may increase the fluid retaining activities of Methyltestosterone.Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Equilin is combined with Metoclopramide.Approved, Investigational
MetolazoneEquilin may increase the hypokalemic activities of Metolazone.Approved
MifepristoneThe therapeutic efficacy of Equilin can be decreased when used in combination with Mifepristone.Approved, Investigational
MinaprineThe risk or severity of adverse effects can be increased when Equilin is combined with Minaprine.Approved
MitotaneThe serum concentration of Equilin can be decreased when it is combined with Mitotane.Approved
MivacuriumMivacurium may increase the adverse neuromuscular activities of Equilin.Approved
MizoribineThe risk or severity of adverse effects can be increased when Mizoribine is combined with Equilin.Investigational
MofebutazoneThe risk or severity of adverse effects can be increased when Mofebutazone is combined with Equilin.Experimental
MoxestrolThe serum concentration of Equilin can be increased when it is combined with Moxestrol.Experimental
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Equilin.Approved, Investigational
Mycophenolic acidThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with Equilin.Approved
NabumetoneThe risk or severity of adverse effects can be increased when Nabumetone is combined with Equilin.Approved
NafamostatThe risk or severity of adverse effects can be increased when Nafamostat is combined with Equilin.Approved, Investigational
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Equilin.Approved
Nalidixic AcidThe risk or severity of adverse effects can be increased when Equilin is combined with Nalidixic Acid.Approved
NandroloneEquilin may increase the fluid retaining activities of Nandrolone.Experimental
NaproxenThe risk or severity of adverse effects can be increased when Naproxen is combined with Equilin.Approved, Vet Approved
NefazodoneThe serum concentration of Equilin can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Equilin can be increased when it is combined with Nelfinavir.Approved
NemonoxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Nemonoxacin.Investigational
NeostigmineThe risk or severity of adverse effects can be increased when Equilin is combined with Neostigmine.Approved, Vet Approved
NepafenacThe risk or severity of adverse effects can be increased when Nepafenac is combined with Equilin.Approved
NevirapineThe serum concentration of Equilin can be decreased when it is combined with Nevirapine.Approved
NicorandilThe risk or severity of adverse effects can be increased when Equilin is combined with Nicorandil.Approved
NifenazoneThe risk or severity of adverse effects can be increased when Nifenazone is combined with Equilin.Experimental
Niflumic AcidThe risk or severity of adverse effects can be increased when Niflumic Acid is combined with Equilin.Approved
NimesulideThe risk or severity of adverse effects can be increased when Nimesulide is combined with Equilin.Approved, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with Equilin.Investigational
NorfloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Norfloxacin.Approved
OlopatadineThe risk or severity of adverse effects can be increased when Olopatadine is combined with Equilin.Approved
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Equilin.Approved
OrgoteinThe risk or severity of adverse effects can be increased when Orgotein is combined with Equilin.Vet Approved
OxandroloneEquilin 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 Equilin.Approved
Oxolinic acidThe risk or severity of adverse effects can be increased when Equilin is combined with Oxolinic acid.Experimental
OxymetholoneEquilin 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 Equilin.Withdrawn
ParaoxonThe risk or severity of adverse effects can be increased when Equilin is combined with Paraoxon.Experimental
ParecoxibThe risk or severity of adverse effects can be increased when Parecoxib is combined with Equilin.Approved
ParthenolideThe risk or severity of adverse effects can be increased when Parthenolide is combined with Equilin.Investigational
PazufloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Pazufloxacin.Investigational
PefloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Pefloxacin.Approved
PentobarbitalThe serum concentration of Equilin can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe serum concentration of Equilin 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 Equilin.Approved
PhenylbutazoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Equilin.Approved, Vet Approved
Phenylbutyric acidThe therapeutic efficacy of Phenylbutyric acid can be decreased when used in combination with Equilin.Approved, Investigational
PhenytoinThe serum concentration of Equilin can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PhysostigmineThe risk or severity of adverse effects can be increased when Equilin is combined with Physostigmine.Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Equilin.Approved, Investigational
Pipemidic acidThe risk or severity of adverse effects can be increased when Equilin is combined with Pipemidic acid.Experimental
PiretanideEquilin may increase the hypokalemic activities of Piretanide.Experimental
PirfenidoneThe risk or severity of adverse effects can be increased when Pirfenidone is combined with Equilin.Investigational
Piromidic acidThe risk or severity of adverse effects can be increased when Equilin is combined with Piromidic acid.Experimental
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with Equilin.Approved, Investigational
PirprofenThe risk or severity of adverse effects can be increased when Pirprofen is combined with Equilin.Experimental
Polyestradiol phosphateThe serum concentration of Equilin can be increased when it is combined with Polyestradiol phosphate.Approved
PolythiazideEquilin may increase the hypokalemic activities of Polythiazide.Approved
PosaconazoleThe serum concentration of Equilin can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PranoprofenThe risk or severity of adverse effects can be increased when Pranoprofen is combined with Equilin.Experimental
PrimidoneThe serum concentration of Equilin can be decreased when it is combined with Primidone.Approved, Vet Approved
ProglumetacinThe risk or severity of adverse effects can be increased when Proglumetacin is combined with Equilin.Experimental
PromestrieneThe serum concentration of Equilin 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 Equilin.Approved
PropyphenazoneThe risk or severity of adverse effects can be increased when Propyphenazone is combined with Equilin.Experimental
ProquazoneThe risk or severity of adverse effects can be increased when Proquazone is combined with Equilin.Experimental
PrulifloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Prulifloxacin.Investigational
PTC299The risk or severity of adverse effects can be increased when PTC299 is combined with Equilin.Investigational
PyridostigmineThe risk or severity of adverse effects can be increased when Equilin is combined with Pyridostigmine.Approved
QuinestrolThe serum concentration of Equilin can be increased when it is combined with Quinestrol.Approved
QuinethazoneEquilin may increase the hypokalemic activities of Quinethazone.Approved
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Equilin is combined with Rabies virus inactivated antigen, A.Approved
RapacuroniumRapacuronium may increase the adverse neuromuscular activities of Equilin.Withdrawn
ResveratrolThe risk or severity of adverse effects can be increased when Resveratrol is combined with Equilin.Experimental, Investigational
RifabutinThe serum concentration of Equilin can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Equilin can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Equilin can be decreased when it is combined with Rifapentine.Approved
RindopepimutThe risk or severity of adverse effects can be increased when Equilin is combined with Rindopepimut.Investigational
RitonavirThe serum concentration of Equilin can be increased when it is combined with Ritonavir.Approved, Investigational
RivastigmineThe risk or severity of adverse effects can be increased when Equilin is combined with Rivastigmine.Approved, Investigational
RofecoxibThe risk or severity of adverse effects can be increased when Rofecoxib is combined with Equilin.Investigational, Withdrawn
RosoxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Rosoxacin.Approved
Rotavirus VaccineThe risk or severity of adverse effects can be increased when Equilin is combined with Rotavirus Vaccine.Approved
Rubella virus vaccineThe risk or severity of adverse effects can be increased when Equilin is combined with Rubella virus vaccine.Approved
RufloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Rufloxacin.Experimental
SalicylamideThe risk or severity of adverse effects can be increased when Salicylamide is combined with Equilin.Approved
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Equilin.Approved, Vet Approved
SalsalateThe risk or severity of adverse effects can be increased when Salsalate is combined with Equilin.Approved
SaquinavirThe serum concentration of Equilin can be increased when it is combined with Saquinavir.Approved, Investigational
SecoisolariciresinolThe serum concentration of Equilin can be increased when it is combined with Secoisolariciresinol.Investigational
SemapimodThe risk or severity of adverse effects can be increased when Semapimod is combined with Equilin.Investigational
SeratrodastThe risk or severity of adverse effects can be increased when Seratrodast is combined with Equilin.Approved
SerrapeptaseThe risk or severity of adverse effects can be increased when Serrapeptase is combined with Equilin.Investigational
SitafloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Sitafloxacin.Experimental
SparfloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Sparfloxacin.Approved
SRP 299The risk or severity of adverse effects can be increased when Equilin is combined with SRP 299.Investigational
SRT501The risk or severity of adverse effects can be increased when SRT501 is combined with Equilin.Investigational
St. John's WortThe serum concentration of Equilin can be decreased when it is combined with St. John's Wort.Nutraceutical
StanozololEquilin may increase the fluid retaining activities of Stanozolol.Approved, Vet Approved
StiripentolThe serum concentration of Equilin 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 Equilin.Approved
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with Equilin.Approved
SuprofenThe risk or severity of adverse effects can be increased when Suprofen is combined with Equilin.Approved, Withdrawn
SuxibuzoneThe risk or severity of adverse effects can be increased when Suxibuzone is combined with Equilin.Experimental
Synthetic Conjugated Estrogens, AThe serum concentration of Equilin can be increased when it is combined with Synthetic Conjugated Estrogens, A.Approved
Synthetic Conjugated Estrogens, BThe serum concentration of Equilin can be increased when it is combined with Synthetic Conjugated Estrogens, B.Approved
TacrineThe risk or severity of adverse effects can be increased when Equilin is combined with Tacrine.Withdrawn
TarenflurbilThe risk or severity of adverse effects can be increased when Tarenflurbil is combined with Equilin.Investigational
TecemotideThe risk or severity of adverse effects can be increased when Equilin is combined with Tecemotide.Investigational
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Equilin.Withdrawn
TelithromycinThe serum concentration of Equilin can be increased when it is combined with Telithromycin.Approved
TemafloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Temafloxacin.Withdrawn
TenidapThe risk or severity of adverse effects can be increased when Tenidap is combined with Equilin.Experimental
TenoxicamThe risk or severity of adverse effects can be increased when Tenoxicam is combined with Equilin.Approved
TepoxalinThe risk or severity of adverse effects can be increased when Tepoxalin is combined with Equilin.Vet Approved
TeriflunomideThe risk or severity of adverse effects can be increased when Teriflunomide is combined with Equilin.Approved
TestosteroneEquilin may increase the fluid retaining activities of Testosterone.Approved, Investigational
TG4010The risk or severity of adverse effects can be increased when Equilin is combined with TG4010.Investigational
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Equilin.Approved
TiboloneThe serum concentration of Equilin 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 Equilin.Investigational
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Tolfenamic Acid is combined with Equilin.Approved
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with Equilin.Approved
TorasemideEquilin may increase the hypokalemic activities of Torasemide.Approved
TranilastThe risk or severity of adverse effects can be increased when Tranilast is combined with Equilin.Approved, Investigational
TribenosideThe risk or severity of adverse effects can be increased when Tribenoside is combined with Equilin.Experimental
TrichlorfonThe risk or severity of adverse effects can be increased when Equilin is combined with Trichlorfon.Vet Approved
TrichlormethiazideEquilin may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TriptolideThe risk or severity of adverse effects can be increased when Triptolide is combined with Equilin.Investigational
TrovafloxacinThe risk or severity of adverse effects can be increased when Equilin is combined with Trovafloxacin.Approved, Withdrawn
TubocurarineThe risk or severity of adverse effects can be increased when Equilin is combined with Tubocurarine.Approved
ValdecoxibThe risk or severity of adverse effects can be increased when Valdecoxib is combined with Equilin.Investigational, Withdrawn
VoriconazoleThe serum concentration of Equilin can be increased when it is combined with Voriconazole.Approved, Investigational
WarfarinEquilin may increase the anticoagulant activities of Warfarin.Approved
Yellow fever vaccineThe risk or severity of adverse effects can be increased when Equilin is combined with Yellow fever vaccine.Approved
ZaltoprofenThe risk or severity of adverse effects can be increased when Zaltoprofen is combined with Equilin.Approved
ZeranolThe serum concentration of Equilin 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 Equilin.Approved, Investigational, Withdrawn
ZomepiracThe risk or severity of adverse effects can be increased when Zomepirac is combined with Equilin.Withdrawn
Zoster vaccineThe risk or severity of adverse effects can be increased when Equilin is combined with Zoster vaccine.Approved
Food Interactions
Not Available

References

General References
  1. Sawicki MW, Erman M, Puranen T, Vihko P, Ghosh D: Structure of the ternary complex of human 17beta-hydroxysteroid dehydrogenase type 1 with 3-hydroxyestra-1,3,5,7-tetraen-17-one (equilin) and NADP+. Proc Natl Acad Sci U S A. 1999 Feb 2;96(3):840-5. [PubMed:9927655]
External Links
KEGG Drug
D04041
KEGG Compound
C14392
PubChem Compound
223368
PubChem Substance
46506633
ChemSpider
193995
BindingDB
50423544
ChEBI
42309
ChEMBL
CHEMBL323533
HET
EQI
Wikipedia
Equilin
PDB Entries
1equ

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)239 °CPhysProp
water solubility1.41 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.0133 mg/mLALOGPS
logP3.8ALOGPS
logP3.9ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.93 m3·mol-1ChemAxon
Polarizability30.55 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9192
Caco-2 permeable+0.875
P-glycoprotein substrateSubstrate0.6807
P-glycoprotein inhibitor INon-inhibitor0.8085
P-glycoprotein inhibitor IINon-inhibitor0.8881
Renal organic cation transporterNon-inhibitor0.6704
CYP450 2C9 substrateNon-substrate0.7245
CYP450 2D6 substrateNon-substrate0.9081
CYP450 3A4 substrateSubstrate0.7666
CYP450 1A2 substrateInhibitor0.9108
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8209
CYP450 3A4 inhibitorNon-inhibitor0.8156
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5528
Ames testNon AMES toxic0.9109
CarcinogenicityNon-carcinogens0.93
BiodegradationNot ready biodegradable0.9319
Rat acute toxicity1.8021 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7619
hERG inhibition (predictor II)Non-inhibitor0.601
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Mass Spectrum (Electron Ionization)MSsplash10-014i-3940000000-b80393e552aa78600070
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Oxosteroids
Direct Parent
Oxosteroids
Alternative Parents
3-hydroxy delta-7-steroids / 17-oxosteroids / Delta-7-steroids / Phenanthrenes and derivatives / Naphthalenes / 1-hydroxy-2-unsubstituted benzenoids / Ketones / Organic oxides / Hydrocarbon derivatives
Substituents
3-hydroxy-delta-7-steroid / 3-hydroxysteroid / Hydroxysteroid / Oxosteroid / 17-oxosteroid / Delta-7-steroid / Phenanthrene / Naphthalene / 1-hydroxy-2-unsubstituted benzenoid / Benzenoid
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
17-oxo steroid, 3-hydroxy steroid (CHEBI:42309) / Estrane and derivatives (C14392) / C18 steroids (estrogens) and derivatives (LMST02010026)

Targets

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
Uniprot Name
Estradiol 17-beta-dehydrogenase 1
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
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 tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Starcevic S, Brozic P, Turk S, Cesar J, Rizner TL, Gobec S: Synthesis and biological evaluation of (6- and 7-phenyl) coumarin derivatives as selective nonsteroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 1. J Med Chem. 2011 Jan 13;54(1):248-61. doi: 10.1021/jm101104z. Epub 2010 Dec 7. [PubMed:21138273]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:07