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Identification
NameClomifene
Accession NumberDB00882  (APRD00880)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionA triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue. [PubChem]
Structure
Thumb
Synonyms
Clomifene
Clomifeno
Clomifenum
Clomiphene
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ClomidTablet50 mgOralSanofi Aventis Canada Inc1995-12-31Not applicableCanada
Clomid 50mgTablet50 mgOralMerrell Pharms Inc., Division Of Merrell Dow (Can)1967-12-311996-09-09Canada
Clomiphene CitrateTablet50 mg/1OralTeva Pharmaceuticals USA Inc1992-11-01Not applicableUs
Clomiphene CitrateTablet50 mg/1OralWatson Laboratories, Inc.1994-09-01Not applicableUs
Clomiphene CitrateTablet50 mg/1OralPd Rx Pharmaceuticals, Inc.1967-02-01Not applicableUs
Serophene Tab 50mgTablet50 mgOralPharmascience Inc1985-12-312014-09-08Canada
Serophene Tab 50mgTablet50 mgOralEmd Serono A Division Of Emd Inc Canada1991-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Clomiphene CitrateTablet50 mg/1OralRebel Distributors Corp1999-08-30Not applicableUs
Clomiphene CitrateTablet50 mg/1OralPar Pharmaceutical Inc1999-08-30Not applicableUs
Clomiphene CitrateTablet50 mg/1OralPhysicians Total Care, Inc.1996-08-22Not applicableUs
Clomiphene CitrateTablet50 mg/1OralA S Medication Solutions1999-08-30Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AndroxalNot Available
ClomifertNot Available
ClostilbegytEgis
OmifinSanofi
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Clomifene citrate
7619-53-6
Thumb
  • InChI Key: PYTMYKVIJXPNBD-OQKDUQJOSA-N
  • Monoisotopic Mass: 597.21294484
  • Average Mass: 598.083
DBSALT000490
Categories
UNIIR6D2UI4FLS
CAS number911-45-5
WeightAverage: 405.96
Monoisotopic: 405.18594223
Chemical FormulaC26H28ClNO
InChI KeyGKIRPKYJQBWNGO-OCEACIFDSA-N
InChI
InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3/b26-25+
IUPAC Name
{2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]ethyl}diethylamine
SMILES
CCN(CC)CCOC1=CC=C(C=C1)C(=C(Cl)C1=CC=CC=C1)C1=CC=CC=C1
Pharmacology
IndicationUsed mainly in female infertility due to anovulation (e.g. due to polycystic ovary syndrome) to induce ovulation.
Structured Indications
PharmacodynamicsClomifene (previously clomiphene) is an orally administered, non steroidal, ovulatory stimulant that acts as a selective estrogen receptor modulator (SERM). Clomifene can lead to multiple ovulation, and hence increase the risk of conceiving twins. In comparison to purified FSH, the rate of ovarian hyperstimulation syndrome is low. There may be an increased risk of ovarian cancer and weight gain. Clomifene is capable of interacting with estrogen-receptor-containing tissues, including the hypothalamus, pituitary, ovary, endometrium, vagina, and cervix. It may compete with estrogen for estrogen-receptor-binding sites and may delay replenishment of intracellular estrogen receptors. Clomifene initiates a series of endocrine events culminating in a preovulatory gonadotropin surge and subsequent follicular rupture. The first endocrine event, in response to a course of clomifene therapy, is an increase in the release of pituitary gonadotropins. This initiates steroidogenesis and folliculogenesis resulting in growth of the ovarian follicle and an increase in the circulating level of estradiol. Following ovulation, plasma progesterone and estradiol rise and fall as they would in a normal ovulatory cycle.
Mechanism of actionClomifene has both estrogenic and anti-estrogenic properties, but its precise mechanism of action has not been determined. Clomifene appears to stumulate the release of gonadotropins, follicle-stimulating hormone (FSH), and leuteinizing hormone (LH), which leads to the development and maturation of ovarian follicle, ovulation, and subsequent development and function of the coprus luteum, thus resulting in pregnancy. Gonadotropin release may result from direct stimulation of the hypothalamic-pituitary axis or from a decreased inhibitory influence of estrogens on the hypothalamic-pituitary axis by competing with the endogenous estrogens of the uterus, pituitary, or hypothalamus. Clomifene has no apparent progestational, androgenic, or antrandrogenic effects and does not appear to interfere with pituitary-adrenal or pituitary-thyroid function.
TargetKindPharmacological actionActionsOrganismUniProt ID
Estrogen receptorProteinyes
antagonist
agonist
HumanP03372 details
Related Articles
AbsorptionBased on early studies with 14 C-labeled clomifene, the drug was shown to be readily absorbed orally in humans.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationBased on early studies with 14C-labeled clomiphene citrate, the drug was shown to be readily absorbed orally in humans and excreted principally in the feces. Mean urinary excretion was approximately 8% with fecal excretion of about 42%.
Half life5-7 days
ClearanceNot Available
ToxicityThe acute oral LD50 of clomifene is 1700 mg/kg in mice and 5750 mg/kg in rats. The toxic dose in humans is not known. Toxic effects accompanying acute overdosage of clomifene have not been reported. Signs and symptoms of overdosage as a result of the use of more than the recommended dose during clomifene therapy include nausea, vomiting, vasomotor flushes, visual blurring, spots or flashes, scotomata, ovarian enlargement with pelvic or abdominal pain.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetaminophenThe serum concentration of Clomifene can be increased when it is combined with Acetaminophen.Approved
AfatinibThe serum concentration of Clomifene can be increased when it is combined with Afatinib.Approved
AlbendazoleThe serum concentration of Clomifene can be increased when it is combined with Albendazole.Approved, Vet Approved
AldosteroneThe serum concentration of Clomifene can be decreased when it is combined with Aldosterone.Experimental
AlectinibThe serum concentration of Clomifene can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Clomifene can be increased when it is combined with Alfentanil.Approved, Illicit
AmantadineThe serum concentration of Clomifene can be increased when it is combined with Amantadine.Approved
Aminohippuric acidThe serum concentration of Clomifene can be increased when it is combined with Aminohippuric acid.Approved
AmiodaroneThe serum concentration of Clomifene can be decreased when it is combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Clomifene can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Clomifene can be increased when it is combined with Amlodipine.Approved
AmprenavirThe serum concentration of Clomifene can be decreased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Clomifene can be increased when it is combined with Amsacrine.Approved
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Clomifene resulting in a loss in efficacy.Approved
AstemizoleThe serum concentration of Clomifene can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe serum concentration of Clomifene can be increased when it is combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Clomifene can be increased when it is combined with Atenolol.Approved
AtorvastatinThe serum concentration of Clomifene can be increased when it is combined with Atorvastatin.Approved
AzelastineThe serum concentration of Clomifene can be increased when it is combined with Azelastine.Approved
AzithromycinThe serum concentration of Clomifene can be increased when it is combined with Azithromycin.Approved
BenzocaineThe serum concentration of Clomifene can be increased when it is combined with Benzocaine.Approved
BepridilThe serum concentration of Clomifene can be increased when it is combined with Bepridil.Approved, Withdrawn
BiperidenThe serum concentration of Clomifene can be increased when it is combined with Biperiden.Approved
BosutinibThe serum concentration of Clomifene can be increased when it is combined with Bosutinib.Approved
BromocriptineThe serum concentration of Clomifene can be increased when it is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe serum concentration of Clomifene can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe serum concentration of Clomifene can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe serum concentration of Clomifene can be increased when it is combined with Cabazitaxel.Approved
CaffeineThe serum concentration of Clomifene can be increased when it is combined with Caffeine.Approved
CanagliflozinThe serum concentration of Clomifene can be increased when it is combined with Canagliflozin.Approved
CandesartanThe serum concentration of Clomifene can be increased when it is combined with Candesartan.Approved
CaptoprilThe serum concentration of Clomifene can be increased when it is combined with Captopril.Approved
CarbamazepineThe serum concentration of Clomifene can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarvedilolThe serum concentration of Clomifene can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Clomifene can be increased when it is combined with Caspofungin.Approved
ChloroquineThe serum concentration of Clomifene can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Clomifene can be increased when it is combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe serum concentration of Clomifene can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Clomifene can be increased when it is combined with Chlorprothixene.Approved, Withdrawn
CholesterolThe serum concentration of Clomifene can be increased when it is combined with Cholesterol.Experimental
Cholic AcidThe serum concentration of Clomifene can be decreased when it is combined with Cholic Acid.Approved
CilazaprilThe serum concentration of Clomifene can be increased when it is combined with Cilazapril.Approved
CimetidineThe serum concentration of Clomifene can be decreased when it is combined with Cimetidine.Approved
CiprofloxacinThe serum concentration of Clomifene can be increased when it is combined with Ciprofloxacin.Approved, Investigational
CitalopramThe serum concentration of Clomifene can be increased when it is combined with Citalopram.Approved
ClarithromycinThe serum concentration of Clomifene can be increased when it is combined with Clarithromycin.Approved
ClofazimineThe serum concentration of Clomifene can be increased when it is combined with Clofazimine.Approved, Investigational
ClomipramineThe serum concentration of Clomifene can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe serum concentration of Clomifene can be decreased when it is combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Clomifene can be increased when it is combined with Cobicistat.Approved
ColchicineThe serum concentration of Clomifene can be increased when it is combined with Colchicine.Approved
ColforsinThe serum concentration of Clomifene can be increased when it is combined with Colforsin.Experimental
CrizotinibThe serum concentration of Clomifene can be increased when it is combined with Crizotinib.Approved
CyclophosphamideThe serum concentration of Clomifene can be increased when it is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe serum concentration of Clomifene can be decreased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
DaclatasvirThe serum concentration of Clomifene can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Clomifene can be increased when it is combined with Dactinomycin.Approved
DasatinibThe serum concentration of Clomifene can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Clomifene can be decreased when it is combined with Daunorubicin.Approved
DesipramineThe serum concentration of Clomifene can be increased when it is combined with Desipramine.Approved
DesloratadineThe serum concentration of Clomifene can be increased when it is combined with Desloratadine.Approved, Investigational
DexamethasoneThe serum concentration of Clomifene can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe serum concentration of Clomifene can be increased when it is combined with Dextromethorphan.Approved
DiclofenacThe serum concentration of Clomifene can be increased when it is combined with Diclofenac.Approved, Vet Approved
DigoxinThe serum concentration of Clomifene can be decreased when it is combined with Digoxin.Approved
DihydroergotamineThe serum concentration of Clomifene can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Clomifene can be increased when it is combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Clomifene can be increased when it is combined with Dipyridamole.Approved
DoxazosinThe serum concentration of Clomifene can be increased when it is combined with Doxazosin.Approved
DoxepinThe serum concentration of Clomifene can be increased when it is combined with Doxepin.Approved
DoxorubicinThe serum concentration of Clomifene can be decreased when it is combined with Doxorubicin.Approved, Investigational
DronabinolThe serum concentration of Clomifene can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneThe serum concentration of Clomifene can be increased when it is combined with Dronedarone.Approved
ElbasvirThe serum concentration of Clomifene can be increased when it is combined with Elbasvir.Approved
EnalaprilThe serum concentration of Clomifene can be increased when it is combined with Enalapril.Approved, Vet Approved
EnzalutamideThe serum concentration of Clomifene can be increased when it is combined with Enzalutamide.Approved
ErgonovineThe serum concentration of Clomifene can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Clomifene can be increased when it is combined with Ergotamine.Approved
ErythromycinThe serum concentration of Clomifene can be decreased when it is combined with Erythromycin.Approved, Vet Approved
EstramustineThe serum concentration of Clomifene can be increased when it is combined with Estramustine.Approved
EstriolThe serum concentration of Clomifene can be decreased when it is combined with Estriol.Approved, Vet Approved
EstroneThe serum concentration of Clomifene can be decreased when it is combined with Estrone.Approved
EtoposideThe serum concentration of Clomifene can be increased when it is combined with Etoposide.Approved
EtravirineThe serum concentration of Clomifene can be increased when it is combined with Etravirine.Approved
FelodipineThe serum concentration of Clomifene can be increased when it is combined with Felodipine.Approved, Investigational
FentanylThe serum concentration of Clomifene can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe serum concentration of Clomifene can be increased when it is combined with Fexofenadine.Approved
FidaxomicinThe serum concentration of Clomifene can be increased when it is combined with Fidaxomicin.Approved
FluconazoleThe serum concentration of Clomifene can be increased when it is combined with Fluconazole.Approved
FluoxetineThe serum concentration of Clomifene can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe serum concentration of Clomifene can be increased when it is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Clomifene can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Clomifene can be increased when it is combined with Flurazepam.Approved, Illicit
FluvoxamineThe serum concentration of Clomifene can be increased when it is combined with Fluvoxamine.Approved, Investigational
GefitinibThe serum concentration of Clomifene can be increased when it is combined with Gefitinib.Approved, Investigational
GenisteinThe serum concentration of Clomifene can be increased when it is combined with Genistein.Investigational
GlyburideThe serum concentration of Clomifene can be increased when it is combined with Glyburide.Approved
GlycerolThe serum concentration of Clomifene can be increased when it is combined with Glycerol.Experimental
Gramicidin DThe serum concentration of Clomifene can be increased when it is combined with Gramicidin D.Approved
GrepafloxacinThe serum concentration of Clomifene can be increased when it is combined with Grepafloxacin.Withdrawn
HaloperidolThe serum concentration of Clomifene can be increased when it is combined with Haloperidol.Approved
HydrocortisoneThe serum concentration of Clomifene can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
IdelalisibThe serum concentration of Clomifene can be increased when it is combined with Idelalisib.Approved
ImatinibThe serum concentration of Clomifene can be increased when it is combined with Imatinib.Approved
ImipramineThe serum concentration of Clomifene can be increased when it is combined with Imipramine.Approved
IndinavirThe serum concentration of Clomifene can be decreased when it is combined with Indinavir.Approved
IndomethacinThe serum concentration of Clomifene can be increased when it is combined with Indomethacin.Approved, Investigational
IsavuconazoniumThe serum concentration of Clomifene can be increased when it is combined with Isavuconazonium.Approved, Investigational
ItraconazoleThe serum concentration of Clomifene can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Clomifene can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Clomifene can be increased when it is combined with Ivermectin.Approved, Vet Approved
KetamineThe serum concentration of Clomifene can be increased when it is combined with Ketamine.Approved, Vet Approved
KetoconazoleThe serum concentration of Clomifene can be increased when it is combined with Ketoconazole.Approved, Investigational
LansoprazoleThe serum concentration of Clomifene can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Clomifene can be increased when it is combined with Lapatinib.Approved, Investigational
LevofloxacinThe serum concentration of Clomifene can be increased when it is combined with Levofloxacin.Approved, Investigational
LevothyroxineThe serum concentration of Clomifene can be decreased when it is combined with Levothyroxine.Approved
LidocaineThe serum concentration of Clomifene can be increased when it is combined with Lidocaine.Approved, Vet Approved
LiothyronineThe serum concentration of Clomifene can be decreased when it is combined with Liothyronine.Approved, Vet Approved
LiotrixThe serum concentration of Clomifene can be decreased when it is combined with Liotrix.Approved
LisinoprilThe serum concentration of Clomifene can be increased when it is combined with Lisinopril.Approved, Investigational
LomitapideThe serum concentration of Clomifene can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Clomifene can be increased when it is combined with Loperamide.Approved
LopinavirThe serum concentration of Clomifene can be increased when it is combined with Lopinavir.Approved
LoratadineThe serum concentration of Clomifene can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Clomifene can be increased when it is combined with Losartan.Approved
LovastatinThe serum concentration of Clomifene can be increased when it is combined with Lovastatin.Approved, Investigational
LumacaftorThe serum concentration of Clomifene can be decreased when it is combined with Lumacaftor.Approved
MaprotilineThe serum concentration of Clomifene can be increased when it is combined with Maprotiline.Approved
MebendazoleThe serum concentration of Clomifene can be increased when it is combined with Mebendazole.Approved, Vet Approved
MefloquineThe serum concentration of Clomifene can be increased when it is combined with Mefloquine.Approved
Megestrol acetateThe serum concentration of Clomifene can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MeprobamateThe serum concentration of Clomifene can be increased when it is combined with Meprobamate.Approved, Illicit
MethadoneThe serum concentration of Clomifene can be increased when it is combined with Methadone.Approved
MetoprololThe serum concentration of Clomifene can be increased when it is combined with Metoprolol.Approved, Investigational
MibefradilThe serum concentration of Clomifene can be increased when it is combined with Mibefradil.Withdrawn
MiconazoleThe serum concentration of Clomifene can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Clomifene can be decreased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Clomifene can be decreased when it is combined with Mifepristone.Approved, Investigational
MitomycinThe serum concentration of Clomifene can be increased when it is combined with Mitomycin.Approved
MitoxantroneThe serum concentration of Clomifene can be decreased when it is combined with Mitoxantrone.Approved, Investigational
MorphineThe serum concentration of Clomifene can be increased when it is combined with Morphine.Approved, Investigational
NaltrexoneThe serum concentration of Clomifene can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaringeninThe serum concentration of Clomifene can be increased when it is combined with Naringenin.Experimental
NefazodoneThe serum concentration of Clomifene can be decreased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Clomifene can be decreased when it is combined with Nelfinavir.Approved
NeostigmineThe serum concentration of Clomifene can be increased when it is combined with Neostigmine.Approved, Vet Approved
NicardipineThe serum concentration of Clomifene can be increased when it is combined with Nicardipine.Approved
NifedipineThe serum concentration of Clomifene can be decreased when it is combined with Nifedipine.Approved
NilotinibThe serum concentration of Clomifene can be increased when it is combined with Nilotinib.Approved, Investigational
NisoldipineThe serum concentration of Clomifene can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Clomifene can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Clomifene can be increased when it is combined with Nitrendipine.Approved
NorethisteroneThe serum concentration of Clomifene can be decreased when it is combined with Norethisterone.Approved
OmeprazoleThe serum concentration of Clomifene can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OspemifeneThe risk or severity of adverse effects can be increased when Clomifene is combined with Ospemifene.Approved
P-NitrophenolThe serum concentration of Clomifene can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe serum concentration of Clomifene can be increased when it is combined with Paclitaxel.Approved, Vet Approved
Palmitic AcidThe serum concentration of Clomifene can be increased when it is combined with Palmitic Acid.Experimental
PantoprazoleThe serum concentration of Clomifene can be increased when it is combined with Pantoprazole.Approved
ParoxetineThe serum concentration of Clomifene can be increased when it is combined with Paroxetine.Approved, Investigational
PerindoprilThe serum concentration of Clomifene can be increased when it is combined with Perindopril.Approved
PhenobarbitalThe serum concentration of Clomifene can be decreased when it is combined with Phenobarbital.Approved
PimozideThe serum concentration of Clomifene can be increased when it is combined with Pimozide.Approved
Platelet Activating FactorThe serum concentration of Clomifene can be decreased when it is combined with Platelet Activating Factor.Experimental
PonatinibThe serum concentration of Clomifene can be increased when it is combined with Ponatinib.Approved
PosaconazoleThe serum concentration of Clomifene can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Clomifene can be increased when it is combined with Pravastatin.Approved
PrazosinThe serum concentration of Clomifene can be increased when it is combined with Prazosin.Approved
PrednisoneThe serum concentration of Clomifene can be increased when it is combined with Prednisone.Approved, Vet Approved
ProbenecidThe serum concentration of Clomifene can be increased when it is combined with Probenecid.Approved
ProgesteroneThe serum concentration of Clomifene can be decreased when it is combined with Progesterone.Approved, Vet Approved
PromethazineThe serum concentration of Clomifene can be increased when it is combined with Promethazine.Approved
PropafenoneThe serum concentration of Clomifene can be increased when it is combined with Propafenone.Approved
PropranololThe serum concentration of Clomifene can be increased when it is combined with Propranolol.Approved, Investigational
ProtriptylineThe serum concentration of Clomifene can be increased when it is combined with Protriptyline.Approved
QuercetinThe serum concentration of Clomifene can be increased when it is combined with Quercetin.Experimental
QuinacrineThe serum concentration of Clomifene can be increased when it is combined with Quinacrine.Approved
QuinidineThe serum concentration of Clomifene can be increased when it is combined with Quinidine.Approved
QuinineThe serum concentration of Clomifene can be increased when it is combined with Quinine.Approved
RanitidineThe serum concentration of Clomifene can be increased when it is combined with Ranitidine.Approved
RanolazineThe serum concentration of Clomifene can be increased when it is combined with Ranolazine.Approved, Investigational
ReboxetineThe serum concentration of Clomifene can be increased when it is combined with Reboxetine.Approved, Investigational
RegorafenibThe serum concentration of Clomifene can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Clomifene can be decreased when it is combined with Reserpine.Approved
RifampicinThe serum concentration of Clomifene can be decreased when it is combined with Rifampicin.Approved
RilpivirineThe serum concentration of Clomifene can be increased when it is combined with Rilpivirine.Approved
RitonavirThe serum concentration of Clomifene can be decreased when it is combined with Ritonavir.Approved, Investigational
RolapitantThe serum concentration of Clomifene can be increased when it is combined with Rolapitant.Approved
SaquinavirThe serum concentration of Clomifene can be decreased when it is combined with Saquinavir.Approved, Investigational
ScopolamineThe serum concentration of Clomifene can be increased when it is combined with Scopolamine.Approved
SelegilineThe serum concentration of Clomifene can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineThe serum concentration of Clomifene can be increased when it is combined with Sertraline.Approved
SimeprevirThe serum concentration of Clomifene can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Clomifene can be increased when it is combined with Simvastatin.Approved
SirolimusThe serum concentration of Clomifene can be decreased when it is combined with Sirolimus.Approved, Investigational
SorafenibThe serum concentration of Clomifene can be increased when it is combined with Sorafenib.Approved, Investigational
SpironolactoneThe serum concentration of Clomifene can be increased when it is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Clomifene can be decreased when it is combined with St. John's Wort.Nutraceutical
StaurosporineThe serum concentration of Clomifene can be increased when it is combined with Staurosporine.Experimental
StreptozocinThe serum concentration of Clomifene can be decreased when it is combined with Streptozocin.Approved
SulfinpyrazoneThe serum concentration of Clomifene can be increased when it is combined with Sulfinpyrazone.Approved
SumatriptanThe serum concentration of Clomifene can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibThe serum concentration of Clomifene can be increased when it is combined with Sunitinib.Approved, Investigational
TacrineThe serum concentration of Clomifene can be increased when it is combined with Tacrine.Withdrawn
TacrolimusThe serum concentration of Clomifene can be decreased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenThe serum concentration of Clomifene can be decreased when it is combined with Tamoxifen.Approved
Taurocholic AcidThe serum concentration of Clomifene can be increased when it is combined with Taurocholic Acid.Experimental
TelmisartanThe serum concentration of Clomifene can be increased when it is combined with Telmisartan.Approved, Investigational
TemsirolimusThe serum concentration of Clomifene can be increased when it is combined with Temsirolimus.Approved
TerazosinThe serum concentration of Clomifene can be increased when it is combined with Terazosin.Approved
TerfenadineThe serum concentration of Clomifene can be increased when it is combined with Terfenadine.Withdrawn
TesmilifeneThe serum concentration of Clomifene can be decreased when it is combined with Tesmilifene.Investigational
TestosteroneThe serum concentration of Clomifene can be increased when it is combined with Testosterone.Approved, Investigational
TicagrelorThe serum concentration of Clomifene can be increased when it is combined with Ticagrelor.Approved
TolvaptanThe serum concentration of Clomifene can be increased when it is combined with Tolvaptan.Approved
TrazodoneThe serum concentration of Clomifene can be decreased when it is combined with Trazodone.Approved, Investigational
TrifluoperazineThe serum concentration of Clomifene can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Clomifene can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimThe serum concentration of Clomifene can be decreased when it is combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe serum concentration of Clomifene can be increased when it is combined with Trimipramine.Approved
TroleandomycinThe serum concentration of Clomifene can be increased when it is combined with Troleandomycin.Approved
VenlafaxineThe serum concentration of Clomifene can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Clomifene can be decreased when it is combined with Verapamil.Approved
VinblastineThe serum concentration of Clomifene can be decreased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Clomifene can be decreased when it is combined with Vincristine.Approved, Investigational
VinorelbineThe serum concentration of Clomifene can be increased when it is combined with Vinorelbine.Approved, Investigational
ZimelidineThe serum concentration of Clomifene can be increased when it is combined with Zimelidine.Withdrawn
Food Interactions
  • Take without regard to meals.
References
Synthesis Reference

Allen, R.E., Palopoli, F.P., Schumann, E.L. and Van Carnpen, M.G. Jr.; US. Patent 2,914,563; November 24, 1959; assigned to The Wrn. S. Merrell Company.

General References
  1. Purvin VA: Visual disturbance secondary to clomiphene citrate. Arch Ophthalmol. 1995 Apr;113(4):482-4. [PubMed:7710399 ]
  2. Hayon T, Atlas L, Levy E, Dvilansky A, Shpilberg O, Nathan I: Multifactorial activities of nonsteroidal antiestrogens against leukemia. Cancer Detect Prev. 2003;27(5):389-96. [PubMed:14585326 ]
  3. Fritz MA, Holmes RT, Keenan EJ: Effect of clomiphene citrate treatment on endometrial estrogen and progesterone receptor induction in women. Am J Obstet Gynecol. 1991 Jul;165(1):177-85. [PubMed:1906682 ]
  4. Hughes E, Brown J, Collins JJ, Vanderkerchove P: Clomiphene citrate for unexplained subfertility in women. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD000057. doi: 10.1002/14651858.CD000057.pub2. [PubMed:20091498 ]
  5. Brown J, Farquhar C, Beck J, Boothroyd C, Hughes E: Clomiphene and anti-oestrogens for ovulation induction in PCOS. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD002249. doi: 10.1002/14651858.CD002249.pub4. [PubMed:19821295 ]
  6. Authors unspecified: Use of clomiphene citrate in women. Fertil Steril. 2006 Nov;86(5 Suppl 1):S187-93. [PubMed:17055820 ]
  7. Homburg R: Oral agents for ovulation induction--clomiphene citrate versus aromatase inhibitors. Hum Fertil (Camb). 2008 Mar;11(1):17-22. doi: 10.1080/14647270701689670. [PubMed:18320435 ]
  8. Homburg R: Clomiphene citrate--end of an era? A mini-review. Hum Reprod. 2005 Aug;20(8):2043-51. Epub 2005 May 5. [PubMed:15878925 ]
External Links
ATC CodesG03GB02
AHFS Codes
  • 68:16.12
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8723
Caco-2 permeable+0.7235
P-glycoprotein substrateSubstrate0.7536
P-glycoprotein inhibitor IInhibitor0.7799
P-glycoprotein inhibitor IINon-inhibitor0.6476
Renal organic cation transporterInhibitor0.7021
CYP450 2C9 substrateNon-substrate0.7972
CYP450 2D6 substrateNon-substrate0.6847
CYP450 3A4 substrateSubstrate0.7021
CYP450 1A2 substrateInhibitor0.9332
CYP450 2C9 inhibitorNon-inhibitor0.6036
CYP450 2D6 inhibitorInhibitor0.8315
CYP450 2C19 inhibitorInhibitor0.7004
CYP450 3A4 inhibitorNon-inhibitor0.8089
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9254
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.621
BiodegradationNot ready biodegradable0.9895
Rat acute toxicity1.8805 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8038
hERG inhibition (predictor II)Inhibitor0.8672
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Par pharmaceutical inc
  • Milex products inc
  • Emd serono inc
Packagers
Dosage forms
FormRouteStrength
TabletOral50 mg/1
TabletOral50 mg
Prices
Unit descriptionCostUnit
ClomiPHENE Citrate 30 50 mg tablet Box215.9USD box
Clomiphene citrate powder47.74USD g
Clomid 50 mg tablet17.1USD tablet
Serophene 50 mg tablet11.08USD tablet
Clomiphene citrate 50 mg tab6.86USD tablet
Clomid 50 mg Tablet6.09USD tablet
Serophene 50 mg Tablet5.52USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point116.5-118Allen, R.E., Palopoli, F.P., Schumann, E.L. and Van Carnpen, M.G. Jr.; US. Patent 2,914,563; November 24, 1959; assigned to The Wrn. S. Merrell Company.
water solubilitySlightly solubleNot Available
logP7.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000414 mg/mLALOGPS
logP6.08ALOGPS
logP6.47ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity133.76 m3·mol-1ChemAxon
Polarizability46.7 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Diphenylmethane
  • Phenylpropene
  • Phenol ether
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonistagonist
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Sasson S: Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor. Pathol Biol (Paris). 1991 Jan;39(1):59-69. [PubMed:2011412 ]
  2. Kurosawa T, Hiroi H, Momoeda M, Inoue S, Taketani Y: Clomiphene citrate elicits estrogen agonistic/antagonistic effects differentially via estrogen receptors alpha and beta. Endocr J. 2010;57(6):517-21. Epub 2010 Apr 6. [PubMed:20379036 ]
  3. Hughes E, Brown J, Collins JJ, Vanderkerchove P: Clomiphene citrate for unexplained subfertility in women. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD000057. doi: 10.1002/14651858.CD000057.pub2. [PubMed:20091498 ]
  4. Brown J, Farquhar C, Beck J, Boothroyd C, Hughes E: Clomiphene and anti-oestrogens for ovulation induction in PCOS. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD002249. doi: 10.1002/14651858.CD002249.pub4. [PubMed:19821295 ]
  5. Authors unspecified: Use of clomiphene citrate in women. Fertil Steril. 2006 Nov;86(5 Suppl 1):S187-93. [PubMed:17055820 ]
  6. Overbeek A, Lambalk N: Pharmacogenomics of ovulation induction: facilitating decisions on who, when and how to treat. Pharmacogenomics. 2009 Sep;10(9):1377-9. doi: 10.2217/pgs.09.110. [PubMed:19761360 ]
  7. Homburg R: Oral agents for ovulation induction--clomiphene citrate versus aromatase inhibitors. Hum Fertil (Camb). 2008 Mar;11(1):17-22. doi: 10.1080/14647270701689670. [PubMed:18320435 ]
  8. Homburg R: Clomiphene citrate--end of an era? A mini-review. Hum Reprod. 2005 Aug;20(8):2043-51. Epub 2005 May 5. [PubMed:15878925 ]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular Weight:
60101.87 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular Weight:
56501.005 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Rao US, Fine RL, Scarborough GA: Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. [PubMed:7914405 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:11