QuickView for Clomifene (compound)

Summary
General Info

PubChem

PubChem Compound 1548953

Name:	Clomiphene
PubChem Compound ID:	1548953
Description:	A triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue.
Molecular formula:	C₂₆H₂₈ClNO
Molecular weight:	405.959 g/mol
Synonyms:	Enclomifeno [INN-Spanish]; Ethanamine, 2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethyl-, (E)-; trans-2-(4-(2-Chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine; ICI 46476; trans-Clomiphene; Clomifene; Enclomifenum [INN-Latin]; Triethylamine, 2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)-, (E)-; Enclomiphene [USAN]; Transclomifenum. show more » Enclomifeno [INN-Spanish]; Ethanamine, 2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethyl-, (E)-; trans-2-(4-(2-Chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine; ICI 46476; trans-Clomiphene; Clomifene; Enclomifenum [INN-Latin]; Triethylamine, 2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)-, (E)-; Enclomiphene [USAN]; Transclomifenum; trans-Clomifene; Enclomiphene; (E)-2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine; RMI 16,289; Transclomiphene; trans-2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine; 15690-57-0 show less «

DrugBank

Identification

Name:	Clomiphene
Name (isomeric):	DB00882
Drug Type:	small molecule
Description:	A triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue.
Synonyms:	Clomiphene citrate (Z,E); Chloramifene; Clomifeno; Chlomaphene; Chloramiphene; Clomifene citrate; Cisclomiphene; clomiphene; Clomiphene dihydrogen citrate; Racemic clomiphene citrate. show more » Clomiphene citrate (Z,E); Chloramifene; Clomifeno; Chlomaphene; Chloramiphene; Clomifene citrate; Cisclomiphene; clomiphene; Clomiphene dihydrogen citrate; Racemic clomiphene citrate; Clomiphene Citrate; Zuclomiphene citrate show less «
Brand:	Clomivid, Clomiphene B, Ikaclomin, Serophene, Dyneric, Milophene, Clomiphene, Clostilbegyt, Omifin, Androxal, Clomphid, Genozym, Clomifert, Clomid
Category:	Estrogen Antagonists, Fertility Agents, Female, Selective Estrogen Receptor Modulators
CAS number:	911-45-5

Pharmacology

Indication:	Used mainly in female infertility due to anovulation (e.g. due to polycystic ovary syndrome) to induce ovulation.
Pharmacology:	Clomifene (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 i... show more » Clomifene (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. show less «
Mechanism of Action:	Clomifene 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 develo... show more » Clomifene 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. show less «
Absorption:	Based on early studies with 14 C-labeled clomifene, the drug was shown to be readily absorbed orally in humans.
Biotransformation:	Hepatic
Route of elimination:	Based 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 Life:	5-7 days
Toxicity:	The 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

Interactions

Food interaction:

Take without regard to meals.

Drug interaction:

Secobarbital	The enzyme inducer, secobarbital, decreases the effect of the hormone agent, clomifene.
Methylphenobarbital	The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, clomifene.
Butabarbital	The enzyme inducer, butabarbital, decreases the effect of the hormone agent, clomifene.
Mephenytoin	The enzyme inducer, mephenytoin, decreases the effect of the hormone agent, clomifene.
Methohexital	The enzyme inducer, methohexital, decreases the effect of the hormone agent, clomifene.

Secobarbital	The enzyme inducer, secobarbital, decreases the effect of the hormone agent, clomifene.
Methylphenobarbital	The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, clomifene.
Butabarbital	The enzyme inducer, butabarbital, decreases the effect of the hormone agent, clomifene.
Mephenytoin	The enzyme inducer, mephenytoin, decreases the effect of the hormone agent, clomifene.
Methohexital	The enzyme inducer, methohexital, decreases the effect of the hormone agent, clomifene.
Heptabarbital	The enzyme inducer, heptabarbital, decreases the effect of the hormone agent, clomifene.
Primidone	The enzyme inducer, primidone, decreases the effect of the hormone agent, clomifene.
Fosphenytoin	The enzyme inducer, fosphenytoin, decreases the effect of the hormone agent, clomifene.
Prednisone	The estrogenic agent, clomifene, may increase the effect of corticosteroid, prednisone.
Phenytoin	The enzyme inducer, phenytoin, decreases the effect of the hormone agent, clomifene.
Butethal	The enzyme inducer, butethal, decreases the effect of the hormone agent, clomifene.
Raloxifene	Association not recommended
Aprobarbital	The enzyme inducer, aprobarbital, decreases the effect of the hormone agent, clomifene.
Ursodeoxycholic acid	Estrogens decreases the effect of ursodiol
Prednisolone	The estrogenic agent, clomifene, may increase the effect of the corticosteroid, prednisolone.
Pentobarbital	The enzyme inducer, pentobarbital, decreases the effect of the hormone agent, clomifene.
Griseofulvin	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, clomifene.
Talbutal	The enzyme inducer, talbutal, decreases the effect of the hormone agent, clomifene.
Butalbital	The enzyme inducer, butalbital, decreases the effect of the hormone agent, clomifene.
Phenobarbital	The enzyme inducer, phenobarbital, decreases the effect of the hormone agent, clomifene.
Amobarbital	The enzyme inducer, amobarbital, decreases the effect of the hormone agent, clomifene.
Ethotoin	The enzyme inducer, ethotoin, decreases the effect of the hormone agent, clomifene.
Hexobarbital	The enzyme inducer, hexobarbital, decreases the effect of the hormone agent, clomifene.

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Targets

Estrogen receptor

Enzymes

Cholesterol side-chain cleavage enzyme, mitochondrial

Transporters

Multidrug resistance protein 1