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药品详细

Clomifene(氯米芬)

化学结构式图
中文名
氯米芬
英文名
Clomifene
分子式
C26H28ClNO
化学名
{2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]ethyl}diethylamine
分子量
Average: 405.96
Monoisotopic: 405.18594223
CAS号
911-45-5
ATC分类
G03G 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

A triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue. [PubChem]

生产厂家
  • Emd serono inc
  • Milex products inc
  • Par pharmaceutical inc
  • Sanofi aventis us llc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Purvin VA: Visual disturbance secondary to clomiphene citrate. Arch Ophthalmol. 1995 Apr;113(4):482-4. Pubmed
  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
  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
  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. Pubmed
  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. Pubmed
  6. Use of clomiphene citrate in women. Fertil Steril. 2006 Nov;86(5 Suppl 1):S187-93. Pubmed
  7. Homburg R: Oral agents for ovulation induction—clomiphene citrate versus aromatase inhibitors. Hum Fertil (Camb). 2008 Mar;11(1):17-22. Pubmed
  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
剂型
规格
化合物类型
Type small molecule
Classes Not Available
Substructures Not Available
适应症
药理
Indication Used mainly in female infertility due to anovulation (e.g. due to polycystic ovary syndrome) to induce ovulation.
Pharmacodynamics 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.
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 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.
Absorption Based on early studies with 14 C-labeled clomifene, the drug was shown to be readily absorbed orally in humans.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
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
Clearance Not Available
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
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
water solubility Slightly soluble Not Available
logP 7.2 Not Available
Predicted Properties
Property Value Source
water solubility 4.14e-04 g/l ALOGPS
logP 6.08 ALOGPS
logP 6.47 ChemAxon
logS -6 ALOGPS
pKa (strongest basic) 9.31 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 12.47 ChemAxon
rotatable bond count 9 ChemAxon
refractivity 133.76 ChemAxon
polarizability 46.7 ChemAxon
药物相互作用
Drug Interaction
Amobarbital The enzyme inducer, amobarbital, decreases the effect of the hormone agent, clomifene.
Aprobarbital The enzyme inducer, aprobarbital, decreases the effect of the hormone agent, clomifene.
Butabarbital The enzyme inducer, butabarbital, decreases the effect of the hormone agent, clomifene.
Butalbital The enzyme inducer, butalbital, decreases the effect of the hormone agent, clomifene.
Butethal The enzyme inducer, butethal, decreases the effect of the hormone agent, clomifene.
Ethotoin The enzyme inducer, ethotoin, decreases the effect of the hormone agent, clomifene.
Fosphenytoin The enzyme inducer, fosphenytoin, decreases the effect of the hormone agent, clomifene.
Griseofulvin The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, clomifene.
Heptabarbital The enzyme inducer, heptabarbital, decreases the effect of the hormone agent, clomifene.
Hexobarbital The enzyme inducer, hexobarbital, 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.
Methylphenobarbital The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, clomifene.
Pentobarbital The enzyme inducer, pentobarbital, decreases the effect of the hormone agent, clomifene.
Phenobarbital The enzyme inducer, phenobarbital, decreases the effect of the hormone agent, clomifene.
Phenytoin The enzyme inducer, phenytoin, decreases the effect of the hormone agent, clomifene.
Prednisolone The estrogenic agent, clomifene, may increase the effect of the corticosteroid, prednisolone.
Prednisone The estrogenic agent, clomifene, may increase the effect of corticosteroid, prednisone.
Primidone The enzyme inducer, primidone, decreases the effect of the hormone agent, clomifene.
Raloxifene Association not recommended
Secobarbital The enzyme inducer, secobarbital, decreases the effect of the hormone agent, clomifene.
Talbutal The enzyme inducer, talbutal, decreases the effect of the hormone agent, clomifene.
Ursodeoxycholic acid Estrogens decreases the effect of ursodiol
食物相互作用
  • Take without regard to meals.

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