clomifene

Also known as Androxal®, Clomifenum, 2-(p-(β-chloro-α-phenylstyryl)phenoxy)triethylamine, Clomiphene, 2-(p-(2-chloro-1,2-diphenylvinyl)phenoxy)triethylamine, Clomifeno, 2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine

Clomifene, also known as clomiphene, is a medication used to treat infertility in women who do not ovulate, including those with polycystic ovary syndrome. It is taken by mouth.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 460044105
Drug.image: Clomiphene.svg
Drug.image_class: skin-invert-image
Drug.width: 250
Drug.class: Selective estrogen receptor modulator; Progonadotropin
Drug.ATC_prefix: G03
Drug.ATC_suffix: GB02
Drug.legal_AU: S4
Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.bioavailability: High (>90%)
Drug.metabolism: Liver CYP2D6 (with enterohepatic circulation)
Drug.metabolites: 4-Hydroxyclomiphene (4-OH-CLO), 4-Hydroxy-N-desethylclomiphene (4-OH-DE-CLO)
Drug.elimination_half life: 4–7 days active metabolites: 4-OH-CLO : 13–34 hrs 4-OH-DE-CLO : 15–37 hrs
Drug.excretion: Mainly feces, some in urine
Drug.CAS_number: 911-45-5

via Wikipedia infobox

Chemical data

Formula: C26H28ClNO
Molecular weight: 406 g/mol
IUPAC name: 2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]-N,N-diethylethanamine
SMILES: CCN(CC)CCOC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3
InChIKey: GKIRPKYJQBWNGO-UHFFFAOYSA-N
XLogP: 7.2
Polar surface area: 12.5 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

7,645 papers

Multiple pregnancy rate in patients undergoing treatment with clomifene citrate for WHO group II ovulatory disorders: a systematic review.Human fertility (Cambridge, England) · 2022
Management strategies for ovulation induction in women with polycystic ovary syndrome and known clomifene citrate resistance.Current opinion in obstetrics & gynecology · 2009
Clomifene and Assisted Reproductive Technology in Humans Are Associated with Sex-Specific Offspring Epigenetic Alterations in Imprinted Control Regions.International journal of molecular sciences · 2022
Ovulation induction with clomifene: a primary care perspective.The journal of family planning and reproductive health care · 2012
The influence of ethnicity on outcomes of ovulation induction with clomifene citrate in women with PCOS.Reproductive biomedicine online · 2022

via PubMed

Wikidata facts

Mass: 405.186

Show 6 more facts

defined daily dose: 9
chemical formula: C₂₆H₂₈ClNO
Commons category: Clomifene
World Health Organisation international non-proprietary name: clomifene
canonical SMILES: CCN(CC)CCOC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3
stylized name: clomiPHENE

Sources (8)

via Wikidata · CC0

~18 min read

Article

19 sections

Contents

Medical uses
Reproductive medicine
Testosterone replacement therapy
Gynecomastia
Prohibited use in sports
Contraindications
Side effects
Cancer risk
Pharmacology
Pharmacodynamics
Selective estrogen receptor modulator activity
Other activities
Pharmacokinetics
Chemistry
History
Society and culture
Brand names
Research
References

Clomifene, also known as clomiphene, is a medication used to treat infertility in women who do not ovulate, including those with polycystic ovary syndrome. It is taken by mouth.

Common side effects include pelvic pain and hot flashes. Other side effects can include changes in vision, vomiting, trouble sleeping, ovarian cancer, and seizures. It is not recommended in people with liver disease or abnormal vaginal bleeding of unknown cause or who are pregnant. Clomifene is in the selective estrogen receptor modulator (SERM) family of medication and is a nonsteroidal medication. It works by causing the release of GnRH by the hypothalamus, and subsequently gonadotropin from the anterior pituitary.