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Details

Stereochemistry ACHIRAL
Molecular Formula C26H28ClNO
Molecular Weight 405.96
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ZUCLOMIPHENE

SMILES

CCN(CC)CCOC1=CC=C(C=C1)C(=C(/Cl)C2=CC=CC=C2)\C3=CC=CC=C3

InChI

InChIKey=GKIRPKYJQBWNGO-QPLCGJKRSA-N
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-

HIDE SMILES / InChI

Molecular Formula C26H28ClNO
Molecular Weight 405.96
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68002996

Clomiphene (CLOMID®) is a triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue. It is an orally administered, nonsteroidal, ovulatory stimulant. Clomiphene (CLOMID®) is a mixture of two geometric isomers [cis (zuclomiphene) and trans (enclomiphene)] containing between 30% and 50% of the cis-isomer. Clomiphene (CLOMID®) 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 clomiphene 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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CLOMID

Approved Use

Clomiphene citrate is indicated for the treatment of ovulatory dysfunction in women desiring pregnancy. Impediments to achieving pregnancy must be excluded or adequately treated before beginning clomiphene citrate therapy. Those patients most likely to achieve success with clomiphene therapy include patients with polycystic ovary syndrome (see WARNINGS: Ovarian Hyperstimulation Syndrome), amenorrhea-galactorrhea syndrome, psychogenic amenorrhea, post-oral-contraceptive amenorrhea, and certain cases of secondary amenorrhea of undetermined etiology. Properly timed coitus in relationship to ovulation is important. A basal body temperature graph or other appropriate tests may help the patient and her physician determine if ovulation occurred. Once ovulation has been established, each course of clomiphene citrate should be started on or about the 5th day of the cycle. Long-term cyclic therapy is not recommended beyond a total of about six cycles (including three ovulatory cycles). (See DOSAGE AND ADMINISTRATION and PRECAUTIONS.) Clomiphene citrate is indicated only in patients with demonstrated ovulatory dysfunction who meet the conditions described below (see CONTRAINDICATIONS): Patients who are not pregnant. Patients without ovarian cysts. Clomiphene citrate should not be used in patients with ovarian enlargement except those with polycystic ovary syndrome. Pelvic examination is necessary prior to the first and each subsequent course of clomiphene citrate treatment. Patients without abnormal vaginal bleeding. If abnormal vaginal bleeding is present, the patient should be carefully evaluated to ensure that neoplastic lesions are not present. Patients with normal liver function. In addition, patients selected for clomiphene citrate therapy should be evaluated in regard to the following: Estrogen Levels. Patients should have adequate levels of endogenous estrogen (as estimated from vaginal smears, endometrial biopsy, assay of urinary estrogen, or from bleeding in response to progesterone). Reduced estrogen levels, while less favorable, do not preclude successful therapy. Primary Pituitary or Ovarian Failure. Clomiphene citrate therapy cannot be expected to substitute for specific treatment of other causes of ovulatory failure. Endometriosis and Endometrial Carcinoma. The incidence of endometriosis and endometrial carcinoma increases with age as does the incidence of ovulatory disorders. Endometrial biopsy should always be performed prior to clomiphene citrate therapy in this population. Other Impediments to Pregnancy. Impediments to pregnancy can include thyroid disorders, adrenal disorders, hyperprolactinemia, and male factor infertility. Uterine Fibroids. Caution should be exercised when using clomiphene citrate in patients with uterine fibroids due to the potential for further enlargement of the fibroids. There are no adequate or well-controlled studies that demonstrate the effectiveness of clomiphene citrate in the treatment of male infertility. In addition, testicular tumors and gynecomastia have been reported in males using clomiphene. The cause and effect relationship between reports of testicular tumors and the administration of clomiphene citrate is not known. Although the medical literature suggests various methods, there is no universally accepted standard regimen for combined therapy (i.e., clomiphene citrate in conjunction with other ovulation-inducing drugs). Similarly, there is no standard clomiphene citrate regimen for ovulation induction in vitro fertilization programs to produce ova for fertilization and reintroduction. Therefore, clomiphene citrate is not recommended for these uses.

Launch Date

-9.2016001E10
PubMed

PubMed

TitleDatePubMed
Visual disturbance secondary to clomiphene citrate.
1995 Apr
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Selective inhibition of hepatitis C virus infection by hydroxyzine and benztropine.
2014 Jun
Patents

Sample Use Guides

Treatment of the selected patient should begin with a low dose, 50 mg daily (1 tablet) for 5 days. The dose should be increased only in those patients who do not ovulate in response to cyclic 50 mg CLOMID®. If ovulation does not appear to occur after the first course of therapy, a second course of 100 mg daily (two 50 mg tablets given as a single daily dose) for 5 days should be given.
Route of Administration: Oral
Clomiphene at lower doses (10^-10 M and 10^-12 M), but not higher doses (10^-6 M and 10^-8 M) elicited estrogenic activity via estrogen receptor alpha (ER alpha). However, clomiphene at concentrations between 10^-6 M and 10^-12 M did not elicit any estrogenic activity via estrogen receptor beta (ER beta). In the presence of 17beta-estradiol (E2), clomiphene behaved either as an agonist or as an antagonist via ER alpha depending on the concentrations of E2, i.e., antagonistic when combined with the higher E2 concentrations, agonistic with the lower E2 concentrations. On the other hand, via ER beta, clomiphene acted as an estrogen antagonist regardless of the concentration of E2 added together. In conclusion, clomiphene acts as an estrogen agonist/antagonist via ER alpha in a coexisting estrogen concentration-dependent way whereas it acts as an estrogen antagonist via ER beta whether or not estrogen is present.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:13:01 UTC 2023
Edited
by admin
on Fri Dec 15 16:13:01 UTC 2023
Record UNII
3JU1DU3652
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZUCLOMIPHENE
USAN  
USAN  
Official Name English
CLOMIPHENE CIS-FORM [MI]
Common Name English
zuclomifene [INN]
Common Name English
TRANSCLOMIPHENE
Common Name English
ETHANAMINE, 2-(4-(2-CHLORO-1,2-DIPHENYLETHENYL)PHENOXY)-N,N-DIETHYL-, (Z)-
Common Name English
RMI-16,312
Code English
RMI 16,312
Code English
ZUCLOMIFENE
INN  
INN  
Official Name English
ZUCLOMIPHENE [USAN]
Common Name English
RMI-16312
Code English
ETHANAMINE, 2-(4-((1Z)-2-CHLORO-1,2-DIPHENYLETHENYL)PHENOXY)-N,N-DIETHYL-
Systematic Name English
ISOMER A
Common Name English
CLOMIPHENE CIS-FORM
MI  
Common Name English
(Z)-2-(P-(2-CHLORO-1,2-DIPHENYLVINYL)PHENOXY)TRIETHYLAMINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1821
Created by admin on Fri Dec 15 16:13:01 UTC 2023 , Edited by admin on Fri Dec 15 16:13:01 UTC 2023
Code System Code Type Description
SMS_ID
100000078821
Created by admin on Fri Dec 15 16:13:01 UTC 2023 , Edited by admin on Fri Dec 15 16:13:01 UTC 2023
PRIMARY
WIKIPEDIA
Zuclomifene
Created by admin on Fri Dec 15 16:13:01 UTC 2023 , Edited by admin on Fri Dec 15 16:13:01 UTC 2023
PRIMARY
NCI_THESAURUS
C66870
Created by admin on Fri Dec 15 16:13:01 UTC 2023 , Edited by admin on Fri Dec 15 16:13:01 UTC 2023
PRIMARY
EVMPD
SUB00194MIG
Created by admin on Fri Dec 15 16:13:01 UTC 2023 , Edited by admin on Fri Dec 15 16:13:01 UTC 2023
PRIMARY
FDA UNII
3JU1DU3652
Created by admin on Fri Dec 15 16:13:01 UTC 2023 , Edited by admin on Fri Dec 15 16:13:01 UTC 2023
PRIMARY
CAS
15690-55-8
Created by admin on Fri Dec 15 16:13:01 UTC 2023 , Edited by admin on Fri Dec 15 16:13:01 UTC 2023
PRIMARY
INN
2335
Created by admin on Fri Dec 15 16:13:01 UTC 2023 , Edited by admin on Fri Dec 15 16:13:01 UTC 2023
PRIMARY
MERCK INDEX
m3647
Created by admin on Fri Dec 15 16:13:01 UTC 2023 , Edited by admin on Fri Dec 15 16:13:01 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL167779
Created by admin on Fri Dec 15 16:13:01 UTC 2023 , Edited by admin on Fri Dec 15 16:13:01 UTC 2023
PRIMARY
PUBCHEM
1548955
Created by admin on Fri Dec 15 16:13:01 UTC 2023 , Edited by admin on Fri Dec 15 16:13:01 UTC 2023
PRIMARY
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