| Record Information |
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| Version | 1.0 |
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| Creation Date | 2014-10-14 21:16:12 UTC |
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| Update Date | 2016-11-09 01:09:15 UTC |
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| Accession Number | CHEM003930 |
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| Identification |
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| Common Name | Clomifene |
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| Class | Small Molecule |
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| Description | A triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue. [PubChem] |
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| Contaminant Sources | - HMDB Contaminants - Urine
- IARC Carcinogens Group 3
- STOFF IDENT Compounds
- T3DB toxins
- ToxCast & Tox21 Chemicals
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| Contaminant Type | - Drug
- Estrogen Antagonist
- Fertility Agent, Female
- Metabolite
- Selective Estrogen Receptor Modulator
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| Clomiphene | Kegg | | Chloramiphene | MeSH | | Gravosan | MeSH | | Hydrochloride, clomiphene | MeSH | | Clomifene | MeSH | | Dyneric | MeSH | | Klostilbegit | MeSH | | Clomid | MeSH | | Clomiphene citrate | MeSH | | Citrate, clomiphene | MeSH | | Clostilbegit | MeSH | | Serophene | MeSH | | Clomifen | MeSH | | Clomiphene hydrochloride | MeSH | | Clomide | MeSH |
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| Chemical Formula | C26H28ClNO |
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| Average Molecular Mass | 405.970 g/mol |
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| Monoisotopic Mass | 405.186 g/mol |
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| CAS Registry Number | 911-45-5 |
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| IUPAC Name | (2-{4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy}ethyl)diethylamine |
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| Traditional Name | clomifene |
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| SMILES | CCN(CC)CCOC1=CC=C(C=C1)C(=C(\Cl)C1=CC=CC=C1)\C1=CC=CC=C1 |
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| InChI Identifier | 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+ |
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| InChI Key | GKIRPKYJQBWNGO-OCEACIFDSA-N |
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| Chemical Taxonomy |
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| Description | 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. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Stilbenes |
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| Sub Class | Not Available |
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| Direct Parent | Stilbenes |
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| Alternative Parents | |
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| Substituents | - Stilbene
- Diphenylmethane
- Phenoxy compound
- Phenol ether
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Tertiary amine
- Tertiary aliphatic amine
- Ether
- Chloroalkene
- Haloalkene
- Vinyl halide
- Vinyl chloride
- Organooxygen compound
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Amine
- Organic oxygen compound
- Organopnictogen compound
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | 116.5-118 °C | | Boiling Point | Not Available | | Solubility | Slightly soluble |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Toxicity Profile |
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| Route of Exposure | Based on early studies with 14 C-labeled clomifene, the drug was shown to be readily absorbed orally in humans. |
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| Mechanism of Toxicity | 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. |
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| Metabolism | Hepatic |
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| Toxicity Values | 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. |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (9) |
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| Uses/Sources | Used mainly in female infertility due to anovulation (e.g. due to polycystic ovary syndrome) to induce ovulation. |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB06735 |
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| HMDB ID | Not Available |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Enclomifene |
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| Chemspider ID | Not Available |
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| ChEBI ID | Not Available |
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| PubChem Compound ID | 1548953 |
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| Kegg Compound ID | C06917 |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| 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. |
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| MSDS | Not Available |
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| General References | Not Available |
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