ZB716 (original) (raw)
ZB716, also known as fulvestrant-3-boronic acid, is a synthetic, steroidal, orally active antiestrogen which is under development for the treatment of estrogen receptor (ER)-positive metastatic breast cancer. The drug is a silent antagonist of the ERα (IC50 = 4.1 nM) as well as a selective estrogen receptor degrader (SERD). It is an analogue of fulvestrant in which the C3 hydroxyl group has been replaced with a boronic acid moiety. In accordance, the two drugs have similar pharmacodynamic properties. However, whereas fulvestrant is not orally active and must be administered via intramuscular injection, ZB716 is less susceptible to first-pass metabolism, and in relation to this, is orally active.
| Property | Value |
|---|---|
| dbo:abstract | ZB716, also known as fulvestrant-3-boronic acid, is a synthetic, steroidal, orally active antiestrogen which is under development for the treatment of estrogen receptor (ER)-positive metastatic breast cancer. The drug is a silent antagonist of the ERα (IC50 = 4.1 nM) as well as a selective estrogen receptor degrader (SERD). It is an analogue of fulvestrant in which the C3 hydroxyl group has been replaced with a boronic acid moiety. In accordance, the two drugs have similar pharmacodynamic properties. However, whereas fulvestrant is not orally active and must be administered via intramuscular injection, ZB716 is less susceptible to first-pass metabolism, and in relation to this, is orally active. A single oral dose of 8.3 mg/kg ZB716 to mice has been found to result in an over 160 ng/mL (160,000 pg/mL) maximal concentration of the drug in circulation, a level far in excess of the 15.2 ng/mL (15,200 pg/mL) concentration achieved with subcutaneous injection of fulvestrant in mice. As such, not only may ZB716 be more convenient to administer in humans, it has far greater bioavailability compared to fulvestrant and hence may allow for greater systemic exposure and therapeutic benefit. ZB716 produces fulvestrant as an active metabolite in vivo in mice, with approximately 10 to 15% of the drug being converted into it. As such, most of the effects are likely due to the parent drug. (en) |
| dbo:casNumber | 1853279-29-4 |
| dbo:class | dbr:Antiestrogen dbr:Selective_estrogen_receptor_degrader |
| dbo:fdaUniiCode | E35ZN95LMT |
| dbo:pubchem | 126480615 |
| dbo:thumbnail | wiki-commons:Special:FilePath/ZB716.svg?width=300 |
| dbo:wikiPageID | 53788580 (xsd:integer) |
| dbo:wikiPageLength | 5234 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1075450277 (xsd:integer) |
| dbo:wikiPageWikiLink | dbc:Selective_estrogen_receptor_degraders dbr:Moiety_(chemistry) dbr:Boronic_acid dbr:Antiestrogen dbr:In_vivo dbr:Intramuscular_injection dbr:Structural_analog dbr:List_of_investigational_sex-hormonal_agents dbc:Alcohols dbc:Antiestrogens dbc:Estranes dbc:Organofluorides dbc:Trifluoromethyl_compounds dbr:Oral_administration dbr:Fulvestrant dbc:Experimental_cancer_drugs dbr:Steroid dbr:Subcutaneous_injection dbc:Hormonal_antineoplastic_drugs dbr:Active_metabolite dbc:Boronic_acids dbr:Estrogen_receptor dbc:Organosulfur_compounds dbr:Bioavailability dbr:Cmax_(pharmacology) dbr:Pharmacodynamic dbr:Metastatic_breast_cancer dbr:IC50 dbr:Selective_estrogen_receptor_degrader dbr:First-pass_metabolism dbr:Synthetic_compound dbr:Hydroxyl_group dbr:Silent_antagonist dbr:ERα |
| dbp:b | 1 (xsd:integer) |
| dbp:c | 32 (xsd:integer) |
| dbp:casNumber | 1853279 (xsd:integer) |
| dbp:class | dbr:Antiestrogen dbr:Selective_estrogen_receptor_degrader |
| dbp:f | 5 (xsd:integer) |
| dbp:h | 48 (xsd:integer) |
| dbp:iupacName | [-17-hydroxy-13-methyl-7-[9-nonyl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]boronic acid (en) |
| dbp:meltingNotes | (en) |
| dbp:meltingPoint | 230 (xsd:integer) |
| dbp:o | 4 (xsd:integer) |
| dbp:pubchem | 126480615 (xsd:integer) |
| dbp:routesOfAdministration | dbr:Oral_administration |
| dbp:s | 1 (xsd:integer) |
| dbp:smiles | BO (en) |
| dbp:stdinchi | 1 (xsd:integer) |
| dbp:stdinchikey | FIAYIYKWRBIBQG-GDWZZRAASA-N (en) |
| dbp:synonyms | Fulvestrant-3-boronic acid; Fulvestrant-3-boronoate; 7α-[9-[-sulfinyl]nonyl]-3-estra-1,3,5-trien-17β-ol (en) |
| dbp:unii | E35ZN95LMT (en) |
| dbp:width | 250 (xsd:integer) |
| dbp:wikiPageUsesTemplate | dbt:Antineoplastic-drug-stub dbt:Drugbox dbt:Estrogen_receptor_modulators dbt:Reflist dbt:Short_description dbt:Steroid-stub dbt:Cascite dbt:Fdacite |
| dct:subject | dbc:Selective_estrogen_receptor_degraders dbc:Alcohols dbc:Antiestrogens dbc:Estranes dbc:Organofluorides dbc:Trifluoromethyl_compounds dbc:Experimental_cancer_drugs dbc:Hormonal_antineoplastic_drugs dbc:Boronic_acids dbc:Organosulfur_compounds |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 dbo:Drug |
| rdfs:comment | ZB716, also known as fulvestrant-3-boronic acid, is a synthetic, steroidal, orally active antiestrogen which is under development for the treatment of estrogen receptor (ER)-positive metastatic breast cancer. The drug is a silent antagonist of the ERα (IC50 = 4.1 nM) as well as a selective estrogen receptor degrader (SERD). It is an analogue of fulvestrant in which the C3 hydroxyl group has been replaced with a boronic acid moiety. In accordance, the two drugs have similar pharmacodynamic properties. However, whereas fulvestrant is not orally active and must be administered via intramuscular injection, ZB716 is less susceptible to first-pass metabolism, and in relation to this, is orally active. (en) |
| rdfs:label | ZB716 (en) |
| owl:sameAs | yago-res:ZB716 wikidata:ZB716 https://global.dbpedia.org/id/2oRAY |
| prov:wasDerivedFrom | wikipedia-en:ZB716?oldid=1075450277&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/ZB716.svg |
| foaf:isPrimaryTopicOf | wikipedia-en:ZB716 |
| is dbo:wikiPageRedirects of | dbr:Fulvestrant-3-boronic_acid dbr:Fulvestrant-3-boronoate dbr:Fulvestrant-3_boronic_acid dbr:Fulvestrant-3_boronoate dbr:Fulvestrant_3-boronic_acid dbr:Fulvestrant_3-boronoate dbr:Fulvestrant_3_boronic_acid dbr:Fulvestrant_3_boronoate dbr:ZB-716 dbr:ZB_716 |
| is dbo:wikiPageWikiLink of | dbr:Fulvestrant dbr:Sex-hormonal_agent dbr:Fulvestrant-3-boronic_acid dbr:Fulvestrant-3-boronoate dbr:Fulvestrant-3_boronic_acid dbr:Fulvestrant-3_boronoate dbr:Fulvestrant_3-boronic_acid dbr:Fulvestrant_3-boronoate dbr:Fulvestrant_3_boronic_acid dbr:Fulvestrant_3_boronoate dbr:ZB-716 dbr:ZB_716 |
| is foaf:primaryTopic of | wikipedia-en:ZB716 |
