4OH

(14beta,15alpha,16alpha,17alpha)-estra-1,3,5(10)-triene-3,15,16,17-tetrol

Created: 2010-01-05
Last modified:  2021-03-13

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Chemical Details

Formal Charge0
Atom Count46
Chiral Atom Count7
Bond Count49
Aromatic Bond Count6
2D diagram of 4OH
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Chemical Component Summary

Name(14beta,15alpha,16alpha,17alpha)-estra-1,3,5(10)-triene-3,15,16,17-tetrol
SynonymsEstra-1,3,5(10)-triene-3,15 alpha,16alpha,17beta-tetrol
Systematic Name (OpenEye OEToolkits)(8R,9S,13S,14S,15R,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,16,17-tetrol
FormulaC18 H24 O4
Molecular Weight304.381
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.352C[C]12CC[CH]3[CH](CCc4cc(O)ccc34)[CH]1[CH](O)[CH](O)[CH]2O
SMILESOpenEye OEToolkits1.7.0CC12CCC3c4ccc(cc4CCC3C1C(C(C2O)O)O)O
Canonical SMILESCACTVS3.352 C[C@]12CC[C@H]3[C@@H](CCc4cc(O)ccc34)[C@@H]1[C@@H](O)[C@@H](O)[C@@H]2O
Canonical SMILESOpenEye OEToolkits1.7.0 C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1[C@H]([C@H]([C@@H]2O)O)O)O
InChIInChI1.03 InChI=1S/C18H24O4/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3/t12-,13-,14-,15-,16-,17+,18+/m1/s1
InChIKeyInChI1.03 AJIPIJNNOJSSQC-NYLIRDPKSA-N

Drug Info: DrugBank

DrugBank IDDB12235 
NameEstetrol
Groups
  • approved
  • investigational
DescriptionNaturally or synthetically produced steroid estrogens have a wide range of pharmaceutical uses ranging from hormonal contraception to the treatment of menopausal symptoms.[L33184] Estetrol (E4) is a native estrogen occurring naturally during pregnancy, but can be synthesized from a plant source and used for contraception.[L33179] It is more potent and is safer than the synthetic estrogen ethinylestradiol (EE2) found in 97% of oral contraceptive pills, reducing the environmental accumulation of unwanted endocrine disrupting chemicals (EDCs) that often lead to harmful epigenetic effects.[L33184] On April 15 2021, Mayne Pharma Group Limited and Mithra Pharmaceuticals were granted FDA approval for the oral contraceptive Estelle/Nextstellis, a combination of [drospirenone] and estetrol. Estetrol is the first new estrogen introduced to the USA in over 50 years and is the first approved estetrol product in the world. The combination of drospirenone and estetrol offers a new choice with a favourable safety profile for women seeking contraceptive therapy.[L33179] In Canada, Nextstellis was approved for use in March 2021; it was developed by Mithra and is marketed by Searchlight Pharma.[L33209]
Synonyms
  • Estetrolum
  • Estétrol
  • Oestetrol
  • Estetrol monohydrate
  • Estetrol
Brand Names
  • Nextstellis
  • Drovelis
  • Lydisilka
IndicationEstetrol is indicated in combination with drospirenone for the prevention of pregnancy.[L33174]
Categories
  • Adrenal Cortex Hormones
  • Contraceptives, Oral
  • Cytochrome P-450 CYP3A Substrates
  • Cytochrome P-450 CYP3A4 Substrates
  • Cytochrome P-450 CYP3A4 Substrates (strength unknown)
ATC-CodeG03AA18
CAS number15183-37-6

Drug Targets

NameTarget SequencePharmacological ActionActions
Estrogen receptor alphaMTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...unknownagonist,modulator,regulator
Estrogen receptor betaMDIKNSPSSLNSPSSYNCSQSILPLEHGSIYIPSSYVDSHHEYPAMTFYS...unknownagonist
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
UDP-glucuronosyltransferase 2B7MSVKWTSVILLIQLSFCFSSGNCGKVLVWAAEYSHWMNIKTILDELIQRG...unknownsubstrate
Serum albuminMKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...unknownbinder
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1230314
PubChem 27125
ChEMBL CHEMBL1230314
ChEBI CHEBI:142773