Details of the Drug

General Information of Drug (ID: DMTB63Q)

Drug Name

Estetrol

Synonyms

Estetrol (oral, contraception/hormone deficiency/osteoporosis/cardiovascular disease/autoimmune disease/breast cancer/prostate cancer); Estetrol (oral, contraception/hormone deficiency/osteoporosis/cardiovascular disease/autoimmune disease/breast cancer/prostate cancer), Pantarhei; Estrogen receptor modulator (oral, contraception/hormone deficiency/autoimmune disease/breast cancer/prostate cancer/osteoporosis/cardiovascular disease), Pantarhei

Indication

Disease Entry	ICD 11	Status	REF
Autoimmune diabetes	5A10	Phase 2	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

304.4

Topological Polar Surface Area (xlogp)

1.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 3-8 h [2]
Bioavailability: The bioavailability of drug is 88% [2]
Elimination: Approximately 69% of a dose of estetrol is excreted in the urine, and about 22% is excreted in the feces as unchanged drug [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 27 hours [4]
Metabolism: The drug is metabolized via the hepatic [5]

Chemical Identifiers

Formula: C18H24O4
IUPAC Name: (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
Canonical SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1[C@H]([C@H]([C@@H]2O)O)O)CCC4=C3C=CC(=C4)O
InChI: 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
InChIKey: AJIPIJNNOJSSQC-NYLIRDPKSA-N

Cross-matching ID

PubChem CID: 27125
ChEBI ID: CHEBI:142773
CAS Number: 15183-37-6
DrugBank ID: DB12235
TTD ID: D0L3TR

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Estrogen receptor (ESR)	TTZAYWL	ESR1_HUMAN	Modulator	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	ClinicalTrials.gov (NCT00563472) Feasibility Study Into the Contraceptive Effect of Estetrol. U.S. National Institutes of Health.
2	Clinical pharmacokinetics and pharmacodynamics of solifenacin. Clin Pharmacokinet. 2009;48(5):281-302. doi: 10.2165/00003088-200948050-00001.
3	Thomas MP, Potter BV: The structural biology of oestrogen metabolism. J Steroid Biochem Mol Biol. 2013 Sep;137:27-49. doi: 10.1016/j.jsbmb.2012.12.014. Epub 2013 Jan 4.
4	FDA Approved Drug Products: NEXTSTELLIS (drospirenone and estetrol) tablets for oral use
5	Product monograph: Nexstellis (estetrol and drospirenone) oral tablets
6	Clinical pipeline report, company report or official report of Pantarhei Bioscience.
7	Modulators of vascular sex hormone receptors and their effects in estrogen-deficiency states associated with menopause. Recent Pat Cardiovasc Drug Discov. 2008 Nov;3(3):165-86.
8	Reprint of Are all estrogens the same Maturitas. 2008 Sep-Oct;61(1-2):195-201.
9	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
10	17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8.
11	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 620).
12	Clinical pipeline report, company report or official report of Shionogi (2011).
13	Effect of selective estrogen receptor modulators on cell proliferation and estrogen receptor activities in normal human prostate stromal and epithe... Prostate Cancer Prostatic Dis. 2009;12(4):375-81.