Details of the Drug

General Information of Drug (ID: DMOEM2I)

Drug Name
Estriol
Synonyms
Aacifemine; Destriol; Estratriol; Estriel; Estriolo; Gynaesan; Hemostyptanon; Holin; Hormomed; Hormonin; Klimoral; Oestratriol; Oestriol; Oestriolum; Orestin; Orgastyptin; Overstin; Ovestin; Ovestrion; Stiptanon; Synapause; Theelol; Thulol; Tridestrin; Trihydroxyestrin; Trihydroxyoestrin; Triodurin; Triovex; Deuslon A; Estriolo [Italian]; Folicular hormone; Follicular hormone hydrate; Oestriol [Steroidal oestrogens]; A 13610; E0218; OE3; Deuslon-A; Estriel (TN); Estriol [USAN:JAN]; Estriol, unconjugated; Ortho-Gynest; Estriol (JP15/USP); Estra-1,3,5(10)-trien-3,16alpha,17beta-triol; Estra-1,3,5(10)-triene-3,16,17-triol; Estra-1,3,5(10)-triene-3,16alpha,17beta-triol; Oestra-1,3,5(10)-triene-3,16alpha,17beta-triol; Oestra-1,3,5(10)-triene-3,16-alpha,17-beta-triol; Estra-1,3,5(10)-trien-3,16.alpha., 17.beta.-triol; Estra-1,3,5(10)-trien-3,16.alpha.,17.beta.-triol; Estra-1,3,5(10)-triene-3,16.alpha., 17.beta.-triol; Estra-1,3,5(10)-triene-3,16.alpha.,17.beta.-triol; Oestra-1,3,5(10)-triene-3,16.alpha., 17.beta.-triol; Oestra-1,3,5(10)-triene-3,16.alpha.,17.beta.-triol; (16.alpha.,17.beta.)-Estra-1,3,5(10)-triene-3,16,17-triol; (16.alpha.,17.beta.)-Oestra-1,3,5(10)-triene-3,16,17-triol; (16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol; (16alpha,17beta)-Oestra-1,3,5(10)-triene-3,16,17-triol; 1,3,5(10)-ESTRATRIENE-3,16,17-TRIOL; 1,3,5(10)-Estratriene-3,16-alpha,17beta-triol; 1,3,5(10)-Estratriene-3,16.alpha., 17.beta.-triol; 1,3,5(10)-Estratriene-3,16.alpha.,17.beta.-triol; 1,3,5(10)-Estratriene-3,16alpha,17beta-Triol; 1,3,5-Estratriene-3.beta.,16-.alpha.,17-.beta.-triol; 1,3,5-Estratriene-3beta,16alpha,17beta-triol; 1,3,5-Oestratriene-3-.beta.,16.alpha.,17.beta.-triol; 1,3,5-Oestratriene-3beta,16alpha,17beta-triol; 16,17-Epiestriol; 16-Epiestriol; 16-Hydroxyestradiol; 16-alpha,17-beta-Estriol; 16-alpha,17-beta-Oestriol; 16-alpha-Hydroxyestradiol; 16-alpha-Hydroxyoestradiol; 16.alpha.,17.beta.-Estriol; 16.alpha.,17.beta.-Oestriol; 16.alpha.-Estriol; 16.alpha.-Hydroxy-17.beta.-estradiol; 16.alpha.-Hydroxyestradiol; 16.alpha.-Hydroxyoestradiol; 16alpha,17beta-Estriol; 16alpha,17beta-Oestriol; 16alpha-Hydroxy-17beta-estradiol; 16alpha-Hydroxyestradiol; 16alpha-Hydroxyoestradiol; 3,16-alpha,17-beta-Estriol; 3,16-alpha,17-beta-Oestriol; 3,16-alpha,17-beta-Trihydroxy-delta-1,3,5-estratriene; 3,16-alpha,17-beta-Trihydroxy-delta-1,3,5-oestratriene; 3,16-alpha,17-beta-Trihydroxyestra-1,3,5(10)-triene; 3,16-alpha,17-beta-Trihydroxyoestra-1,3,5(10)-triene; 3,16.alpha.,17.beta.-Estriol; 3,16.alpha.,17.beta.-Trihydroxy-.delta.-1,3,5-estratriene; 3,16.alpha.,17.beta.-Trihydroxy-.delta.-1,3,5-oestratriene; 3,16.alpha.,17.beta.-Trihydroxy-1,3,5(10)-estratriene; 3,16.alpha.,17.beta.-Trihydroxyestra-1,3,5(10)-triene; 3,16alpha,17beta-Estriol; 3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratriene; 3,16alpha,17beta-Trihydroxy-delta-1,3,5-oestratriene; 3,16alpha,17beta-trihydroxy-Delta(1,3,5)-estratriene
Indication
Disease Entry ICD 11 Status REF
Hormone deficiency 5A61.1 Approved [1]
Multiple sclerosis 8A40 Phase 2 [2]
Therapeutic Class
Estrogens
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 288.4
Logarithm of the Partition Coefficient (xlogp) 2.5
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C18H24O3
IUPAC Name
(8R,9S,13S,14S,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O
InChI
InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
InChIKey
PROQIPRRNZUXQM-ZXXIGWHRSA-N
Cross-matching ID
PubChem CID
5756
ChEBI ID
CHEBI:27974
CAS Number
50-27-1
DrugBank ID
DB04573
TTD ID
D0Z1FX
VARIDT ID
DR01435
INTEDE ID
DR0646
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Agonist [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [5]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Actin, alpha cardiac muscle 1 (ACTC1) OTJU04B1 ACTC_HUMAN Gene/Protein Processing [7]
Advanced glycosylation end product-specific receptor (AGER) OTPY0IH7 RAGE_HUMAN Gene/Protein Processing [8]
Alpha-fetoprotein (AFP) OT9GG3ZI FETA_HUMAN Gene/Protein Processing [9]
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Gene/Protein Processing [10]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [4]
Beta-1,4-galactosyltransferase 1 (B4GALT1) OTBCXEK7 B4GT1_HUMAN Gene/Protein Processing [11]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [12]
Coagulation factor X (F10) OT2BLK17 FA10_HUMAN Gene/Protein Processing [13]
Cystine/glutamate transporter (SLC7A11) OTKJ6PXW XCT_HUMAN Gene/Protein Processing [14]
Early estrogen-induced gene 1 protein (EEIG1) OT2BMEAE EEIG1_HUMAN Gene/Protein Processing [11]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Hormone deficiency
ICD Disease Classification 5A61.1
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Estrogen receptor (ESR) DTT ESR1 2.05E-08 -0.08 -0.31
P-glycoprotein 1 (ABCB1) DTP P-GP 3.39E-11 -2.93E-01 -6.11E-01
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME UGT1A1 6.50E-01 1.30E-02 5.24E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 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. (Ligand id: 2821).
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800026520)
3 Reprint of Are all estrogens the same Maturitas. 2008 Sep-Oct;61(1-2):195-201.
4 P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93.
5 Stimulation of microsomal uridine diphosphate glucuronyltransferase by glucuronic acid derivatives. Biochem J. 1974 Apr;139(1):243-9.
6 Expression and cyclic variability of CYP3A4 and CYP3A7 isoforms in human endometrium and cervix during the menstrual cycle. Drug Metab Dispos. 2003 Jan;31(1):1-6.
7 The effect of estrogen compounds on human embryoid bodies. Reprod Sci. 2013 Jun;20(6):661-9. doi: 10.1177/1933719112462630. Epub 2012 Nov 26.
8 Differential effect of estrogen receptor alpha and beta agonists on the receptor for advanced glycation end product expression in human microvascular endothelial cells. Biochim Biophys Acta. 2005 Sep 30;1745(3):300-9. doi: 10.1016/j.bbamcr.2005.03.012. Epub 2005 Apr 12.
9 Hormones of pregnancy, alpha-feto protein, and reduction of breast cancer risk. Adv Exp Med Biol. 2008;617:477-84. doi: 10.1007/978-0-387-69080-3_47.
10 Aflatoxin B1--a potential endocrine disruptor--up-regulates CYP19A1 in JEG-3 cells. Toxicol Lett. 2011 May 10;202(3):161-7.
11 Identification of estrogen-responsive genes by complementary deoxyribonucleic acid microarray and characterization of a novel early estrogen-induced gene: EEIG1. Mol Endocrinol. 2004 Feb;18(2):402-11. doi: 10.1210/me.2003-0202. Epub 2003 Nov 6.
12 Effects of sex hormones on regulation of ABCG2 expression in the placental cell line BeWo. J Pharm Pharm Sci. 2006;9(1):133-9.
13 Vascular complications of long-term oestrogen therapy. Front Horm Res. 1977;5:174-91. doi: 10.1159/000401993.
14 Using a customized DNA microarray for expression profiling of the estrogen-responsive genes to evaluate estrogen activity among natural estrogens and industrial chemicals. Environ Health Perspect. 2004 May;112(7):773-81. doi: 10.1289/ehp.6753.