Details of the Drug

General Information of Drug (ID: DMVBIZL)

Drug Name
Estrone sulfate
Synonyms Estrone 3-sulfate; Estrone hydrogen sulfate; Estrone sulphate; [3H]-estrone hydrogen sulfate; [3H]-estrone-3-sulphate; [3H]estrone-3-sulfate; [3H]estrone-3-sulphate
Indication
Disease Entry ICD 11 Status REF
Atrophic vaginitis GA30.2 Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 350.429
Logarithm of the Partition Coefficient (xlogp) 2.5
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Metabolism
The drug is metabolized via the liver []
Chemical Identifiers
Formula
C18H22O5S
IUPAC Name
[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Canonical SMILES
CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)OS(=O)(=O)O
InChI
InChI=1S/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1
InChIKey
JKKFKPJIXZFSSB-CBZIJGRNSA-N
Cross-matching ID
PubChem CID
3001028
ChEBI ID
CHEBI:17474
CAS Number
481-97-0
VARIDT ID
DR00019

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic solute transporter subunit alpha (SLC51A) DTMEQ32 OSTA_HUMAN Substrate [2]
Organic anion transporter 6 (SLC22A20) DTT3IKQ S22AK_HUMAN Substrate [3]
ATP-binding cassette sub-family A member 8 (ABCA8) DT9NXMV ABCA8_HUMAN Substrate [4]
Organic anion transporting polypeptide 3A1 (SLCO3A1) DTVNRXW SO3A1_HUMAN Substrate [5]
Organic solute transporter subunit beta (SLC51B) DT1V9AJ OSTB_HUMAN Substrate [2]
Organic anion transporting polypeptide 4A1 (SLCO4A1) DT8H2IC SO4A1_HUMAN Substrate [6]
Organic anion transporting polypeptide 4C1 (SLCO4C1) DTY0QMU SO4C1_HUMAN Substrate [7]
Sodium/taurocholate cotransporting polypeptide (SLC10A1) DT56EKP NTCP_HUMAN Substrate [8]
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [9]
Organic anion transporter 4 (SLC22A11) DT06JWZ S22AB_HUMAN Substrate [10]
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTPFTEQ SO2B1_HUMAN Substrate [11]
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTE2B1D SO1A2_HUMAN Substrate [12]
Multidrug resistance-associated protein 1 (ABCC1) DTSYQGK MRP1_HUMAN Substrate [13]
Multidrug and toxin extrusion protein 2 (SLC47A2) DT3TX4H S47A2_HUMAN Substrate [14]
Multidrug and toxin extrusion protein 1 (SLC47A1) DTZGT0P S47A1_HUMAN Substrate [14]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [15]
Organic anion transporting polypeptide 1B1 (SLCO1B1) DT3D8F0 SO1B1_HUMAN Substrate [16]
Organic anion transporting polypeptide 1B3 (SLCO1B3) DT9C1TS SO1B3_HUMAN Substrate [17]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [18]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [19]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta. J Biol Chem. 2003 Jul 25;278(30):27473-82.
3 Transport of estrone sulfate by the novel organic anion transporter Oat6 (Slc22a20). Am J Physiol Renal Physiol. 2006 Aug;291(2):F314-21.
4 Functional analysis of ABCA8, a new drug transporter. Biochem Biophys Res Commun. 2002 Oct 18;298(1):41-5.
5 Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60.
6 Involvement of estrone-3-sulfate transporters in proliferation of hormone-dependent breast cancer cells. J Pharmacol Exp Ther. 2004 Dec;311(3):1032-7.
7 Transport of estrone 3-sulfate mediated by organic anion transporter OATP4C1: estrone 3-sulfate binds to the different recognition site for digoxin in OATP4C1. Drug Metab Pharmacokinet. 2010;25(3):314-7.
8 Ethnicity-dependent polymorphism in Na+-taurocholate cotransporting polypeptide (SLC10A1) reveals a domain critical for bile acid substrate recognition. J Biol Chem. 2004 Feb 20;279(8):7213-22.
9 Human hepatobiliary transport of organic anions analyzed by quadruple-transfected cells. Mol Pharmacol. 2005 Oct;68(4):1031-8.
10 Inhibitory effects of angiotensin II receptor antagonists and leukotriene receptor antagonists on the transport of human organic anion transporter 4. J Pharm Pharmacol. 2006 Nov;58(11):1499-505.
11 Substrate-dependent drug-drug interactions between gemfibrozil, fluvastatin and other organic anion-transporting peptide (OATP) substrates on OATP1B1, OATP2B1, and OATP1B3. Drug Metab Dispos. 2007 Aug;35(8):1308-14.
12 Determination of OATP-, NTCP- and OCT-mediated substrate uptake activities in individual and pooled batches of cryopreserved human hepatocytes. Eur J Pharm Sci. 2011 Jul 17;43(4):297-307.
13 Molecular cloning and pharmacological characterization of rat multidrug resistance protein 1 (mrp1). Drug Metab Dispos. 2003 Aug;31(8):1016-26.
14 Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71.
15 ABCG2 transports sulfated conjugates of steroids and xenobiotics. J Biol Chem. 2003 Jun 20;278(25):22644-9.
16 Role of transmembrane domain 10 for the function of organic anion transporting polypeptide 1B1. Protein Sci. 2009 Nov;18(11):2298-306.
17 Effect of pregnane X receptor ligands on transport mediated by human OATP1B1 and OATP1B3. Eur J Pharmacol. 2008 Apr 14;584(1):57-65.
18 Involvement of tyrosine kinase and PI3K in the regulation of OAT3-mediated estrone sulfate transport in isolated rabbit renal proximal tubules. Am J Physiol Renal Physiol. 2005 Nov;289(5):F1057-64.
19 Identification of the hepatic efflux transporters of organic anions using double-transfected Madin-Darby canine kidney II cells expressing human organic anion-transporting polypeptide 1B1 (OATP1B1)/multidrug resistance-associated protein 2, OATP1B1/multidrug resistance 1, and OATP1B1/breast cancer resistance protein. J Pharmacol Exp Ther. 2005 Sep;314(3):1059-67.