Estriol
Explore a selection of our essential drug information below, or:
Identification
- Summary
Estriol is a weak estrogen used to treat vaginal dryness and estrogen deficiency conditions, such as vaginitis and vulvar itching.
- Generic Name
- Estriol
- DrugBank Accession Number
- DB04573
- Background
A hydroxylated metabolite of estradiol or estrone that has a hydroxyl group at C3-beta, 16-alpha, and 17-beta position. Estriol is a major urinary estrogen. During pregnancy, large amount of estriol is produced by the placenta. Isomers with inversion of the hydroxyl group or groups are called epiestriol. Though estriol is used as part of the primarily North American phenomenon of bioidentical hormone replacement therapy, it is not approved for use by the FDA or Health Canada. It is however available in the United States by prescription filled only by compounding pharmacies. It has also been approved and marketed throughout Europe and Asia for approximately 40 years for the treatment of post-menopausal hot flashes.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
- Weight
- Average: 288.3814
Monoisotopic: 288.172544634 - Chemical Formula
- C18H24O3
- Synonyms
- (16α,17β)-estra-1,3,5(10)-triene-3,16,17-triol
- 1,3,5(10)-Estratriene-3,16-alpha,17beta-triol
- 16-alpha-Hydroxyestradiol
- 16alpha-hydroxyestradiol
- 16α-hydroxyestradiol
- 16α,17β-estriol
- 3,16alpha,17beta-Trihydroxy-delta(1,3,5)-estratriene
- Estriol
- Oestriol
- Östriol
- Trihydroxyestrin
Pharmacology
- Indication
Used as a test to determine the general health of an unborn fetus.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Cervicitis •••••••••••• •••••• •••••• Treatment of Menopausal and postmenopausal disorders •••••••••••• •••••••••••••• •••••• •••• ••••••• ••••••••••• Treatment of Menopausal and postmenopausal disorders •••••••••••• •••••••••••••• •••••• •••• ••••••• ••••••••••• Treatment of Menopausal and postmenopausal disorders •••••••••••• •••••••••••••• •••••• •••• ••••••• ••••••••••• Management of Hypoestrogenism •••••••••••• •••••• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Estriol (also oestriol) is one of the three main estrogens produced by the human body. It is only produced in significant amounts during pregnancy as it is made by the placenta. In pregnant women with multiple sclerosis (MS), estriol reduces the disease's symptoms noticeably, according to researchers at UCLA's Geffen Medical School.
- Mechanism of action
Estriol levels can be measured to give an indication of the general health of the fetus. DHEA-S is produced by the adrenal cortex of the fetus. This is converted to estriol by the placenta. If levels of "unconjugated estriol" are abnormally low in a pregnant woman, this may indicate a problem with the development of the child. The drug interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estriol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary.
Target Actions Organism AEstrogen receptor agonistHumans UEstrogen receptor beta agonistHumans USex hormone-binding globulin Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
ORAL (LD50): Acute: >2000 mg/kg [Rat].
- Pathways
Pathway Category Estrone Metabolism Metabolic - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab Estriol may decrease the anticoagulant activities of Abciximab. Aceclofenac Aceclofenac may increase the thrombogenic activities of Estriol. Acenocoumarol Estriol may decrease the anticoagulant activities of Acenocoumarol. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Estriol. Adalimumab Estriol may increase the thrombogenic activities of Adalimumab. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Aacifemine (Organon) / Colpoestriol (Temis-Lostalo) / Estriel / Ovestin (Merck Sharp & Dohme) / Synapause E (Organon)
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Advanced Formula Estro-Life Cream 1.69 mg/1mL Topical Smoky Mountain Naturals, LLC - DBA SMNutrition 2022-04-01 Not applicable US Estriol 5.0 Cream Cream 5 mg/85g Transdermal SHYNE BRANDS 2021-06-15 Not applicable US Estro-Life Cream 1.69 mg/1mL Topical Smoky Mountain Naturals, LLC - DBA SMNutrition 2022-04-01 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BiEST 2.5 Estrogen Cream Estriol (2 mg/85g) + Estradiol (0.5 mg/85g) Cream Transdermal SHYNE BRANDS 2021-06-15 Not applicable US BiEST 2.5 Estrogen Cream (Lavender scented) Estriol (2 mg/85g) + Estradiol (0.5 mg/85g) Cream Transdermal SHYNE BRANDS 2021-06-15 Not applicable US BiEST 5.0 Estrogen Cream Estriol (4 mg/85g) + Estradiol (1 mg/85g) Cream Transdermal SHYNE BRANDS 2021-06-15 Not applicable US Gynoflor - Vaginaltabletten Estriol (0.03 mg) + Lactobacillus acidophilus (50 mg) Tablet Vaginal Gedeon Richter Plc 1990-02-09 Not applicable Austria GYNOFLOR 50 MG/0.03 MG VAJİNAL TABLET, 12 ADET Estriol (0.03 mg) + Lactobacillus acidophilus (50 mg) Suppository Vaginal ABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş. 1996-12-11 Not applicable Turkey - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Advanced Formula Estro-Life Estriol (1.69 mg/1mL) Cream Topical Smoky Mountain Naturals, LLC - DBA SMNutrition 2022-04-01 Not applicable US BiEST 2.5 Estrogen Cream Estriol (2 mg/85g) + Estradiol (0.5 mg/85g) Cream Transdermal SHYNE BRANDS 2021-06-15 Not applicable US BiEST 2.5 Estrogen Cream (Lavender scented) Estriol (2 mg/85g) + Estradiol (0.5 mg/85g) Cream Transdermal SHYNE BRANDS 2021-06-15 Not applicable US BiEST 5.0 Estrogen Cream Estriol (4 mg/85g) + Estradiol (1 mg/85g) Cream Transdermal SHYNE BRANDS 2021-06-15 Not applicable US Estriol 5.0 Cream Estriol (5 mg/85g) Cream Transdermal SHYNE BRANDS 2021-06-15 Not applicable US
Categories
- ATC Codes
- G03CC06 — Estriol
- G03CC — Estrogens, combinations with other drugs
- G03C — ESTROGENS
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Estradiol Congeners
- Estranes
- Estrenes
- Estrogens
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Gonadal Hormones
- Gonadal Steroid Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Natural and Semisynthetic Estrogens, Plain
- P-glycoprotein inducers
- P-glycoprotein substrates
- Sex Hormones and Modulators of the Genital System
- Steroids
- Thyroxine-binding globulin inducers
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Estrane steroids
- Direct Parent
- Estrogens and derivatives
- Alternative Parents
- 3-hydroxysteroids / 17-hydroxysteroids / 16-alpha-hydroxysteroids / Phenanthrenes and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / Cyclic alcohols and derivatives / 1,2-diols / Hydrocarbon derivatives
- Substituents
- 1,2-diol / 1-hydroxy-2-unsubstituted benzenoid / 16-alpha-hydroxysteroid / 16-hydroxysteroid / 17-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aromatic homopolycyclic compound / Benzenoid / Cyclic alcohol
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- 17beta-hydroxy steroid, 3-hydroxy steroid, 16alpha-hydroxy steroid (CHEBI:27974) / C18 steroids (estrogens) and derivatives, Estrane and derivatives, Estrogens (C05141) / C18 steroids (estrogens) and derivatives (LMST02010003)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- FB33469R8E
- CAS number
- 50-27-1
- InChI Key
- PROQIPRRNZUXQM-ZXXIGWHRSA-N
- 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
- IUPAC Name
- (1R,2R,3aS,3bR,9bS,11aS)-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,2,7-triol
- SMILES
- [H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
References
- Synthesis Reference
James V. Freeman, Gary M. Johnson, "Synthesis of 6.alpha.-functionalized estriol haptens and protein conjugates thereof." U.S. Patent US5902888, issued June, 1973.
US5902888- General References
- External Links
- Human Metabolome Database
- HMDB0000153
- KEGG Drug
- D00185
- KEGG Compound
- C05141
- PubChem Compound
- 5756
- PubChem Substance
- 46505881
- ChemSpider
- 5553
- BindingDB
- 50410506
- 4094
- ChEBI
- 27974
- ChEMBL
- CHEMBL193482
- ZINC
- ZINC000003815418
- Therapeutic Targets Database
- DAP001019
- PharmGKB
- PA164769104
- PDBe Ligand
- ESL
- Wikipedia
- Estriol
- PDB Entries
- 1x8v / 3q95
- MSDS
- Download (75.9 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Dyspareunia Among Puerperal Women / Vulvo Vaginal Atrophy 1 somestatus stop reason just information to hide Not Available Completed Not Available Provoked, Localized Vulvodynia 1 somestatus stop reason just information to hide Not Available Completed Supportive Care Postmenopausal / Urogenital Disease, Female / Vulvo Vaginal Atrophy 1 somestatus stop reason just information to hide Not Available Enrolling by Invitation Treatment Genitourinary Symptoms / Postmenopausal Atrophic Vaginitis / Postmenopausal Syndrome 1 somestatus stop reason just information to hide Not Available Recruiting Supportive Care Postmenopausal / Vaginal Prolapse / Vulvo Vaginal Atrophy 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Jiangxi Yuneng Pharmchem Co. Ltd.
- NutriScience Innovations LLC
- Dosage Forms
Form Route Strength Insert Vaginal Cream Transdermal Gel Vaginal 50 mcg/g Gel Vaginal 50 MICROGRAMMI/G Cream Vaginal 0.0125 % Insert Vaginal 1 MG Tablet Vaginal Cream Vaginal 0.050 g Cream Vaginal 0.100 g Insert Vaginal 3.500 mg Cream Transdermal 5 mg/85g Cream Vaginal 50 g Cream Vaginal 0.5 MG/G Cream Topical 1.69 mg/1mL Suppository Vaginal Cream Vaginal 0.1 g Capsule Vaginal Gel Vaginal Suppository Vaginal Cream Vaginal 1 mg/g Suppository Vaginal 0.5 MG Suppository Vaginal 0.03 MG Tablet Oral 2 MG Cream Vaginal 1.0 MG/G Insert Vaginal 3.5 mg Cream; gel Vaginal 1 MG/G Cream Vaginal Tablet Oral Tablet Oral 1 MG Cream Vaginal 100 mg Insert Vaginal 0.5 mg Cream Vaginal 1.000 mg Insert Vaginal 0.500 mg Cream Vaginal 1 MG/1G - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 82-86 Organon Laboratories Limited, England; British Patent 879,014; October 4, 1961. logP 2.45 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.119 mg/mL ALOGPS logP 2.54 ALOGPS logP 2.67 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 10.33 Chemaxon pKa (Strongest Basic) -3.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 60.69 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 81.27 m3·mol-1 Chemaxon Polarizability 33.08 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9966 Blood Brain Barrier + 0.7057 Caco-2 permeable + 0.7591 P-glycoprotein substrate Substrate 0.7862 P-glycoprotein inhibitor I Non-inhibitor 0.9208 P-glycoprotein inhibitor II Non-inhibitor 0.9805 Renal organic cation transporter Non-inhibitor 0.8619 CYP450 2C9 substrate Non-substrate 0.7536 CYP450 2D6 substrate Non-substrate 0.7993 CYP450 3A4 substrate Substrate 0.6892 CYP450 1A2 substrate Non-inhibitor 0.6618 CYP450 2C9 inhibitor Non-inhibitor 0.9399 CYP450 2D6 inhibitor Non-inhibitor 0.9619 CYP450 2C19 inhibitor Non-inhibitor 0.7086 CYP450 3A4 inhibitor Non-inhibitor 0.8932 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9152 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.9147 Biodegradation Not ready biodegradable 0.9811 Rat acute toxicity 1.9758 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.948 hERG inhibition (predictor II) Inhibitor 0.7684
Spectra
- Mass Spec (NIST)
- Download (2.96 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 178.8088921 predictedDarkChem Lite v0.1.0 [M-H]- 179.4440921 predictedDarkChem Lite v0.1.0 [M-H]- 178.5921921 predictedDarkChem Lite v0.1.0 [M-H]- 179.1051921 predictedDarkChem Lite v0.1.0 [M-H]- 179.4016 predictedDeepCCS 1.0 (2019) [M-H]- 178.8088921 predictedDarkChem Lite v0.1.0 [M-H]- 179.4440921 predictedDarkChem Lite v0.1.0 [M-H]- 178.5921921 predictedDarkChem Lite v0.1.0 [M-H]- 179.1051921 predictedDarkChem Lite v0.1.0 [M-H]- 179.4016 predictedDeepCCS 1.0 (2019) [M+H]+ 180.3004921 predictedDarkChem Lite v0.1.0 [M+H]+ 180.8460921 predictedDarkChem Lite v0.1.0 [M+H]+ 181.3761921 predictedDarkChem Lite v0.1.0 [M+H]+ 181.5291921 predictedDarkChem Lite v0.1.0 [M+H]+ 181.54332 predictedDeepCCS 1.0 (2019) [M+H]+ 180.3004921 predictedDarkChem Lite v0.1.0 [M+H]+ 180.8460921 predictedDarkChem Lite v0.1.0 [M+H]+ 181.3761921 predictedDarkChem Lite v0.1.0 [M+H]+ 181.5291921 predictedDarkChem Lite v0.1.0 [M+H]+ 181.54332 predictedDeepCCS 1.0 (2019) [M+Na]+ 179.3961921 predictedDarkChem Lite v0.1.0 [M+Na]+ 179.8062921 predictedDarkChem Lite v0.1.0 [M+Na]+ 179.1691921 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.45587 predictedDeepCCS 1.0 (2019) [M+Na]+ 179.3961921 predictedDarkChem Lite v0.1.0 [M+Na]+ 179.8062921 predictedDarkChem Lite v0.1.0 [M+Na]+ 179.1691921 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.45587 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity)
- Specific Function
- 14-3-3 protein binding
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- Sasson S: Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor. Pathol Biol (Paris). 1991 Jan;39(1):59-69. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1/ER-alpha, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560)
- Specific Function
- DNA binding
- Gene Name
- ESR2
- Uniprot ID
- Q92731
- Uniprot Name
- Estrogen receptor beta
- Molecular Weight
- 59215.765 Da
References
- Mishra RG, Stanczyk FZ, Burry KA, Oparil S, Katzenellenbogen BS, Nealen ML, Katzenellenbogen JA, Hermsmeyer RK: Metabolite ligands of estrogen receptor-beta reduce primate coronary hyperreactivity. Am J Physiol Heart Circ Physiol. 2006 Jan;290(1):H295-303. Epub 2005 Sep 30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration
- Specific Function
- androgen binding
- Gene Name
- SHBG
- Uniprot ID
- P04278
- Uniprot Name
- Sex hormone-binding globulin
- Molecular Weight
- 43778.755 Da
References
- Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Na(+)-independent transporter that mediates the cellular uptake of a broad range of organic anions such as the endogenous bile salts cholate and deoxycholate, either in their unconjugated or conjugated forms (taurocholate and glycocholate), at the plasmam membrane (PubMed:19129463, PubMed:7557095). Responsible for intestinal absorption of bile acids (By similarity). Transports dehydroepiandrosterone 3-sulfate (DHEAS), a major circulating steroid secreted by the adrenal cortex, as well as estrone 3-sulfate and 17beta-estradiol 17-O-(beta-D-glucuronate) (PubMed:11159893, PubMed:12568656, PubMed:19129463, PubMed:23918469, PubMed:25560245, PubMed:9539145). Mediates apical uptake of all-trans-retinol (atROL) across human retinal pigment epithelium, which is essential to maintaining the integrity of the visual cycle and thus vision (PubMed:25560245). Involved in the uptake of clinically used drugs (PubMed:17301733, PubMed:20686826, PubMed:27777271). Capable of thyroid hormone transport (both T3 or 3,3',5'-triiodo-L-thyronine, and T4 or L-tyroxine) (PubMed:19129463, PubMed:20358049). Also transports prostaglandin E2 (PubMed:19129463). Plays roles in blood-brain and -cerebrospinal fluid barrier transport of organic anions and signal mediators, and in hormone uptake by neural cells (By similarity). May also play a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL: Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol. 1996 Feb;270(2 Pt 2):F326-31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- Kim WY, Benet LZ: 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. [Article]
Drug created at September 07, 2007 21:04 / Updated at June 12, 2021 10:53