Gadoxetic acid
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Identification
- Summary
Gadoxetic acid is a gadolinium-based contrast agent (GBCA) used with contrasted magnetic resonance imaging (MRI) to detect and visualize the liver.
- Brand Names
- Eovist, Primovist
- Generic Name
- Gadoxetic acid
- DrugBank Accession Number
- DB08884
- Background
Gadoxetic acid (gadoxetate) is a paramagnetic gadolinium-containing ionic linear contrast agent in which its salt form, gadoxetate disodium, is used for intravenous injection. Ethoxybenzyl diethylenetriaminepentaacetic acid is the moiety that chelates with a gadolinium ion and forms a stable complex with it to make up the drug.4 Gadoxetate is a unique gadolinium-based contrasting agent (GBCA) with both dynamic phase and hepatobiliary phase and thus has different pharmacokinetic and pharmacodynamic properties compared to other GBCAs.2 Since gadoxetate uptake is mediated by organic anion-transporting polypeptides (OATPs) and liver tumor cells lack OATPs, liver tumors show a lack of contrast of enhancement and therefore heightening the liver parenchyma-liver tumours contrast.2
Gadoxetic acid, under the form gadoxetate disodium, is marketed by Bayer HealthCare Pharmaceuticals under the brand name EOVIST and FDA approved in 2008.3
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 681.75
Monoisotopic: 682.11214 - Chemical Formula
- C23H30GdN3O11
- Synonyms
- Gadoxetate
- Gadoxetic acid
- Gd-EOB-DTPA
Pharmacology
- Indication
Gadoxetate is indicated for intravenous use in magnetic resonance imaging (MRI) of the liver to detect and characterize lesions in patients with known or suspected focal liver disease.5
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Focal liver disease •••••••••••• ••••••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
EOB-DTPA forms a stable complex with the paramagnetic gadolinium ion with a thermodynamic stability of log KGdL=-23.46. Gadoxetate disodium is a highly water-soluble, hydrophilic compound with a lipophilic moiety, the ethoxybenzyl group (EOB).5
Gadoxetate disodium is selectively taken up by hepatocytes resulting in increased signal intensity in liver tissue.5
Gadoxetate disodium exhibits a biphasic mode of action: first, distribution in the extracellular space after injection and subsequently, selective uptake by hepatocytes (and biliary excretion) due to the lipophilic (EOB) moiety.5
- Mechanism of action
Gadoxetate disodium is a paramagnetic compound and develops a magnetic moment when placed in a magnetic field. The relatively large magnetic moment produced by gadoxetate disodium results in a local magnetic field, yielding enhanced relaxation rates (shortening of relaxation times) of water protons in the vicinity of the paramagnetic agent, which leads to an increase in signal intensity (brightening) of blood and tissue.5
In MRI, visualization of normal and pathological tissue depends in part on variations in the radiofrequency signal intensity that occur with 1) differences in proton density; 2) differences of the spin-lattice or longitudinal relaxation times (T1); and 3) differences in the spin-spin or transverse relaxation time (T2). When placed in a magnetic field, gadoxetate disodium decreases the T1 and T2 relaxation time in target tissue. At the recommended dose, the effect is observed with the greatest sensitivity in T1-weighted MR sequences.5
- Absorption
After intravenous administration, the plasma concentration-time profile of gadoxetate disodium is characterized by a biexponential decline.5
- Volume of distribution
The total volume of distribution at steady state of gadoxetate disodium is 0.21 L/kg.5
- Protein binding
Gadoxetate disodium shows a weak (<10%), transient protein binding and the relaxivity in plasma is about 8.7 L/mmol/sec at pH 7, 39°C and 0.47 T.5 Because it is more protein-bound than other gadolinium-based contrast agents, gadoxetate disodium has increased T1 relaxivity and thus enhanced signal generation.2
- Metabolism
Gadoxetate disodium is not metabolized.5
- Route of elimination
Gadoxetate disodium is equally eliminated via the renal and hepatobiliary routes.5 Biliary excretion is attributed to the Multidrug Resistance Protein 2.1
- Half-life
The mean terminal elimination half-life of gadoxetate disodium (0.01 to 0.1 mmol/kg) has been observed in healthy volunteers of 22–39 years of age to be 0.91 to 0.95 hours.5
- Clearance
A total serum clearance (Cltot) was 250 mL/min, whereas the renal clearance (Clr) corresponds to about 120 mL/min, a value similar to the glomerular filtration rate in healthy subjects. Clearance appeared to decrease slightly with increasing age.5
- Adverse Effects
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- Toxicity
GBCAs have been shown to cross the human placenta and result in fetal exposure and gadolinium retention. The human data on the association between GBCAs and adverse fetal outcomes are limited and inconclusive. In animal reproduction studies, no teratogenicity was observed with repeated daily intravenous administration of gadoxetate disodium to rats during organogenesis at doses up to 32 times the recommended single human dose; however, an increase in preimplantation loss was noted at doses 3.2 times the single human dose. Post-implantation loss was observed with repeated daily intravenous administration of gadoxetate disodium to rabbits on gestation days 6 through 18 at doses 26 times the recommended single human dose (see Data). Because of the potential risks of gadolinium to the fetus, use gadoxetate disodium only if imaging is essential during pregnancy and cannot be delayed.5
The maximum dose studied in MR imaging was 0.4 mL/kg (0.1 mmol/kg) body weight and was tolerated in a manner similar to lower doses. In case of inadvertent overdosage in patients with severely impaired renal and/or hepatic function, gadoxetate disodium can be partially removed by hemodialysis.5
No carcinogenicity studies of gadoxetate disodium have been conducted.5
Gadoxetate disodium was not mutagenic in in vitro reverse mutation tests in bacteria, or in chromosome aberration tests in human peripheral blood lymphocytes, and was negative in an in vivo micronucleus test in mice after intravenous injection of doses up to 4 mmol/kg.5
Gadoxetate disodium had no effect on fertility and general reproductive performance of male and female rats when given in doses 6.5 times the human dose (based on body surface area).5
A dose-related increase in QTc which was resolved by 30 minutes post dosing was observed in dogs when given a single dose of gadoxetate disodium. The increase was noted when given in doses equal to or greater than 0.1 mmol/kg (2.2 times the human dose). Maximum increase in QTcF was equal to or less than 20 ms at doses up to 0.5 mmol/kg (11 times the human dose).5
A gait disturbance was observed in 1 of 3 mice when given gadoxetate disodium at a dose of approximately 1.1 mmol/kg (3.6 times the human dose); the disturbance occurred at 30 minutes post dosing and resolved at 4 hours post dosing.5
Local intolerance reactions, including moderate interstitial hemorrhage, edema, and focal muscle fiber necrosis, were observed after intramuscular administration of gadoxetate disodium.5
- Pathways
- Not Available
- 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 softwareAcetylcysteine The excretion of Gadoxetic acid can be decreased when combined with Acetylcysteine. Amprenavir The excretion of Gadoxetic acid can be decreased when combined with Amprenavir. Apalutamide The serum concentration of Gadoxetic acid can be decreased when it is combined with Apalutamide. Asunaprevir The excretion of Gadoxetic acid can be decreased when combined with Asunaprevir. Ataluren The excretion of Gadoxetic acid can be decreased when combined with Ataluren. - Food Interactions
- No interactions found.
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.
- Product Ingredients
Ingredient UNII CAS InChI Key Gadoxetate disodium HOY74VZE0M 135326-22-6 SLYTULCOCGSBBJ-UHFFFAOYSA-I - Active Moieties
Name Kind UNII CAS InChI Key Gadolinium cation (3+) ionic AZV954TZ9N 22541-19-1 RJOJUSXNYCILHH-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Eovist Injection, solution 181.43 mg/1mL Intravenous Bayer HealthCare Pharmaceuticals Inc. 2008-07-03 Not applicable US Primovist Solution 181.43 mg / mL Intravenous Bayer Ag 2010-02-04 Not applicable Canada
Categories
- ATC Codes
- V08CA10 — Gadoxetic acid
- Drug Categories
- Acetates
- Acids, Acyclic
- Amines
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Coordination Complexes
- Diagnostic Uses of Chemicals
- Gadolinium-based Contrast Agent
- Magnetic Resonance Contrast Activity
- Magnetic Resonance Imaging Contrast Media
- OATP1B1/SLCO1B1 Substrates
- OATP1B3 substrates
- Other Diagnostics
- Paramagnetic Contrast Agent
- Paramagnetic Contrast Media
- Polyamines
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 3QJA87N40S
- CAS number
- 135326-11-3
- InChI Key
- PCZHWPSNPWAQNF-LMOVPXPDSA-K
- InChI
- InChI=1S/C23H33N3O11.Gd/c1-2-37-18-5-3-16(4-6-18)9-17(26(14-22(33)34)15-23(35)36)10-24(11-19(27)28)7-8-25(12-20(29)30)13-21(31)32;/h3-6,17H,2,7-15H2,1H3,(H,27,28)(H,29,30)(H,31,32)(H,33,34)(H,35,36);/q;+3/p-3/t17-;/m0./s1
- IUPAC Name
- gadolinium(3+) ion 2-[(2-{[(2S)-2-[bis(carboxymethyl)amino]-3-(4-ethoxyphenyl)propyl](carboxylatomethyl)amino}ethyl)(carboxylatomethyl)amino]acetate
- SMILES
- [Gd+3].[H][C@@](CN(CCN(CC([O-])=O)CC([O-])=O)CC([O-])=O)(CC1=CC=C(OCC)C=C1)N(CC(O)=O)CC(O)=O
References
- General References
- Van Beers BE, Pastor CM, Hussain HK: Primovist, Eovist: what to expect? J Hepatol. 2012 Aug;57(2):421-9. doi: 10.1016/j.jhep.2012.01.031. Epub 2012 Apr 12. [Article]
- Choi Y, Huh J, Woo DC, Kim KW: Use of gadoxetate disodium for functional MRI based on its unique molecular mechanism. Br J Radiol. 2016;89(1058):20150666. doi: 10.1259/bjr.20150666. Epub 2015 Dec 23. [Article]
- Ringe KI, Boll DT, Husarik DB, Bashir MR, Gupta RT, Merkle EM: Lesion detection and assessment of extrahepatic findings in abdominal MRI using hepatocyte specific contrast agents--comparison of Gd-EOB-DTPA and Gd-BOPTA. BMC Med Imaging. 2013 Mar 18;13:10. doi: 10.1186/1471-2342-13-10. [Article]
- Ye F, Liu J, Ouyang H: Gadolinium Ethoxybenzyl Diethylenetriamine Pentaacetic Acid (Gd-EOB-DTPA)-Enhanced Magnetic Resonance Imaging and Multidetector-Row Computed Tomography for the Diagnosis of Hepatocellular Carcinoma: A Systematic Review and Meta-analysis. Medicine (Baltimore). 2015 Aug;94(32):e1157. doi: 10.1097/MD.0000000000001157. [Article]
- FDA Approved Drug Products: EOVIST (gadoxetate disodium) injection, for intravenous use [Link]
- External Links
- KEGG Drug
- D04288
- PubChem Compound
- 131704314
- PubChem Substance
- 175427133
- ChemSpider
- 189907
- 802624
- ChEMBL
- CHEMBL1201768
- PharmGKB
- PA165985534
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Gadoxetic_acid
- FDA label
- Download (223 KB)
- MSDS
- Download (114 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 Active Not Recruiting Diagnostic Hepatic Metastases / Hepatocellular Carcinoma / Liver and Intrahepatic Bile Duct Disorder / Primary Malignant Liver Neoplasm 1 somestatus stop reason just information to hide Not Available Completed Not Available Adenoma benign / Carcinoma / Hepatic abscess / Neoplasms, Hepatic 1 somestatus stop reason just information to hide Not Available Completed Not Available Dyspnea 1 somestatus stop reason just information to hide Not Available Completed Not Available Hepatic dysfunction / Hepatocellular Carcinoma 1 somestatus stop reason just information to hide Not Available Completed Not Available Imaging procedure 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous 181.43 mg/1mL Injection 0.25 MMOL/ML Injection, solution Solution Intravenous 181.43 mg / mL Injection, solution Intravenous 0.25 mmol Injection, solution Parenteral 0.25 mmol/ml Injection, solution Intravenous 181.43 mg Injection, solution Intravenous bolus 0.25 mmol/mL Solution Intravenous 0.25 mmol Solution Intravenous 181.43 mg/1ml - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6039931 No 2000-03-21 2021-11-13 US US5798092 No 1998-08-25 2015-08-25 US
Properties
- State
- Liquid
- Experimental Properties
Property Value Source pKa 6.8-8 MSDS - Predicted Properties
Property Value Source Water Solubility 0.497 mg/mL ALOGPS logP 1.24 ALOGPS logP -4.3 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 1.98 Chemaxon pKa (Strongest Basic) 9.99 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 14 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 213.94 Å2 Chemaxon Rotatable Bond Count 20 Chemaxon Refractivity 159.21 m3·mol-1 Chemaxon Polarizability 50.67 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6058 Blood Brain Barrier + 0.6251 Caco-2 permeable - 0.5137 P-glycoprotein substrate Substrate 0.6927 P-glycoprotein inhibitor I Non-inhibitor 0.6538 P-glycoprotein inhibitor II Non-inhibitor 0.9495 Renal organic cation transporter Non-inhibitor 0.6488 CYP450 2C9 substrate Non-substrate 0.8375 CYP450 2D6 substrate Non-substrate 0.8177 CYP450 3A4 substrate Non-substrate 0.6054 CYP450 1A2 substrate Non-inhibitor 0.6386 CYP450 2C9 inhibitor Non-inhibitor 0.7982 CYP450 2D6 inhibitor Non-inhibitor 0.6855 CYP450 2C19 inhibitor Non-inhibitor 0.781 CYP450 3A4 inhibitor Non-inhibitor 0.9528 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7762 Ames test Non AMES toxic 0.6871 Carcinogenicity Non-carcinogens 0.8385 Biodegradation Not ready biodegradable 0.6465 Rat acute toxicity 2.2477 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5 hERG inhibition (predictor II) Non-inhibitor 0.7809
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that binds and hydrolyzes ATP to enable active transport of various substrates including many drugs, toxicants and endogenous compound across cell membranes. Transports a wide variety of conjugated organic anions such as sulfate-, glucuronide- and glutathione (GSH)-conjugates of endo- and xenobiotics substrates (PubMed:10220572, PubMed:10421658, PubMed:11500505, PubMed:16332456). Mediates hepatobiliary excretion of mono- and bis-glucuronidated bilirubin molecules and therefore play an important role in bilirubin detoxification (PubMed:10421658). Mediates also hepatobiliary excretion of others glucuronide conjugates such as 17beta-estradiol 17-glucosiduronic acid and leukotriene C4 (PubMed:11500505). Transports sulfated bile salt such as taurolithocholate sulfate (PubMed:16332456). Transports various anticancer drugs, such as anthracycline, vinca alkaloid and methotrexate and HIV-drugs such as protease inhibitors (PubMed:10220572, PubMed:11500505, PubMed:12441801). Confers resistance to several anti-cancer drugs including cisplatin, doxorubicin, epirubicin, methotrexate, etoposide and vincristine (PubMed:10220572, PubMed:11500505)
- Specific Function
- ABC-type glutathione S-conjugate transporter activity
- Gene Name
- ABCC2
- Uniprot ID
- Q92887
- Uniprot Name
- ATP-binding cassette sub-family C member 2
- Molecular Weight
- 174205.64 Da
References
- Van Beers BE, Pastor CM, Hussain HK: Primovist, Eovist: what to expect? J Hepatol. 2012 Aug;57(2):421-9. doi: 10.1016/j.jhep.2012.01.031. Epub 2012 Apr 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that binds and hydrolyzes ATP to enable active transport of various substrates including many drugs, toxicants and endogenous compound across cell membranes (PubMed:10359813, PubMed:11581266, PubMed:15083066). Transports glucuronide conjugates such as bilirubin diglucuronide, estradiol-17-beta-o-glucuronide and GSH conjugates such as leukotriene C4 (LTC4) (PubMed:11581266, PubMed:15083066). Transports also various bile salts (taurocholate, glycocholate, taurochenodeoxycholate-3-sulfate, taurolithocholate- 3-sulfate) (By similarity). Does not contribute substantially to bile salt physiology but provides an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes (By similarity). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can confer resistance to various anticancer drugs, methotrexate, tenoposide and etoposide, by decreasing accumulation of these drugs in cells (PubMed:10359813, PubMed:11581266)
- Specific Function
- ABC-type bile acid transporter activity
- Gene Name
- ABCC3
- Uniprot ID
- O15438
- Uniprot Name
- ATP-binding cassette sub-family C member 3
- Molecular Weight
- 169341.14 Da
References
- Van Beers BE, Pastor CM, Hussain HK: Primovist, Eovist: what to expect? J Hepatol. 2012 Aug;57(2):421-9. doi: 10.1016/j.jhep.2012.01.031. Epub 2012 Apr 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds and xenobiotics from cells. Transports a range of endogenous molecules that have a key role in cellular communication and signaling, including cyclic nucleotides such as cyclic AMP (cAMP) and cyclic GMP (cGMP), bile acids, steroid conjugates, urate, and prostaglandins (PubMed:11856762, PubMed:12523936, PubMed:12835412, PubMed:12883481, PubMed:15364914, PubMed:15454390, PubMed:16282361, PubMed:17959747, PubMed:18300232, PubMed:26721430). Mediates the ATP-dependent efflux of glutathione conjugates such as leukotriene C4 (LTC4) and leukotriene B4 (LTB4) too. The presence of GSH is necessary for the ATP-dependent transport of LTB4, whereas GSH is not required for the transport of LTC4 (PubMed:17959747). Mediates the cotransport of bile acids with reduced glutathione (GSH) (PubMed:12523936, PubMed:12883481, PubMed:16282361). Transports a wide range of drugs and their metabolites, including anticancer, antiviral and antibiotics molecules (PubMed:11856762, PubMed:12105214, PubMed:15454390, PubMed:17344354, PubMed:18300232). Confers resistance to anticancer agents such as methotrexate (PubMed:11106685)
- Specific Function
- 15-hydroxyprostaglandin dehydrogenase (NAD+) activity
- Gene Name
- ABCC4
- Uniprot ID
- O15439
- Uniprot Name
- ATP-binding cassette sub-family C member 4
- Molecular Weight
- 149525.33 Da
References
- Van Beers BE, Pastor CM, Hussain HK: Primovist, Eovist: what to expect? J Hepatol. 2012 Aug;57(2):421-9. doi: 10.1016/j.jhep.2012.01.031. Epub 2012 Apr 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10358072, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (dehydroepiandrosterone 3-sulfate, 17-beta-glucuronosyl estradiol, and estrone 3-sulfate), as well as eicosanoids (prostaglandin E2, thromboxane B2, leukotriene C4, and leukotriene E4), and thyroid hormones (T4/L-thyroxine, and T3/3,3',5'-triiodo-L-thyronine) (PubMed:10358072, PubMed:10601278, PubMed:10873595, PubMed:11159893, PubMed:12196548, PubMed:12568656, PubMed:15159445, PubMed:15970799, PubMed:16627748, PubMed:17412826, PubMed:19129463, PubMed:26979622). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Involved in the clearance of endogenous and exogenous substrates from the liver (PubMed:10358072, PubMed:10601278). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins), such as pravastatin and pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:10601278, PubMed:15159445, PubMed:15970799). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drug methotrexate (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748). Shows a pH-sensitive substrate specificity towards prostaglandin E2 and T4 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)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Nassif A, Jia J, Keiser M, Oswald S, Modess C, Nagel S, Weitschies W, Hosten N, Siegmund W, Kuhn JP: Visualization of hepatic uptake transporter function in healthy subjects by using gadoxetic acid-enhanced MR imaging. Radiology. 2012 Sep;264(3):741-50. doi: 10.1148/radiol.12112061. Epub 2012 Jul 6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10779507, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (17-beta-glucuronosyl estradiol, dehydroepiandrosterone sulfate (DHEAS), and estrone 3-sulfate), as well as eicosanoid leukotriene C4, prostaglandin E2 and L-thyroxine (T4) (PubMed:10779507, PubMed:11159893, PubMed:12568656, PubMed:15159445, PubMed:17412826, PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). Shows a pH-sensitive substrate specificity towards sulfated steroids, taurocholate and T4 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). Involved in the clearance of bile acids and organic anions from the liver (PubMed:22232210). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins) such as pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:15159445). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Nassif A, Jia J, Keiser M, Oswald S, Modess C, Nagel S, Weitschies W, Hosten N, Siegmund W, Kuhn JP: Visualization of hepatic uptake transporter function in healthy subjects by using gadoxetic acid-enhanced MR imaging. Radiology. 2012 Sep;264(3):741-50. doi: 10.1148/radiol.12112061. Epub 2012 Jul 6. [Article]
Drug created at May 22, 2013 21:49 / Updated at October 29, 2024 18:06