NAV

Ivosidenib

Identification

Summary

Ivosidenib is an isocitrate dehydrogenase-1 inhibitor used to treat acute myeloid leukemia and cholangiocarcinoma in adults with a susceptible IDH1 mutation.

Brand Names
Tibsovo
Generic Name
Ivosidenib
DrugBank Accession Number
DB14568
Background

Ivosidenib is a first-in-class isocitrate dehydrogenase-1 (IDH1) inhibitor. IDH1 is an enzyme that is often mutated and overexpressed in some cancers, leading to aberrant cell growth and proliferation.6 Ivosidenib inhibits mutated IDH1, blocking the enzymatic activity and further differentiation of cancer cells.5

Ivosidenib was granted accelerated approval by the FDA in July 2018 for the treatment of relapsed of refractory acute myeloid leukemia in adults.5 It is currently approved to also treat newly diagnosed acute myeloid leukemia in older adults in combination azacitidine or as monotherapy, as well as locally advanced or metastatic cholangiocarcinoma in adults. The drug is only effective in patients with a susceptible IDH1 mutation.9

Type
Small Molecule
Groups
Approved, Investigational
Structure
3D
Similar Structures
Weight
Average: 582.97
Monoisotopic: 582.1394008
Chemical Formula
C28H22ClF3N6O3
Synonyms
  • Ivosidenib
External IDs
  • AG-120

Pharmacology

Indication

Ivosidenib is an isocitrate dehydrogenase-1 (IDH1) inhibitor indicated for the treatment of patients with a susceptible IDH1 mutation as detected by an FDA-approved test with:

  • Newly Diagnosed Acute Myeloid Leukemia (AML) in combination azacitidine or as monotherapy for the treatment of newly diagnosed AML in adults 75 years or older, or who have comorbidities that preclude use of intensive induction chemotherapy.9

  • Relapsed or refractory AML in adults.9

  • Locally Advanced or Metastatic Cholangiocarcinoma in adults who have been previously treated.9

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Ivosidenib is an antineoplastic agent that is effective in cancers with a susceptible IDH1 mutation, which indicates increased levels of oncometabolite D-2-hydroxyglutarate (D-2HG) in cancer cells.5 Ivosidenib decreases D-2HG levels in a dose-dependent manner by inhibiting the IDH1 enzyme. Ivosidenib inhibits both the mutant and wild-type IDH1 but does not inhibit IDH2.7

Mechanism of action

Isocitrate dehydrogenase 1 (IDH1) is a metabolic enzyme in the cytoplasm and peroxisomes that plays a role in many cellular processes, including mitochondrial oxidative phosphorylation, glutamine metabolism, lipogenesis, glucose sensing, and regulation of cellular redox status.1 IDH1 converts isocitrate to α-ketoglutarate (α-KG), a normal metabolite in the carboxylic acid cycle.1 Multiple cancers are associated with missense mutations in IDH1, leading to the substitution of the amino acid arginine 132 in the enzyme active site, acquired gain-of-function activity, and increased enzyme activity.5,7 IDH1 mutation results in the accumulation of D-2-hydroxyglutarate (D-2HG), an oncometabolite that is structurally similar to α-KG.1,4 D-2HG inhibits α-KG-dependent dioxygenases, including histone and DNA demethylases, which play a role in histone and DNA demethylation along with other cellular processes.4 Inhibition of these enzymes leads to histone and DNA hypermethylation and a block in cell differentiation,1 including hematopoietic differentiation.3 With histone hypermethylation, methylation-sensitive insulators cannot regulate the activation of oncogenes.2 Excess D-2HG ultimately interferes with cellular metabolism and alters epigenetic regulation towards oncogenesis.1,4

Ivosidenib inhibits the mutant IDH1 at much lower concentrations than the wild-type enzyme.9 It targets gene mutations at position R132, with R132H and R132C being the most common mutations.5 In mouse xenograft models of IDH1-mutated AML, ivosidenib caused a decrease in D-2HG levels in a dose-dependent manner and induced myeloid differentiation in vitro and in vivo.9 Ivosidenib works to inhibit histone demethylases and restore normal methylation conditions to promote cell differentiation and oncogene regulation.4

TargetActionsOrganism
AIsocitrate dehydrogenase [NADP] cytoplasmic
inhibitor
Humans
Absorption

Following oral administration, ivosidenib is rapidly absorbed.7 The Cmax following a single oral dose is 4503 ng/mL in patients with relapsed or refractory AML, 4820 ng/mL in patients with newly diagnosed AML who were also treated with azacitidine, and 4060 ng/mL in patients with cholangiocarcinoma. The steady-state was reached within 14 days. The steady-state Cmax is 6551 ng/mL in patients with relapsed or refractory AML, 6145 ng/mL in patients with newly diagnosed AML who were also treated with azacitidine, and 4799 ng/mL in patients with cholangiocarcinoma. The Tmax ranges from two to three hours.9

A high-fat meal increases ivosidenib exposure.9

Volume of distribution

The apparent volume of distribution at steady state is 403 L in patients with relapsed or refractory AML, 504 L in patients with newly diagnosed AML who were also treated with azacitidine, and 706 L in patients with cholangiocarcinoma.9

Protein binding

In vitro, ivosidenib is 92-96% bound to plasma proteins.9

Metabolism

Ivosidenib is predominantly metabolized by CYP3A4 via oxidation. The exact chemical structures of the metabolites formed from CYP3A4-mediated oxidation have not been fully characterized. Ivosidenib can also undergo N-dealkylation and hydrolysis as minor metabolic pathways.7,8,9

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Route of elimination

Following oral administration of ivosidenib, about 77% of the dose was eliminated in feces, where 67% was in the form of unchanged parent drug. About 17% of the dose was excreted in urine, where 10% was in the form of unchanged ivosidenib.9

Half-life

The terminal half-life at steady state is 58 hours in patients with relapsed or refractory AML, 98 hours in patients with newly diagnosed AML who were also treated with azacitidine, and 129 hours in patients with cholangiocarcinoma.9

Clearance

The apparent clearance at steady state is 5.6 L/h in patients with relapsed or refractory AML, 4.6 L/h in patients with newly diagnosed AML who were also treated with azacitidine, and 6.1 L/h in patients with cholangiocarcinoma.9

Adverse Effects
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Toxicity

There is limited information regarding the LD50 or overdose of ivosidenib.

Ivosidenib is associated with a risk of differentiation syndrome, Guillain-Barre syndrome, and embryo-fetal toxicity.6,9

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.
DrugInteraction
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interactions in your software
1,2-BenzodiazepineThe metabolism of 1,2-Benzodiazepine can be increased when combined with Ivosidenib.
AbametapirThe serum concentration of Ivosidenib can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Ivosidenib can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Ivosidenib.
AbirateroneThe metabolism of Abiraterone can be increased when combined with Ivosidenib.
AbrocitinibThe metabolism of Abrocitinib can be increased when combined with Ivosidenib.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Ivosidenib.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Ivosidenib.
AcetaminophenThe metabolism of Acetaminophen can be increased when combined with Ivosidenib.
AcetazolamideThe metabolism of Ivosidenib can be decreased when combined with Acetazolamide.
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Food Interactions
  • Do not take with or immediately after a high-fat meal. Administration of ivosidenib with a high-fat meal increases the Cmax and AUC of ivosidenib by 98 and 25%, respectively.
  • Exercise caution with grapefruit products. Grapefruit inhibits CYP3A metabolism, which may increase the serum concentration of ivosidenib. Dose adjustment may be necessary if co-administered.
  • Exercise caution with St. John's Wort. This herb induces CYP3A metabolism and may reduce serum levels of ivosidenib.
  • Take at the same time every day.
  • Take with or without food.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TibsovoTablet, film coated250 mg/1OralAgios Pharmaceuticals, Inc.2018-07-202024-11-30US flag
TibsovoTablet, film coated250 mg/1OralServier Pharmaceutical LLC2021-10-19Not applicableUS flag

Categories

ATC Codes
L01XX62 — Ivosidenib
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Proline and derivatives
Alternative Parents
Alpha amino acid amides / Phenylacetamides / Pyrrolidinecarboxamides / Chlorobenzenes / Pyrrolidine-2-ones / Pyridines and derivatives / Aryl chlorides / Aryl fluorides / Imidolactams / Tertiary carboxylic acid amides
show 11 more
Substituents
2-pyrrolidone / Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Aromatic heteromonocyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 30 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Q2PCN8MAM6
CAS number
1448347-49-6
InChI Key
WIJZXSAJMHAVGX-DHLKQENFSA-N
InChI
InChI=1S/C28H22ClF3N6O3/c29-21-4-2-1-3-20(21)25(26(40)36-18-11-28(31,32)12-18)37(19-10-17(30)14-34-15-19)27(41)22-5-6-24(39)38(22)23-9-16(13-33)7-8-35-23/h1-4,7-10,14-15,18,22,25H,5-6,11-12H2,(H,36,40)/t22-,25-/m0/s1
IUPAC Name
(2S)-2-(2-chlorophenyl)-2-{1-[(2S)-1-(4-cyanopyridin-2-yl)-5-oxopyrrolidin-2-yl]-N-(5-fluoropyridin-3-yl)formamido}-N-(3,3-difluorocyclobutyl)acetamide
SMILES
[H][C@@](N(C(=O)[C@]1([H])CCC(=O)N1C1=NC=CC(=C1)C#N)C1=CC(F)=CN=C1)(C(=O)NC1CC(F)(F)C1)C1=C(Cl)C=CC=C1

References

General References
  1. Mondesir J, Willekens C, Touat M, de Botton S: IDH1 and IDH2 mutations as novel therapeutic targets: current perspectives. J Blood Med. 2016 Sep 2;7:171-80. doi: 10.2147/JBM.S70716. eCollection 2016. [Article]
  2. Flavahan WA, Drier Y, Liau BB, Gillespie SM, Venteicher AS, Stemmer-Rachamimov AO, Suva ML, Bernstein BE: Insulator dysfunction and oncogene activation in IDH mutant gliomas. Nature. 2016 Jan 7;529(7584):110-4. doi: 10.1038/nature16490. Epub 2015 Dec 23. [Article]
  3. Figueroa ME, Abdel-Wahab O, Lu C, Ward PS, Patel J, Shih A, Li Y, Bhagwat N, Vasanthakumar A, Fernandez HF, Tallman MS, Sun Z, Wolniak K, Peeters JK, Liu W, Choe SE, Fantin VR, Paietta E, Lowenberg B, Licht JD, Godley LA, Delwel R, Valk PJ, Thompson CB, Levine RL, Melnick A: Leukemic IDH1 and IDH2 mutations result in a hypermethylation phenotype, disrupt TET2 function, and impair hematopoietic differentiation. Cancer Cell. 2010 Dec 14;18(6):553-67. doi: 10.1016/j.ccr.2010.11.015. Epub 2010 Dec 9. [Article]
  4. Popovici-Muller J, Lemieux RM, Artin E, Saunders JO, Salituro FG, Travins J, Cianchetta G, Cai Z, Zhou D, Cui D, Chen P, Straley K, Tobin E, Wang F, David MD, Penard-Lacronique V, Quivoron C, Saada V, de Botton S, Gross S, Dang L, Yang H, Utley L, Chen Y, Kim H, Jin S, Gu Z, Yao G, Luo Z, Lv X, Fang C, Yan L, Olaharski A, Silverman L, Biller S, Su SM, Yen K: Discovery of AG-120 (Ivosidenib): A First-in-Class Mutant IDH1 Inhibitor for the Treatment of IDH1 Mutant Cancers. ACS Med Chem Lett. 2018 Jan 19;9(4):300-305. doi: 10.1021/acsmedchemlett.7b00421. eCollection 2018 Apr 12. [Article]
  5. Merchant SL, Culos K, Wyatt H: Ivosidenib: IDH1 Inhibitor for the Treatment of Acute Myeloid Leukemia. J Adv Pract Oncol. 2019 Jul;10(5):494-500. doi: 10.6004/jadpro.2019.10.5.7. Epub 2019 Jul 1. [Article]
  6. Authors unspecified: Ivosidenib . [Article]
  7. Dhillon S: Ivosidenib: First Global Approval. Drugs. 2018 Sep;78(14):1509-1516. doi: 10.1007/s40265-018-0978-3. [Article]
  8. Prakash C, Fan B, Altaf S, Agresta S, Liu H, Yang H: Pharmacokinetics, absorption, metabolism, and excretion of [(14)C]ivosidenib (AG-120) in healthy male subjects. Cancer Chemother Pharmacol. 2019 May;83(5):837-848. doi: 10.1007/s00280-019-03793-7. Epub 2019 Feb 13. [Article]
  9. FDA Approved Drug Products: TIBSOVO (ivosidenib) tablets, for oral use [Link]
ChemSpider
38772333
BindingDB
363689
RxNav
2049873
ChEBI
145430
ChEMBL
CHEMBL3989958
ZINC
ZINC000205136523
Wikipedia
Ivosidenib

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Active Not RecruitingTreatmentAcute Myeloid Leukemia (AML) / AML Arising From Myelodysplastic Syndrome (MDS) / Newly Diagnosed Acute Myeloid Leukemia (AML) / Untreated AML1
3CompletedTreatmentCholangiocarcinoma Advanced / Metastatic Cholangiocarcinoma1
3RecruitingTreatmentAcute Myeloid Leukemia (AML) / Myelodysplastic Syndrome With Excess Blasts-21
2Not Yet RecruitingTreatmentAcute Myeloid Leukemia (AML)1
2RecruitingTreatmentAcute Myeloid Leukemia (AML) / Myelodysplastic Syndromes (MDS)1
2RecruitingTreatmentAcute Myeloid Leukemia With Gene Mutations / Acute, recurrent Myeloid Leukemia / Myelodysplastic Syndromes (MDS) / Myeloproliferative Neoplasms (MPNs) / Refractory Acute Myeloid Leukemia (AML)1
2RecruitingTreatmentCancer of Unknown Primary Site1
2RecruitingTreatmentChondrosarcoma, Grade 2 / Chondrosarcoma, Grade 3 / Chondrosarcomas / IDH1 Gene Mutation1
2RecruitingTreatmentClonal Cytopenia of Undetermined Significance1
2RecruitingTreatmentEpendymoma, Recurrent / Recurrent Ewing's Sarcoma / Recurrent Hepatoblastoma / Recurrent Langerhans Cell Histiocytosis / Recurrent Malignant Germ Cell Tumor / Recurrent Malignant Gliomas / Recurrent Malignant Solid Neoplasm / Recurrent Medulloblastoma / Recurrent Neuroblastoma / Recurrent Non-Hodgkin Lymphoma / Recurrent Osteosarcoma / Recurrent Peripheral Primitive Neuroectodermal Tumor / Recurrent Rhabdoid Tumor / Recurrent Rhabdomyosarcoma / Recurrent Soft Tissue Sarcoma / Recurrent WHO Grade 2 Glioma / Refractory Ependymoma / Refractory Ewing Sarcoma / Refractory Hepatoblastoma / Refractory Langerhans cell histiocytosis / Refractory Malignant Germ Cell Tumor / Refractory Malignant Glioma / Refractory Malignant Solid Neoplasm / Refractory Medulloblastoma / Refractory Neuroblastoma / Refractory Non-Hodgkin's lymphoma / Refractory Osteosarcoma / Refractory Peripheral Primitive Neuroectodermal Tumor / Refractory Rhabdoid Tumor / Refractory Rhabdomyosarcoma / Refractory Soft Tissue Sarcomas / Refractory WHO Grade 2 Glioma / Wilms' tumor1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral250 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US9474779No2016-10-252033-08-19US flag
US9850277No2017-12-262033-01-18US flag
US9968595No2018-05-152035-03-13US flag
US10449184No2019-10-222035-03-13US flag
US10610125No2020-04-072030-06-21US flag
US10799490No2020-10-132035-03-13US flag
US10980788No2021-04-202039-06-07US flag
US10717764No2020-07-212033-01-18US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility<1 mg/mLhttps://www.selleck.cn/msds/MSDS_S8206.pdf
Predicted Properties
PropertyValueSource
Water Solubility0.0208 mg/mLALOGPS
logP2.52ALOGPS
logP3.01ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)12.14ChemAxon
pKa (Strongest Basic)1.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area119.29 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity139.33 m3·mol-1ChemAxon
Polarizability53.42 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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insights and accelerate drug research.
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Details1. Isocitrate dehydrogenase [NADP] cytoplasmic
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Ivosidenib inhibits both the wild-type and mutant forms of IDH1 with varying affinities.
General Function
Receptor binding
Specific Function
Not Available
Gene Name
IDH1
Uniprot ID
O75874
Uniprot Name
Isocitrate dehydrogenase [NADP] cytoplasmic
Molecular Weight
46659.005 Da
References
  1. Megias-Vericat JE, Ballesta-Lopez O, Barragan E, Montesinos P: IDH1-mutated relapsed or refractory AML: current challenges and future prospects. Blood Lymphat Cancer. 2019 Jun 27;9:19-32. doi: 10.2147/BLCTT.S177913. eCollection 2019. [Article]
  2. Merchant SL, Culos K, Wyatt H: Ivosidenib: IDH1 Inhibitor for the Treatment of Acute Myeloid Leukemia. J Adv Pract Oncol. 2019 Jul;10(5):494-500. doi: 10.6004/jadpro.2019.10.5.7. Epub 2019 Jul 1. [Article]
  3. FDA Approved Drug Products: TIBSOVO (ivosidenib) tablets, for oral use [Link]

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Prakash C, Fan B, Altaf S, Agresta S, Liu H, Yang H: Pharmacokinetics, absorption, metabolism, and excretion of [(14)C]ivosidenib (AG-120) in healthy male subjects. Cancer Chemother Pharmacol. 2019 May;83(5):837-848. doi: 10.1007/s00280-019-03793-7. Epub 2019 Feb 13. [Article]
  2. FDA Approved Drug Products: TIBSOVO (ivosidenib) tablets, for oral use [Link]
Details2. Cytochrome P450 2B6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. FDA Approved Drug Products: TIBSOVO (ivosidenib) tablets, for oral use [Link]
Details3. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
Curator comments
There are limited data in the literature supporting this enzyme action, however the FDA label states that ivosidenib may induce CYP2C9.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. FDA Approved Drug Products: TIBSOVO (ivosidenib) tablets, for oral use [Link]
Details4. Cytochrome P450 2C8
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. FDA Approved Drug Products: TIBSOVO (ivosidenib) tablets, for oral use [Link]

Transporters

Details1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. FDA Approved Drug Products: TIBSOVO (ivosidenib) tablets, for oral use [Link]
Details2. Solute carrier family 22 member 8
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. FDA Approved Drug Products: TIBSOVO (ivosidenib) tablets, for oral use [Link]

Drug created at July 20, 2018 16:42 / Updated at May 30, 2022 20:15