Eliglustat
Identification
- Name
- Eliglustat
- Accession Number
- DB09039
- Description
Eliglustat, marketed by Genzyme as CERDELGA, is a glucosylceramide synthase inhibitor indicated for the long-term treatment of type 1 Gaucher disease. Patients selected for treatment with Eliglustat undergo an FDA approved genotype test to establish if they are CYP2D6 EM (extensive metabolizers), IM (intermediate metabolizers), or PM (poor metabolizers), as the results of this test dictate the dosage of Eliglustat recommended. There are no recommended dosing guidelines for CYP2D6 ultra-rapid or indeterminate metabolizers. Eliglustat was approved for use by the FDA in August 2014.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Eliglustat (DB09039)
- Weight
- Average: 404.551
Monoisotopic: 404.267507647 - Chemical Formula
- C23H36N2O4
- Synonyms
- Eliglustat
- éliglustat
- Eliglustatum
- N-[(1R,2R)-1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(1-pyrrolidinyl)-2-propanyl]octanamide
- External IDs
- GENZ 99067
- GENZ-99067
Pharmacology
- Indication
Eliglustat is indicated for the long-term treatment of type 1 Gaucher disease in adult patients who are CYP2D6 extensive metabolizers (EMs), intermediate metabolizers (IMs), or poor metabolizers (PMs) as detected by an FDA-cleared test.Label
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
According to pharmacokinetic and pharmacodynamic modelling, plasma concentrations of 500ng/mL of eliglustat are predicted to increase mean concentration in the PR, QRS, and QTcF intervals of 22, 7, and 13 msec, respectively. (Taken from Cerdelga prescribing information).
- Mechanism of action
Eliglustat is a glucosylceramide synthase (IC50 = 10 ng/mL) specific inhibitor that acts as a substrate inhibitor of glucosylceramide.
Target Actions Organism ACeramide glucosyltransferase antagonistHumans - Absorption
In CYP2D6 EMs (extensive metabolizers), median time to reach maximum plasma concentrations (tmax) occurs at 1.5 to 2 hours following multiple doses of eliglustat 84 mg twice daily.
- Volume of distribution
835 L in CYP2D6 EMs (extensive metabolizers).
- Protein binding
76 to 83%.
- Metabolism
Extensively metabolized, primarily by CYP2D6 and less so by CYP3A4. No active metabolites have been identified.
- Route of elimination
Urine (41.8%) and feces (51.4%), mainly as metabolites after oral administration.
- Half-life
6.5 hours in EM (extensive metabolizers) and 8.9 hours in PM (poor metabolizers).
- Clearance
88 L/h (8.8%) in CYP2D6 EM (extensive metabolizers).
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
In rats, eliglustat increased pre-implantation loss at 30 and 100 mg/kg/day. In male mature rats, eliglustat showed reversible adverse affects on sperm morphology, germ cell necrosis, and sloughed cells in the epididymis.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2D6 CYP2D6*3 Not Available C allele Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*4 Not Available C allele Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*5 Not Available Whole-gene deletion Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*6 Not Available 1707delT Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*7 Not Available 2935A>C Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*8 Not Available 1758G>T Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*11 Not Available 883G>C Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*12 Not Available 124G>A Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*13 Not Available CYP2D7/2D6 hybrid gene structure Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*14A Not Available 1758G>A Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*15 Not Available 137insT, 137_138insT Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*19 Not Available 2539_2542delAACT Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*20 Not Available 1973_1974insG Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*21 Not Available 2573insC Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*31 Not Available -1770G>A / -1584C>G … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*36 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*38 Not Available 2587_2590delGACT Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*40 Not Available 1863_1864ins(TTT CGC CCC)2 Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*42 Not Available 3259_3260insGT Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*44 Not Available 2950G>C Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*47 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*51 Not Available -1584C>G / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*56 Not Available 3201C>T Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*57 Not Available 100C>T / 310G>T … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*62 Not Available 4044C>T Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*68A Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*68B Not Available Similar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4. Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*69 Not Available 2988G>A / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*92 Not Available 1995delC Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*100 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*101 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*1XN Not Available Normal allele duplicated. Effect Inferred Reduced efficacy. Details Cytochrome P450 2D6 CYP2D6*2XN Not Available 2850C>T / 4180G>C … show all Effect Inferred Reduced efficacy. Details
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 Unlock Additional DataAbametapir The serum concentration of Eliglustat can be increased when it is combined with Abametapir. Abatacept The metabolism of Eliglustat can be increased when combined with Abatacept. Abiraterone The metabolism of Eliglustat can be decreased when combined with Abiraterone. Acalabrutinib The metabolism of Eliglustat can be decreased when combined with Acalabrutinib. Acebutolol The risk or severity of QTc prolongation can be increased when Acebutolol is combined with Eliglustat. Acetaminophen The metabolism of Eliglustat can be decreased when combined with Acetaminophen. Acetazolamide The metabolism of Eliglustat can be decreased when combined with Acetazolamide. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Eliglustat. Adalimumab The metabolism of Eliglustat can be increased when combined with Adalimumab. Adenosine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Eliglustat. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid grapefruit products. Grapefruit inhibits the CYP3A4 metabolism of eliglustat, which may increase its serum concentration.
- Avoid St. John's Wort. This herb induces the CYP3A metabolism of eliglustat and may reduce its serum concentration.
- Take with or without food.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Eliglustat tartrate N0493335P3 928659-70-5 KUBARPMUNHKBIQ-VTHUDJRQSA-N - International/Other Brands
- Cerdelga (Genzyme Corporation)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataCerdelga Capsule 84 mg Oral Genzyme Europe Bv 2015-01-19 Not applicable EU 
Cerdelga Capsule 84 mg Oral Genzyme Europe Bv 2015-01-19 Not applicable EU Cerdelga Capsule 84 mg Oral Sanofi Genzyme, a Division of Sanofi Aventis Canada Inc 2017-07-26 Not applicable Canada 
Cerdelga Capsule 84 mg Oral Genzyme Europe Bv 2015-01-19 Not applicable EU Cerdelga Capsule 84 mg/1 Oral Genzyme Corporation 2014-09-03 Not applicable US 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- A16AX10 — Eliglustat
- Drug Categories
- Alimentary Tract and Metabolism
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Enzyme Inhibitors
- Gaucher Disease
- Glucosylceramide Synthase Inhibitor
- Glucosylceramide Synthase Inhibitors
- Highest Risk QTc-Prolonging Agents
- Other Miscellaneous Therapeutic Agents
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- QTc Prolonging Agents
- Various Alimentary Tract and Metabolism Products
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzo-1,4-dioxanes. These are heterocyclic compounds containing a benzene ring fused to a 1,4-dioxane ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzodioxanes
- Sub Class
- Benzo-1,4-dioxanes
- Direct Parent
- Benzo-1,4-dioxanes
- Alternative Parents
- Alkyl aryl ethers / Aralkylamines / Para dioxins / N-alkylpyrrolidines / N-acyl amines / Benzenoids / 1,3-aminoalcohols / Trialkylamines / Secondary carboxylic acid amides / Secondary alcohols show 8 more
- Substituents
- 1,3-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Amino acid or derivatives / Aralkylamine / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Benzenoid show 23 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- secondary alcohol, carboxamide, N-alkylpyrrolidine, benzodioxine (CHEBI:82752)
Chemical Identifiers
- UNII
- DR40J4WA67
- CAS number
- 491833-29-5
- InChI Key
- FJZZPCZKBUKGGU-AUSIDOKSSA-N
- InChI
- InChI=1S/C23H36N2O4/c1-2-3-4-5-6-9-22(26)24-19(17-25-12-7-8-13-25)23(27)18-10-11-20-21(16-18)29-15-14-28-20/h10-11,16,19,23,27H,2-9,12-15,17H2,1H3,(H,24,26)/t19-,23-/m1/s1
- IUPAC Name
- N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl]octanamide
- SMILES
- CCCCCCCC(=O)N[[email protected]](CN1CCCC1)[[email protected]](O)C1=CC=C2OCCOC2=C1
References
- General References
- Poole RM: Eliglustat: first global approval. Drugs. 2014 Oct;74(15):1829-36. doi: 10.1007/s40265-014-0296-3. [PubMed:25239269]
- McEachern KA, Fung J, Komarnitsky S, Siegel CS, Chuang WL, Hutto E, Shayman JA, Grabowski GA, Aerts JM, Cheng SH, Copeland DP, Marshall J: A specific and potent inhibitor of glucosylceramide synthase for substrate inhibition therapy of Gaucher disease. Mol Genet Metab. 2007 Jul;91(3):259-67. Epub 2007 May 16. [PubMed:17509920]
- External Links
- KEGG Drug
- D09893
- PubChem Compound
- 23652731
- PubChem Substance
- 310264987
- ChemSpider
- 28475348
- 1547220
- ChEBI
- 82752
- ChEMBL
- CHEMBL2110588
- ZINC
- ZINC000072267023
- PharmGKB
- PA166123486
- Wikipedia
- Eliglustat
- AHFS Codes
- 92:92.00 — Other Miscellaneous Therapeutic Agents
- FDA label
- Download (376 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Active Not Recruiting Treatment Gaucher's Disease 1 3 Completed Treatment Gaucher Disease, Type 1 / Gaucher's Disease Type 1 2 3 Completed Treatment Gaucher's Disease 1 3 Recruiting Treatment Gaucher's Disease Type 1 / Gaucher's disease type III 1 2 Completed Treatment Cerebroside Lipidosis Syndrome / Gaucher Disease, Non-Neuronopathic Form / Gaucher Disease, Type 1 / Gaucher's Disease Type 1 / Glucocerebrosidase Deficiency Disease / Glucosylceramide Beta-Glucosidase Deficiency Disease 1 1 Completed Not Available Healthy Volunteers 1 1 Completed Basic Science Healthy Volunteers 1 1 Completed Treatment Gaucher's Disease 3 1 Completed Treatment Healthy Volunteers 1 Not Available Active Not Recruiting Treatment Gaucher Disease, Type III 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral 84 mg Capsule Oral 84 mg/1 Capsule 84 mg Capsule, coated Oral 84 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS6916802 No 2005-07-12 2022-04-29 US US7615573 No 2009-11-10 2022-04-29 US US7196205 No 2007-03-27 2022-04-29 US US7253185 No 2007-08-07 2022-04-29 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.113 mg/mL ALOGPS logP 3.44 ALOGPS logP 3.21 ChemAxon logS -3.6 ALOGPS pKa (Strongest Acidic) 13.51 ChemAxon pKa (Strongest Basic) 8.17 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 71.03 Å2 ChemAxon Rotatable Bond Count 11 ChemAxon Refractivity 113.76 m3·mol-1 ChemAxon Polarizability 46.82 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Ceramide glucosyltransferase activity
- Specific Function
- Catalyzes the first glycosylation step in glycosphingolipid biosynthesis, the transfer of glucose to ceramide. May also serve as a "flippase".
- Gene Name
- UGCG
- Uniprot ID
- Q16739
- Uniprot Name
- Ceramide glucosyltransferase
- Molecular Weight
- 44853.255 Da
References
- Poole RM: Eliglustat: first global approval. Drugs. 2014 Oct;74(15):1829-36. doi: 10.1007/s40265-014-0296-3. [PubMed:25239269]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Poole RM: Eliglustat: first global approval. Drugs. 2014 Oct;74(15):1829-36. doi: 10.1007/s40265-014-0296-3. [PubMed:25239269]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Poole RM: Eliglustat: first global approval. Drugs. 2014 Oct;74(15):1829-36. doi: 10.1007/s40265-014-0296-3. [PubMed:25239269]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
Drug created on April 02, 2015 10:54 / Updated on October 21, 2020 01:55
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