Futibatinib

Identification

Summary

Futibatinib is a kinase inhibitor used to treat intrahepatic cholangiocarcinoma in previously treated adults.

Brand Names

Lytgobi 20 Mg Daily Dose

Generic Name

Futibatinib

DrugBank Accession Number

DB15149

Background

Futibatinib is an inhibitor of Fibroblast Growth Factor receptor (FGFR), which comprises a group of receptor tyrosine kinases that play a key role in cell proliferation, differentiation, migration, and survival. FGFR was investigated in oncology as a therapeutic target, as FGFR genomic aberrations and dysregulated FGFR signalling pathways are observed in some cancers such as cholangiocarcinoma and urothelial malignancies.^1,2

As a novel inhibitor of FGFR, futibatinib was first approved by the FDA in September 2022 to treat different types of intrahepatic cholangiocarcinoma.⁴ On July 4, 2023, the European Commission granted Conditional Marketing Authorization for futibatinib for the treatment of cholangiocarcinoma.⁶

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 418.457
Monoisotopic: 418.175338592
Chemical Formula: C₂₂H₂₂N₆O₃

Synonyms

1-((3S)-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo(3, 4-d) pyrimidin-1-yl)-1-pyrrolidinyl)-2-propen-1-one
1-[(3S)-3-{4-amino-3-[(3,5-dimethoxyphenyl)ethynyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}pyrrolidin-1-yl]prop-2-en-1-one
Futibatinib

External IDs

TAS-120

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Pharmacology

Indication

Futibatinib is indicated to treat adults with previously treated, unresectable, locally advanced or metastatic intrahepatic cholangiocarcinoma harbouring fibroblast growth factor receptor 2 (FGFR2) gene fusions or other rearrangements.⁴ In Europe, it is indicated in patients whose disease has progressed after at least one prior line of systemic therapy.⁵

Futibatinib is approved in the US under accelerated approval and in Europe under conditional marketing authorization. This currently approved indication is subject to change, as it may be contingent upon verification and description of clinical benefit in a confirmatory trial(s).⁴

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Associated Conditions

Indication Type	Indication	Approval Level	Age Group	Patient Characteristics
Treatment of	Locally advanced intrahepatic cholangiocarcinoma	••••••••••••	•••••	•••••••••• •••••••
Treatment of	Locally advanced intrahepatic cholangiocarcinoma	••••••••••••	•••••	•• ••••• ••• ••••• •••••••• •••••••• ••••••• ••••••••••• ••••• •••••••• •••••••••
Treatment of	Metastatic intrahepatic cholangiocarcinoma	••••••••••••	•••••	•••••••••• •••••••
Treatment of	Metastatic intrahepatic cholangiocarcinoma	••••••••••••	•••••	••••••• ••••••••••• ••••• •••••••• •••••••••• •• ••••• ••• ••••• •••••••• •••••••
Treatment of	Unresectable intrahepatic cholangiocarcinoma	••••••••••••	•••••	•••••••••• •••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Futibatinib is an anticancer agent with demonstrated anti-tumour activity in mouse and rat xenograft models of human tumours with activating FGFR genetic alterations.⁴ Futibatinib is not expected to affect cell lines with no FGFR genomic aberrations.² It suppresses the growth of tumours in a dose-dependent manner.²

Mechanism of action

Fibroblast Growth Factor receptor (FGFR) pathway play a key role in cell proliferation, differentiation, migration, and survival. Notably, FGFR genomic aberrations and aberrant FGFR signalling pathways are observed in some cancers,^1,2 as constitutive FGFR signalling can support the proliferation and survival of malignant cells.⁴

Futibatinib is a selective, irreversible inhibitor of FGFR 1, 2, 3, and 4 with IC₅₀ values of less than 4 nM.^2,4 It binds to the FGFR kinase domain by forming a covalent bond with cysteine in the ATP-binding pocket.² Upon binding to FGFR, futibatinib blocks FGFR phosphorylation and downstream signalling pathways,⁴ such as the RAS-dependent mitogen-activated protein kinase (MAPK), phosphatidylinositol 3-kinase (PI3KCA)/Akt/mTOR, phospholipase Cγ (PLCγ), and JAK/STAT.³ Futibatinib ultimately decreases cell viability in cancer cell lines with FGFR alterations, including FGFR fusions or rearrangements, amplifications, and mutations.⁴

Target	Actions	Organism
AFibroblast growth factor receptor 1	inhibitor	Humans
AFibroblast growth factor receptor 2	inhibitor	Humans
AFibroblast growth factor receptor 3	inhibitor	Humans
AFibroblast growth factor receptor 4	inhibitor	Humans

Absorption

T_max ranges from 1.2 to 22.8 hours, with a median value of two hours. In healthy subjects, a high-fat and high-calorie meal (900 to 1000 calories with approximately 50% of total caloric content from fat) decreased futibatinib AUC by 11% and C_max by 42%.⁴

Volume of distribution

The geometric mean (CV%) apparent volume of distribution (Vc/F) is 66 L (18%).⁴

Protein binding

Futibatinib is 95% bound to human plasma protein at 0.2 to 5 µmol/L in vitro, primarily to albumin and α1-acid glycoprotein.⁴

Metabolism

In vitro, futibatinib is primarily metabolized by CYP3A and to a lesser extent by CYP2C9 and CYP2D6. Unchanged futibatinib is the major drug-related moiety in plasma (accounting for 59% of radioactivity) in healthy subjects.⁴

Route of elimination

Following a single oral dose of 20 mg radiolabeled futibatinib, approximately 91% of the total recovered radioactivity was observed in feces and 9% in urine, with negligible unchanged futibatinib in urine or feces.⁴

Half-life

The mean (CV%) elimination half-life (t_1/2) of futibatinib is 2.9 hours (27%).⁴

Clearance

The geometric mean (CV%) apparent clearance (CL/F) is 20 L/h (23%).⁴

Adverse Effects

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Toxicity

There is no information available regarding acute toxicity and overdose of futibatinib.

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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
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Abametapir	The serum concentration of Futibatinib can be increased when it is combined with Abametapir.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Futibatinib.
Abrocitinib	The serum concentration of Futibatinib can be increased when it is combined with Abrocitinib.
Adagrasib	The serum concentration of Futibatinib can be increased when it is combined with Adagrasib.
Afatinib	The serum concentration of Futibatinib can be increased when it is combined with Afatinib.

Food Interactions

Take at the same time every day.
Take with or without food. A high-fat and high-calorie meal decreases drug exposure, but not to a clinically significant extent.

Products

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Lytgobi	Tablet, film coated	4 mg	Oral	Taiho Pharma Netherlands B.V.	2023-07-22	Not applicable
Lytgobi	Tablet	4 mg/1	Oral	Taiho Pharmaceutical Co., Ltd.	2023-02-03	Not applicable
Lytgobi	Tablet, film coated	4 mg	Oral	Taiho Pharma Netherlands B.V.	2023-07-22	Not applicable
Lytgobi	Tablet, film coated	4 mg	Oral	Taiho Pharma Netherlands B.V.	2023-07-22	Not applicable

Chemical Identifiers

UNII: 4B93MGE4AL
CAS number: 1448169-71-8
InChI Key: KEIPNCCJPRMIAX-HNNXBMFYSA-N
InChI: InChI=1S/C22H22N6O3/c1-4-19(29)27-8-7-15(12-27)28-22-20(21(23)24-13-25-22)18(26-28)6-5-14-9-16(30-2)11-17(10-14)31-3/h4,9-11,13,15H,1,7-8,12H2,2-3H3,(H2,23,24,25)/t15-/m0/s1
IUPAC Name: 1-[(3S)-3-{4-amino-3-[2-(3,5-dimethoxyphenyl)ethynyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}pyrrolidin-1-yl]prop-2-en-1-one
SMILES: COC1=CC(=CC(OC)=C1)C#CC1=NN([C@H]2CCN(C2)C(=O)C=C)C2=C1C(N)=NC=N2

References

General References

Kommalapati A, Tella SH, Borad M, Javle M, Mahipal A: FGFR Inhibitors in Oncology: Insight on the Management of Toxicities in Clinical Practice. Cancers (Basel). 2021 Jun 13;13(12). pii: cancers13122968. doi: 10.3390/cancers13122968. [Article]
Sootome H, Fujita H, Ito K, Ochiiwa H, Fujioka Y, Ito K, Miura A, Sagara T, Ito S, Ohsawa H, Otsuki S, Funabashi K, Yashiro M, Matsuo K, Yonekura K, Hirai H: Futibatinib Is a Novel Irreversible FGFR 1-4 Inhibitor That Shows Selective Antitumor Activity against FGFR-Deregulated Tumors. Cancer Res. 2020 Nov 15;80(22):4986-4997. doi: 10.1158/0008-5472.CAN-19-2568. Epub 2020 Sep 24. [Article]
Rizzo A, Ricci AD, Brandi G: Futibatinib, an investigational agent for the treatment of intrahepatic cholangiocarcinoma: evidence to date and future perspectives. Expert Opin Investig Drugs. 2021 Apr;30(4):317-324. doi: 10.1080/13543784.2021.1837774. Epub 2020 Oct 25. [Article]
FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]
EMA Approved Drug Products: LYTGOBI (futibatinib) Oral Tablets [Link]
PR Newswire: European Commission Grants Conditional Marketing Authorization for Taiho's LYTGOBI® Tablets for the Treatment of Adults With Cholangiocarcinoma [Link]

External Links

ChemSpider: 58877816
BindingDB: 161389
RxNav: 2628190
ChEMBL: CHEMBL3701238
ZINC: ZINC000207800318
PharmGKB: PA166293381
PDBe Ligand: TZ0
Wikipedia: Futibatinib

PDB Entries

6mzq / 6mzw / 7d5o

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
3	Active Not Recruiting	Treatment	Cholangiocarcinoma Advanced / FGFR2 Gene Rearrangements	1
3	Not Yet Recruiting	Treatment	Biliary Tract Neoplasms	1
3	Recruiting	Health Services Research	Soft Tissue Sarcoma	1
2	Active Not Recruiting	Treatment	Advanced or Metastatic Gastric or Gastroesophageal Cancer / Advanced or Metastatic Solid Tumor / Myeloid/lymphoid neoplasms	1
2	Active Not Recruiting	Treatment	FGFR 1 High Amplification / FGFR2 Amplification / Metastatic Breast Cancer	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral	4 mg/1
Tablet, film coated	Oral	4 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US9108973	No	2015-08-18	2033-02-23
US10434103	No	2019-10-08	2036-03-31
US11833151	No	2019-11-05	2039-11-05

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0398 mg/mL	ALOGPS
logP	1.79	ALOGPS
logP	1.77	Chemaxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	19.22	Chemaxon
pKa (Strongest Basic)	2.58	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	7	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	108.39 Å²	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	122.82 m³·mol^-1	Chemaxon
Polarizability	45.57 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	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	splash10-014i-0002900000-6840c919b3866fc7b65a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0005900000-d06403b9be88f2a9de7a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00lr-0009100000-991cbf5fc77bea1aac01
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0029400000-8c439a0490926c391a3d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-007k-1196100000-4afe1457eedee4892db5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000w-2189000000-eba1f0e52df16e833b1d
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Not Available

Targets

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Details1. Fibroblast growth factor receptor 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Protein tyrosine kinase activity
Specific Function: Tyrosine-protein kinase that acts as cell-surface receptor for fibroblast growth factors and plays an essential role in the regulation of embryonic development, cell proliferation, differentiation ...
Gene Name: FGFR1
Uniprot ID: P11362
Uniprot Name: Fibroblast growth factor receptor 1
Molecular Weight: 91866.935 Da

References

Sootome H, Fujita H, Ito K, Ochiiwa H, Fujioka Y, Ito K, Miura A, Sagara T, Ito S, Ohsawa H, Otsuki S, Funabashi K, Yashiro M, Matsuo K, Yonekura K, Hirai H: Futibatinib Is a Novel Irreversible FGFR 1-4 Inhibitor That Shows Selective Antitumor Activity against FGFR-Deregulated Tumors. Cancer Res. 2020 Nov 15;80(22):4986-4997. doi: 10.1158/0008-5472.CAN-19-2568. Epub 2020 Sep 24. [Article]
FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]

Details2. Fibroblast growth factor receptor 2

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Protein tyrosine kinase activity
Specific Function: Tyrosine-protein kinase that acts as cell-surface receptor for fibroblast growth factors and plays an essential role in the regulation of cell proliferation, differentiation, migration and apoptosi...
Gene Name: FGFR2
Uniprot ID: P21802
Uniprot Name: Fibroblast growth factor receptor 2
Molecular Weight: 92024.29 Da

References

Sootome H, Fujita H, Ito K, Ochiiwa H, Fujioka Y, Ito K, Miura A, Sagara T, Ito S, Ohsawa H, Otsuki S, Funabashi K, Yashiro M, Matsuo K, Yonekura K, Hirai H: Futibatinib Is a Novel Irreversible FGFR 1-4 Inhibitor That Shows Selective Antitumor Activity against FGFR-Deregulated Tumors. Cancer Res. 2020 Nov 15;80(22):4986-4997. doi: 10.1158/0008-5472.CAN-19-2568. Epub 2020 Sep 24. [Article]
FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]

Details3. Fibroblast growth factor receptor 3

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Protein tyrosine kinase activity
Specific Function: Tyrosine-protein kinase that acts as cell-surface receptor for fibroblast growth factors and plays an essential role in the regulation of cell proliferation, differentiation and apoptosis. Plays an...
Gene Name: FGFR3
Uniprot ID: P22607
Uniprot Name: Fibroblast growth factor receptor 3
Molecular Weight: 87708.905 Da

References

Sootome H, Fujita H, Ito K, Ochiiwa H, Fujioka Y, Ito K, Miura A, Sagara T, Ito S, Ohsawa H, Otsuki S, Funabashi K, Yashiro M, Matsuo K, Yonekura K, Hirai H: Futibatinib Is a Novel Irreversible FGFR 1-4 Inhibitor That Shows Selective Antitumor Activity against FGFR-Deregulated Tumors. Cancer Res. 2020 Nov 15;80(22):4986-4997. doi: 10.1158/0008-5472.CAN-19-2568. Epub 2020 Sep 24. [Article]
FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]

Details4. Fibroblast growth factor receptor 4

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Protein tyrosine kinase activity
Specific Function: Tyrosine-protein kinase that acts as cell-surface receptor for fibroblast growth factors and plays a role in the regulation of cell proliferation, differentiation and migration, and in regulation o...
Gene Name: FGFR4
Uniprot ID: P22455
Uniprot Name: Fibroblast growth factor receptor 4
Molecular Weight: 87953.535 Da

References

Sootome H, Fujita H, Ito K, Ochiiwa H, Fujioka Y, Ito K, Miura A, Sagara T, Ito S, Ohsawa H, Otsuki S, Funabashi K, Yashiro M, Matsuo K, Yonekura K, Hirai H: Futibatinib Is a Novel Irreversible FGFR 1-4 Inhibitor That Shows Selective Antitumor Activity against FGFR-Deregulated Tumors. Cancer Res. 2020 Nov 15;80(22):4986-4997. doi: 10.1158/0008-5472.CAN-19-2568. Epub 2020 Sep 24. [Article]
FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]

Enzymes

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: No
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

FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]

Details2. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

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

FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]

Details3. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

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

FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Binder

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]

Details2. Alpha-1-acid glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Binder

General Function: Not Available
Specific Function: Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name: ORM1
Uniprot ID: P02763
Uniprot Name: Alpha-1-acid glycoprotein 1
Molecular Weight: 23511.38 Da

References

FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]

Transporters

Details1. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: No
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

FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]

Details2. ATP-binding cassette sub-family G member 2

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Xenobiotic-transporting atpase activity
Specific Function: High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name: ABCG2
Uniprot ID: Q9UNQ0
Uniprot Name: ATP-binding cassette sub-family G member 2
Molecular Weight: 72313.47 Da

References

FDA Approved Drug Products: LYTGOBI (futibatinib) tablets, for oral use [Link]

Drug created at May 20, 2019 14:54 / Updated at August 19, 2023 10:38

Futibatinib

Identification

Structure for Futibatinib (DB15149)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

Enzymes

References

References

References

Carriers

References

References

Transporters

References

References