Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H26FN6O9P |
Molecular Weight | 580.4595 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(NC2=NC=C(F)C(NC3=NC4=C(OC(C)(C)C(=O)N4COP(O)(O)=O)C=C3)=N2)=CC(OC)=C1OC
InChI
InChIKey=GKDRMWXFWHEQQT-UHFFFAOYSA-N
InChI=1S/C23H26FN6O9P/c1-23(2)21(31)30(11-38-40(32,33)34)20-14(39-23)6-7-17(28-20)27-19-13(24)10-25-22(29-19)26-12-8-15(35-3)18(37-5)16(9-12)36-4/h6-10H,11H2,1-5H3,(H2,32,33,34)(H2,25,26,27,28,29)
Molecular Formula | C23H26FN6O9P |
Molecular Weight | 580.4595 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Fostamatinib is a pro-drug of a Syk inhibitor R406 initially developed by Rigel Pharmaceuticals, but then in-licensed by AstraZeneca. It reached phase III of clinical trials for such diseases as Rheumatoid Arthritis and Immune Thrombocytopenic Purpura, however, AstraZeneca decided not to proceed with regulatory filings and return the rights to the compound to Rigel Pharmaceuticals. In 2018 the drug was approved by the FDA for treatment of chronic immune thrombocytopenia. Fostamatinib is being developed for Autoimmune Hemolytic Anemia (phase II), graft versus host disease (phase I) and ovarian cancer (phase I).
CNS Activity
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209299Orig1s000MultidisciplineR.pdf
Curator's Comment: Non CNS penetrant in rats
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2599 |
41.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Tavalisse Approved UseTAVALISSE is a kinase inhibitor indicated for the treatment of thrombocytopenia in adult patients with chronic immune thrombocytopenia (ITP) who have had an insufficient response to a previous treatment. Launch Date2018 |
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Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
605 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23190017 |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
R406 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6490 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23190017 |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
R406 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
17.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23190017 |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
R406 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
Other AEs: Lymphopenia, Hypertension... Other AEs: Lymphopenia (grade 3-5, 14%) Sources: Hypertension (grade 3-5, 29%) Aspartate aminotransferase increased (grade 3-5, 14%) Alkaline phosphatase increased (grade 3-5, 29%) Hyperbilirubinemia (grade 3-5, 14%) Anemia (grade 1-2, 29%) Leukopenia (grade 1-2, 57%) Neutropenia (grade 1-2, 14%) Thrombocytopenia (grade 1-2, 29%) Diarrhea (grade 1-2, 14%) Fatigue (grade 1-2, 14%) ALT increased (grade 1-2, 71%) |
260 mg 1 times / day multiple, oral (median) Dose: 260 mg, 1 times / day Route: oral Route: multiple Dose: 260 mg, 1 times / day Sources: Page: p. 166 |
unhealthy, 53.5 years (range: 20 - 88 years) n = 102 Health Status: unhealthy Age Group: 53.5 years (range: 20 - 88 years) Sex: M+F Population Size: 102 Sources: Page: p. 166 |
Disc. AE: Abdominal pain, ALT increased... AEs leading to discontinuation/dose reduction: Abdominal pain (1%) Sources: Page: p. 166ALT increased (1%) Chest pain (1%) Headache (1%) Neutropenia (1%) Pneumonia (1%) Plasma cell myeloma (1%) Syncope (1%) Thrombocytopenia (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Diarrhea | grade 1-2, 14% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
Fatigue | grade 1-2, 14% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
Neutropenia | grade 1-2, 14% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
Anemia | grade 1-2, 29% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
Thrombocytopenia | grade 1-2, 29% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
Leukopenia | grade 1-2, 57% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
ALT increased | grade 1-2, 71% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
Aspartate aminotransferase increased | grade 3-5, 14% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
Hyperbilirubinemia | grade 3-5, 14% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
Lymphopenia | grade 3-5, 14% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
Alkaline phosphatase increased | grade 3-5, 29% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
Hypertension | grade 3-5, 29% | 200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 34-82 years n = 7 Health Status: unhealthy Age Group: 34-82 years Sex: M+F Population Size: 7 Sources: |
ALT increased | 1% Disc. AE |
260 mg 1 times / day multiple, oral (median) Dose: 260 mg, 1 times / day Route: oral Route: multiple Dose: 260 mg, 1 times / day Sources: Page: p. 166 |
unhealthy, 53.5 years (range: 20 - 88 years) n = 102 Health Status: unhealthy Age Group: 53.5 years (range: 20 - 88 years) Sex: M+F Population Size: 102 Sources: Page: p. 166 |
Abdominal pain | 1% Disc. AE |
260 mg 1 times / day multiple, oral (median) Dose: 260 mg, 1 times / day Route: oral Route: multiple Dose: 260 mg, 1 times / day Sources: Page: p. 166 |
unhealthy, 53.5 years (range: 20 - 88 years) n = 102 Health Status: unhealthy Age Group: 53.5 years (range: 20 - 88 years) Sex: M+F Population Size: 102 Sources: Page: p. 166 |
Chest pain | 1% Disc. AE |
260 mg 1 times / day multiple, oral (median) Dose: 260 mg, 1 times / day Route: oral Route: multiple Dose: 260 mg, 1 times / day Sources: Page: p. 166 |
unhealthy, 53.5 years (range: 20 - 88 years) n = 102 Health Status: unhealthy Age Group: 53.5 years (range: 20 - 88 years) Sex: M+F Population Size: 102 Sources: Page: p. 166 |
Headache | 1% Disc. AE |
260 mg 1 times / day multiple, oral (median) Dose: 260 mg, 1 times / day Route: oral Route: multiple Dose: 260 mg, 1 times / day Sources: Page: p. 166 |
unhealthy, 53.5 years (range: 20 - 88 years) n = 102 Health Status: unhealthy Age Group: 53.5 years (range: 20 - 88 years) Sex: M+F Population Size: 102 Sources: Page: p. 166 |
Neutropenia | 1% Disc. AE |
260 mg 1 times / day multiple, oral (median) Dose: 260 mg, 1 times / day Route: oral Route: multiple Dose: 260 mg, 1 times / day Sources: Page: p. 166 |
unhealthy, 53.5 years (range: 20 - 88 years) n = 102 Health Status: unhealthy Age Group: 53.5 years (range: 20 - 88 years) Sex: M+F Population Size: 102 Sources: Page: p. 166 |
Plasma cell myeloma | 1% Disc. AE |
260 mg 1 times / day multiple, oral (median) Dose: 260 mg, 1 times / day Route: oral Route: multiple Dose: 260 mg, 1 times / day Sources: Page: p. 166 |
unhealthy, 53.5 years (range: 20 - 88 years) n = 102 Health Status: unhealthy Age Group: 53.5 years (range: 20 - 88 years) Sex: M+F Population Size: 102 Sources: Page: p. 166 |
Pneumonia | 1% Disc. AE |
260 mg 1 times / day multiple, oral (median) Dose: 260 mg, 1 times / day Route: oral Route: multiple Dose: 260 mg, 1 times / day Sources: Page: p. 166 |
unhealthy, 53.5 years (range: 20 - 88 years) n = 102 Health Status: unhealthy Age Group: 53.5 years (range: 20 - 88 years) Sex: M+F Population Size: 102 Sources: Page: p. 166 |
Syncope | 1% Disc. AE |
260 mg 1 times / day multiple, oral (median) Dose: 260 mg, 1 times / day Route: oral Route: multiple Dose: 260 mg, 1 times / day Sources: Page: p. 166 |
unhealthy, 53.5 years (range: 20 - 88 years) n = 102 Health Status: unhealthy Age Group: 53.5 years (range: 20 - 88 years) Sex: M+F Population Size: 102 Sources: Page: p. 166 |
Thrombocytopenia | 1% Disc. AE |
260 mg 1 times / day multiple, oral (median) Dose: 260 mg, 1 times / day Route: oral Route: multiple Dose: 260 mg, 1 times / day Sources: Page: p. 166 |
unhealthy, 53.5 years (range: 20 - 88 years) n = 102 Health Status: unhealthy Age Group: 53.5 years (range: 20 - 88 years) Sex: M+F Population Size: 102 Sources: Page: p. 166 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.ema.europa.eu/en/documents/product-information/tavlesse-epar-product-information_en.pdf#page=8 Page: (EMA product info) 8 |
no | |||
Sources: https://www.ema.europa.eu/en/documents/product-information/tavlesse-epar-product-information_en.pdf#page=8 Page: (EMA product info) 8 |
no | |||
yes | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209299Orig1s000MultidisciplineR.pdf#page=79 Page: 68, 78 |
yes | no (co-administration study) Comment: Coadministration of fostamatinib (100 mg BID x 8 days) decreased mean Cmax of pioglitazone and hydroxypioglitazone by 117% and 9%. The mean AUC was increased by 18% and decreased 10% for pioglitazone (AUC(0-inf)) and hydroxypioglitazone (AUC(0-48hr)), respectively. No dose modification of fostamatinib is needed when co-administering with CYP2C8 substrates. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209299Orig1s000MultidisciplineR.pdf#page=79 Page: 68, 78 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209299Orig1s000MultidisciplineR.pdf#page=69 Page: 68, 78-79 |
yes | yes (co-administration study) Comment: Coadministration of fostamatinib (100 mg BID x 9 days) increased mean rosuvastatin (20 mg on Day 6) Cmax by 88% and mean AUC(0-inf) by 96%. Monitor for toxicities that may require dosage reduction of BCRP substrates (such as, rosuvastatin) when co-administering with fostamatinib. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209299Orig1s000MultidisciplineR.pdf#page=69 Page: 68, 78-79 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209299Orig1s000MultidisciplineR.pdf#page=78 Page: 68, 77-78 |
yes | yes (co-administration study) Comment: Coadministration of fostamatinib (100 mg BID x 6 days) increased mean midazolam (7.5 mg on Day 7) Cmax by 9% and mean AUC(0-inf) by 25%. Coadministration of fostamatinib (100 mg BID x 7 days) increased mean Cmax of simvastatin (40mg on Day 6) and simvastatin acid by 113% and 83% and mean AUC(0-inf) by 64% and 66%. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209299Orig1s000MultidisciplineR.pdf#page=78 Page: 68, 77-78 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209299Orig1s000MultidisciplineR.pdf#page=80 Page: 68, 79 |
yes | yes (co-administration study) Comment: Coadministration of fostamatinib (100 mg BID on Day 9 to Day 15) increased mean Cmax,ss of digoxin (a loading dose of 0.25 mg BID on Day 1 and 0.25 mg QD on Day 2 to Day 15) by 70% and mean AUCss by 37%. Monitor for toxicities that may require dosage reduction of P-gp substrates (such as, digoxin) when co-administering with fostamatinib. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209299Orig1s000MultidisciplineR.pdf#page=80 Page: 68, 79 |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
major | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209299Orig1s000MultidisciplineR.pdf#page=76 Page: 64, 68, 75, 76 |
major | yes (co-administration study) Comment: The AUC(0-inf) and Cmax of R406 (Fostamatinib 80mg, 2 hr after the 2nd dose of ketoconazole) was increased by 102% and 37% when fostamatinib was co-administered with ketoconazole (200 mg BID x 7 days, strong CYP3A4 inhibitor). The mean terminal t1/2 increased from 14 hr to 18 hr. Co-administration of verapamil (80 mg TID x 4 days, moderate CYP3A4 inhibitor) increased mean Cmax of R406 (fostamatinib 150 mg on the 2nd day w/verapamil) by 6% and mean AUC(0-inf) by 39%. The mean terminal t1/2 increased from 14 hours to 19 hours. Avoid concomitant use of strong CYP3A inducer due to the concern of loss of efficacy as the mean AUC(0-inf) of R406 (fostamatinib 150 mg on Day 6) was decreased by 75% and Cmax by 59% when fostamatinib was co-administration with rifampicin (600 mg QD x 8 days, strong CYP3A4 inducer). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209299Orig1s000MultidisciplineR.pdf#page=76 Page: 64, 68, 75, 76 |
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Page: 13.0 |
no | |||
Page: 13.0 |
no | |||
Page: 13.0 |
no | |||
Page: 13.0 |
no | |||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
R406, an orally available spleen tyrosine kinase inhibitor blocks fc receptor signaling and reduces immune complex-mediated inflammation. | 2006 Dec |
|
Metabolism of fostamatinib, the oral methylene phosphate prodrug of the spleen tyrosine kinase inhibitor R406 in humans: contribution of hepatic and gut bacterial processes to the overall biotransformation. | 2010 Jul |
Patents
Sample Use Guides
Rheumatoid Arthritis: 100 mg twice daily or 150 mg once daily. Immune Thrombocytopenic Purpura: 100 mg or 150 mg twice daily for 24 weeks. IGA Nephropathy: 100 mg or 150 mg twice daily for 15 months. Autoimmune Hemolytic Anemia: 100 mg or 150 mg twice daily for 12 weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23284223
In primary human B cells, active metabolite of fostamatinib, R406, inhibited CD69 up-regulation in response to anti-IgM with an EC50 of 48 nM. EC50 for IgE-induced degranulation of primary human mast cells in vitro was 56 nM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:37:04 GMT 2023
by
admin
on
Fri Dec 15 16:37:04 GMT 2023
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Record UNII |
SQ8A3S5101
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Record Status |
Validated (UNII)
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B02BX09
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FDA ORPHAN DRUG |
544516
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NCI_THESAURUS |
C1967
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CHEMBL2103830
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
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METABOLIC ENZYME -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE ACTIVE -> PRODRUG |
MAJOR
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
PLASMA
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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DOSE |
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