General Information of Drug (ID: DR3419)
Drug Name
Fruquintinib
Synonyms HMPL-013
Indication Solid tumour/cancer [ICD11: 2A00-2F9Z] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 393.4 Topological Polar Surface Area 95.7
Heavy Atom Count 29 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
44480399
CAS Number
1194506-26-7
TTD Drug ID
D03JTG
Formula
C21H19N3O5
Canonical SMILES
CC1=C(C2=C(O1)C=C(C=C2)OC3=NC=NC4=CC(=C(C=C43)OC)OC)C(=O)NC
InChI
InChI=1S/C21H19N3O5/c1-11-19(20(25)22-2)13-6-5-12(7-16(13)28-11)29-21-14-8-17(26-3)18(27-4)9-15(14)23-10-24-21/h5-10H,1-4H3,(H,22,25)
InChIKey
BALLNEJQLSTPIO-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
M205 DM019450 N. A. Unclear - Unclear 1 [3]
M379-1 DM019439 N. A. Unclear - Unclear 1 [4] , [2]
M379-2 DM019441 N. A. Oxidation - O-desmethylation 1 [5]
M380 DM019448 N. A. Unclear - Unclear 1 [6]
M409-1 DM019454 N. A. Unclear - Unclear 1 [7] , [2]
M409-2 DM019443 N. A. Oxidation - Mono-oxidation 1 [8] , [2]
M409-3 DM019434 N. A. Oxidation - Mono-oxidation 1 [9]
M409-4 DM019453 N. A. Oxidation - Mono-oxidation 1 [10] , [2]
M285 DM019451 N. A. Conjugation - Sulfation 2 [11]
M365-1 DM019437 N. A. Unclear - Unclear 2 [12]
M365-1 DM019437 N. A. Unclear - Unclear 2 [13]
M365-2/3 DM019436 N. A. Unclear - Unclear 2 [14]
M365-2/3 DM019436 N. A. Unclear - Unclear 2 [15]
M379 DM019435 N. A. Oxidation - Mono-oxidation 2 [16]
M381 DM019452 N. A. Conjugation - Glucuronidation 2 [17]
M395-1 DM019446 N. A. Unclear - Unclear 2 [18]
M425-2 DM019444 N. A. Unclear - Unclear 2 [19]
M555-1 DM019440 N. A. Unclear - Unclear 2 [20]
M555-2 DM019442 N. A. Unclear - Unclear 2 [21]
M556 DM019449 N. A. Unclear - Unclear 2 [22]
M585 DM019447 N. A. Unclear - Unclear 2 [23]
M351 DM019438 N. A. Unclear - Unclear 3 [24]
M351 DM019438 N. A. Unclear - Unclear 3 [25]
M365-1 DM019437 N. A. Unclear - Unclear 3 [26]
M365-1 DM019437 N. A. Unclear - Unclear 3 [27]
M365-2/3 DM019436 N. A. Unclear - Unclear 3 [28]
M395-2 DM019445 N. A. Unclear - Unclear 3 [29]
M351 DM019438 N. A. Unclear - Unclear 4 [30]
M351 DM019438 N. A. Unclear - Unclear 4 [31]
M365-1 DM019437 N. A. Unclear - Unclear 4 [32]
M351 DM019438 N. A. Unclear - Unclear 5 [33]
⏷ Show the Full List of 31  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012010 Fruquintinib M409-3 Oxidation - Mono-oxidation Unclear [9]
MR012015 Fruquintinib M379-1 Unclear - Unclear CYP3A4 ... [4], [2]
MR012019 Fruquintinib M379-2 Oxidation - O-desmethylation Unclear [5]
MR012023 Fruquintinib M409-2 Oxidation - Mono-oxidation CYP3A4 ... [8], [2]
MR012028 Fruquintinib M380 Unclear - Unclear Unclear [6]
MR012030 Fruquintinib M205 Unclear - Unclear Unclear [3]
MR012033 Fruquintinib M409-4 Oxidation - Mono-oxidation CYP3A4 ... [10], [2]
MR012034 Fruquintinib M409-1 Unclear - Unclear CYP3A4 ... [7], [2]
MR012031 M205 M285 Conjugation - Sulfation Unclear [11]
MR012032 M205 M381 Conjugation - Glucuronidation Unclear [17]
MR012016 M379-1 M365-2/3 Unclear - Unclear Unclear [15]
MR012017 M379-1 M365-1 Unclear - Unclear Unclear [13]
MR012018 M379-1 M555-1 Unclear - Unclear Unclear [20]
MR012020 M379-2 M365-2/3 Unclear - Unclear Unclear [14]
MR012021 M379-2 M365-1 Unclear - Unclear Unclear [12]
MR012022 M379-2 M555-2 Unclear - Unclear Unclear [21]
MR012029 M380 M556 Unclear - Unclear Unclear [22]
MR012024 M409-2 M425-2 Unclear - Unclear Unclear [19]
MR012026 M409-2 M395-1 Unclear - Unclear Unclear [18]
MR012027 M409-2 M585 Unclear - Unclear Unclear [23]
MR012011 M409-3 M379 Oxidation - Mono-oxidation Unclear [16]
MR012012 M379 M365-2/3 Unclear - Unclear Unclear [28]
MR012025 M425-2 M395-2 Unclear - Unclear Unclear [29]
MR012013 M365-2/3 M365-1 Unclear - Unclear Unclear [32]
MR012014 M365-1 M351 Unclear - Unclear Unclear [33]
⏷ Show the Full List of 25 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 ClinicalTrials.gov (NCT02314819) A Phase III Trial Evaluating Fruquintinib Efficacy and Safety in 3+ Line Colorectal Cancer Patients RESCO). U.S. National Institutes of Health.
2 Preclinical pharmacokinetics and disposition of a novel selective VEGFR inhibitor fruquintinib (HMPL-013) and the prediction of its human pharmacokinetics
3 Locus coeruleus neuronal activity correlates with behavioral response to acute and chronic doses of methylphenidate (Ritalin) in adolescent rats
4 Incarceration of the medial collateral ligament in the intercondylar notch following proximal avulsion
5 Internal resources among informal caregivers: trajectories and associations with well-being
6 Spontaneous thrombosis of a giant cerebral varix in a pediatric patient
7 Esophageal bezoar due to karaya gum granules used as a laxative
8 A simple and rapid infrared-assisted self enzymolysis extraction method for total flavonoid aglycones extraction from Scutellariae Radix and mechanism exploration
9 A phase I study to investigate the metabolism, excretion, and pharmacokinetics of [(14)C]fruquintinib, a novel oral selective VEGFR inhibitor, in healthy Chinese male volunteers
10 Management of postoperative junctional ectopic tachycardia in pediatric patients: a survey of 30 centers in Germany, Austria, and Switzerland
11 Assessment of hepatitis B virus antibody titers in childhood cancer survivors
12 Disposable electrochemical immunosensor for Brettanomyces bruxellensis based on nanogold-reduced graphene oxide hybrid nanomaterial
13 Prophylactic etanercept treatment in cisplatin ototoxicity
14 Exhaled breath online measurement for cervical cancer patients and healthy subjects by proton transfer reaction mass spectrometry
15 Early computed tomography or focused assessment with sonography in abdominal trauma: what are the leading opinions?
16 Electrolyte disorders with platinum-based chemotherapy: mechanisms, manifestations and management
17 Renal function in neonates with twin-twin transfusion syndrome treated with or without fetoscopic laser surgery
18 Hydrophilic interaction liquid chromatography-tandem mass spectrometry for quantitation of paralytic shellfish toxins: validation and application to reference materials
19 Optical biosensor optimized for continuous in-line glucose monitoring in animal cell culture
20 Biopsychosocial factors predict quality of life in thoracolumbar spine surgery
21 TLC surface integrity affects the detection of alkali adduct ions in TLC-MALDI analysis
22 Comparison of Nellcor? PM1000N and Masimo Radical-7(?) for detecting apnea in volunteers
23 Derivatization-free LC-MS/MS method for estrogen quantification in mouse brain highlights a local metabolic regulation after oral versus subcutaneous administration
24 Experiences and benefits of a career development course for undergraduate chemistry students
25 Health-related quality of life in paediatric patients with congenital heart defects: association with the type of heart defect and the surgical technique
26 Novel ribonuclease activity of cusativin from Cucumis sativus for mapping nucleoside modifications in RNA
27 Trauma to the bladder and ureter: a review of diagnosis, management, and prognosis
28 Efficacy and safety of taxane monotherapy in advanced gastric cancer refractory to triplet chemotherapy with docetaxel, cisplatin, and S-1: a multicenter retrospective study
29 Aptamer-based fluorescence-quenching lateral flow strip for rapid detection of mercury (II) ion in water samples
30 Self-assembly of the polymer brush-grafted silica colloidal?array for recognition of proteins
31 #N/A
32 Clinical predictors of survival in patients with castration-resistant prostate cancer receiving sipuleucel-T cellular immunotherapy
33 Two-year follow-up study of subchondral surface irregularities of the capitellum on ultrasonography in baseball players under the age of 10 years

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