1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl)-N-methylmethanamine: a proton pump inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 15981397 |
| CHEMBL ID | 2079130 |
| CHEBI ID | 136048 |
| SCHEMBL ID | 194487 |
| MeSH ID | M000609957 |
| Synonym |
|---|
| CHEBI:136048 |
| vonoprazan |
| 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl)-n-methylmethanamine |
| who 9535 |
| 1r5l3j156g , |
| 1-(5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1h-pyrrol-3-yl)-n-methylmethanamine |
| vonoprazan [usan:inn] |
| unii-1r5l3j156g |
| 1h-pyrrole-3-methanamine, 5-(2-fluorophenyl)-n-methyl-1-(3-pyridinylsulfonyl)- |
| vonoprazan [usan] |
| vonoprazan [inn] |
| 881681-00-1 |
| SCHEMBL194487 |
| vonoprazan [mi] |
| vonoprazan [who-dd] |
| CHEMBL2079130 |
| CS-5555 |
| HY-100007 |
| tak-438 (free base) |
| DTXSID20236869 , |
| 1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]-n-methylmethanamine |
| HKT , |
| 1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonyl-pyrrol-3-yl]-~{n}-methyl-methanamine |
| (5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl)-n-methylmethanamine |
| 1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl]-n-methylmethanamine |
| 881681-00-1 (free base) |
| NCGC00386236-05 |
| AKOS030632802 |
| tak-438 free base |
| DB11739 |
| vonoprazan; tak-438 free base |
| 5-(2-fluorophenyl)-n-methyl-1-(3-pyridinylsulfonyl)-1h-pyrrole-3-methanamine |
| Q27887191 |
| vonoprazan free base |
| DS-19419 |
| bdbm394392 |
| us10308605, example 166 |
| EX-A4002 |
| tak-438;tak 438;tak438 |
| BCP13240 |
| SB16719 |
| vonoprazan (usan/inn) |
| D11784 |
| NCGC00386236-02 |
| voquezna® |
| compound 13e [pmid: 22512618] |
| gtpl11549 |
| EN300-7360476 |
| {[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1h-pyrrol-3-yl]methyl}(methyl)amine |
| GLXC-25655 |
| AC-36443 |
| vonoprazanum |
| dtxcid00159360 |
| a02bc08 |
Vonoprazan is a potassium competitive acid blocker (P-CAB) approved in Japan in 2014 to treat endoscopic submucosal dissection (ESD)-induced ulcers and bleeding or perforation. When combined with antibiotics has been used to eradicate Helicobacter pylori (H.pylori) infection.
Vonoprazan 20 mg has a similar tolerability profile to lansoprazole 30 mg and is non-inferior with respect to GU healing and has similar efficacy for DU healing.
Vonoprazan (VON) has been approved recently via US-FDA in 2015 as the first in class of potassium competitive acid blocker group. Vonoprazin has been widely used for H and is an alternative to proton-pump inhibitors (PPIs)
Vonoprazan can produce reversible hyperplastic polyps and anemia. It has a lower post-ESD bleeding rate than PPIs.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Vonoprazan can produce reversible hyperplastic polyps and anemia." | ( Long-term vonoprazan administration causes gastric fundic gland-type hyperplastic polyps and chronic bleeding. Akizue, N; Goto, C; Kato, J; Kato, N; Matsumura, T; Matsusaka, K; Ohta, Y; Okimoto, K; Saito, K; Taida, T, 2023) | 2.03 |
| "Vonoprazan has a lower post-ESD bleeding rate than PPIs. " | ( Vonoprazan versus proton pump inhibitors for postendoscopic submucosal dissection bleeding in the stomach: a multicenter population-based comparative study. Arai, M; Fukuda, K; Hasatani, K; Honda, T; Ikeya, T; Ishii, N; Kawai, T; Kiyotoki, S; Niikura, R; Nishida, T; Shiratori, Y; Sumiyoshi, T; Yoshida, N, 2022) | 3.61 |
Vonoprazan treatment significantly decreased scores of FSSG, nighttime symptom, and Athens Insomnia Scale. Treatment with vonopraza favorably affects gastrointestinal symptoms in patients with GERD. VonoprazAn treatment might be appropriate as a promising new strategy for PPI-refractoryGERD.
Oral vonoprazan treatment showed no significant increase in the incidence of adverse effects. For the rate of adverse events, there was no significant difference among all the PPIs and placebo. The incidences of treatment-emergent adverse events were slightly lower for GU than with lansoprazole.
Pharmacokinetic parameters for vonoprazan, amoxicillin, clarithromycin and metronidazole in single therapy or triple therapies were assessed. Clinicians should pay attention to the resulting changes in pharmacokinetics parameters and accordingly, adjust the dose of vonoprizan in clinical settings.
No clinically meaningful drug-drug interactions were observed. Vonoprazan was well tolerated when administered with LDA or NSAIDs. A tiered approach was applied to understand the CYP3A victim and perpetrator drug-Drug interaction (DDI) potential.
Vonoprazan (Takecab(®) is an orally bioavailable potassium-competitive acid blocker (P-CAB) Being developed by Takeda for the treatment and prevention of acid-related diseases.
This study aimed to evaluate the efficacy and safety of 10-day vonoprazan-amoxicillin dual therapy as a first-line treatment of Helicobacter pylori infection. The aim was to explore the optimal dosage of amoxicillin in the dual therapy.
| Class | Description |
|---|---|
| pyrroles | An azole that includes only one N atom and no other heteroatom as a part of the aromatic skeleton. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| cytochrome P450 family 3 subfamily A polypeptide 4 | Homo sapiens (human) | Potency | 1.0684 | 0.0123 | 7.9835 | 43.2770 | AID1645841 |
| cytochrome P450 2D6 | Homo sapiens (human) | Potency | 18.9991 | 0.0010 | 8.3798 | 61.1304 | AID1645840 |
| Spike glycoprotein | Severe acute respiratory syndrome-related coronavirus | Potency | 39.8107 | 0.0096 | 10.5250 | 35.4813 | AID1479145 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| virion membrane | Spike glycoprotein | Severe acute respiratory syndrome-related coronavirus |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1347159 | Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1347160 | Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1910980 | Inhibition of N-terminal Flag-GFP-TEV site-Met48 recombinant pig gastric H(+)/K(+) ATPase alpha/beta subunit in HEK293 cells by colorimetric microplate reader | 2022 | Journal of medicinal chemistry, 06-09, Volume: 65, Issue:11 | Structural Basis for Binding of Potassium-Competitive Acid Blockers to the Gastric Proton Pump. |
| AID1891804 | Half life in Sprague-Dawley rat at 0.75 mg/kg, iv measured up to 24 hrs | |||
| AID1891802 | Inhibition of gastric acid secretion in histamine induced Sprague-Dawley rat at 1 mg/kg, iv pretreated with compound for 15 mins followed by histamine dihydrochloride injection and measured after 3 hrs | |||
| AID1891808 | Oral bioavailability in Sprague-Dawley rat at 2 mg/kg | |||
| AID1891805 | AUC (0 to infinity) in Sprague-Dawley rat at 2 mg/kg, po | |||
| AID1891807 | Cmax in Sprague-Dawley rat at 2 mg/kg, po | |||
| AID1466557 | Dissociation constant, pKa of the compound | 2017 | Bioorganic & medicinal chemistry, 07-01, Volume: 25, Issue:13 | Identification of a novel fluoropyrrole derivative as a potassium-competitive acid blocker with long duration of action. |
| AID1891806 | Half life in Sprague-Dawley rat at 2 mg/kg, po | |||
| AID1891801 | Inhibition of rabbit stomach K+ stimulated H(+)/K(+) ATPase activity incubated for 30 mins in presence of ATP and KCl by malachite green reagent based assay | |||
| AID1466558 | Lipophilicity, log D of the compound at pH 7.4 by HPLC analysis | 2017 | Bioorganic & medicinal chemistry, 07-01, Volume: 25, Issue:13 | Identification of a novel fluoropyrrole derivative as a potassium-competitive acid blocker with long duration of action. |
| AID1891803 | AUC (0 to infinity) in Sprague-Dawley rat at 0.75 mg/kg, iv measured up to 24 hrs | |||
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 0 (0.00) | 29.6817 |
| 2010's | 137 (46.13) | 24.3611 |
| 2020's | 160 (53.87) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.
| This Compound (88.05) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 78 (26.09%) | 5.53% |
| Reviews | 53 (17.73%) | 6.00% |
| Case Studies | 15 (5.02%) | 4.05% |
| Observational | 8 (2.68%) | 0.25% |
| Other | 145 (48.49%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||