Identification
- Summary
Baloxavir marboxil is a polymerase acidic endonuclease inhibitor used to treat uncomplicated influenza.
- Brand Names
- Xofluza
- Generic Name
- Baloxavir marboxil
- DrugBank Accession Number
- DB13997
- Background
Baloxavir marboxil is an antiviral drug used to treat influenza. More specifically, it is a first-in-class cap-dependent endonuclease inhibitor that works to block influenza virus proliferation.2,3 It is a prodrug of baloxavir 6 with an improved absorption profile than its active metabolite due to the addition of a phenolic hydroxyl group to its structure.4 Baloxavir marboxil was first globally approved in Japan in February 2018,2 followed by the US approval in October, 2018.5 It was also approved by the European Commission on January 7, 2021.8
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Baloxavir marboxil (DB13997)
- Weight
- Average: 571.55
Monoisotopic: 571.122477593 - Chemical Formula
- C27H23F2N3O7S
- Synonyms
- Baloxavir marboxil
- External IDs
- S-033188
Pharmacology
- Indication
Baloxavir marboxil is an influenza virus polymerase acidic (PA) endonuclease inhibitor indicated for the treatment of acute uncomplicated influenza in patients who have been symptomatic for no more than 48 hours and who are otherwise healthy adults and pediatric patients five years of age and older, or patients 12 years of age and older who are at high risk of developing influenza-related complications.6
The drug is also indicated for post-exposure prophylaxis of influenza in patients five years of age and older following contact with an individual who has influenza.6 In Europe, it is approved for use in patients aged one year and above for these indications.8
Baloxavir marboxil is associated with a risk for loss of efficacy due to changes in influenza virus such as changes in virus subtypes, emergence of virus resistance, and changes in viral virulence; therefore, the drug should be used after considering available information on drug susceptibility patterns for circulating influenza virus strains.6
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- Contraindications & Blackbox Warnings
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Baloxavir marboxil is an antiviral drug that works against influenza virus to block viral replication. It has an 50% inhibitory concentration (IC50) of 1.4 to 3.1 nM for influenza A viruses and 4.5 to 8.9 nM for influenza B viruses in a polymerase acidic (PA) endonuclease assay.6 In murine models of influenza and avian influenza A, baloxavir reduced pulmonary viral loads and increased survival rates of mice.1 The reduction of viral titer was observed within 24 hours of administration, in a dose-dependent manner.2
- Mechanism of action
The influenza virus RNA polymerase complex is a heterotrimer made up of three protein subunits - polymerase basic protein 1 (PB1), polymerase basic protein 2 (PB2), and polymerase acidic protein (PA).1 This polymerase complex is an influenza virus-specific enzyme essential for viral gene transcription and replication,6 with its subunits playing different roles in viral mRNA synthesis. The PB2 subunit binds to the cap of host cellular pre-messenger RNA, allowing the PA protein - a cap-dependent endonuclease - to cleave the capped pre-messenger RNA.1,4 This initial step of mRNA synthesis by the PA protein, also known as the "cap-snatching process," provides an RNA primer for the PB1 subunit, which carries out its RNA-dependent RNA polymerase function to proceed with viral mRNA transcription.1
After administration, the prodrug baloxavir marboxil is almost completely hydrolyzed by esterases in the gastrointestinal lumen, intestinal epithelium, liver and blood 3 to its active metabolite, baloxavir.6 Baloxavir selectively inhibits the PA protein,6 blocking the initiation of mRNA synthesis and ultimately influenza virus proliferation.2 Cap-dependent endonuclease is a highly conserved region across influenza strains;4 however, baloxavir is still vulnerable to resistance because amino acid substitutions in the PA protein can lead to reduced viral susceptibility to baloxavir.6
Target Actions Organism APolymerase acidic protein inhibitorInfluenza A virus (strain A/Puerto Rico/8/1934 H1N1) - Absorption
Following oral administration of 40 mg baloxavir marboxil in adolescents and adults aged 12 years and older, the AUC was 5520 ng x hr/mL and the Cmax was 68.9 ng/mL. Following a 80 mg dose, the the AUC was 6930 ng x hr/mL and the Cmax was 82.5 ng/mL. The Tmax is about four hours. Food decreased Cmax by 48% and AUC0-inf by 36%.6
In pediatric patients aged five to 12 years of age weighing less than 20 kg, the AUCinf was 5830 ng x hr/mL and the Cmax was 148 ng/mL following a 2 mg/kg dose. The AUCinf was 4360 ng x hr/mL and the Cmax was 81.1 ng/mL following a 40 mg dose in pediatric patients who weigh greater than or equal to 20 kg. The Tmax ranged from 3.5 to 4.5 hours.6
- Volume of distribution
The volume of distribution is 1180 L.6
- Protein binding
Baloxavir, the active metabolite, is 92.9–93.9% bound to human serum proteins. The ratio of blood cell to blood is 48.5–54.4%.6
- Metabolism
Baloxavir predominantly undergoes UGT1A3-mediated metabolism to form glucuronic acid conjugate. It is subsequently metabolized by CYP3A4 to form sulfoxide.2,6
Hover over products below to view reaction partners
- Route of elimination
Baloxavir is primarily eliminated by biliary excretion. About 80.1% of the total dose is excreted in feces. About 14.7% of the dose is excreted in urine, where 3.3% of the recovered dose is the unchanged parent drug.6
- Half-life
The apparent terminal elimination half-life of baloxavir is 79.1 hours.6
- Clearance
Clearance of baloxavir is 10.3 L/h.6
- Adverse Effects
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Oral LD50 is >2000 mg/kg in rats.7
There is limited clinical experience with baloxavir overdose. In one ascending single-dose study involving healthy volunteers, up to 80 mg dose of baloxavir was administered without notable safety concerns.1 Treatment of an overdose of baloxavir marboxil should consist of general supportive measures, including monitoring of vital signs and observation of the clinical status of the patient. There is no specific antidote for overdose with baloxavir marboxil. Baloxavir, the active ingredient, is unlikely to be significantly removed by dialysis due to high serum protein binding.6
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
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 Integrate drug-drug
interactions in your softwareAdenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Baloxavir marboxil. Anthrax vaccine The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Baloxavir marboxil. Bacillus calmette-guerin substrain connaught live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Baloxavir marboxil. Bacillus calmette-guerin substrain russian BCG-I live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Baloxavir marboxil. Bacillus calmette-guerin substrain tice live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Baloxavir marboxil. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Baloxavir marboxil. Human adenovirus e serotype 4 strain cl-68578 antigen The therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Baloxavir marboxil. Rubella virus vaccine The therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Baloxavir marboxil. Typhoid Vaccine Live The therapeutic efficacy of Typhoid Vaccine Live can be decreased when used in combination with Baloxavir marboxil. Varicella zoster vaccine (live/attenuated) The therapeutic efficacy of Varicella zoster vaccine (live/attenuated) can be decreased when used in combination with Baloxavir marboxil. 
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- Avoid antacids. Baloxavir may form a chelate with polyvalent cations in antacids, which may decrease plasma concentrations of baloxavir.
- Avoid milk and dairy products. Baloxavir may form a chelate with polyvalent cations such as calcium in dairy products, which may decrease plasma concentrations of baloxavir.
- Avoid multivalent ions. Multivalent ions such as magnesium, calcium, and aluminum can form a chelate with baloxavir, which can reduce the absorption of baloxavir.
- Take with or without food. Food reduces drug absorption, but not to a clinically significant extent.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Active Moieties
Name Kind UNII CAS InChI Key Baloxavir prodrug 4G86Y4JT3F 1985605-59-1 FIDLLEYNNRGVFR-CTNGQTDRSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Xofluza Tablet, film coated 40 mg Oral Roche Registration Gmb H 2022-07-25 Not applicable EU 
Xofluza Tablet, film coated 20 mg Oral Roche Registration Gmb H 2021-01-28 Not applicable EU Xofluza Tablet, film coated 20 mg/1 Oral Genentech, Inc. 2018-10-24 2022-07-31 US 
Xofluza Tablet 20 mg Oral Hoffmann La Roche Not applicable Not applicable Canada 
Xofluza Tablet, film coated 80 mg Oral Roche Registration Gmb H 2022-07-25 Not applicable EU Xofluza Tablet 80 mg Oral Hoffmann La Roche Not applicable Not applicable Canada Xofluza Tablet, film coated 20 mg/1 Oral A-S Medication Solutions 2018-10-24 Not applicable US Xofluza Tablet, film coated 80 mg/1 Oral Genentech, Inc. 2018-10-24 Not applicable US Xofluza Granule 2 mg/ml Oral Roche Registration Gmb H 2023-02-08 Not applicable EU Xofluza Tablet, film coated 40 mg Oral Roche Registration Gmb H 2021-01-28 Not applicable EU
Categories
- ATC Codes
- J05AX25 — Baloxavir marboxil
- Drug Categories
- Anti-Infective Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Baloxavir and prodrugs
- BCRP/ABCG2 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (weak)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (weak)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Direct Acting Antivirals
- Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Oxazines
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Polymerase Acidic Endonuclease Inhibitors
- Pyridines
- Sulfur Compounds
- Thiepins
- UGT1A3 substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dibenzothiepins. These are compounds containing a dibenzothiepin moiety, which consists of two benzene connected by a thiepine ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzothiepins
- Sub Class
- Dibenzothiepins
- Direct Parent
- Dibenzothiepins
- Alternative Parents
- 2-heteroaryl carboxamides / Alkylarylthioethers / Pyridines and derivatives / Morpholines / Carbonic acid diesters / Benzenoids / Aryl fluorides / 1,2,4-triazines / Vinylogous amides / Tertiary carboxylic acid amides show 12 more
- Substituents
- 1,2,4-triazine / 2-heteroaryl carboxamide / Acetal / Alkylarylthioether / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Aryl thioether / Azacycle / Benzenoid show 28 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans
Chemical Identifiers
- UNII
- 505CXM6OHG
- CAS number
- 1985606-14-1
- InChI Key
- RZVPBGBYGMDSBG-GGAORHGYSA-N
- InChI
- InChI=1S/C27H23F2N3O7S/c1-36-27(35)39-14-38-25-19(33)8-9-31-24(25)26(34)30-10-11-37-12-21(30)32(31)23-15-6-7-18(28)22(29)17(15)13-40-20-5-3-2-4-16(20)23/h2-9,21,23H,10-14H2,1H3/t21-,23+/m1/s1
- IUPAC Name
- {[(3R)-2-[(2S)-12,13-difluoro-9-thiatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl]-9,12-dioxo-5-oxa-1,2,8-triazatricyclo[8.4.0.0^{3,8}]tetradeca-10,13-dien-11-yl]oxy}methyl methyl carbonate
- SMILES
- [H][C@@]12COCCN1C(=O)C1=C(OCOC(=O)OC)C(=O)C=CN1N2[C@H]1C2=CC=C(F)C(F)=C2CSC2=CC=CC=C12
References
- General References
- Hayden FG, Sugaya N, Hirotsu N, Lee N, de Jong MD, Hurt AC, Ishida T, Sekino H, Yamada K, Portsmouth S, Kawaguchi K, Shishido T, Arai M, Tsuchiya K, Uehara T, Watanabe A: Baloxavir Marboxil for Uncomplicated Influenza in Adults and Adolescents. N Engl J Med. 2018 Sep 6;379(10):913-923. doi: 10.1056/NEJMoa1716197. [Article]
- Heo YA: Baloxavir: First Global Approval. Drugs. 2018 Apr;78(6):693-697. doi: 10.1007/s40265-018-0899-1. [Article]
- Shirley M: Baloxavir Marboxil: A Review in Acute Uncomplicated Influenza. Drugs. 2020 Jul;80(11):1109-1118. doi: 10.1007/s40265-020-01350-8. [Article]
- Abraham GM, Morton JB, Saravolatz LD: Baloxavir: A Novel Antiviral Agent in the Treatment of Influenza. Clin Infect Dis. 2020 Oct 23;71(7):1790-1794. doi: 10.1093/cid/ciaa107. [Article]
- FDA NEWS RELEASE: FDA Approves New Drug to Treat Influenza [Link]
- FDA Approved Drug Products: XOFLUZA (baloxavir marboxil) tablets or suspension, for oral use (August 2022) [Link]
- Genentech: XOFLUZA (Baloxavir Marboxil) MSDS [Link]
- EMA Approved Drug Products: Xofluza (baloxavir marboxil) Oral Tablets [Link]
- External Links
- KEGG Drug
- D11021
- ChemSpider
- 59718643
- 2099995
- ChEMBL
- CHEMBL4297503
- Wikipedia
- Baloxavir_marboxil
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Flu caused by Influenza / Viral Respiratory Tract Infection 1 3 Completed Treatment Flu caused by Influenza 4 3 Recruiting Treatment Flu caused by Influenza 2 2 Recruiting Treatment Coronavirus Disease 2019 (COVID‑19) / Flu caused by Influenza / Influenza, Human 1 2 Recruiting Treatment Flu caused by Influenza / Hematopoietic and Lymphoid System Neoplasm 1 2, 3 Recruiting Treatment Flu caused by Influenza 1 Not Available Completed Other Healthy Subjects (HS) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Granule Oral 2 mg/ml Granule, for solution Oral 40 mg/1mL Powder 1 kg/1kg Tablet Oral 20 mg Tablet Oral 40 mg Tablet Oral 80 mg Tablet, coated Oral 20 mg Tablet, film coated Oral 20 MG Tablet, film coated Oral 20 mg/1 Tablet, film coated Oral 40 mg/1 Tablet, film coated Oral 40 mg Tablet, film coated Oral 80 mg/1 Tablet, film coated Oral 80 mg Tablet, film coated Oral - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8927710 No 2015-01-06 2031-05-05 US US9815835 No 2017-11-14 2030-06-14 US US8987441 No 2015-03-24 2031-09-21 US US10392406 No 2019-08-27 2036-04-27 US US10633397 No 2020-04-28 2036-04-27 US US10759814 No 2020-09-01 2037-08-09 US US11261198 No 2018-09-25 2038-09-25 US US11306106 No 2017-08-09 2037-08-09 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 0.015 mg/mL https://toku-e.com/content/product-documents/1SDS/B079%20Baloxavir%20Marboxil%20A.0%20CLP.pdf logP 2.26 https://www.accessdata.fda.gov/drugsatfda_docs/label/2022/214410Orig2s000lbl.pdf - Predicted Properties
Property Value Source Water Solubility 0.0412 mg/mL ALOGPS logP 2.12 ALOGPS logP 3.38 Chemaxon logS -4.1 ALOGPS pKa (Strongest Basic) -0.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 97.85 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 140.76 m3·mol-1 Chemaxon Polarizability 53.87 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
- Kind
- Protein
- Organism
- Influenza A virus (strain A/Puerto Rico/8/1934 H1N1)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- Curator comments
- This is a representative protein from the polymerase acidic proteins group.
- General Function
- Plays an essential role in viral RNA transcription and replication by forming the heterotrimeric polymerase complex together with PB1 and PB2 subunits. The complex transcribes viral mRNAs by using a unique mechanism called cap-snatching. It consists in the hijacking and cleavage of host capped pre-mRNAs. These short capped RNAs are then used as primers for viral mRNAs. The PB2 subunit is responsible for the binding of the 5' cap of cellular pre-mRNAs which are subsequently cleaved after 10-13 nucleotides by the PA subunit that carries the endonuclease activity.
- Specific Function
- Endonuclease activity
- Gene Name
- PA
- Uniprot ID
- P03433
- Uniprot Name
- Polymerase acidic protein
- Molecular Weight
- 82587.575 Da
References
- Hayden FG, Sugaya N, Hirotsu N, Lee N, de Jong MD, Hurt AC, Ishida T, Sekino H, Yamada K, Portsmouth S, Kawaguchi K, Shishido T, Arai M, Tsuchiya K, Uehara T, Watanabe A: Baloxavir Marboxil for Uncomplicated Influenza in Adults and Adolescents. N Engl J Med. 2018 Sep 6;379(10):913-923. doi: 10.1056/NEJMoa1716197. [Article]
- Shirley M: Baloxavir Marboxil: A Review in Acute Uncomplicated Influenza. Drugs. 2020 Jul;80(11):1109-1118. doi: 10.1007/s40265-020-01350-8. [Article]
- FDA Approved Drug Products: XOFLUZA (baloxavir marboxil) tablets or suspension, for oral use (August 2022) [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
- Gene Name
- UGT1A3
- Uniprot ID
- P35503
- Uniprot Name
- UDP-glucuronosyltransferase 1-3
- Molecular Weight
- 60337.835 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- Curator comments
- In vitro, baloxavir was a weak inhibitor of CYP3A but it is unlikely to cause clinically relevant drug-drug interactions.
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro, baloxavir was a weak inhibitor of CYP2B6 but it is unlikely to cause clinically relevant drug-drug interactions.
- 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
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Heo YA: Baloxavir: First Global Approval. Drugs. 2018 Apr;78(6):693-697. doi: 10.1007/s40265-018-0899-1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro, baloxavir was a weak inhibitor of CYP2C8 but it is unlikely to cause clinically relevant drug-drug interactions.
- 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
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Heo YA: Baloxavir: First Global Approval. Drugs. 2018 Apr;78(6):693-697. doi: 10.1007/s40265-018-0899-1. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Both baloxavir marboxil and baloxavir are substrates of P-glycoprotein (P-gp). In vitro, baloxavir was a weak inhibitor of P-gp but it is unlikely to cause clinically relevant drug-drug interactions.
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro, baloxavir was a weak inhibitor of BCRP but it is unlikely to cause clinically relevant drug-drug interactions.
- 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
- Heo YA: Baloxavir: First Global Approval. Drugs. 2018 Apr;78(6):693-697. doi: 10.1007/s40265-018-0899-1. [Article]
Drug created at February 28, 2018 15:53 / Updated at February 18, 2023 02:02