Ensifentrine
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Identification
- Summary
Ensifentrine is a phosphodiesterase inhibitor used for the maintenance treatment of chronic obstructive pulmonary disease (COPD) in adults.
- Brand Names
- Ohtuvayre
- Generic Name
- Ensifentrine
- DrugBank Accession Number
- DB16157
- Background
Ensifentrine is a first-in-class, selective dual inhibitor of the phosphodiesterase 3 (PDE3) and phosphodiesterase 4 (PDE4) enzymes.6 On June 26, 2024, the FDA announced the approval of an inhaled product of ensifentrine for the treatment of chronic obstructive pulmonary disease (COPD) in adults, which allows the drug to be directly delivered to the lungs.6 It works to induce bronchodilator and reduce inflammation in COPD.3
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 477.565
Monoisotopic: 477.237604498 - Chemical Formula
- C26H31N5O4
- Synonyms
- 2-(9,10-DIMETHOXY-4-OXO-2-(2,4,6-TRIMETHYLPHENYL)IMINO-6,7-DIHYDROPYRIMIDO(6,1-A)ISOQUINOLIN-3-YL)ETHYLUREA
- Ensifentrine
- N-(2-((2E)-9,10-DIMETOXI-4-OXO-2-((2,4,6-TRIMETILFENIL)IMINO)-6,7-DIHIDRO-2H-PIRIMIDO(6,1-A)ISOQUINOLEIN-3(4H)-IL)ETIL)UREA
- UREA, N-(2-(6,7-DIHYDRO-9,10-DIMETHOXY-4-OXO-2-((2,4,6-TRIMETHYLPHENYL)IMINO)-2H-PYRIMIDO(6,1-A)ISOQUINOLIN-3(4H)-YL)ETHYL)-
- External IDs
- LS-193,855
- LS-193855
- RPL 554
- RPL-554
- RPL554
Pharmacology
- Indication
Ensifentrine is indicated for the maintenance treatment of chronic obstructive pulmonary disease (COPD) in adult patients.5
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Chronic obstructive pulmonary disease (copd) •••••••••••• ••••• - Associated Therapies
- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Ensifentrine causes bronchodilation in chronic obstructive pulmonary disease (COPD) and asthma.1 Ensifentrine was shown to mediate anti-inflammatory effects by reducing the levels of proinflammatory cytokines such as granulocyte-macrophage colony-stimulating factor (GM-CSF) in cystic fibrosis bronchial epithelial cells.1
In vitro, ensifentrine activates the CFTR-mediated chloride ion secretion in bronchial epithelial cells, increasing ciliary beat frequency and potentially enhancing mucociliary clearance.3 In guinea pig models, ensifentrine demonstrated bronchoprotective properties against airway constriction caused by spasmogens and antigens: It caused dose-dependent relaxation of the airways.3,4
- Mechanism of action
COPD is characterized by progressive airflow obstruction and chronic inflammation of the respiratory tract. Because PDE3 and PDE4 are expressed in airway smooth muscle, inflammatory cells, and bronchial epithelial cells to drive inflammation and bronchial muscle tone, these two PDE isoforms have been identified as therapeutic targets in the treatment of COPD.3 PDE3 primarily hydrolyzes the second-messenger molecule cyclic adenosine monophosphate (cAMP) in airway smooth muscle, mediating muscle tone.2,3 PDE3 can also hydrolyze cyclic guanosine monophosphate (cGMP).2 PDE4 regulates cAMP only and is involved in inflammatory cell activation and migration, as well as Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) stimulation in bronchial epithelial cells.2,3,4
Ensifentrine is a drug that selectively inhibits the PDE3 and PDE4 enzymes.5 Dual inhibition of PDE3 and PDE4 results in the accumulation of intracellular levels of cAMP and/or cGMP, causing a synergistic effect in contracting airway smooth muscle and suppressing inflammatory response.2,5
Target Actions Organism APhosphodiesterase 3 inhibitorHumans APhosphodiesterase 4 inhibitorHumans - Absorption
Following inhaled administration of ensifentrine in healthy subjects and subjects with COPD, ensifentrine Cmax was attained around 0.6 to 1.5 hours after dosing. A randomized, two-period, cross-over study assessing systemic exposure following inhalation of two times the recommended dose of ensifentrine with and without charcoal block demonstrated that the majority of an inhaled dose (approximately 90%) is delivered to the lung from which it is absorbed.5
Population pharmacokinetic analysis indicates that relative bioavailability in subjects with COPD is approximately 35% lower when compared to healthy subjects. Exposure to ensifentrine was associated with high inter-subject variability.5
- Volume of distribution
Apparent central and peripheral volume of distribution for ensifentrine in healthy subjects were 2700 L and 1820 L, respectively, as estimated in population PK analysis. In patients with COPD, apparent central and peripheral volumes were estimated as 8150 L and 5490 L, respectively.5
- Protein binding
In vitro plasma protein binding of ensifentrine is approximately 90%.5
- Metabolism
Following administration of a single nebulized dose, 8 times the recommended dose of ensifentrine, unchanged ensifentrine was identified as the major drug-related component in human plasma, accounting for 96 and 99% of the drug-related material identified in Tmax and time normalized (0-24 h) plasma samples, respectively. The primary metabolic routes for ensifentrine are oxidative (hydroxylation, O-demethylation) followed by conjugation (e.g., glucuronidation). In vitro results indicate that, at physiologically relevant concentrations, ensifentrine was predominantly metabolized by CYP2C9 and to a lesser extent by CYP2D6.5
- Route of elimination
The majority of ensifentrine is excreted in feces. After a 3 mg nebulized dose, urinary elimination of unchanged ensifentrine was negligible (<0.3% of the dose).5
- Half-life
Following twice-daily administration for 6 days, terminal elimination half-life ranged from 10.6 to 12.6 hours in healthy subjects and subjects with COPD (1.5 mg to 12 mg twice daily).5
- Clearance
Not Available
- Adverse Effects
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- Toxicity
There is no information regarding the lethal dose 50 of ensifentrine. An overdosage of ensifentrine may lead to signs and symptoms such as headache, tachycardia, and palpitations. Treatment of overdosage consists of temporary interruption of ensifentrine along with appropriate symptomatic and/or supportive therapy.5
- 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 softwareIsosorbide mononitrate Ensifentrine may increase the hypotensive activities of Isosorbide mononitrate. - Food Interactions
- No interactions found.
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.
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ohtuvayre Suspension 3 mg/2.5mL Respiratory (inhalation) Verona Pharma, Inc. 2024-06-26 Not applicable US
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 3E3D8T1GIX
- CAS number
- 1884461-72-6
- InChI Key
- CSOBIBXVIYAXFM-BYNJWEBRSA-N
- InChI
- InChI=1S/C26H31N5O4/c1-15-10-16(2)24(17(3)11-15)29-23-14-20-19-13-22(35-5)21(34-4)12-18(19)6-8-30(20)26(33)31(23)9-7-28-25(27)32/h10-14H,6-9H2,1-5H3,(H3,27,28,32)/b29-23+
- IUPAC Name
- {2-[(2E)-9,10-dimethoxy-4-oxo-2-[(2,4,6-trimethylphenyl)imino]-2H,3H,4H,6H,7H-pyrimido[4,3-a]isoquinolin-3-yl]ethyl}urea
- SMILES
- COC1=C(OC)C=C2C(CCN3C(=O)N(CCNC(N)=O)\C(C=C23)=N\C2=C(C)C=C(C)C=C2C)=C1
References
- General References
- Turner MJ, Dauletbaev N, Lands LC, Hanrahan JW: The Phosphodiesterase Inhibitor Ensifentrine Reduces Production of Proinflammatory Mediators in Well Differentiated Bronchial Epithelial Cells by Inhibiting PDE4. J Pharmacol Exp Ther. 2020 Dec;375(3):414-429. doi: 10.1124/jpet.120.000080. Epub 2020 Oct 4. [Article]
- Anzueto A, Barjaktarevic IZ, Siler TM, Rheault T, Bengtsson T, Rickard K, Sciurba F: Ensifentrine, a Novel Phosphodiesterase 3 and 4 Inhibitor for the Treatment of Chronic Obstructive Pulmonary Disease: Randomized, Double-Blind, Placebo-controlled, Multicenter Phase III Trials (the ENHANCE Trials). Am J Respir Crit Care Med. 2023 Aug 15;208(4):406-416. doi: 10.1164/rccm.202306-0944OC. [Article]
- Donohue JF, Rheault T, MacDonald-Berko M, Bengtsson T, Rickard K: Ensifentrine as a Novel, Inhaled Treatment for Patients with COPD. Int J Chron Obstruct Pulmon Dis. 2023 Jul 28;18:1611-1622. doi: 10.2147/COPD.S413436. eCollection 2023. [Article]
- Faruqi MA, Khan MMKS, Mannino DM: Perspectives on Ensifentrine and Its Therapeutic Potential in the Treatment of COPD: Evidence to Date. Int J Chron Obstruct Pulmon Dis. 2024 Jan 3;19:11-16. doi: 10.2147/COPD.S385811. eCollection 2024. [Article]
- FDA Approved Drug Products: OHTUVAYRE (ensifentrine) inhalation suspension, for oral inhalation use [Link]
- Verona Pharma: Verona Pharma Announces US FDA Approval of Ohtuvayre™ (ensifentrine) [Link]
- External Links
- ChemSpider
- 8110374
- 2687215
- ChEMBL
- CHEMBL4594287
- ZINC
- ZINC000000602859
- Wikipedia
- Ensifentrine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Completed Treatment Chronic Obstructive Pulmonary Disease (COPD) 2 somestatus stop reason just information to hide 3 Recruiting Treatment Chronic Obstructive Pulmonary Disease (COPD) 2 somestatus stop reason just information to hide 2 Completed Treatment Asthma 1 somestatus stop reason just information to hide 2 Completed Treatment Chronic Obstructive Pulmonary Disease (COPD) 6 somestatus stop reason just information to hide 2 Completed Treatment Coronavirus Disease 2019 (COVID‑19) / Infections, Coronavirus 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Suspension Respiratory (inhalation) 3 mg/2.5mL - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US9956171 No 2015-09-15 2035-09-15 US US9062047 No 2011-08-21 2031-08-21 US US10945950 No 2015-09-15 2035-09-15 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0218 mg/mL ALOGPS logP 3.12 ALOGPS logP 3.27 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 14.74 Chemaxon pKa (Strongest Basic) 5.23 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 109.49 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 137.62 m3·mol-1 Chemaxon Polarizability 52.81 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes 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
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0000900000-99596635c6ac65c94072 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-056r-0000900000-130cc4dc89e8cd6cd45c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-02br-0000900000-603aa7243cdf4d761bb8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-4002900000-02b21be3458d5852eda3 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0gb9-0115900000-18e78d6f1953405ac22c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000x-4003900000-d00ef3296d039c495f12 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 233.8289078 predictedDarkChem Lite v0.1.0 [M+H]+ 232.9659078 predictedDarkChem Lite v0.1.0 [M+Na]+ 234.4190078 predictedDarkChem Lite v0.1.0
Targets
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Cyclic nucleotide phosphodiesterase with specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes (PubMed:1315035, PubMed:25961942, PubMed:8155697, PubMed:8695850). Has also activity toward cUMP (PubMed:27975297). Independently of its catalytic activity it is part of an E2/17beta-estradiol-induced pro-apoptotic signaling pathway. E2 stabilizes the PDE3A/SLFN12 complex in the cytosol, promoting the dephosphorylation of SLFN12 and activating its pro-apoptotic ribosomal RNA/rRNA ribonuclease activity. This apoptotic pathway might be relevant in tissues with high concentration of E2 and be for instance involved in placenta remodeling (PubMed:31420216, PubMed:34707099)
- Specific Function
- 3',5'-cyclic-AMP phosphodiesterase activity
Components:
Name | UniProt ID |
---|---|
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A | Q14432 |
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B | Q13370 |
References
- Donohue JF, Rheault T, MacDonald-Berko M, Bengtsson T, Rickard K: Ensifentrine as a Novel, Inhaled Treatment for Patients with COPD. Int J Chron Obstruct Pulmon Dis. 2023 Jul 28;18:1611-1622. doi: 10.2147/COPD.S413436. eCollection 2023. [Article]
- Faruqi MA, Khan MMKS, Mannino DM: Perspectives on Ensifentrine and Its Therapeutic Potential in the Treatment of COPD: Evidence to Date. Int J Chron Obstruct Pulmon Dis. 2024 Jan 3;19:11-16. doi: 10.2147/COPD.S385811. eCollection 2024. [Article]
- FDA Approved Drug Products: OHTUVAYRE (ensifentrine) inhalation suspension, for oral inhalation use [Link]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Hydrolyzes the second messenger 3',5'-cyclic AMP (cAMP), which is a key regulator of many important physiological processes
- Specific Function
- 3',5'-cyclic-AMP phosphodiesterase activity
Components:
Name | UniProt ID |
---|---|
3',5'-cyclic-AMP phosphodiesterase 4A | P27815 |
3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 |
3',5'-cyclic-AMP phosphodiesterase 4C | Q08493 |
3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 |
References
- Donohue JF, Rheault T, MacDonald-Berko M, Bengtsson T, Rickard K: Ensifentrine as a Novel, Inhaled Treatment for Patients with COPD. Int J Chron Obstruct Pulmon Dis. 2023 Jul 28;18:1611-1622. doi: 10.2147/COPD.S413436. eCollection 2023. [Article]
- Faruqi MA, Khan MMKS, Mannino DM: Perspectives on Ensifentrine and Its Therapeutic Potential in the Treatment of COPD: Evidence to Date. Int J Chron Obstruct Pulmon Dis. 2024 Jan 3;19:11-16. doi: 10.2147/COPD.S385811. eCollection 2024. [Article]
- FDA Approved Drug Products: OHTUVAYRE (ensifentrine) inhalation suspension, for oral inhalation use [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- FDA Approved Drug Products: OHTUVAYRE (ensifentrine) inhalation suspension, for oral inhalation use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- FDA Approved Drug Products: OHTUVAYRE (ensifentrine) inhalation suspension, for oral inhalation use [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:11306452, PubMed:12958161, PubMed:19506252, PubMed:20705604, PubMed:28554189, PubMed:30405239, PubMed:31003562). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:20705604, PubMed:23189181). Also mediates the efflux of sphingosine-1-P from cells (PubMed:20110355). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (PubMed:19506252, PubMed:20368174, PubMed:22132962, PubMed:31003562, PubMed:36749388). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (By similarity). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (PubMed:12682043, PubMed:28554189, PubMed:30405239). Mediates the secretion of the riboflavin and biotin vitamins into milk (By similarity). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (By similarity). Plays an important role in the exclusion of xenobiotics from the brain (Probable). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:11306452, PubMed:12477054, PubMed:15670731, PubMed:18056989, PubMed:31254042). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (By similarity). May play a role in early stem cell self-renewal by blocking differentiation (By similarity)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- Broad substrate specificity ATP-binding cassette transporter ABCG2
- Molecular Weight
- 72313.47 Da
References
- FDA Approved Drug Products: OHTUVAYRE (ensifentrine) inhalation suspension, for oral inhalation use [Link]
Drug created at December 15, 2020 18:14 / Updated at August 08, 2024 23:11