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Identification
- Summary
Molsidomine is a long-acting vasodilator used to treat angina pectoris, including in association with left heart failure and acute myocardial infarction.
- Generic Name
- Molsidomine
- DrugBank Accession Number
- DB09282
- Background
Molsidomine is an orally active, long-acting vasodilator, which belongs to the class of medications known as syndnones. Interestingly, it is being studied as being a preventive measure in cerebral infarction 1.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Molsidomine (DB09282)
- Weight
- Average: 242.235
Monoisotopic: 242.101504947 - Chemical Formula
- C9H14N4O4
- Synonyms
- Molsidomina
- Molsidomine
- Molsidominum
- External IDs
- CAS 276
- CAS-276
- SIN-10
Pharmacology
- Indication
The indications for use of molsidomine include ischemic heart disease, angina, chronic heart failure, and pulmonary hypertension 9,10.
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 Treatment of Angina pectoris •••••••••••• ••••• •••••••••• •••••••••• •••••• •••••• ••••••••••• ••••••• •••••••• ••••••• Treatment of Chronic stable angina pectoris •••••••••••• ••••• •••••••• •••••••••• ••••••• •••••••• ••••••• Treatment of Chronic stable angina pectoris •••••••••••• ••••••• •••••••• ••••••• Treatment of Unstable angina pectoris •••••••••••• ••••••• •••••••• ••••••• Treatment of Unstable angina pectoris •••••••••••• ••••• •••••••• •••••••••• ••••••• •••••••• ••••••• - 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
Molsidomine leads to smooth muscle relaxation in the coronary blood vessels, relieving symptoms of angina and increasing blood flow to the coronary arteries.
- Mechanism of action
Molsidomine, a cardiovascular drug, acts in a similar fashion to organic nitrates. The SIN-1A metabolite of molsidomine has a pharmacologically active group of nitric oxide, which increases levels of cyclic GMP, and decreases intracellular calcium ions in smooth muscle cells. This leads to relaxation of smooth muscle in the blood vessels, and inhibits platelet aggregation.
Target Actions Organism UGuanylate cyclase soluble subunit alpha-2 agonistHumans - Absorption
Peak plasma drug concentration (tmax) occurs from 1 to 2 hours after administration.
- Volume of distribution
98 L 8
- Protein binding
Not Available
- Metabolism
Molsidomine hepatically metabolized to linsidomine. Linsidomine releases nitric oxide (NO) from endothelial cells when it decays, and acts as the active vasodilating metabolite responsible for molsidomine's pharmacological effects.
Oral absorption of Molsidomine is found to be 95.5% ±4.5. Presystemic metabolism is noted to be 56% and metabolism is reported extensive by Liver. Renal Excretion accounts for 95 % and plasma half-life is 5 hr. Back to top
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- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
renal excretion is the main route of elimination of the metabolites in humans (90% to 95%) About 2% of the ingested drug is excreted unchanged in the urine.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- 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 softwareAcebutolol Molsidomine may increase the hypotensive activities of Acebutolol. Aliskiren Molsidomine may increase the hypotensive activities of Aliskiren. Ambrisentan Molsidomine may increase the hypotensive activities of Ambrisentan. Amlodipine Molsidomine may increase the hypotensive activities of Amlodipine. Amyl Nitrite Molsidomine may increase the hypotensive activities of Amyl Nitrite. - Food Interactions
- Not Available
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.- International/Other Brands
- Angoral (Pharmaghreb) / Cardamine (ADWYA) / Corvasal (Benta) / Dilacor (Saiph) / Molsicor (IBN) / Molsidomina Polfa (Polfa) / Molsidomine Arrow (Arrow)
Categories
- ATC Codes
- C01DX12 — Molsidomine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Oxazinanes
- Sub Class
- Morpholines
- Direct Parent
- Morpholines
- Alternative Parents
- Organic carbonic acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic heteromonocyclic compound / Azacycle / Carbonic acid derivative / Carbonyl group / Dialkyl ether / Ether / Hydrocarbon derivative / Morpholine / Organic 1,3-dipolar compound / Organic nitrogen compound
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- D46583G77X
- CAS number
- 25717-80-0
- InChI Key
- XLFWDASMENKTKL-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H14N4O4/c1-2-16-9(14)10-8-7-13(11-17-8)12-3-5-15-6-4-12/h7H,2-6H2,1H3
- IUPAC Name
- 5-[(ethoxycarbonyl)azanidyl]-3-(morpholin-4-yl)-1,2,3lambda5-oxadiazol-3-ylium
- SMILES
- CCOC(=O)[N-]C1=C[N+](=NO1)N1CCOCC1
References
- General References
- Ehlert A, Schmidt C, Wolfer J, Manthei G, Jacobs AH, Bruning R, Heindel W, Ringelstein EB, Stummer W, Pluta RM, Hesselmann V: Molsidomine for the prevention of vasospasm-related delayed ischemic neurological deficits and delayed brain infarction and the improvement of clinical outcome after subarachnoid hemorrhage: a single-center clinical observational study. J Neurosurg. 2016 Jan;124(1):51-8. doi: 10.3171/2014.12.JNS13846. Epub 2015 Jul 10. [Article]
- Lorenc-Koci E, Czarnecka A, Lenda T, Kaminska K, Konieczny J: Molsidomine, a nitric oxide donor, modulates rotational behavior and monoamine metabolism in 6-OHDA lesioned rats treated chronically with L-DOPA. Neurochem Int. 2013 Dec;63(8):790-804. doi: 10.1016/j.neuint.2013.09.021. Epub 2013 Sep 30. [Article]
- Rosenkranz B, Winkelmann BR, Parnham MJ: Clinical pharmacokinetics of molsidomine. Clin Pharmacokinet. 1996 May;30(5):372-84. [Article]
- Ostrowski J, Resag K: Pharmacokinetics of molsidomine in humans. Am Heart J. 1985 Mar;109(3 Pt 2):641-3. [Article]
- Molsidomine [Link]
- Update: Molsidomine [Link]
- EPA Chemistry Dashboard: Molsidomine [Link]
- Molsidomine [Link]
- Molsidomide: an overview [Link]
- Molsidomine [Link]
- Relationship between pharmacokinetics and pharmacodynamics of molsidomine and its metabolites in humans [Link]
- Molsidomine 2/4 mg tablets [Link]
- Clinical Pharmacology of Antianginal Drugs [Link]
- External Links
- Human Metabolome Database
- HMDB0245703
- KEGG Drug
- D01320
- PubChem Compound
- 5353788
- PubChem Substance
- 310265175
- ChemSpider
- 4090
- BindingDB
- 39912
- 7023
- ChEBI
- 92623
- ChEMBL
- CHEMBL1329455
- Wikipedia
- Molsidomine
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 dataNot Available Completed Treatment Myocardial Ischemia 1 somestatus stop reason just information to hide 4 Completed Treatment Atherosclerosis / Chronic Stable Angina Pectoris 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Tablet 2 MG Tablet 4 MG Tablet, extended release Oral 8 MG Tablet, extended release Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 156 [L1368] boiling point (°C) 266 to 368 [L1368] water solubility 4.65e-03 to 1.74 [L1368] logP -1.61 [L1368] - Predicted Properties
Property Value Source Water Solubility 13.3 mg/mL ALOGPS logP -1 ALOGPS logP -1 Chemaxon logS -1.4 ALOGPS pKa (Strongest Acidic) 9.94 Chemaxon pKa (Strongest Basic) -3.2 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 77.91 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 76.99 m3·mol-1 Chemaxon Polarizability 23.94 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key 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]- 164.4346423 predictedDarkChem Lite v0.1.0 [M-H]- 149.04094 predictedDeepCCS 1.0 (2019) [M+H]+ 164.7970423 predictedDarkChem Lite v0.1.0 [M+H]+ 151.43651 predictedDeepCCS 1.0 (2019) [M+Na]+ 164.1821423 predictedDarkChem Lite v0.1.0 [M+Na]+ 157.34904 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Has guanylyl cyclase on binding to the beta-1 subunit
- Specific Function
- GTP binding
- Gene Name
- GUCY1A2
- Uniprot ID
- P33402
- Uniprot Name
- Guanylate cyclase soluble subunit alpha-2
- Molecular Weight
- 81749.185 Da
References
- Kukovetz WR, Holzmann S: Mechanism of vasodilation by molsidomine. Am Heart J. 1985 Mar;109(3 Pt 2):637-40. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Has guanylyl cyclase on binding to the beta-1 subunit
- Specific Function
- GTP binding
- Gene Name
- GUCY1A2
- Uniprot ID
- P33402
- Uniprot Name
- Guanylate cyclase soluble subunit alpha-2
- Molecular Weight
- 81749.185 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:15489334, PubMed:9714779). Specifically regulates nitric-oxide-generated cGMP (PubMed:15489334)
- Specific Function
- 3',5'-cyclic-AMP phosphodiesterase activity
- Gene Name
- PDE5A
- Uniprot ID
- O76074
- Uniprot Name
- cGMP-specific 3',5'-cyclic phosphodiesterase
- Molecular Weight
- 99984.14 Da
Drug created at October 29, 2015 16:02 / Updated at September 05, 2022 12:50