5-[(ethoxycarbonyl)azanidyl]-3-(morpholin-4-yl)-1,2,3λ5-oxadiazol-3-ylium

• ChemBase ID: 133974
• Molecular Formular: C9H14N4O4
• Molecular Mass: 242.23186
• Monoisotopic Mass: 242.10150495
• SMILES: CCOC(=O)[N-]c1c[n+](no1)N1CCOCC1
• Canonical SMILES: CCOC(=O)[N-]c1on[n+](c1)N1CCOCC1
• 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
• InChIKey: XLFWDASMENKTKL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(ethoxycarbonyl)azanidyl]-3-(morpholin-4-yl)-1,2,3λ^5-oxadiazol-3-ylium
• IUPAC Traditional name: 5-[(ethoxycarbonyl)azanidyl]-3-(morpholin-4-yl)-1,2,3λ^5-oxadiazol-3-ylium
• Synonyms: N-(Ethoxycarbonyl)-3-(4-morpholino)sydnone imine; SIN-10; Molsidomine; 5-[(Ethoxycarbonyl)amino]-3-(4-morpholinyl)-1,2,3-oxadiazolium Inner Salt; CAS 276; Corraton; Coruno; Corvasal; Corvaton; Molsidolat; Morial; Morsydomine; Motazomin; N-(Ethoxycarbonyl)-3-morpholinosydnone imine; N-Ethoxycarbonyl-3-morpholinosydnonimine; SIN 10 (pharmaceutical); Sydnopharm; Molsidomine

Database IDs

• CAS Number: 25717-80-0
• EC Number: 247-207-4
• MDL Number: MFCD00869301
• PubChem SID: 162228251; 24278544
• PubChem CID: 5353788

CALCULATED PROPERTIES

• Acid pKa: 7.9913807
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -1.0171243
• LogD (pH = 7.4): -1.0268412
• Log P: -1.0168914
• Molar Refractivity: 76.9908 cm^3
• Polarizability: 21.543848 Å^3
• Polar Surface Area: 77.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: WU7677400
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - M2901

Biochem/physiol Actions
Orally active, long acting vasodilator; antianginal; converted by the liver to the active metabolite, SIN-1

Toronto Research Chemicals - M488000

Molsidomine is an antianginal agent. Molsidomine is an effective therapeutic agents in the treatment of angina pectoris. Molsidomine is a sydnonimine derivative that acts as a heterocyclic direct nitric oxide donor.

REFERENCES

• Tanayama, S. et al.: Xenobiotica, 4, 175 (1974)
• Yamada, M. et al.: Chem. Pharmac. Bull., 35, 3390 (1974)
• Messin, R. et al.: Adv. Ther., 23, 107 (1974)