Compound: ISOSORBIDE MONONITRATE
SMILES: O=[N+](O[C@H]1[C@H]2OC[C@@H]([C@H]2OC1)O)[O-]
InChIKey: YWXYYJSYQOXTPL-SLPGGIOYSA-N
Synonyms: ISOSORBIDE MONONITRATE, 16051-77-7, Isosorbide 5-mononitrate, Imdur, Monosorbitrate, Isosorbide 5-nitrate, Corangin, Monoket, ISMN, Isosorbide-5-mononitrate, ISMO, Monolong, Monopront, Monosordil, Orasorbil, Promocard, Sigacora, Sorbimon, Turimonit, Vasdilat, Duride, Imtrate, Ismexin, Medocor, Monicor, Olicard, Pertil, Uniket, Ismox, Monodur Durules, Mono Corax, 1,4:3,6-Dianhydro-D-glucitol 5-nitrate, Monocord, 5-Ismn, isosorbide-5-nitrate, IS 5MN, IS 5-MN, Iso-5-mononitrate, IS-5-MN, AHR-4698, IS-5MN, D-Glucitol, 1,4:3,6-dianhydro-, 5-nitrate, Monosorb XL 60, AHR 4698, DTXSID9023176, BM 22-145, BM 22.145, BM-22-145, Diluted isosorbide mononitrate, NSC-758619, (3R,3aS,6S,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl nitrate, LX1OH63030, [(3S,3aR,6R,6aS)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] nitrate, BM-22145, BM-22.145, CHEBI:6062, DTXCID003176, BM 22.145IS 5-MNAHR-4698, monocinque, Monit, Isosorbide dinitrate isosorbide-5-mononitrate, Angitate, Dynamin, Ketanodur, Monodur, Tenkosorb, Astrodur mr, Relosorb xl, Trangina xl, (3R,3aS,6S,6aR)-6-hydroxy-hexahydrofuro(3,2-b)furan-3-yl nitrate, Monomax xl, Monomil xl, Pertil ret, Tardisc xl, Carmil xl, Ziotan xl, Ismo ret, Monit ls, Monit sr, Imo la, ((3R,3aS,6S,6aR)-6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro(2,3-d)furan-3-yl) nitrate, ((3S,3aR,6R,6aS)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro(3,2-b)furan-6-yl) nitrate, [(3R,3aS,6S,6aR)-6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[2,3-d]furan-3-yl] nitrate, Vasotrate 60 sr, Chemydur 60 xl, Mono-cedocard 10, Mono-cedocard 20, Mono-cedocard 40, Phasonit la 50, Dynamin xl 25, Dynamin xl 50, Elantan 10, Elantan 20, Elantan 40, Elantan la 25, Elantan la 50, Isotard 25 xl, Isotard 40 xl, Isotard 50 xl, Isotard 60 xl, Modisal 40 xl, Modisal 60 xl, Modisal la 25, Modisal la 50, Monigen xl 60, Monomax sr 40, Monomax sr 60, Angeze sr 40, Angeze sr 60, Cibral xl 60, Isodur 25 xl, Isodur 50 xl, Slomon xl 60, Xismox xl 60, Angeze 10, Angeze 20, Angeze 40, Cibral 10, Cibral 20, Cibral 40, Eumon 40 xl, Eumon 60 xl, Monit xl 60, Zemon 40 xl, Zemon 60 xl, Isib 50 xl, Isib 60 xl, Isib 20, Isib 40, Ismo 10, Ismo 20, Ismo 40, RefChem:55422, Mcr 50, 240-197-2, Elantan, Mononit, Monisid, Mononitrate d'isosorbide, Isosorbidi mononitras [Latin], Mononitrato de isosorbida, Isosorbidi mononitras, Mononitrate d'isosorbide [French], Mononitrato de isosorbida [Spanish], Isomonit, Monizid, vasotrate, Epicordin, Monoclair, Monotrate, Olicardin, Percorina, Edistol, Etimonis, Isomonat, MFCD00143462, Multitab, Titarane, Conpin, Imazin, Imodur, Isomon, Iturol, Monis, Nitex, Plodin, IHD, MonoSigma, Elantan Retard, Mono-Sanorania, Monoket Retard, Elantan Long, Imdur Durules, Corangin SR, Mono Mack, Mono-Mack, Conpin Retardkaps, Fem-Mono, ISMN Lannacher, Monoket OD, ISMN Apogepha, ISMN Heumann, ISMN Basics, Pentacard 20, 1,4:3,6-dianhydro-5-O-nitro-D-glucitol, Mono Corax Retard, ISMN Hexal, ISMN Stada, Monocord 20, Monocord 40, Monolong 40, Monolong 60, ISMN Atid, Mononit 20, Mononit 40, Isopen-20, Monocord 50 SR, Mononit Retard 50, Imdur 60, ISMN AbZ, Monit 20, ISMN AL, Ismo-20, Monocedocard, Monosorb, (3r,3as,6s,6ar)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl nitrate, Glucitol, 1,4:3,6-dianhydro-, 5-nitrate, D-, Monomax, 1,4:3,6-dianhydro-5-O-nitro-D-erythro-hexitol, CCRIS 1911, Imdur (TN), Ismo (TN), SR-05000001872, EINECS 240-197-2, UN3251, BRN 5851319, Leicester, Isosorbide 5-Mononitrate (1.0 mg/mL in Dimethyl Sulfoxide), UNII-LX1OH63030, NCGC00159334-02, isorbide mononitrate, isosorbide-mononitrate, Isosobide-5-mononitrate, Isosorbide mononitrate CRS, CHEMBL1311, Isosorbide mononitrate [USAN:USP:INN:BAN:JAN], SCHEMBL26781, GTPL7052, Isosorbide Mononitrate, Diluted, NIOSH/LZ4385560, HY-B0642R, Isosorbide Dinitrate Impurity 13, Isosorbide mononitrate (Standard), Isosorbide-5-nitrate (IS-5-N), HMS2093K07, HMS3715I08, Pharmakon1600-01503807, HY-B0642, MSK15666, ISOSORBIDE MONONITRATE [INN], ISOSORBIDE MONONITRATE [JAN], Tox21_111581, EBC-26168, ISOSORBIDE MONONITRATE [USAN], NSC758619, s4633, SBB080596, ISOSORBIDE MONONITRATE [VANDF], AKOS005110986, ISOSORBIDE MONONITRATE [MART.], AC-8830, CCG-213200, CS-3495, DB01020, ISOSORBIDE MONONITRATE [WHO-DD], MD09906, NSC 758619, Isosorbide mononitrate (JP18/USP/INN), NCGC00167981-01, NCGC00167981-03, 1,4:3,6-Dianhydro-5-nitro-D-glucitol, D-1,4:3,6-Dianhydroglucitol 5-nitrate, DA-74592, 1,4:3,6-Dianhydrosorbitol 5-mononitrate, SBI-0206724.P001, CAS-16051-77-7, ISOSORBIDE MONONITRATE [ORANGE BOOK], I0403, ISOSORBIDE MONONITRATE [USP IMPURITY], LZ43855600, NS00004528, C07714, D00630, DILUTED ISOSORBIDE MONONITRATE [USP-RS], W15583, AB01563284_01, EN300-19636279, Q423401, SR-05000001872-1, SR-05000001872-2, BRD-K82225283-001-01-5, BRD-K82225283-001-03-1, DILUTED ISOSORBIDE MONONITRATE [USP MONOGRAPH], Isosobide-5-mononitrate [UN3251]  [Flammable solid], Isosorbide 5-Nitrate(Discontinued,See C4X-223813), Isosorbide Mononitrate 1.0 mg/ml in Dimethyl Sulfoxide, Isosorbide 5-Mononitrate (1 mg/mL in Dimethyl Sulfoxide), ISOSORBIDE DINITRATE ISOSORBIDE-5-MONONITRATE [MI], ISOSORBIDE DINITRATE, DILUTED IMPURITY C [EP IMPURITY], (2S,5S,1R,6R)-6-(nitrooxy)-4,8-dioxabicyclo[3.3.0]octan-2-ol
Theoretical properties:
molecular_formula: C6H9NO6
molecular_weight: 191.14 g/mol
exact_mass: 191.04298701 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 1
heavy_atom_count: 13
topological_polar_surface_area: 93.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 88 - 91 °C
solubility: 5.70e+01 g/L
Descriptions:
pubchem: Isosorbide mononitrate is a nitrate ester and a glucitol derivative. It has a role as a vasodilator agent and a nitric oxide donor.
chembl: ISOSORBIDE MONONITRATE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Isosorbide mononitrate, sold under many brand names, is a medication used for heart-related chest pain (angina), heart failure and esophageal spasms. It can be used both to treat and to prevent heart-related chest pain; however, it is generally less preferred than beta blockers or calcium channel blockers. It is taken by mouth.
Common side effects include headache, low blood pressure with standing, blurry vision, and skin flushing. Serious side effects may include low blood pressure especially if also exposed to PDE5 inhibitors such as sildenafil. Use is not recommended in pregnancy. It is believed to work by relaxing smooth muscle within blood vessels.
It was patented in 1971 and approved for medical use in 1981. It is available as a generic medication. In 2023, isosorbide was the 125th most commonly prescribed medication in the United States, with more than 5 million prescriptions.