Compound: isosorbide
SMILES: O1[C@H]2[C@H](OC[C@H]2O)[C@H](C1)O
InChIKey: KLDXJTOLSGUMSJ-JGWLITMVSA-N
Synonyms: isosorbide, 652-67-5, Isobide, 1,4:3,6-Dianhydro-D-glucitol, Devicoran, (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol, Hydronol, Ismotic, (+)-D-Isosorbide, D-Glucitol, 1,4:3,6-dianhydro-, 1,4:3,6-Dianhydro-D-sorbitol, 1,4:3,6-Dianhydrosorbitol, NSC-40725, DTXSID5046196, Glucitol, 1,4:3,6-dianhydro-, D-, WXR179L51S, NSC40725, DTXCID3026196, (3R,3aR,6S,6aR)-hexahydrofuro(3,2-b)furan-3,6-diol, RefChem:55420, GlyTouCan:G82967ZA, G82967ZA, 211-492-3, Sorbid, Vascardin dinitrate, 1,4-Dianhydrosorbitol, Dianhydro-D-glucitol, Isosorbida, (3S,3aR,6R,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol, D-Isosorbide, MFCD00064827, D-Isosorbide;Dianhydro-D-glucitol, Sorbitol, 1,4:3,6-dianhydro-, D-1,4:3,6-Dianhydroglucitol, NCGC00160508-01, Isosorbide 100 microg/mL in Acetonitrile, Hydronol (VAN), Isosorbidum, Isosorbidum [INN-Latin], Isosorbida [INN-Spanish], CAS-652-67-5, HSDB 3105, EINECS 211-492-3, NSC 40725, BRN 0080510, lsosorbide, UNII-WXR179L51S, Devicoran;, Hydronol;, Ismotic;, Sorbide (obsol.), Ismotic (TN), Isobide (TN), Isobide. Isorgen G;, Isosorbide [USAN:USP:INN:BAN:JAN], 1,6-Dianhydrosorbitol, ISOSORBIDE [MI], ISOSORBIDE [INN], ISOSORBIDE [JAN], ISOSORBIDE [HSDB], ISOSORBIDE [USAN], ISOSORBIDE [VANDF], 1,6-Dianhydro-D-glucitol, 1,6-Dianhydro-D-sorbitol, EC 211-492-3, ISOSORBIDE [MART.], ISOSORBIDE [USP-RS], ISOSORBIDE [WHO-DD], Dianhydro-D-glucitol, 98%, SCHEMBL15495, 1,4:3,6-Dianhydroglucitol, 5-19-03-00201 (Beilstein Handbook Reference), BIDD:GT0695, 1,4; 3,6-dianhydrosorbitol, CHEBI:6060, Isosorbide (JP18/USP/INN), orb1300667, D-Glucitol,4:3,6-dianhydro-, CHEMBL1200660, ISOSORBIDE [ORANGE BOOK], 1.4:3.6-dianhydro-D-glucitol, 1.4;3.6-dianhydro-D-glucitol, ISOSORBIDE [USP IMPURITY], GLXC-08174, Glucitol,4:3,6-dianhydro-, D-, HY-B1469, Tox21_111861, BBL029591, EBC-04434, s4204, STK801813, AKOS005622709, Tox21_111861_1, CCG-266173, CS-5157, DB09401, MD07153, SMP1_000177, NCGC00160508-02, NCGC00160508-03, AS-14140, DA-61279, I0407, NS00002879, D00347, EN300-170910, AB01566931_01, F242232, Q1243800, BRD-K47178855-001-01-8, BRD-K47178855-001-02-6, Z1216815730, A912284D-27E1-4FB0-91B8-86C8AB905297, Rel-(3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol, D-Sorbitol, {1,4:3,6-dianhydro(furo[3,2-b]furan-3,6-diol,} hexahydro-), D-Sorbitol,4:3,6-dianhydro(furo[3,2-b]furan-3,6-diol, hexahydro-), 28980-83-8
Theoretical properties:
molecular_formula: C6H10O4
molecular_weight: 146.14 g/mol
exact_mass: 146.05790880 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 10
topological_polar_surface_area: 58.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: CRYSTALS
color: CRYSTALS
melting_point: 60-63
Descriptions:
pubchem: Isosorbide is an organic molecular entity.
chembl: ISOSORBIDE 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.