IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data
Identification
Product NameDorzolamide HydrochlorideIUPAC Name(4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxo-5,6-dihydro-4H-thienothiopyran-2-sulfonamide;hydrochloride Molecular StructureCAS Registry Number 130693-82-2EINECS Number620-304-2MDL NumberMFCD00884659Beilstein Registry Number5896026SynonymsDORZOLAMIDE HYDROCHLORIDE130693-82-2Dorzolamide HClTrusoptDorzolomide hydrochlorideCosoptDorzolamide (hydrochloride)MK-507Dorzolomide HCl(4S,6S)-4-(ethylamino)-6-methyl-5,6-dihydro-4H-thienothiopyran-2-sulfonamide 7,7-dioxide hydrochlorideDorzolamide (as hydrochloride)QZO5366EW7Trusopt (TN)CHEBI:4703(4S,6S)-4-(Ethylamino)-5,6-dihydro-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulfonamide 7,7-dioxide, monohydrochloride(4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxo-5,6-dihydro-4H-thienothiopyran-2-sulfonamide;hydrochloride4H-Thieno(2,3-b)thiopyran-2-sulfonamide, 4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, monohydrochloride, (4S-trans)-UNII-QZO5366EW7SR-05000001449Dorzolamide hydrochloride (4S,6S)-4-(Ethylamino)-5,6-dihydro-6-methyl-4H-thienothiopyran-2-sulfonamide 7,7-dioxide, monohydrochlorideL 671152L-671,152Dorzolamide HCl saltDorzolamide hydrochloride MK507 hydrochlorideMK 0507MK-0507L671152 hydrochlorideNCGC00016977-01CAS-130693-82-2SCHEMBL41152MLS002154162CHEMBL1201162DTXSID1045530Dorzolamide hydrochloride- Bio-XHY-B0109AHMS1571O14EX-A3987Tox21_110720MFCD00884659s1375DORZOLAMIDE HYDROCHLORIDE AKOS005146235AKOS015895951Dorzolamide hydrochloride (JP17/USP)Tox21_110720_1AC-5244CCG-221116CS-1858DORZOLAMIDE HYDROCHLORIDE KS-1348DORZOLAMIDE HYDROCHLORIDE DORZOLAMIDE HYDROCHLORIDE NCGC00179244-03BD164381DORZOLAMIDE HYDROCHLORIDE DORZOLAMIDE HYDROCHLORIDE SMR001233461MK-507 (L-671152) HClD4189DORZOLAMIDE HYDROCHLORIDE, TRANS-(-)-C72221D00653DORZOLAMIDE HYDROCHLORIDE DORZOLAMIDE HYDROCHLORIDE COSOPT COMPONENT DORZOLAMIDE HYDROCHLORIDEDORZOLAMIDE HYDROCHLORIDE 279D961EN300-19768601DORZOLAMIDE HYDROCHLORIDE COMPONENT OF COSOPTL-671152SR-05000001449-3Q27106441Dorzolamide hydrochloride, European Pharmacopoeia (EP) Reference StandardDorzolamide for system suitability, European Pharmacopoeia (EP) Reference StandardDorzolamide hydrochloride, United States Pharmacopeia (USP) Reference Standard(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1lambda6-thienothiopyran-6-sulfonamide hydrochloride(4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide 4H-Thienothiopyran-2-sulfonamide hydrochloride122028-16-44H-Thieno(2,3-b)thiopyran-2-sulfonamide, 5,6-dihydro-4-(ethylamino)-6-methyl-, 7,7-dioxide, monohydrochloride, (4S,6S)-Molecular FormulaC10H17ClN2O4S3Molecular Weight360.901InChIInChI=1S/C10H16N2O4S3.ClH/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16;/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16);1H/t6-,8-;/m0./s1InChI KeyOSRUSFPMRGDLAG-QMGYSKNISA-NCanonical SMILES
Patent InformationPatent IDTitlePublication DateUS2015/191485Process for Preparing Enantiomerically Enriched Oxamides2015WO2008/75155CARBONIC ANHYDRASE INHIBITORS DERIVATIVES2008US2006/142595Process for preparing 5,6-dihydro-4-(S)-(ethylamino)-6-(S) methyl-4H-thienothiopyran-2-sulphonamide-7,7-dioxide HCI2006US2006/155132PYRROLOTRIAZINE DERIVATIVES2006
Physical Data
AppearanceA white to off white c1ystalline powder.
Melting Point, °C Solvent (Melting Point) 283 - 285238H2O
Density, g·cm-3Reference Temperature, °CMeasurement Temperature, °C1.60619.85
Spectra
Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Frequency (NMR Spectroscopy), MHzChemical shifts1Hdimethylsulfoxide-d6400Chemical shifts1Hdimethylsulfoxide-d6400Chemical shifts1Hdimethylsulfoxide-d6Chemical shifts13Cdimethylsulfoxide-d6
3-Aminopyridine CAS#: 462-08-8 NMR
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Temperature (IR Spectroscopy), °CFT-IRBandsKBr14.85 - 54.85
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nmExt./Abs. Coefficient, l·mol-1cm-1Absorption maximaaq. HCl, methanol254
Route of Synthesis (ROS)
Route of Dorzolamide Hydrochloride CAS#：130693-82-2
ConditionsYieldStage #1: 5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thienothiopyran-2-sulfonamide 7,7-dioxide maleate salt With hydrogenchloride; sodium hydroxide In water at 52℃; pH=7.7; Inert atmosphere;Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20 - 75℃;99.2%Stage #1: 5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thienothiopyran-2-sulfonamide 7,7-dioxide maleate salt With sodium hydroxide In water at 52℃; Inert atmosphere;Stage #2: With hydrogenchloride In water; isopropyl alcohol at 75℃;8.1 gExperimental Procedure 10 (4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thienothiopyran-2-sulfonamide-7,7-dioxide, monochloride Dorzolamide HydrochlorideExample 10(4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thienothiopyran-2-sulfonamide-7,7-dioxide, monochloride Dorzolamide HydrochlorideSodium hydroxide (8.0 g, 30% aqueous solution) was added to a suspension of trans-(6S)-4-ethylamino-5,6-dihydro-6-methyl-7,7-dioxo-4H-thienothiopyran-2-sulfonamide maleate salt (12.0 g, 27.2 mmol) in water (35 mL) at 52° C. under nitrogen atmosphere.The pH was adjusted to 7.7 with hydrochloric acid (2.3 g, 31.5% aqueous solution) and the mixture was diluted with ethyl acetate (36.1 g).The phases were separated and the aqueous phase counter-extracted with ethyl acetate (24.8 g).The phases were separated and the combined organic phases were washed with water (10.2 g) and concentrated up to a volume of approximately 30 mL.The mixture was then diluted with isopropyl alcohol (26.5 g) and the distillation process continued.The residue was diluted with isopropyl alcohol (33.0 g), and hydrochloric acid (4.6 g, 31.5% aqueous solution) was added to the mixture at 75° C.The temperature was brought to 20° C., the solid was filtered and washed with isopropyl alcohol (14.6 g, in 2 portions), then dried to give (4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thienothiopyran-2-sulfonamide-7,7-dioxide, monochloride (8.1 g, titre 99.2%, ee 100%).1H NMR: δH (ppm) (400 MHz, DMSO) 9.9 (bs, 1H, -NH2+Cl-), 9.6 (bs, 1H, -NH2+Cl-), 8.2 (s, 2H, SO2NH2), 8.0 (s, 1H, CH), 4.7 (bs, 1H, CH), 4.35 (m, 1H, CH), 3.2 (bs, 1H, NH-CH2), 3.0 (bs, 1H, NH-CH2), 2.8 (m, 1H, CH2), 2.6-2.5 (m, 1H, CH2), 1.4 (d, 3H, J=6 Hz, CH3), 1.3 (t, 3H, J=7 Hz, CH3).
Safety and Hazards
Pictogram(s)SignalWarningGHS Hazard StatementsH302 (100%): Harmful if swallowed H373 (89.69%): Causes damage to organs through prolonged or repeated exposure Precautionary Statement CodesP260, P264, P270, P301+P317, P319, P330, and P501(The corresponding statement to each P-code can be found at the GHS Classification page.)
Other Data
TransportationUnder the room temperature and away from lightHS CodeStorageUnder the room temperature and away from lightShelf Life1 yearMarket Price
DruglikenessLipinski rules componentMolecular Weight360.907logP-0.23HBA6HBD2Matching Lipinski Rules4Veber rules componentPolar Surface Area (PSA)151.33Rotatable Bond (RotB)3Matching Veber Rules1
BioactivityIn vitro: EfficacyQuantitative Results
Quantitative Results1 of 31Comment (Pharmacological Data)Bioactivities presentReferenceOphthalmic composition containing a carbonic anhydrase inhibitor and xanthan gum2 of 10 Comment (Pharmacological Data)Bioactivities presentReferenceCarbonic anhydrase inhibitors: Water-soluble 4-sulfamoylphenylthioureas as topical intraocular pressure-lowering agents with long-lasting effects3 of 31Comment (Pharmacological Data)Bioactivities presentReferenceEffects of some ophthalmic medications on pupil size: A literature review4 of 31Comment (Pharmacological Data)Bioactivities presentReferencePROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED OXAMIDES5 of 31Comment (Pharmacological Data)Bioactivities presentReferenceCost-utility of primary open-angle glaucoma in Brazil6 of 31Comment (Pharmacological Data)Bioactivities presentReferenceBenzenesulfonamides Incorporating Flexible Triazole Moieties Are Highly Effective Carbonic Anhydrase Inhibitors: Synthesis and Kinetic, Crystallographic, Computational, and Intraocular Pressure Lowering Investigations
Toxicity/Safety PharmacologyQuantitative Results
Use PatternDorzolamide Hydrochloride CAS#：130693-82-2 is a carbonic anhydrase inhibitor. Dorzolamide hydrochloride is an anti-glaucoma topical eye drops. Dorzolamide hydrochloride is used to reduce the increased intraocular pressure in open angle glaucoma and ocular hypertension
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