Dorzolamide Hydrochloride CAS#：130693-82-2; ChemWhat Code: 1411214

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NameDorzolamide Hydrochloride
IUPAC Name(4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide;hydrochloride  
Molecular Structure
CAS Registry Number 130693-82-2
EINECS Number620-304-2
MDL NumberMFCD00884659
Beilstein Registry Number5896026
SynonymsDORZOLAMIDE HYDROCHLORIDE
130693-82-2
Dorzolamide HCl
Trusopt
Dorzolomide hydrochloride
Cosopt
Dorzolamide (hydrochloride)
MK-507
Dorzolomide HCl
(4S,6S)-4-(ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride
Dorzolamide (as hydrochloride)
QZO5366EW7
Trusopt (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-thieno[2,3-b]thiopyran-2-sulfonamide;hydrochloride
4H-Thieno(2,3-b)thiopyran-2-sulfonamide, 4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, monohydrochloride, (4S-trans)-
UNII-QZO5366EW7
SR-05000001449
Dorzolamide hydrochloride [USAN]
(4S,6S)-4-(Ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide, monohydrochloride
L 671152
L-671,152
Dorzolamide HCl salt
Dorzolamide hydrochloride [USAN:USP]
MK507 hydrochloride
MK 0507
MK-0507
L671152 hydrochloride
NCGC00016977-01
CAS-130693-82-2
SCHEMBL41152
MLS002154162
CHEMBL1201162
DTXSID1045530
Dorzolamide hydrochloride- Bio-X
HY-B0109A
HMS1571O14
EX-A3987
Tox21_110720
MFCD00884659
s1375
DORZOLAMIDE HYDROCHLORIDE [MI]
AKOS005146235
AKOS015895951
Dorzolamide hydrochloride (JP17/USP)
Tox21_110720_1
AC-5244
CCG-221116
CS-1858
DORZOLAMIDE HYDROCHLORIDE [JAN]
KS-1348
DORZOLAMIDE HYDROCHLORIDE [MART.]
DORZOLAMIDE HYDROCHLORIDE [VANDF]
NCGC00179244-03
BD164381
DORZOLAMIDE HYDROCHLORIDE [USP-RS]
DORZOLAMIDE HYDROCHLORIDE [WHO-DD]
SMR001233461
MK-507 (L-671152) HCl
D4189
DORZOLAMIDE HYDROCHLORIDE, TRANS-(-)-
C72221
D00653
DORZOLAMIDE HYDROCHLORIDE [ORANGE BOOK]
DORZOLAMIDE HYDROCHLORIDE [USP IMPURITY]
COSOPT COMPONENT DORZOLAMIDE HYDROCHLORIDE
DORZOLAMIDE HYDROCHLORIDE [USP MONOGRAPH]
279D961
EN300-19768601
DORZOLAMIDE HYDROCHLORIDE COMPONENT OF COSOPT
L-671152
SR-05000001449-3
Q27106441
Dorzolamide hydrochloride, European Pharmacopoeia (EP) Reference Standard
Dorzolamide for system suitability, European Pharmacopoeia (EP) Reference Standard
Dorzolamide hydrochloride, United States Pharmacopeia (USP) Reference Standard
(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1lambda6-thieno[2,3-b]thiopyran-6-sulfonamide hydrochloride
(4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide 4H-Thieno[2,3-b]thiopyran-2-sulfonamide hydrochloride
122028-16-4
4H-Thieno(2,3-b)thiopyran-2-sulfonamide, 5,6-dihydro-4-(ethylamino)-6-methyl-, 7,7-dioxide, monohydrochloride, (4S,6S)-
Molecular FormulaC10H17ClN2O4S3
Molecular Weight360.901
InChIInChI=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./s1
InChI KeyOSRUSFPMRGDLAG-QMGYSKNISA-N
Canonical SMILES
Patent Information
Patent IDTitlePublication Date
US2015/191485Process for Preparing Enantiomerically Enriched Oxamides2015
WO2008/75155CARBONIC ANHYDRASE INHIBITORS DERIVATIVES2008
US2006/142595Process for preparing 5,6-dihydro-4-(S)-(ethylamino)-6-(S) methyl-4H-thieno[2,3b]thiopyran-2-sulphonamide-7,7-dioxide HCI2006
US2006/155132PYRROLOTRIAZINE DERIVATIVES2006

Physical Data

AppearanceA white to off white c1ystalline powder.
Melting Point, °C Solvent (Melting Point)
283 – 285
238H2O
Density, g·cm-3Reference Temperature, °CMeasurement Temperature, °C
1.60619.85

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Frequency (NMR Spectroscopy), MHz
Chemical shifts1Hdimethylsulfoxide-d6400
Chemical shifts1Hdimethylsulfoxide-d6400
Chemical shifts1Hdimethylsulfoxide-d6
Chemical shifts13Cdimethylsulfoxide-d6
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Temperature (IR Spectroscopy), °C
FT-IR
BandsKBr14.85 – 54.85
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nmExt./Abs. Coefficient, l·mol-1cm-1
Absorption maximaaq. HCl, methanol254

Route of Synthesis (ROS)

Route of Dorzolamide Hydrochloride CAS#：130693-82-2

ConditionsYield
Stage #1: 5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-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-thieno<2,3-b>thiopyran-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 g
Experimental Procedure

10 (4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide, monochloride Dorzolamide Hydrochloride
Example 10
(4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide, monochloride Dorzolamide Hydrochloride
Sodium 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-thieno[2,3-b]thiopyran-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-thieno[2,3-b]thiopyran-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)exclamation-markhealth-hazard
SignalWarning
GHS Hazard StatementsH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H373 (89.69%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, 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 light
HS Code
StorageUnder the room temperature and away from light
Shelf Life1 year
Market Price
Druglikeness
Lipinski rules component
Molecular Weight360.907
logP-0.23
HBA6
HBD2
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)151.33
Rotatable Bond (RotB)3
Matching Veber Rules1
Bioactivity
In vitro: Efficacy
Quantitative Results
Quantitative Results
1 of 31Comment (Pharmacological Data)Bioactivities present
ReferenceOphthalmic composition containing a carbonic anhydrase inhibitor and xanthan gum
2 of 10
Comment (Pharmacological Data)		Bioactivities present
ReferenceCarbonic anhydrase inhibitors: Water-soluble 4-sulfamoylphenylthioureas as topical intraocular pressure-lowering agents with long-lasting effects
3 of 31Comment (Pharmacological Data)Bioactivities present
ReferenceEffects of some ophthalmic medications on pupil size: A literature review
4 of 31Comment (Pharmacological Data)Bioactivities present
ReferencePROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED OXAMIDES
5 of 31Comment (Pharmacological Data)Bioactivities present
ReferenceCost-utility of primary open-angle glaucoma in Brazil
6 of 31Comment (Pharmacological Data)Bioactivities present
ReferenceBenzenesulfonamides Incorporating Flexible Triazole Moieties Are Highly Effective Carbonic Anhydrase Inhibitors: Synthesis and Kinetic, Crystallographic, Computational, and Intraocular Pressure Lowering Investigations
Toxicity/Safety Pharmacology
Quantitative Results
Use Pattern
Dorzolamide 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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