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Basic Information

Molecular Structure:
CAS No.:	130693-82-2
Name:	Dorzolomide hydrochloride
Article Data:	13

Formula:	C₁₀H₁₆N₂O₄S₃^.HCl
Molecular Weight:	360.907
Synonyms:	4H-Thieno[2,3-b]thiopyran-2-sulfonamide,4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, monohydrochloride, (4S,6S)-(9CI);(S,S)-(-)-5,6-Dihydro-4-ethylamino-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxidemonohydrochloride;L 671152;MK 507;Trusopt;
EINECS:	620-304-2
Density:	1.53 g/cm³
Melting Point:	265-267 °C
Boiling Point:	575.8 °C at 760 mmHg
Flash Point:	302 °C
Appearance:	White off-white crystalline powder.

Synthetic route

: 1227941-29-8
(4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno-[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide di-p-toluyl-L-tartate salt

: 130693-82-2
dorzolamide hydrochloride

Conditions

Conditions	Yield
Stage #1: (4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno-[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide di-p-toluyl-L-tartate salt With sodium hydrogencarbonate In water; ethyl acetate at 25 - 30℃; for 0.25h; Stage #2: With hydrogenchloride In ethyl acetate; isopropyl alcohol at 25 - 85℃; for 12.5h; Product distribution / selectivity;	100%
With hydrogenchloride In isopropyl alcohol at 80℃; for 0.0833333 - 0.166667h; pH=3 - 4; Product distribution / selectivity; Heating / reflux;
Stage #1: (4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno-[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide di-p-toluyl-L-tartate salt With sodium hydrogencarbonate In ethyl acetate at 20℃; Stage #2: With hydrogenchloride In methanol; isopropyl alcohol for 0.666667h;

: 5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-dioxide maleate salt

: 130693-82-2
dorzolamide hydrochloride

Conditions

Conditions	Yield
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

: 120279-96-1
dorzolamide

: 130693-82-2
dorzolamide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethyl acetate pH=1;	95%
With hydrogenchloride In water; dimethyl sulfoxide at 5 - 10℃; for 3h; pH=1.0;

: 5,6-dihydro-4-(S)-ethylamino-6-(S)-methyl-4H-thieno[2,3-b]thiopyran-7,7-dioxide hydrochloride

: 130693-82-2
dorzolamide hydrochloride

Conditions

Conditions	Yield
Stage #1: 5,6-dihydro-4-(S)-ethylamino-6-(S)-methyl-4H-thieno[2,3-b]thiopyran-7,7-dioxide hydrochloride With sulfuric acid; sulfur trioxide at 20℃; for 2 - 3h; Stage #2: With thionyl chloride for 3 - 6h; Heating / reflux; Stage #3: With hydrogenchloride; ammonia Product distribution / selectivity; more than 3 stages;	70%
Stage #1: 5,6-dihydro-4-(S)-ethylamino-6-(S)-methyl-4H-thieno[2,3-b]thiopyran-7,7-dioxide hydrochloride With sulfuric acid; sulfur trioxide at -7 - 20℃; for 22h; Stage #2: With thionyl chloride at 20 - 65℃; for 24h; Stage #3: With hydrogenchloride; ammonia Product distribution / selectivity; more than 3 stages;

Reaxys ID: 11712783: Reaxys ID: 11712783

: 130693-82-2
dorzolamide hydrochloride

Conditions

Conditions	Yield
With (-)-di-p-toluoyl-L-tartaric acid	22.48%

: trans-5,6-dihydro-4-ethylamino-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

: 130693-82-2
dorzolamide hydrochloride

Conditions

Conditions	Yield
Stage #1: trans-5,6-dihydro-4-ethylamino-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide; Di-p-toluoyl-L-tartaric acid In propan-1-ol Heating / reflux; Stage #2: With sodium hydrogencarbonate In water Stage #3: With hydrogenchloride In ethanol	22.48%

: 2C10H16N2O4S3*C11H10O7

: 130693-82-2
dorzolamide hydrochloride

Conditions

Conditions	Yield
Stage #1: 2C10H16N2O4S3*C11H10O7 With sodium carbonate In water; ethyl acetate Stage #2: With hydrogenchloride In ethyl acetate; isopropyl alcohol pH=1 - 2;

: 5,6-dihydro-6-methyl-4-oxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide

: 130693-82-2
dorzolamide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: dihydrogen peroxide / sodium tungstate (VI) dihydrate / ethyl acetate; water / -20 °C 2.1: water; sodium tetrahydroborate; methanol / ethyl acetate / 10 - 20 °C 3.1: sulfuric acid / 0 - 30 °C 3.2: 10 °C / pH 7 - 8 4.1: sodium tetrahydroborate / tetrahydrofuran / -5 - 5 °C 4.2: 5 - 20 °C 5.1: sodium hydroxide / 20 °C / pH 7.5 - 8 6.1: isopropyl alcohol; acetonitrile / 1 h / 70 °C / Reflux 7.1: sodium hydrogencarbonate / ethyl acetate / 20 °C 7.2: 0.67 h View Scheme

Yield

Multi-step reaction with 7 steps
1.1: dihydrogen peroxide / sodium tungstate (VI) dihydrate / ethyl acetate; water / -20 °C
2.1: water; sodium tetrahydroborate; methanol / ethyl acetate / 10 - 20 °C
3.1: sulfuric acid / 0 - 30 °C
3.2: 10 °C / pH 7 - 8
4.1: sodium tetrahydroborate / tetrahydrofuran / -5 - 5 °C
4.2: 5 - 20 °C
5.1: sodium hydroxide / 20 °C / pH 7.5 - 8
6.1: isopropyl alcohol; acetonitrile / 1 h / 70 °C / Reflux
7.1: sodium hydrogencarbonate / ethyl acetate / 20 °C
7.2: 0.67 h
View Scheme

: 4-hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

: 130693-82-2
dorzolamide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sulfuric acid / 0 - 30 °C 1.2: 10 °C / pH 7 - 8 2.1: sodium tetrahydroborate / tetrahydrofuran / -5 - 5 °C 2.2: 5 - 20 °C 3.1: sodium hydroxide / 20 °C / pH 7.5 - 8 4.1: isopropyl alcohol; acetonitrile / 1 h / 70 °C / Reflux 5.1: sodium hydrogencarbonate / ethyl acetate / 20 °C 5.2: 0.67 h View Scheme

: (+/-)-(4S,6S;4R,6R)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide

: 130693-82-2
dorzolamide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: isopropyl alcohol; acetonitrile / 1 h / 70 °C / Reflux 2.1: sodium hydrogencarbonate / ethyl acetate / 20 °C 2.2: 0.67 h View Scheme

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Chemistry

IUPAC Name:(4R,6R)-?4-?(ethylamino)-?6-?methyl-?7,7-?dioxo-?5,6-?dihydro-?4H-?thieno[2,3-?b]thiopyran-?2-?sulfonamide hydrochloride
Molecular Formula:C₁₀H₁₇ClN₂O₄S₃
Molecular Weight:360.900980 g/mol
Appearance:White off-white crystalline powder
Density:1.53 g/cm³
Melting Point:283~285 oC
Boiling Point:575.8 °C at 760 mmHg
Flash Point:302 °C
Synonyms of Dorzolamide hydrochloride(130693-82-2):
3-b)thiopyran-2-sulfonamide,5,6-dihydro-4-(ethylamino)-6-methyl-4h-thieno(;mk-0507;monohydrochloride,(4s-trans)-7-dioxide;(2s,4s)-2-ethylamino-4-methyl-5,5-dioxo-5,7-dithiabicyclo[4.3.0]nona-8,10-diene-8-sulfonamide hydrochloride;DORZOLAMIDE HCL;DORZOLAMIDE HYDROCHLORIDE;dorzolomide hydrochloride;DorzolomideHcl,Usp
Categories of Dorzolamide hydrochloride(130693-82-2):
Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Dorzolamide

Uses

Dorzolamide hydrochloride(130693-82-2) is used for treatment of glaucoma.

Toxicity Data With Reference

Toxicity Information of Dorzolamide hydrochloride(130693-82-2):
1.dog LD50 oral > 250mg/kg (250mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 1241, 1994.
2.mouse LD50 intravenous 469mg/kg (469mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)LUNGS, THORAX, OR RESPIRATION: DYSPNEA Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 1241, 1994.
3.mouse LD50 oral 1320mg/kg (1320mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYEBEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: ATAXIA Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 1241, 1994.
4.mouse LD50 subcutaneous > 2gm/kg (2000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE,BEHAVIORAL: ATAXIA,BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 1241, 1994.
5.rat LD50 intravenous 726mg/kg (726mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: DYSPNEA Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 1241, 1994.
6.rat LD50 oral 1927mg/kg (1927mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)BEHAVIORAL: ATAXIA Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 1241, 1994.
7.rat LD50 subcutaneous > 2gm/kg (2000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 1241, 1994.

Analytical Methods

TRUSOPT is a sulfonamide and, although administered topically, is absorbed systemically. Therefore, the same types of adverse reactions that are attributable to sulfonamides may occur with topical administration with TRUSOPT. Fatalities have occurred, although rarely, due to severe reactions to sulfonamides including Stevens-Johnson syndrome, toxic epidermal necrolysis, fulminant hepatic necrosis, agranulocytosis, aplastic anemia, and other blood dyscrasias. Sensitization may recur when a sulfonamide is readministered irrespective of the route of administration. If signs of serious reactions or hypersensitivity occur, discontinue the use of this preparation.