ETS

(4S-TRANS)-4-(ETHYLAMINO)-5,6-DIHYDRO-6-METHYL-4H-THIENO(2,3-B)THIOPYRAN-2-SULFONAMIDE-7,7-DIOXIDE

Created: 1999-07-08
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count35
Chiral Atom Count2
Bond Count36
Aromatic Bond Count5
2D diagram of ETS
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Chemical Component Summary

Name(4S-TRANS)-4-(ETHYLAMINO)-5,6-DIHYDRO-6-METHYL-4H-THIENO(2,3-B)THIOPYRAN-2-SULFONAMIDE-7,7-DIOXIDE
SynonymsDorzolamide
Systematic Name (OpenEye OEToolkits)(4S,6S)-4-(ethylamino)-6-methyl-7,7-bis(oxidanylidene)-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide
FormulaC10 H16 N2 O4 S3
Molecular Weight324.44
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=S(=O)(c1sc2c(c1)C(NCC)CC(S2(=O)=O)C)N
SMILESCACTVS3.385CCN[CH]1C[CH](C)[S](=O)(=O)c2sc(cc12)[S](N)(=O)=O
SMILESOpenEye OEToolkits1.7.6CCNC1CC(S(=O)(=O)c2c1cc(s2)S(=O)(=O)N)C
Canonical SMILESCACTVS3.385 CCN[C@H]1C[C@H](C)[S](=O)(=O)c2sc(cc12)[S](N)(=O)=O
Canonical SMILESOpenEye OEToolkits1.7.6 CCN[C@H]1C[C@@H](S(=O)(=O)c2c1cc(s2)S(=O)(=O)N)C
InChIInChI1.03 InChI=1S/C10H16N2O4S3/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)/t6-,8-/m0/s1
InChIKeyInChI1.03 IAVUPMFITXYVAF-XPUUQOCRSA-N

Drug Info: DrugBank

DrugBank IDDB00869 
NameDorzolamide
Groups approved
DescriptionDorzolamide is a non-bacteriostatic sulfonamide derivative [A1304] and topical carbonic anhydrase (CA) inhibitor that treats elevated intraocular pressure (IOP) associated with open-angle glaucoma and ocular hypertension.[L11377] It works by blocking an enzyme in the ciliary process that regulates ion balance and fluid pressure in the eyes.[A1303] Unlike oral CA inhibitors, dorzolamide has negligible effects of acid-base or electrolyte disturbances and other systemic adverse effects.[A1304] First marketed in 1995,[A190624] dorzolamide is available in ophthalmic solutions as monotherapy marketed as Trusopt [L11377] or in combination with [timolol] as Cosopt PF.[L11380]
Synonyms
  • (4S,6S)-4-ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonic acid amide
  • 4S,6S-dorzolamide
  • Dorzolamida
  • (4S,trans)-4-(ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide
  • Dorzolamidum
Brand Names
  • Trusopt Preservative-free
  • Act Dorzotimolol
  • Van-dorzolamide-timolol
  • Dorzolamide Hydrochloride Timolol Maleate
  • Cosopt
IndicationDorzolamide is indicated for the management of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma.[L11377] It can also be used in combination with [timolol] for the same indication in patients who are insufficiently responsive to ophthalmic beta-blockers.[L11380] Its pre-operative use was also investigated to prevent elevated intraocular pressure after neodynium yttrium aluminum garnet laser posterior capsulotomy.[A190183]
Categories
  • Amides
  • Antiglaucoma Preparations and Miotics
  • Antihypertensive Agents
  • Carbonic Anhydrase Inhibitors
  • Cardiovascular Agents
ATC-Code
  • G01AE10
  • S01EC03
CAS number120279-96-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Carbonic anhydrase 2MSHHWGYGKHNGPEHWHKDFPIAKGERQSPVDIDTHTAKYDPSLKPLSVS...unknowninhibitor
Carbonic anhydrase 4MRMLLALLALSAARPSASAESHWCYEVQAESSNYPCLVPVKWGGNCQKDR...unknowninhibitor
Carbonic anhydrase 1MASPDWGYDDKNGPEQWSKLYPIANGNNQSPVDIKTSETKHDTSLKPISV...unknowninhibitor
Carbonic anhydrase 3MAKEWGYASHNGPDHWHELFPNAKGENQSPVELHTKDIRHDPSLQPWSVS...unknowninhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL218490
PubChem 5284549
ChEMBL CHEMBL218490
ChEBI CHEBI:4702
CCDC/CSD SETSOA