Dorzolamide (CED0004724)

Record Information
Version1.0
Creation Date2016-05-25 18:23:21 UTC
Update Date2026-08-18 01:56:50 UTC
Accession NumberCHEM022193
Identification
Common NameDorzolamide
ClassSmall Molecule
Description
Dorzolamide is an organic compound with the chemical formula C10H16N2O4S3 and an average molecular weight of 324.44 g/mol. Dorzolamide belongs to the 2,3,5-trisubstituted thiophenes, a subclass of thiophenes within the organic compounds. It is categorized as an organoheterocyclic compound. The compound is identified as an inhibitor of four protein targets: Carbonic anhydrase 1 (CA1), Carbonic anhydrase 2 (CA2), Carbonic anhydrase 3 (CA3), and Carbonic anhydrase 4 (CA4). Regarding its presence in commercial products, it is found in or released from four recorded sources. These include household cleaning and consumer products, specifically other smoking requisites and non electric simulated smoking devices, as well as healthcare, pharmaceuticals and veterinary products, specifically miotics and antiglaucoma preparations and gynecologicals. The recorded exposure route for this compound is ophthalmic.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonic acid amideChEBI
(4S,trans)-4-(Ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxideChEBI
(4S-trans)-4-(ETHYLAMINO)-5,6-dihydro-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxideChEBI
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonic acid amideChEBI
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonic acid amideChEBI
4S,6S-DorzolamideChEBI
TrusoptKegg
(4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonate amideGenerator
(4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulphonate amideGenerator
(4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulphonic acid amideGenerator
(4S,trans)-4-(Ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulphonamide 7,7-dioxideGenerator
(4S-trans)-4-(ETHYLAMINO)-5,6-dihydro-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulphonamide-7,7-dioxideGenerator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonate amideGenerator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulphonate amideGenerator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulphonic acid amideGenerator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonate amideGenerator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulphonate amideGenerator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulphonic acid amideGenerator
5,6-Dihydro-4-ethylamino-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxideHMDB
Dorzolamide hydrochlorideHMDB
Dorzolamide chibretHMDB
Dorzolamide, (trans)-isomerHMDB
4-Ethylamino-5,6-dihydro-6-methyl-7,7-dioxide-4H-thieno(2,3-b)thiopyran-2-sulfonamideHMDB
Chemical FormulaC10H16N2O4S3
Average Molecular Mass324.440 g/mol
Monoisotopic Mass324.027 g/mol
CAS Registry Number120279-96-1
IUPAC Name(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ⁶-thieno[2,3-b]thiopyran-6-sulfonamide
Traditional Namedorzolamide
SMILESCCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O
InChI IdentifierInChI=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
InChI KeyIAVUPMFITXYVAF-XPUUQOCRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,3,5-trisubstituted thiophenes. These are organic compounds containing a thiophene that is trisubstituted at the C-2, C3- and C5-positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiophenes
Sub Class2,3,5-trisubstituted thiophenes
Direct Parent2,3,5-trisubstituted thiophenes
Alternative Parents
Substituents
  • 2,3,5-trisubstituted thiophene
  • Aralkylamine
  • Organosulfonic acid amide
  • Thiopyran
  • Sulfone
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Secondary aliphatic amine
  • Secondary amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.7 g/LALOGPS
logP-0.5ALOGPS
logP-0.15ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)8.18ChemAxon
pKa (Strongest Basic)7.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area106.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.46 m³·mol⁻¹ChemAxon
Polarizability31.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0ar3-2393000000-5fee748c257c96fe4cc6Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1039000000-bc26f50a987e66b2d85fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1940000000-b593686cdeed391e6252Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-37bcca2a8a93f29e705eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00b9-7495000000-d579bf9a53d7355310beNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fa9-5960000000-4180bf8ab95c96f57f15Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9010000000-0ef2ea7db65e541aecefNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0009000000-2467b7c2962f7a83efdcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0097000000-a04c8c4869eb06d72260Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016r-0390000000-5e9ea339d753845f7c98Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-77ced8018945af0b8737Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dr-4439000000-3349264d7067d02efbcaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9740000000-a0afe72c11e381401a2fNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1359.0Log mg/kg[760:2400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
398Antiglaucoma preparations and mioticsHealthcare, pharmaceuticals & veterinary productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
Pathways
1 pathway
Dorzolamide Drug Metabolism Action Pathway
Dorzolamide Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)31.4511
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)29.5049
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)26.3909
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)14.5578
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)7.78492
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)22.9655
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)8.32987
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)10.6653
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)8.01847
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)9.6533
Carbonic anhydrase 13 structureClick to view 3D structureCarbonic anhydrase 13Q8N1Q1HumansPredicted (SEA)2.17978
Click to view 3D structureCarbonate dehydrataseB2V8E3Sulfurihydrogenibium sp. (strain YO3AOP1)Predicted (SEA)2.33548
Click to view 3D structureAstrosclerin-3A6YCJ1Astrosclera willeyanaPredicted (SEA)2.72472
Click to view 3D structureDelta carbonic anhydraseQ5U9J1Conticribra weissflogiiPredicted (SEA)1.86838
Click to view 3D structureCarbonic anhydrase, alpha familyQ31FD6Thiomicrospira crunogenaPredicted (SEA)2.33548
Click to view 3D structureAGAP002992-PAQ5TU56Anopheles gambiaePredicted (SEA)1.08989
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)8.79696
Click to view 3D structureCarbonic anhydrase 13Q9D6N1Mus musculusPredicted (SEA)3.50322
Click to view 3D structureCarbonic anhydrase 15Q99N23Mus musculusPredicted (SEA)5.0602
Click to view 3D structureCarbonic anhydraseO24855Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)Predicted (SEA)3.03612
Click to view 3D structureCarbonic anhydraseQ6FTL6Candida glabrata CBS 138Predicted (SEA)4.43741
Click to view 3D structureAlpha carbonic anhydraseB5SU02Stylophora pistillataPredicted (SEA)2.33548
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)2.88042
Click to view 3D structureCarbonic anhydraseP53615Saccharomyces cerevisiae S288cPredicted (SEA)1.63483
Click to view 3D structureCarbonic anhydrase 2P9WPJ9Mycobacterium tuberculosisPredicted (SEA)0.233548
Concentrations
Not Available
External Links
DrugBank IDDB00869
HMDB IDHMDB0015007
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDorzolamide
Chemspider ID4447604
ChEBI ID4702
PubChem Compound ID5284549
Kegg Compound IDC06969
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Balfour JA, Wilde MI: Dorzolamide. A review of its pharmacology and therapeutic potential in the management of glaucoma and ocular hypertension. Drugs Aging. 1997 May;10(5):384-403.
2. Ponticello GS, Sugrue MF, Plazonnet B, Durand-Cavagna G: Dorzolamide, a 40-year wait. From an oral to a topical carbonic anhydrase inhibitor for the treatment of glaucoma. Pharm Biotechnol. 1998;11:555-74.
3. Martens-Lobenhoffer J, Banditt P: Clinical pharmacokinetics of dorzolamide. Clin Pharmacokinet. 2002;41(3):197-205.
4. Almeida GC Jr, Faria e Souza SJ: Effect of topical dorzolamide on rabbit central corneal thickness. Braz J Med Biol Res. 2006 Feb;39(2):277-81. Epub 2006 Feb 2.
5. Grover S, Apushkin MA, Fishman GA: Topical dorzolamide for the treatment of cystoid macular edema in patients with retinitis pigmentosa. Am J Ophthalmol. 2006 May;141(5):850-8. Epub 2006 Mar 20.
6. Plummer CE, MacKay EO, Gelatt KN: Comparison of the effects of topical administration of a fixed combination of dorzolamide-timolol to monotherapy with timolol or dorzolamide on IOP, pupil size, and heart rate in glaucomatous dogs. Vet Ophthalmol. 2006 Jul-Aug;9(4):245-9.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=10762051
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=11229775
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=11425561
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=11906288
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=14611846
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=14684332