Dorzolamide (CHEM022193)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:23:21 UTC
Update Date2016-11-09 01:17:26 UTC
Accession NumberCHEM022193
Identification
Common NameDorzolamide
ClassSmall Molecule
DescriptionDorzolamide is a non-bacteriostatic sulfonamide derivative and topical carbonic anhydrase (CA) inhibitor that treats elevated intraocular pressure (IOP) associated with open-angle glaucoma and ocular hypertension. It works by blocking an enzyme in the ciliary process that regulates ion balance and fluid pressure in the eyes. Unlike oral CA inhibitors, dorzolamide has negligible effects of acid-base or electrolyte disturbances and other systemic adverse effects. First marketed in 1995, dorzolamide is available in ophthalmic solutions as monotherapy marketed as Dorzolamide or in combination with as Cosopt PF.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ar3-2393000000-5fee748c257c96fe4cc6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1039000000-bc26f50a987e66b2d85fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1940000000-b593686cdeed391e6252Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-37bcca2a8a93f29e705eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-7495000000-d579bf9a53d7355310beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fa9-5960000000-4180bf8ab95c96f57f15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-0ef2ea7db65e541aecefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-2467b7c2962f7a83efdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0097000000-a04c8c4869eb06d72260Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-0390000000-5e9ea339d753845f7c98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-77ced8018945af0b8737Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-4439000000-3349264d7067d02efbcaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9740000000-a0afe72c11e381401a2fSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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