Identification

Name
Dorzolamide
Accession Number
DB00869  (APRD00577, DB04507)
Type
Small Molecule
Groups
Approved
Description

Dorzolamide is a carbonic anhydrase (CA) inhibitor. It is used in ophthalmic solutions (Trusopt) to lower intraocular pressure (IOP) in open-angle glaucoma and ocular hypertension.

Structure
Thumb
Synonyms
  • (4S-trans)-4-(ETHYLAMINO)-5,6-dihydro-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide
  • (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,trans)-4-(Ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide
  • 4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonic acid amide
  • 4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonic acid amide
  • 4S,6S-Dorzolamide
  • Dorzolamid
  • Dorzolamida
  • Dorzolamide
  • Dorzolamidum
External IDs
L 671152 / MK 507
Product Ingredients
IngredientUNIICASInChI Key
Dorzolamide HydrochlorideQZO5366EW7130693-82-2OSRUSFPMRGDLAG-QMGYSKNISA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DorzolamideSolution2.0 %OphthalmicAlcon, Inc.Not applicableNot applicableCanada
Dorzolamide HydrochlorideSolution20 mg/mLOphthalmicPrasco, Laboratories1994-12-092017-01-10Us
Dorzolamide Hydrochloride Ophthalmic SolutionSolution20 mgOphthalmicBausch & Lomb IncNot applicableNot applicableCanada
Jamp-dorzolamideSolution2 %OphthalmicJamp Pharma CorporationNot applicableNot applicableCanada
Med-dorzolamideSolution2 %OphthalmicGeneric Medical Partners IncNot applicableNot applicableCanada
Riva-dorzolamideSolution2 %OphthalmicLaboratoire Riva Inc2017-01-03Not applicableCanada
Sandoz DorzolamideSolution20 mgOphthalmicSandoz Canada Incorporated2010-10-25Not applicableCanada
TrusoptSolution20 mg/mLOphthalmicMerck Sharp & Dohme Limited1994-12-09Not applicableUs
TrusoptSolution2 %OphthalmicPurdue Pharma1996-12-31Not applicableCanada
TrusoptSolution2 %OphthalmicPurdue Pharma2006-02-01Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-dorzolamideSolution2 %OphthalmicApotex CorporationNot applicableNot applicableCanada
Dorzolamide HClSolution20 mg/mLOphthalmicActavis Pharma Company2015-02-17Not applicableUs
Dorzolamide HClSolution20 mg/mLOphthalmicA S Medication Solutions2015-02-172017-06-20Us
Dorzolamide HClSolution / drops20 mg/mLOphthalmicA S Medication Solutions2009-06-252017-06-20Us
Dorzolamide HClSolution / drops22.3 mg/mLOphthalmicPhysicians Total Care, Inc.2012-02-21Not applicableUs
Dorzolamide HClSolution / drops20 mg/mLOphthalmicBauch & Lomb Incorporated2009-06-25Not applicableUs
Dorzolamide HydrochlorideSolution20 mg/mLOphthalmicTeva2010-01-28Not applicableUs
Dorzolamide HydrochlorideSolution / drops20 mg/mLOphthalmicSandoz2009-06-01Not applicableUs
Dorzolamide HydrochlorideSolution / drops20 mg/mLOphthalmicA S Medication Solutions2008-10-282017-06-20Us
Dorzolamide HydrochlorideSolution / drops20 mg/mLOphthalmicRemedy Repack2013-11-182017-01-10Us
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Act DorzotimololDorzolamide (20 mg) + Timolol (5 mg)SolutionOphthalmicActavis Pharma Company2013-05-01Not applicableCanada
Apo-dorzo-timopDorzolamide (20 mg) + Timolol (5 mg)SolutionOphthalmicApotex Corporation2010-12-15Not applicableCanada
CosoptDorzolamide Hydrochloride (20 mg/mL) + Timolol maleate (5 mg/mL)SolutionOphthalmicMerck Sharp & Dohme Limited1998-04-072016-02-22Us
CosoptDorzolamide Hydrochloride (20 mg/mL) + Timolol maleate (5 mg/mL)Solution / dropsOphthalmicAkorn2014-04-30Not applicableUs
CosoptDorzolamide (20 mg) + Timolol (5 mg)SolutionOphthalmicPurdue Pharma2005-11-02Not applicableCanada
CosoptDorzolamide (20 mg) + Timolol (5 mg)SolutionOphthalmicPurdue Pharma1999-05-27Not applicableCanada
CosoptDorzolamide Hydrochloride (20 mg/mL) + Timolol maleate (5 mg/mL)SolutionOphthalmicPhysicians Total Care, Inc.2002-10-29Not applicableUs
Cosopt PFDorzolamide Hydrochloride (20 mg/mL) + Timolol maleate (5 mg/mL)SolutionOphthalmicMerck Sharp & Dohme Limited2012-02-012016-04-13Us
Cosopt PFDorzolamide Hydrochloride (20 mg/mL) + Timolol maleate (5 mg/mL)Solution / dropsOphthalmicAkorn2014-05-14Not applicableUs
Dorzolamide HCl /Timolol MaleateDorzolamide Hydrochloride (20 mg/mL) + Timolol maleate (6.83 mg/mL)Solution / dropsOphthalmicRemedy Repack2015-06-222017-02-15Us
Categories
UNII
9JDX055TW1
CAS number
120279-96-1
Weight
Average: 324.44
Monoisotopic: 324.02721908
Chemical Formula
C10H16N2O4S3
InChI Key
IAVUPMFITXYVAF-XPUUQOCRSA-N
InChI
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
IUPAC Name
(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ⁶-thieno[2,3-b]thiopyran-6-sulfonamide
SMILES
CCN[[email protected]]1C[[email protected]](C)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O

Pharmacology

Indication

For the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Also used prophylatically for the inhibition of perioperative IOP increase (before neodynium yttrium aluminum garnet laser posterior capsulotomy).

Structured Indications
Pharmacodynamics

Dorzolamide is topical CA inhibitor that is indicated for the reduction of elevated IOP in patients with open-angle glaucoma or ocular hypertension who are insufficiently responsive to beta-blockers. Dorzolamide reduces IOP by approximately 17-23% in patients with elevater IOP.

Mechanism of action

Dorzolamide is a sulfonamide and a highly specific carbonic anhydrase II (CA-II) inhibitor, which is the main CA isoenzyme involved in aqueous humor secretion. Inhibition of CA-II in the ciliary processes of the eye decreases aqueous humor secretion, presumably by slowing the formation of bicarbonate ions with subsequent reduction in sodium and fluid transport. Dorzolamide also accumulates in red blood cells as a result of CA-II binding, as CA-II is found predominantly in erythrocytes. However, sufficient CA-II activity remains so that adverse effects due to systemic CA inhibition are not observed.

TargetActionsOrganism
ACarbonic anhydrase 2
inhibitor
Human
UCarbonic anhydrase 4
inhibitor
Human
UCarbonic anhydrase 1
inhibitor
Human
UCarbonic anhydrase 3
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

~33%

Metabolism
Not Available
Route of elimination

Dorzolamide is primarily excreted unchanged in the urine; the metabolite also is excreted in urine.

Half life

4 months

Clearance
Not Available
Toxicity

Dizziness, headache, shortness of breath, slow heartbeat, severe asthma, cardiac arrest

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Dorzolamide.Experimental
AbirateroneThe metabolism of Dorzolamide can be decreased when combined with Abiraterone.Approved
AcebutololDorzolamide may increase the hypotensive activities of Acebutolol.Approved
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Dorzolamide.Approved, Vet Approved
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Dorzolamide.Approved, Vet Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Dorzolamide.Approved, Investigational
AliskirenDorzolamide may increase the hypotensive activities of Aliskiren.Approved, Investigational
AloxiprinThe risk or severity of adverse effects can be increased when Aloxiprin is combined with Dorzolamide.Experimental
AlprenololAlprenolol may increase the hypotensive activities of Dorzolamide.Approved, Withdrawn
AmbrisentanDorzolamide may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostineDorzolamide may increase the hypotensive activities of Amifostine.Approved, Investigational
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Dorzolamide.Approved
AmiodaroneThe metabolism of Dorzolamide can be decreased when combined with Amiodarone.Approved, Investigational
AmlodipineAmlodipine may increase the hypotensive activities of Dorzolamide.Approved
AprepitantThe serum concentration of Dorzolamide can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Dorzolamide can be decreased when combined with Atazanavir.Approved, Investigational
AtenololAtenolol may increase the hypotensive activities of Dorzolamide.Approved
AtomoxetineThe metabolism of Dorzolamide can be decreased when combined with Atomoxetine.Approved
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Dorzolamide.Approved, Investigational
BenazeprilBenazepril may increase the hypotensive activities of Dorzolamide.Approved, Investigational
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Dorzolamide.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Dorzolamide.Withdrawn
BepridilDorzolamide may increase the hypotensive activities of Bepridil.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Dorzolamide.Approved
BethanidineBethanidine may increase the hypotensive activities of Dorzolamide.Approved
BietaserpineBietaserpine may increase the hypotensive activities of Dorzolamide.Experimental
BimatoprostDorzolamide may increase the hypotensive activities of Bimatoprost.Approved, Investigational
BisoprololBisoprolol may increase the hypotensive activities of Dorzolamide.Approved
BoceprevirThe metabolism of Dorzolamide can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Dorzolamide can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Dorzolamide can be decreased when it is combined with Bosentan.Approved, Investigational
BQ-123Dorzolamide may increase the hypotensive activities of BQ-123.Investigational
BretyliumDorzolamide may increase the hypotensive activities of Bretylium.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Dorzolamide.Approved
BrinzolamideThe risk or severity of adverse effects can be increased when Dorzolamide is combined with Brinzolamide.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Dorzolamide.Experimental
BupranololDorzolamide may increase the hypotensive activities of Bupranolol.Approved
CadralazineCadralazine may increase the hypotensive activities of Dorzolamide.Experimental
CafedrineDorzolamide may increase the hypotensive activities of Cafedrine.Investigational
Candesartan cilexetilCandesartan may increase the hypotensive activities of Dorzolamide.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Dorzolamide.Experimental
CapecitabineThe metabolism of Dorzolamide can be decreased when combined with Capecitabine.Approved, Investigational
CaptoprilDorzolamide may increase the hypotensive activities of Captopril.Approved
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Dorzolamide.Approved, Investigational
Carbaspirin calciumThe risk or severity of adverse effects can be increased when Carbaspirin calcium is combined with Dorzolamide.Experimental, Investigational
CaroxazoneCaroxazone may increase the hypotensive activities of Dorzolamide.Withdrawn
CarteololCarteolol may increase the hypotensive activities of Dorzolamide.Approved
CarvedilolDorzolamide may increase the hypotensive activities of Carvedilol.Approved, Investigational
CeliprololDorzolamide may increase the hypotensive activities of Celiprolol.Approved, Investigational
CeritinibThe serum concentration of Dorzolamide can be increased when it is combined with Ceritinib.Approved
ChlorothiazideDorzolamide may increase the hypotensive activities of Chlorothiazide.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Dorzolamide.Approved
CholecalciferolThe metabolism of Dorzolamide can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CicletanineDorzolamide may increase the hypotensive activities of Cicletanine.Investigational
CilazaprilDorzolamide may increase the hypotensive activities of Cilazapril.Approved
ClarithromycinThe metabolism of Dorzolamide can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Dorzolamide can be decreased when combined with Clemastine.Approved
ClonidineClonidine may increase the hypotensive activities of Dorzolamide.Approved
CloranololDorzolamide may increase the hypotensive activities of Cloranolol.Experimental
ClotrimazoleThe metabolism of Dorzolamide can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Dorzolamide can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Dorzolamide can be increased when it is combined with Conivaptan.Approved, Investigational
CrisaboroleThe metabolism of Dorzolamide can be decreased when combined with Crisaborole.Approved
CrizotinibThe metabolism of Dorzolamide can be decreased when combined with Crizotinib.Approved
CryptenamineCryptenamine may increase the hypotensive activities of Dorzolamide.Approved
CyclopenthiazideDorzolamide may increase the hypotensive activities of Cyclopenthiazide.Experimental
CyclosporineThe metabolism of Dorzolamide can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CyclothiazideCyclothiazide may increase the hypotensive activities of Dorzolamide.Approved
DabrafenibThe serum concentration of Dorzolamide can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Dorzolamide can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Dorzolamide can be increased when it is combined with Dasatinib.Approved, Investigational
DebrisoquinDebrisoquin may increase the hypotensive activities of Dorzolamide.Approved, Investigational
DeferasiroxThe serum concentration of Dorzolamide can be decreased when it is combined with Deferasirox.Approved, Investigational
DelaprilDorzolamide may increase the hypotensive activities of Delapril.Experimental
DelavirdineThe metabolism of Dorzolamide can be decreased when combined with Delavirdine.Approved
dersalazineThe risk or severity of adverse effects can be increased when dersalazine is combined with Dorzolamide.Investigational
DeserpidineDorzolamide may increase the hypotensive activities of Deserpidine.Approved
DiazoxideDiazoxide may increase the hypotensive activities of Dorzolamide.Approved
DiclofenamideThe risk or severity of adverse effects can be increased when Dorzolamide is combined with Diclofenamide.Approved
diethylnorspermineDorzolamide may increase the hypotensive activities of diethylnorspermine.Investigational
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Dorzolamide.Approved
DihydralazineDihydralazine may increase the hypotensive activities of Dorzolamide.Investigational
DihydroergotamineThe metabolism of Dorzolamide can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Dorzolamide can be decreased when combined with Diltiazem.Approved
DosulepinThe metabolism of Dorzolamide can be decreased when combined with Dosulepin.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Dorzolamide.Approved
DoxycyclineThe metabolism of Dorzolamide can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Dorzolamide can be decreased when combined with Dronedarone.Approved
EfavirenzThe metabolism of Dorzolamide can be decreased when combined with Efavirenz.Approved, Investigational
EfonidipineDorzolamide may increase the hypotensive activities of Efonidipine.Approved
EnalaprilEnalapril may increase the hypotensive activities of Dorzolamide.Approved, Vet Approved
EnalaprilatDorzolamide may increase the hypotensive activities of Enalaprilat.Approved
EndralazineEndralazine may increase the hypotensive activities of Dorzolamide.Experimental
EnzalutamideThe serum concentration of Dorzolamide can be decreased when it is combined with Enzalutamide.Approved
EpanololDorzolamide may increase the hypotensive activities of Epanolol.Experimental
EpoprostenolDorzolamide may increase the hypotensive activities of Epoprostenol.Approved
EprosartanDorzolamide may increase the hypotensive activities of Eprosartan.Approved
ErythromycinThe metabolism of Dorzolamide can be decreased when combined with Erythromycin.Approved, Vet Approved
EthoxzolamideThe risk or severity of adverse effects can be increased when Dorzolamide is combined with Ethoxzolamide.Withdrawn
EtravirineThe metabolism of Dorzolamide can be decreased when combined with Etravirine.Approved
FelodipineDorzolamide may increase the hypotensive activities of Felodipine.Approved, Investigational
FenoldopamFenoldopam may increase the hypotensive activities of Dorzolamide.Approved
Ferulic acidDorzolamide may increase the hypotensive activities of Ferulic acid.Experimental
FlecainideThe serum concentration of Flecainide can be increased when it is combined with Dorzolamide.Approved, Withdrawn
FloxuridineThe metabolism of Dorzolamide can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Dorzolamide can be decreased when combined with Fluconazole.Approved
FluorouracilThe metabolism of Dorzolamide can be decreased when combined with Fluorouracil.Approved
FluvastatinThe metabolism of Dorzolamide can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Dorzolamide can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Dorzolamide can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Dorzolamide can be increased when it is combined with Fosaprepitant.Approved
FosinoprilFosinopril may increase the hypotensive activities of Dorzolamide.Approved
FosphenytoinThe metabolism of Dorzolamide can be increased when combined with Fosphenytoin.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Dorzolamide.Approved, Investigational, Vet Approved
Fusidic AcidThe serum concentration of Dorzolamide can be increased when it is combined with Fusidic Acid.Approved
GemfibrozilThe metabolism of Dorzolamide can be decreased when combined with Gemfibrozil.Approved
GuacetisalThe risk or severity of adverse effects can be increased when Guacetisal is combined with Dorzolamide.Experimental
GuanabenzGuanabenz may increase the hypotensive activities of Dorzolamide.Approved, Investigational
GuanadrelGuanadrel may increase the hypotensive activities of Dorzolamide.Approved
GuanazodineDorzolamide may increase the hypotensive activities of Guanazodine.Experimental
GuanethidineGuanethidine may increase the hypotensive activities of Dorzolamide.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Dorzolamide.Approved, Investigational
GuanoclorDorzolamide may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzDorzolamide may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanDorzolamide may increase the hypotensive activities of Guanoxan.Experimental
HarmalineHarmaline may increase the hypotensive activities of Dorzolamide.Experimental
Hemoglobin crosfumarilThe risk or severity of adverse effects can be increased when Hemoglobin crosfumaril is combined with Dorzolamide.Experimental
HexamethoniumDorzolamide may increase the hypotensive activities of Hexamethonium.Experimental
HydracarbazineHydracarbazine may increase the hypotensive activities of Dorzolamide.Experimental
HydralazineHydralazine may increase the hypotensive activities of Dorzolamide.Approved
HydrochlorothiazideDorzolamide may increase the hypotensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Dorzolamide.Approved, Investigational
IdelalisibThe serum concentration of Dorzolamide can be increased when it is combined with Idelalisib.Approved
IloprostIloprost may increase the hypotensive activities of Dorzolamide.Approved, Investigational
ImatinibThe metabolism of Dorzolamide can be decreased when combined with Imatinib.Approved
ImidaprilDorzolamide may increase the hypotensive activities of Imidapril.Investigational
IndapamideIndapamide may increase the hypotensive activities of Dorzolamide.Approved
IndenololDorzolamide may increase the hypotensive activities of Indenolol.Withdrawn
IndinavirThe metabolism of Dorzolamide can be decreased when combined with Indinavir.Approved
IndoraminIndoramin may increase the hypotensive activities of Dorzolamide.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Dorzolamide.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Dorzolamide.Withdrawn
IrbesartanThe metabolism of Dorzolamide can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Dorzolamide can be decreased when combined with Isavuconazonium.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Dorzolamide.Approved
IsradipineThe metabolism of Dorzolamide can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Dorzolamide can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Dorzolamide can be increased when it is combined with Ivacaftor.Approved
KetanserinKetanserin may increase the hypotensive activities of Dorzolamide.Investigational
KetoconazoleThe metabolism of Dorzolamide can be decreased when combined with Ketoconazole.Approved, Investigational
LabetalolLabetalol may increase the hypotensive activities of Dorzolamide.Approved
LacidipineDorzolamide may increase the hypotensive activities of Lacidipine.Approved, Investigational
LatanoprostLatanoprost may increase the hypotensive activities of Dorzolamide.Approved, Investigational
LeflunomideThe metabolism of Dorzolamide can be decreased when combined with Leflunomide.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Dorzolamide.Approved, Investigational
LinsidomineDorzolamide may increase the hypotensive activities of Linsidomine.Experimental
LisinoprilLisinopril may increase the hypotensive activities of Dorzolamide.Approved, Investigational
LithiumThe serum concentration of Lithium can be decreased when it is combined with Dorzolamide.Approved
LobeglitazoneThe metabolism of Dorzolamide can be decreased when combined with Lobeglitazone.Approved, Investigational
LofexidineDorzolamide may increase the hypotensive activities of Lofexidine.Approved, Investigational
LopinavirThe metabolism of Dorzolamide can be decreased when combined with Lopinavir.Approved
LosartanThe metabolism of Dorzolamide can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Dorzolamide can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Dorzolamide can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Dorzolamide can be decreased when it is combined with Lumacaftor.Approved
MacitentanDorzolamide may increase the hypotensive activities of Macitentan.Approved
ManidipineDorzolamide may increase the hypotensive activities of Manidipine.Approved, Investigational
MebanazineMebanazine may increase the hypotensive activities of Dorzolamide.Withdrawn
MecamylamineMecamylamine may increase the hypotensive activities of Dorzolamide.Approved
MemantineDorzolamide may decrease the excretion rate of Memantine which could result in a higher serum level.Approved, Investigational
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Dorzolamide.Approved
MetforminThe risk or severity of adverse effects can be increased when Dorzolamide is combined with Metformin.Approved
MethazolamideThe risk or severity of adverse effects can be increased when Methazolamide is combined with Dorzolamide.Approved
MethenamineThe therapeutic efficacy of Methenamine can be decreased when used in combination with Dorzolamide.Approved, Vet Approved
MethoserpidineDorzolamide may increase the hypotensive activities of Methoserpidine.Experimental
MethyldopaDorzolamide may increase the hypotensive activities of Methyldopa.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Dorzolamide.Approved, Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Dorzolamide.Approved, Investigational
MetipranololDorzolamide may increase the hypotensive activities of Metipranolol.Approved
MetolazoneMetolazone may increase the hypotensive activities of Dorzolamide.Approved
MetoprololMetoprolol may increase the hypotensive activities of Dorzolamide.Approved, Investigational
MetyrosineDorzolamide may increase the hypotensive activities of Metyrosine.Approved
MibefradilDorzolamide may increase the hypotensive activities of Mibefradil.Investigational, Withdrawn
MidostaurinThe metabolism of Dorzolamide can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Dorzolamide can be increased when it is combined with Mifepristone.Approved, Investigational
MinaprineMinaprine may increase the hypotensive activities of Dorzolamide.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Dorzolamide.Approved
MirodenafilMirodenafil may increase the antihypertensive activities of Dorzolamide.Investigational
MitotaneThe serum concentration of Dorzolamide can be decreased when it is combined with Mitotane.Approved
MoclobemideMoclobemide may increase the hypotensive activities of Dorzolamide.Approved
MoexiprilMoexipril may increase the hypotensive activities of Dorzolamide.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Dorzolamide.Approved, Investigational
MoxonidineMoxonidine may increase the hypotensive activities of Dorzolamide.Approved, Investigational
MuzolimineDorzolamide may increase the hypotensive activities of Muzolimine.Experimental
NadololDorzolamide may increase the hypotensive activities of Nadolol.Approved
NaftopidilDorzolamide may increase the hypotensive activities of Naftopidil.Investigational
NebivololDorzolamide may increase the hypotensive activities of Nebivolol.Approved, Investigational
NefazodoneThe metabolism of Dorzolamide can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Dorzolamide can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Dorzolamide can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Dorzolamide can be increased when combined with Nevirapine.Approved
NialamideNialamide may increase the hypotensive activities of Dorzolamide.Withdrawn
NicardipineThe metabolism of Dorzolamide can be decreased when combined with Nicardipine.Approved
NicorandilDorzolamide may increase the hypotensive activities of Nicorandil.Approved, Investigational
NiguldipineDorzolamide may increase the hypotensive activities of Niguldipine.Experimental
NilotinibThe metabolism of Dorzolamide can be decreased when combined with Nilotinib.Approved, Investigational
NilvadipineDorzolamide may increase the hypotensive activities of Nilvadipine.Approved, Investigational
NimodipineNimodipine may increase the hypotensive activities of Dorzolamide.Approved
NisoldipineNisoldipine may increase the hypotensive activities of Dorzolamide.Approved
NitrendipineDorzolamide may increase the hypotensive activities of Nitrendipine.Approved, Investigational
NitroaspirinThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with Dorzolamide.Investigational
NitroprussideNitroprusside may increase the hypotensive activities of Dorzolamide.Approved
ObinutuzumabDorzolamide may increase the hypotensive activities of Obinutuzumab.Approved
OctamoxinOctamoxin may increase the hypotensive activities of Dorzolamide.Withdrawn
OlaparibThe metabolism of Dorzolamide can be decreased when combined with Olaparib.Approved
OlmesartanOlmesartan may increase the hypotensive activities of Dorzolamide.Approved, Investigational
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Dorzolamide.Approved
OmapatrilatDorzolamide may increase the hypotensive activities of Omapatrilat.Investigational
OmeprazoleThe metabolism of Dorzolamide can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Dorzolamide can be increased when it is combined with Osimertinib.Approved
OxprenololDorzolamide may increase the hypotensive activities of Oxprenolol.Approved
PalbociclibThe serum concentration of Dorzolamide can be increased when it is combined with Palbociclib.Approved
PargylinePargyline may increase the hypotensive activities of Dorzolamide.Approved
PenbutololDorzolamide may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentobarbitalThe metabolism of Dorzolamide can be increased when combined with Pentobarbital.Approved, Vet Approved
PentoliniumDorzolamide may increase the hypotensive activities of Pentolinium.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Dorzolamide.Approved, Investigational
PerindoprilPerindopril may increase the hypotensive activities of Dorzolamide.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Dorzolamide.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Dorzolamide.Withdrawn
PhenobarbitalThe metabolism of Dorzolamide can be increased when combined with Phenobarbital.Approved
PhenoxybenzamineDorzolamide may increase the hypotensive activities of Phenoxybenzamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Dorzolamide.Withdrawn
PhentolaminePhentolamine may increase the hypotensive activities of Dorzolamide.Approved
PhenytoinThe metabolism of Dorzolamide can be increased when combined with Phenytoin.Approved, Vet Approved
PinacidilPinacidil may increase the hypotensive activities of Dorzolamide.Withdrawn
PindololDorzolamide may increase the hypotensive activities of Pindolol.Approved
PirlindolePirlindole may increase the hypotensive activities of Dorzolamide.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Dorzolamide.Withdrawn
PolythiazideDorzolamide may increase the hypotensive activities of Polythiazide.Approved
PosaconazoleThe metabolism of Dorzolamide can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrazosinPrazosin may increase the hypotensive activities of Dorzolamide.Approved
PrimidoneThe risk or severity of adverse effects can be increased when Dorzolamide is combined with Primidone.Approved, Vet Approved
PropranololPropranolol may increase the hypotensive activities of Dorzolamide.Approved, Investigational
PyrimethamineThe metabolism of Dorzolamide can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinaprilDorzolamide may increase the hypotensive activities of Quinapril.Approved, Investigational
QuinidineDorzolamide may decrease the excretion rate of Quinidine which could result in a higher serum level.Approved
QuinineQuinine may increase the hypotensive activities of Dorzolamide.Approved
RamiprilRamipril may increase the hypotensive activities of Dorzolamide.Approved
RanolazineThe metabolism of Dorzolamide can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineRasagiline may increase the hypotensive activities of Dorzolamide.Approved
RemikirenRemikiren may increase the hypotensive activities of Dorzolamide.Approved
RescinnamineDorzolamide may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Dorzolamide.Approved, Investigational
RifabutinThe metabolism of Dorzolamide can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Dorzolamide can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Dorzolamide can be increased when combined with Rifapentine.Approved
RilmenidineRilmenidine may increase the hypotensive activities of Dorzolamide.Investigational
RiociguatDorzolamide may increase the hypotensive activities of Riociguat.Approved
RitonavirThe metabolism of Dorzolamide can be decreased when combined with Ritonavir.Approved, Investigational
RituximabDorzolamide may increase the hypotensive activities of Rituximab.Approved
SafrazineSafrazine may increase the hypotensive activities of Dorzolamide.Withdrawn
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Dorzolamide.Approved, Vet Approved
SaprisartanDorzolamide may increase the hypotensive activities of Saprisartan.Experimental
SaquinavirThe metabolism of Dorzolamide can be decreased when combined with Saquinavir.Approved, Investigational
SecobarbitalThe metabolism of Dorzolamide can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineSelegiline may increase the hypotensive activities of Dorzolamide.Approved, Investigational, Vet Approved
SelexipagDorzolamide may increase the hypotensive activities of Selexipag.Approved
SildenafilSildenafil may increase the antihypertensive activities of Dorzolamide.Approved, Investigational
SiltuximabThe serum concentration of Dorzolamide can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Dorzolamide can be increased when it is combined with Simeprevir.Approved
SitaxentanDorzolamide may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SorafenibThe metabolism of Dorzolamide can be decreased when combined with Sorafenib.Approved, Investigational
SpiraprilDorzolamide may increase the hypotensive activities of Spirapril.Approved
St. John's WortThe serum concentration of Dorzolamide can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Dorzolamide can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Dorzolamide can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Dorzolamide can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Dorzolamide can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TadalafilTadalafil may increase the antihypertensive activities of Dorzolamide.Approved, Investigational
TalinololDorzolamide may increase the hypotensive activities of Talinolol.Investigational
TelaprevirThe metabolism of Dorzolamide can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Dorzolamide can be decreased when combined with Telithromycin.Approved
TelmisartanDorzolamide may increase the hypotensive activities of Telmisartan.Approved, Investigational
TemocaprilDorzolamide may increase the hypotensive activities of Temocapril.Experimental, Investigational
TerlipressinDorzolamide may increase the hypotensive activities of Terlipressin.Approved, Investigational
TetrahydropalmatineDorzolamide may increase the hypotensive activities of Tetrahydropalmatine.Investigational
TheodrenalineDorzolamide may increase the hypotensive activities of Theodrenaline.Investigational
TiboloneDorzolamide may increase the hypotensive activities of Tibolone.Approved, Investigational
TicagrelorThe metabolism of Dorzolamide can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Dorzolamide can be decreased when combined with Ticlopidine.Approved
TicrynafenDorzolamide may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololTimolol may increase the hypotensive activities of Dorzolamide.Approved
TocilizumabThe serum concentration of Dorzolamide can be decreased when it is combined with Tocilizumab.Approved
TolazolineTolazoline may increase the hypotensive activities of Dorzolamide.Approved, Vet Approved
TolbutamideThe metabolism of Dorzolamide can be decreased when combined with Tolbutamide.Approved
TolonidineDorzolamide may increase the hypotensive activities of Tolonidine.Experimental
ToloxatoneToloxatone may increase the hypotensive activities of Dorzolamide.Approved
TopiroxostatThe metabolism of Dorzolamide can be decreased when combined with Topiroxostat.Approved, Investigational
TorasemideTorasemide may increase the hypotensive activities of Dorzolamide.Approved
TrandolaprilTrandolapril may increase the hypotensive activities of Dorzolamide.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Dorzolamide.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Dorzolamide.Approved
TravoprostTravoprost may increase the hypotensive activities of Dorzolamide.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Dorzolamide.Approved, Investigational
TrichlormethiazideDorzolamide may increase the hypotensive activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Dorzolamide.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Dorzolamide.Approved, Investigational
TrimethoprimThe metabolism of Dorzolamide can be decreased when combined with Trimethoprim.Approved, Vet Approved
UdenafilUdenafil may increase the antihypertensive activities of Dorzolamide.Approved, Investigational
UnoprostoneDorzolamide may increase the hypotensive activities of Unoprostone.Approved
UrapidilUrapidil may increase the hypotensive activities of Dorzolamide.Investigational
Valproic AcidThe metabolism of Dorzolamide can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Dorzolamide can be decreased when combined with Valsartan.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Dorzolamide.Approved
VenlafaxineThe metabolism of Dorzolamide can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Dorzolamide can be decreased when combined with Verapamil.Approved
VincamineDorzolamide may increase the hypotensive activities of Vincamine.Experimental
VinpocetineDorzolamide may increase the hypotensive activities of Vinpocetine.Investigational
VoriconazoleThe metabolism of Dorzolamide can be decreased when combined with Voriconazole.Approved, Investigational
XipamideDorzolamide may increase the hypotensive activities of Xipamide.Experimental
XylometazolineDorzolamide may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Dorzolamide.Approved, Vet Approved
ZafirlukastThe metabolism of Dorzolamide can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe metabolism of Dorzolamide can be decreased when combined with Ziprasidone.Approved
ZofenoprilDorzolamide may increase the hypotensive activities of Zofenopril.Experimental
Food Interactions
Not Available

References

Synthesis Reference

Laszlo Kovacs, Csaba Szabo, Erika Molnarne, Adrienne Kovacsne-Mezei, Claude Singer, Judith Aronhime, "Method of making dorzolamide hydrochloride." U.S. Patent US20060155132, issued July 13, 2006.

US20060155132
General References
  1. 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. [PubMed:16771760]
  2. 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. [PubMed:16546110]
  3. 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. [PubMed:16470316]
  4. Martens-Lobenhoffer J, Banditt P: Clinical pharmacokinetics of dorzolamide. Clin Pharmacokinet. 2002;41(3):197-205. [PubMed:11929320]
  5. 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. [PubMed:9143858]
  6. 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. [PubMed:9760696]
External Links
Human Metabolome Database
HMDB15007
KEGG Drug
D07871
KEGG Compound
C06969
PubChem Compound
5284549
PubChem Substance
46506754
ChemSpider
4447604
BindingDB
10884
ChEBI
4702
ChEMBL
CHEMBL218490
Therapeutic Targets Database
DAP000775
PharmGKB
PA164748765
HET
ETS
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Dorzolamide
ATC Codes
S01EC03 — Dorzolamide
AHFS Codes
  • 52:40.12 — Carbonic Anhydrase Inhibitors
PDB Entries
1cil / 3fw3 / 4k13 / 4m2u / 4m2w
FDA label
Download (569 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Not Yet RecruitingTreatmentGlaucoma1
1RecruitingTreatmentEye Diseases / Glaucoma / Ocular Hypertension1
2Active Not RecruitingTreatmentChildhood Glaucoma1
2CompletedTreatmentGlaucoma2
2CompletedTreatmentGlaucoma, Primary Open Angle (POAG)1
2CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
2RecruitingTreatmentAge-Related Macular Degeneration (ARMD) / Diabetic Macular Edema (DME) / Retinal Vein Occlusions(RVO) / Wet Macular Degeneration1
2Unknown StatusTreatmentHypertensive Phase1
2, 3CompletedBasic ScienceOpen-angle Glaucoma (OAG)1
2, 3RecruitingTreatmentNeovascular Age-Related Macular Degeneration / Wet Macular Degeneration1
3CompletedTreatmentGlaucoma1
3CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
3CompletedTreatmentGlaucoma / Ocular Hypertension3
3CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)1
3CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
3Not Yet RecruitingTreatmentGlaucoma, Primary Open Angle (POAG)1
3RecruitingPreventionGlaucoma1
3TerminatedTreatmentGlaucoma / Ocular Hypertension1
4CompletedNot AvailableOcular Hypertension / Open-angle Glaucoma (OAG)1
4CompletedBasic ScienceGlaucoma1
4CompletedOtherEye Disease1
4CompletedTreatmentGlaucoma5
4CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
4CompletedTreatmentGlaucoma / Ocular Hypertension2
4CompletedTreatmentGlaucoma / Ocular Surface Disease1
4CompletedTreatmentOcular Hypertension1
4CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)2
4CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)3
4CompletedTreatmentOpen-angle Glaucoma (OAG)1
4RecruitingTreatmentGlaucoma1
4TerminatedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
4Unknown StatusBasic ScienceOpen Angle Glaucoma (OAG)1
4Unknown StatusTreatmentGlaucoma1
4Unknown StatusTreatmentRetinal Degenerations1
Not AvailableCompletedBasic ScienceDrug Effect (Glaucoma Drugs)1
Not AvailableCompletedBasic ScienceGlaucoma1
Not AvailableCompletedPreventionRetinopathy, Diabetic1
Not AvailableCompletedTreatmentMacular Hole / Retinal Detachment1
Not AvailableCompletedTreatmentNormal Tension Glaucoma1
Not AvailableCompletedTreatmentScleral Buckling1
Not AvailableRecruitingNot AvailableDiabetic Macular Edema (DME) / Retinopathy, Diabetic1
Not AvailableUnknown StatusHealth Services ResearchOpen Angle Glaucoma (OAG)1
Not AvailableUnknown StatusTreatmentExfoliation Syndrome / Glaucoma / Ocular Hypertension1
Not AvailableWithdrawnNot AvailableOcular Hypertension / Open-angle Glaucoma (OAG)1
Not AvailableWithdrawnBasic ScienceGlaucoma1

Pharmacoeconomics

Manufacturers
  • Alcon inc
  • Apotex inc
  • Bausch and lomb inc
  • Hi tech pharmacal co inc
  • Pharmaforce inc
  • Sandoz canada inc
  • Teva pharmaceuticals usa
  • Merck research laboratories div merck co inc
Packagers
Dosage forms
FormRouteStrength
SolutionOphthalmic2 %
SolutionOphthalmic
SolutionOphthalmic2.0 %
Solution / dropsOphthalmic22.3 mg/mL
SolutionOphthalmic20 mg/mL
Solution / dropsOphthalmic20 mg/mL
Solution / dropsOphthalmic
SolutionOphthalmic22.3 mg/mL
SolutionOphthalmic20 mg
Prices
Unit descriptionCostUnit
Trusopt 2% Solution 10ml79.25USD bottle
Dorzolamide HCl 2% Solution 10ml Bottle69.42USD bottle
Dorzolamide hcl 2% eye drops6.86USD ml
Trusopt 2% eye drops6.73USD ml
Trusopt (Preservative-Free) 2 % Solution3.93USD ml
Trusopt 2 % Solution3.93USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1329211No1994-05-032011-05-03Canada

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)283-285 °CNot Available
logP-1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.699 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.46 m3·mol-1ChemAxon
Polarizability31.55 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier+0.6697
Caco-2 permeable-0.6627
P-glycoprotein substrateSubstrate0.5389
P-glycoprotein inhibitor INon-inhibitor0.8855
P-glycoprotein inhibitor IINon-inhibitor0.8398
Renal organic cation transporterNon-inhibitor0.9011
CYP450 2C9 substrateNon-substrate0.7755
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5096
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7547
Ames testNon AMES toxic0.6397
CarcinogenicityNon-carcinogens0.6933
BiodegradationNot ready biodegradable0.9946
Rat acute toxicity2.2365 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9446
hERG inhibition (predictor II)Non-inhibitor0.8706
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thiophenes
Sub Class
2,3,5-trisubstituted thiophenes
Direct Parent
2,3,5-trisubstituted thiophenes
Alternative Parents
Aralkylamines / Thiopyrans / Organosulfonamides / Sulfones / Heteroaromatic compounds / Aminosulfonyl compounds / Dialkylamines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
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
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfonamide, thiophenes (CHEBI:4702)

Targets

Details
1. Carbonic anhydrase 2
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 Da
References
  1. Lachmann C, Jorg KM, Trinkmann R: [Postoperative behavior of intraocular pressure after posterior Nd:YAG laser capsulotomy--critical evaluation in preventive administration of local carbonic anhydrase II inhibitor dorzolamide hydrochloride (Trusopt)]. Klin Monbl Augenheilkd. 1998 Dec;213(6):326-30. [PubMed:10048009]
  2. Wong BK, Bruhin PJ, Barrish A, Lin JH: Nonlinear dorzolamide pharmacokinetics in rats: concentration-dependent erythrocyte distribution and drug-metabolite displacement interaction. Drug Metab Dispos. 1996 Jun;24(6):659-63. [PubMed:8781782]
  3. Berg JT, Ramanathan S, Gabrielli MG, Swenson ER: Carbonic anhydrase in mammalian vascular smooth muscle. J Histochem Cytochem. 2004 Aug;52(8):1101-6. [PubMed:15258186]
  4. Hasegawa T, Hara K, Hata S: Binding of dorzolamide and its metabolite, N-deethylated dorzolamide, to human erythrocytes in vitro. Drug Metab Dispos. 1994 May-Jun;22(3):377-82. [PubMed:8070313]
  5. Maren TH, Conroy CW, Wynns GC, Levy NS: Ocular absorption, blood levels, and excretion of dorzolamide, a topically active carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1997 Feb;13(1):23-30. [PubMed:9029437]
  6. Sugrue MF: Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors. Prog Retin Eye Res. 2000 Jan;19(1):87-112. [PubMed:10614682]
  7. Sugrue MF: The preclinical pharmacology of dorzolamide hydrochloride, a topical carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1996 Fall;12(3):363-76. [PubMed:8875343]
  8. Srinivas SP, Ong A, Zhai CB, Bonanno JA: Inhibition of carbonic anhydrase activity in cultured bovine corneal endothelial cells by dorzolamide. Invest Ophthalmol Vis Sci. 2002 Oct;43(10):3273-8. [PubMed:12356834]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Details
2. Carbonic anhydrase 4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina an...
Gene Name
CA4
Uniprot ID
P22748
Uniprot Name
Carbonic anhydrase 4
Molecular Weight
35032.075 Da
References
  1. Sugrue MF: The preclinical pharmacology of dorzolamide hydrochloride, a topical carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1996 Fall;12(3):363-76. [PubMed:8875343]
Details
3. Carbonic anhydrase 1
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name
CA1
Uniprot ID
P00915
Uniprot Name
Carbonic anhydrase 1
Molecular Weight
28870.0 Da
References
  1. Hasegawa T, Hara K, Hata S: Binding of dorzolamide and its metabolite, N-deethylated dorzolamide, to human erythrocytes in vitro. Drug Metab Dispos. 1994 May-Jun;22(3):377-82. [PubMed:8070313]
  2. Maren TH, Conroy CW, Wynns GC, Levy NS: Ocular absorption, blood levels, and excretion of dorzolamide, a topically active carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1997 Feb;13(1):23-30. [PubMed:9029437]
  3. Sugrue MF: The preclinical pharmacology of dorzolamide hydrochloride, a topical carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1996 Fall;12(3):363-76. [PubMed:8875343]
Details
4. Carbonic anhydrase 3
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide.
Gene Name
CA3
Uniprot ID
P07451
Uniprot Name
Carbonic anhydrase 3
Molecular Weight
29557.215 Da
References
  1. Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25. [PubMed:17826101]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on November 13, 2017 21:49