Dorzolamide

Identification

Summary

Dorzolamide is a carbonic anhydrase inhibitor used to treat high intraocular pressure in ocular hypertension and open angle glaucoma.

Brand Names

Cosopt, Trusopt

Generic Name

Dorzolamide

DrugBank Accession Number

DB00869

Background

Dorzolamide is a non-bacteriostatic sulfonamide derivative ² and topical carbonic anhydrase (CA) inhibitor that treats elevated intraocular pressure (IOP) associated with open-angle glaucoma and ocular hypertension.⁶ It works by blocking an enzyme in the ciliary process that regulates ion balance and fluid pressure in the eyes.¹ Unlike oral CA inhibitors, dorzolamide has negligible effects of acid-base or electrolyte disturbances and other systemic adverse effects.² First marketed in 1995,⁵ dorzolamide is available in ophthalmic solutions as monotherapy marketed as Trusopt ⁶ or in combination with timolol as Cosopt PF.⁷

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 324.44
Monoisotopic: 324.02721908
Chemical Formula: C₁₀H₁₆N₂O₄S₃

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,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

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Pharmacology

Indication

Dorzolamide is indicated for the management of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma.⁶ It can also be used in combination with timolol for the same indication in patients who are insufficiently responsive to ophthalmic beta-blockers.⁷

Its pre-operative use was also investigated to prevent elevated intraocular pressure after neodynium yttrium aluminum garnet laser posterior capsulotomy.³

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Patient Characteristics	Dose Form
Prophylaxis of	Elevated intraocular pressure		••• •••••		•••••••• • •••••
Used in combination to manage	Elevated intraocular pressure	Combination Product in combination with: Timolol (DB00373)	••••••••••••	•••••••••••• •••••••• •• •••••••••••••	•••••••• • •••••
Used in combination to manage	Elevated intraocular pressure	Combination Product in combination with: Timolol (DB00373)	••••••••••••	•••••••••••• •••••••• •• •••••••••••••	••••••••
Management of	Elevated intraocular pressure		••••••••••••		•••••••• • •••••
Management of	Elevated intraocular pressure		••••••••••••		•••••••• • •••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Dorzolamide is a carbonic anhydrase inhibitor that reduces elevated intraocular pressure in open-angle glaucoma or ocular hypertension. When used in combination with topic beta-adrenergic antagonists, dorzolamide has an additive effect of lowering intraocular pressure. The peak ocular hypotensive effect of dorzolamide is observed at about 2 hours following ophthalmic administration.²

Mechanism of action

Elevated intraocular pressure is a characteristic manifestation of ocular hypertension or open-angle glaucoma. The level of intraocular pressure (IOP) is governed by the balance between the production of aqueous humour (by ocular ciliary processes) and its outflow from the anterior segment of the eye via trabecular (conventional) or uveoscleral (unconventional) pathways. When there is an increase in the resistance to the trabecular outflow of aqueous humour, the intraocular pressure is elevated. Subsequently, optic nerve damage can occur from blood flow restrictions and mechanical distortion of ocular structures. Optic nerve damage can further result in optic disc cupping and progressive visual field loss (and blindness in some cases).²

Carbonic anhydrase (CA) is a ubiquitous enzyme that catalyzes the reversible hydration of carbon dioxide to bicarbonate ions and dehydration of carbonic acid.^2,6 In the ocular ciliary processes, the local production of bicarbonate by CAs promotes sodium and fluid transport. CA-II is a key isoenzyme found primarily in red blood cells (RBCs) that regulates aqueous humour production.² Dorzolamide is a highly specific CA-II inhibitor, where it displays a 4000-fold higher affinity for carbonic anhydrase II than carbonic anhydrase I.² The inhibition of CA-II in the ciliary process disrupts the formation of bicarbonate ions and reduces sodium and fluid transport, which leads to decreased aqueous humour secretion and reduced intraocular pressure.^2,6

Target	Actions	Organism
ACarbonic anhydrase 2	inhibitor	Humans
ACarbonic anhydrase 4	inhibitor	Humans
ACarbonic anhydrase 1	inhibitor	Humans
UCarbonic anhydrase 3	inhibitor	Humans

Absorption

Dorzolamide readily penetrated into the eye in animal studies.² Upon ophthalmic administration, dorzolamide is absorbed via the cornea and stroma.¹ Dorzolamide is reported to be absorbed systematically following topical administration.⁶ The systemic exposure of dorzolamide following long-term administration was assessed in healthy subjects receiving an oral dose of 2 mg dorzolamide twice daily, which equates to the ophthalmic dose of 2% dorzolamide three times daily. In these subjects receiving the treatment for 20 weeks, the steady-state was reached within 8 weeks.⁶

Volume of distribution

There is limited information on the volume of distribution of dorzolamide; however, the plasma concentrations of dorzolamide and its main metabolite are generally below the assay limit of quantitation, which is 15nM. Dorzolamide accumulates in red blood cells following chronic administration as a result of binding to CA-II, which is contained in peripheral red blood cells (RBCs).⁶

Protein binding

Dorzolamide is approximately 33% bound to plasma proteins.⁶

Metabolism

Dorzolamide is slowly metabolised to N-desethyldorzolamide, which has a less potent pharmacological activity on CA-II and some inhibitory effect on CA-I.⁶ Like the parent drug, N-desethyldorzolamide is also stored in RBCs, where it binds to CA-I.^1,6 The findings of an in vitro study using liver microsomes from Sprague-Dawley rats suggest the involvement of CYP2B1, CYP2E1, and CYP3A2 in the metabolism of dorzolamide in rat liver.⁴

Hover over products below to view reaction partners

Dorzolamide
- N-desethyldorzolamide

Route of elimination

Dorzolamide is primarily excreted unchanged in the urine; however, N-desethyldorzolamide is also detected in the urine.⁶

Half-life

As the drug administration is stopped, dorzolamide stored in RBCs is washed out of RBCs in a non-linear fashion,⁶ with the terminal elimination half-life of ≥120 days in RBCs.² This initial rapid decline in drug concentrations is followed by the slow elimination phase, where the elimination half-life of the drug is about >4 months.¹

Clearance

There is limited information on the clearance rate of dorzolamide.

Adverse Effects

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Toxicity

The oral LD₅₀ of dorzolamide is 1927 mg/kg in rats and 1320 mg/kg in mice. The subcutaneous LD₅₀ is >2 g/kg in both rats and mice.⁸

Overdose may result in electrolyte imbalance, acidosis, and possibly central nervous system effects; these symptoms should be responded with appropriate supportive treatment. It is advised that the patient's serum electrolyte (particularly potassium) levels and blood pH levels are monitored in the case of a suspected overdose.⁶

Pathways

Not Available

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Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Acebutolol	Dorzolamide may increase the hypotensive activities of Acebutolol.
Acetazolamide	The risk or severity of adverse effects can be increased when Acetazolamide is combined with Dorzolamide.
Acetylsalicylic acid	The risk or severity of metabolic acidosis can be increased when Dorzolamide is combined with Acetylsalicylic acid.
Aliskiren	Dorzolamide may increase the hypotensive activities of Aliskiren.
Ambrisentan	Dorzolamide may increase the hypotensive activities of Ambrisentan.

Food Interactions

No interactions found.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Dorzolamide hydrochloride	QZO5366EW7	130693-82-2	OSRUSFPMRGDLAG-QMGYSKNISA-N

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Dorzolamide	Solution	2 % w/v	Ophthalmic	Micro Labs Limited	Not applicable	Not applicable
Dorzolamide	Solution	2.0 % w/v	Ophthalmic	Alcon, Inc.	Not applicable	Not applicable
Dorzolamide	Solution	20 mg / mL	Ophthalmic	Jamp Pharma Corporation	2023-09-28	Not applicable
Dorzolamide Eye Drops BP	Solution	2 % w/v	Ophthalmic	Hikma Canada Limited	Not applicable	Not applicable
Dorzolamide Hydrochloride	Solution	20 mg/1mL	Ophthalmic	Prasco, Laboratories	1994-12-09	2014-08-31

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-dorzolamide	Solution	2 %	Ophthalmic	Apotex Corporation	Not applicable	Not applicable
Dorzolamide HCl	Solution / drops	20 mg/1mL	Ophthalmic	A-S Medication Solutions	2009-06-25	2019-11-30
Dorzolamide HCl	Solution	20 mg/1mL	Ophthalmic	Actavis Pharma Company	2015-02-17	2019-02-28
Dorzolamide HCl	Solution / drops	20 mg/1mL	Ophthalmic	Bausch & Lomb Incorporated	2009-06-25	Not applicable
Dorzolamide HCl	Solution / drops	22.3 mg/1mL	Ophthalmic	Physicians Total Care, Inc.	2012-02-21	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Act Dorzotimolol	Dorzolamide hydrochloride (20 mg / mL) + Timolol maleate (5 mg / mL)	Solution	Ophthalmic	TEVA Canada Limited	2013-05-01	Not applicable
Ag-dorzolamide Timolol	Dorzolamide hydrochloride (20 mg / mL) + Timolol maleate (5 mg / mL)	Solution	Ophthalmic	Angita Pharma Inc.	Not applicable	Not applicable
Apo-dorzo-timop	Dorzolamide hydrochloride (20 mg / mL) + Timolol maleate (5 mg / mL)	Solution	Ophthalmic	Apotex Corporation	2010-12-15	Not applicable
ARUDOR % 2 + % 0.5 GOZ DAMLASI, 5 ML	Dorzolamide hydrochloride (20 mg/ml) + Timolol maleate (5 mg/ml)	Solution / drops	Ophthalmic	GENVEON İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
ARUTIDOR	Dorzolamide hydrochloride (20 mg/mL) + Timolol maleate (5 mg/mL)	Solution / drops; Suspension / drops	Ophthalmic		2017-01-01	2021-11-15

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Brim-Dor PF	Dorzolamide hydrochloride (20 mg/1mL) + Brimonidine tartrate (1.5 mg/1mL)	Solution / drops	Ophthalmic	ImprimisRx NJ	2018-01-01	Not applicable
Dorzolamide PF	Dorzolamide hydrochloride (20 mg/1mL)	Solution / drops	Ophthalmic	ImprimisRx NJ	2018-01-01	Not applicable
DORZOTIM GOZ DAMLASI 5 ML	Dorzolamide (22.25 mg) + Timolol maleate (6.83 mg)	Solution / drops	Ophthalmic	TEKA TEKNİK CİHAZLAR SAN.VE TİC. A.Ş.	2014-02-23	Not applicable
Tim-Brim-Dor PF	Dorzolamide hydrochloride (20 mg/1mL) + Brimonidine tartrate (1.5 mg/1mL) + Timolol maleate (5 mg/1mL)	Solution / drops	Ophthalmic	ImprimisRx NJ	2018-01-01	Not applicable
Tim-Brim-Dor-Lat	Dorzolamide hydrochloride (20 mg/1mL) + Brimonidine tartrate (1.5 mg/1mL) + Latanoprost (0.05 mg/1mL) + Timolol maleate (5 mg/1mL)	Solution / drops	Ophthalmic	ImprimisRx NJ	2018-01-01	Not applicable

Chemical Identifiers

UNII: 9JDX055TW1
CAS number: 120279-96-1
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-1lambda6-thieno[2,3-b]thiopyran-6-sulfonamide
SMILES: CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O

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

Martens-Lobenhoffer J, Banditt P: Clinical pharmacokinetics of dorzolamide. Clin Pharmacokinet. 2002;41(3):197-205. [Article]
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. [Article]
Arieta C, Amaral M, Matuda E, Crosta C, de Carvalho Moreira Filho D, Jose N: Dorzolamide X apraclonidine in the prevention of the intraocular pressure spike after Nd : YAG laser posterior capsulotomy. Curr Eye Res. 2002 Oct;25(4):237-41. doi: 10.1076/ceyr.25.4.237.13484. [Article]
Hasegawa T, Hara K, Kenmochi T, Hata S: In vitro metabolism of dorzolamide, a novel potent carbonic anhydrase inhibitor, in rat liver microsomes. Drug Metab Dispos. 1994 Nov-Dec;22(6):916-21. [Article]
Loftsson T, Jansook P, Stefansson E: Topical drug delivery to the eye: dorzolamide. Acta Ophthalmol. 2012 Nov;90(7):603-8. doi: 10.1111/j.1755-3768.2011.02299.x. Epub 2012 Jan 23. [Article]
FDA Approved Drug Products: TRUSOPT (dorzolamide hydrochloride) ophthalmic solution [Link]
FDA Approved Drug Products: COSOPT PF (dorzolamide hydrochloride, timolol maleate) ophthalmic solution [Link]
Cayman Chemical Safety Data Sheet: Dorzolamide (hydrochloride) [Link]

External Links

Human Metabolome Database: HMDB0015007
KEGG Drug: D07871
KEGG Compound: C06969
PubChem Compound: 5284549
PubChem Substance: 46506754
ChemSpider: 4447604
BindingDB: 10884
RxNav: 60207
ChEBI: 4702
ChEMBL: CHEMBL218490
ZINC: ZINC000001530621
Therapeutic Targets Database: DAP000775
PharmGKB: PA164748765
PDBe Ligand: ETS
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Dorzolamide

PDB Entries

1cil / 3fw3 / 4k13 / 4m2u / 4m2w / 6bc9

FDA label

Download (569 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Glaucoma	1
4	Completed	Not Available	Ocular Hypertension / Open Angle Glaucoma (OAG)	1
4	Completed	Basic Science	Glaucoma	1
4	Completed	Other	Eye Diseases	1
4	Completed	Treatment	Exfoliation Syndrome / Ocular Hypertension / Open Angle Glaucoma (OAG) / Pigmentary Glaucoma	1

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

Apotex Inc.
Dispensing Solutions
Falcon Pharmaceuticals Ltd.
Hi Tech Pharmacal Co. Inc.
Lake Erie Medical and Surgical Supply
Merck & Co.
Physicians Total Care Inc.
Prasco Labs
Sandoz
Teva Pharmaceutical Industries Ltd.

Dosage Forms

Form	Route	Strength
Solution	Ophthalmic	20.000 mg
Solution	Ophthalmic	2 %
Solution / drops; suspension / drops	Ophthalmic
Solution	Ophthalmic
Solution	Ophthalmic	2 %
Solution	Ophthalmic	20 mg/ml
Solution / drops; suspension / drops	Ophthalmic	20 MG/ML
Solution	Ophthalmic	20.00 mg
Solution	Intraocular; Ophthalmic	20 mg
Solution	Ophthalmic	20 mg
Solution / drops	Ophthalmic
Solution	Ophthalmic	2.0 % w/v
Solution / drops	Ophthalmic	20 mg/1mL
Solution / drops	Ophthalmic	22.3 mg/1mL
Solution	Ophthalmic	20 mg/1mL
Solution / drops	Ophthalmic
Solution	Ophthalmic	20 mg / mL
Solution	Ophthalmic	22.3 mg/1mL
Solution / drops	Ophthalmic	2 %
Solution	Conjunctival; Ophthalmic
Solution	Ophthalmic	2 % w/v
Solution	Ophthalmic; Topical
Liquid	Ophthalmic	20 mg/1ml
Solution	Ophthalmic	20.000 mg
Solution	Conjunctival; Ophthalmic	20 mg
Solution	Conjunctival; Ophthalmic	22.26 mg
Solution / drops	Ophthalmic	2 % w/v
Solution	Ophthalmic	20 mg/ml
Solution / drops	Ophthalmic	20 MG/ML
Liquid	Ophthalmic

Prices

Unit description	Cost	Unit
Trusopt 2% Solution 10ml	79.25USD	bottle
Dorzolamide HCl 2% Solution 10ml Bottle	69.42USD	bottle
Dorzolamide hcl 2% eye drops	6.86USD	ml
Trusopt 2% eye drops	6.73USD	ml
Trusopt (Preservative-Free) 2 % Solution	3.93USD	ml
Trusopt 2 % Solution	3.93USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
CA1329211	No	1994-05-03	2011-05-03

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	264	FDA Label

Predicted Properties

Property	Value	Source
Water Solubility	0.699 mg/mL	ALOGPS
logP	-0.5	ALOGPS
logP	-0.12	Chemaxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.16	Chemaxon
pKa (Strongest Basic)	6.88	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	106.33 Å²	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	72.46 m³·mol^-1	Chemaxon
Polarizability	31.55 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9944
Blood Brain Barrier	+	0.6697
Caco-2 permeable	-	0.6627
P-glycoprotein substrate	Substrate	0.5389
P-glycoprotein inhibitor I	Non-inhibitor	0.8855
P-glycoprotein inhibitor II	Non-inhibitor	0.8398
Renal organic cation transporter	Non-inhibitor	0.9011
CYP450 2C9 substrate	Non-substrate	0.7755
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.5096
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.831
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7547
Ames test	Non AMES toxic	0.6397
Carcinogenicity	Non-carcinogens	0.6933
Biodegradation	Not ready biodegradable	0.9946
Rat acute toxicity	2.2365 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9446
hERG inhibition (predictor II)	Non-inhibitor	0.8706

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0ar3-2393000000-5fee748c257c96fe4cc6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0009000000-a00b23b67f0305b8f2cc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-0019000000-6b04b60bdbabef9cfa1f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0049000000-5909ffd0fb60fdbb4429
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-4009000000-2d3f392657b48f7d9c39
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-08mi-0390000000-415cac5a06247aeb93bd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-01ti-9731000000-a689fc2b487424da9633
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	176.4205401	predicted	DarkChem Lite v0.1.0
[M-H]-	169.74689	predicted	DeepCCS 1.0 (2019)
[M+H]+	176.8264401	predicted	DarkChem Lite v0.1.0
[M+H]+	172.10489	predicted	DeepCCS 1.0 (2019)
[M+Na]+	176.6062401	predicted	DarkChem Lite v0.1.0
[M+Na]+	178.503	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	1.1	N/A	N/A	A29178
IC 50 (nM)	30	N/A	N/A	A29178
IC 50 (nM)	3.74	7.2	4	A28814
Ki (nM)	0.37	N/A	N/A	A29178
Ki (nM)	15	N/A	N/A	A29178
Ki (nM)	0.28	N/A	N/A	A29179
Ki (nM)	9	N/A	N/A	A29172 / A29173 / A29174 / A29175 / A27678 / A27679 / A28998 / A29176 / A27680 / A27681 / A27682 / A27683 / A27685 / A5448 / A27688 / A27689 / A28628 / A27690 / A27691 / A27693 / A27694 / A27518 / A27519 / A27520 / A27697 / A27701 / A28427 / A27521 / A6377 / A27525 / A27708 / A27710 / A27711 / A27713 / A27529 / A29013 / A4564 / A29062 / A27554 / A29177 / A27537 / A27538 / A27720 / A29035 / A27545 / A27556 / A27547
Ki (nM)	0.51	7.4	37	A28814
Ki (nM)	9	7.5	22	A27684 / A27523
Ki (nM)	9	7.4	25	A10350 / A29020
Ki (nM)	9000	N/A	N/A	A27517 / A27544
Ki (nM)	9	7.5	20	A27695 / A28029
Ki (nM)	9	7.5	25	A27549 / A27522
Ki (nM)	9	7.5	23	A29018

Details1. Carbonic anhydrase 2

Kind: Protein
Organism: Humans
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

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. [Article]
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. [Article]
Berg JT, Ramanathan S, Gabrielli MG, Swenson ER: Carbonic anhydrase in mammalian vascular smooth muscle. J Histochem Cytochem. 2004 Aug;52(8):1101-6. [Article]
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. [Article]
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. [Article]
Sugrue MF: Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors. Prog Retin Eye Res. 2000 Jan;19(1):87-112. [Article]
Sugrue MF: The preclinical pharmacology of dorzolamide hydrochloride, a topical carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1996 Fall;12(3):363-76. [Article]
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. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	32	7.2	4	A28814
IC 50 (nM)	43	N/A	N/A	A29180
Ki (nM)	43	N/A	N/A	A28998 / A29177
Ki (nM)	8530	N/A	N/A	A27520
Ki (nM)	8500	7.5	22	A27523
Ki (nM)	8500	N/A	N/A	A27525 / A27711 / A29035
Ki (nM)	8500	7.5	23	A29018

Details2. Carbonic anhydrase 4

Kind: Protein
Organism: Humans
Pharmacological action: Yes
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

Sugrue MF: The preclinical pharmacology of dorzolamide hydrochloride, a topical carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1996 Fall;12(3):363-76. [Article]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	50000	N/A	N/A	A29172 / A29173 / A29174 / A29175 / A27678 / A27679 / A29176 / A27683 / A27685 / A27688 / A27689 / A28628 / A27690 / A27691 / A27693 / A27694 / A27518 / A27519 / A27697 / A27701 / A28427 / A27521 / A6377 / A27525 / A27711 / A27713 / A27529 / A4564 / A29177 / A27537 / A27538 / A27720 / A29035 / A27545 / A27547
Ki (nM)	>50000	N/A	N/A	A28998 / A27680 / A27681 / A27682 / A5448
Ki (nM)	50000	7.5	22	A27684 / A27523
Ki (nM)	50000	7.4	25	A10350 / A29020
Ki (nM)	50000000	N/A	N/A	A27517 / A27520 / A27544
Ki (nM)	50000	7.5	20	A27695 / A28029
Ki (nM)	50000	7.5	25	A27522
Ki (nM)	500	N/A	N/A	A27708 / A27710 / A29013
Ki (nM)	50000	7.5	23	A29018

Details3. Carbonic anhydrase 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor
Curator comments: In vitro, dorzolamide is a much weaker inhibitor of human carbonic anhydrase isoenzyme I (IC50 value of 600 nM).

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

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. [Article]
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. [Article]
Sugrue MF: The preclinical pharmacology of dorzolamide hydrochloride, a topical carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1996 Fall;12(3):363-76. [Article]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	8000	N/A	N/A	A27525
Ki (nM)	770000	N/A	N/A	A20066 / A27711
Ki (nM)	770000	7.5	23	A29018

Details4. Carbonic anhydrase 3

Kind: Protein
Organism: Humans
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

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. [Article]

Enzymes

Details1. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: No
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

Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]

Details2. Cytochrome P450 2B1

Kind: Protein
Organism: Rat
Pharmacological action: No
Actions: Substrate
Curator comments: An in vitro study using liver microsomes from Sprague-Dawley rats suggest the involvement of this enzyme in the metabolism of dorzolamide. It is unclear whether this drug-enzyme interaction can be expected with human liver enzymes.

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: Cyp2b1
Uniprot ID: P00176
Uniprot Name: Cytochrome P450 2B1
Molecular Weight: 55933.06 Da

References

Hasegawa T, Hara K, Kenmochi T, Hata S: In vitro metabolism of dorzolamide, a novel potent carbonic anhydrase inhibitor, in rat liver microsomes. Drug Metab Dispos. 1994 Nov-Dec;22(6):916-21. [Article]

Details3. Cytochrome P450 2E1

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate
Curator comments: An in vitro study using liver microsomes from Sprague-Dawley rats suggest the involvement of this enzyme in the metabolism of dorzolamide. It is unclear whether this drug-enzyme interaction can be expected with human liver enzymes.

General Function: Steroid hydroxylase activity
Specific Function: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name: CYP2E1
Uniprot ID: P05181
Uniprot Name: Cytochrome P450 2E1
Molecular Weight: 56848.42 Da

References

Hasegawa T, Hara K, Kenmochi T, Hata S: In vitro metabolism of dorzolamide, a novel potent carbonic anhydrase inhibitor, in rat liver microsomes. Drug Metab Dispos. 1994 Nov-Dec;22(6):916-21. [Article]

Details4. Cytochrome P450 3A2

Kind: Protein
Organism: Rat
Pharmacological action: No
Actions: Substrate
Curator comments: An in vitro study using liver microsomes from Sprague-Dawley rats suggest the involvement of this enzyme in the metabolism of dorzolamide. It is unclear whether this drug-enzyme interaction can be expected with human liver enzymes.

General Function: Testosterone 6-beta-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: Cyp3a2
Uniprot ID: P05183
Uniprot Name: Cytochrome P450 3A2
Molecular Weight: 57731.215 Da

References

Hasegawa T, Hara K, Kenmochi T, Hata S: In vitro metabolism of dorzolamide, a novel potent carbonic anhydrase inhibitor, in rat liver microsomes. Drug Metab Dispos. 1994 Nov-Dec;22(6):916-21. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Dorzolamide

Identification

Structure for Dorzolamide (DB00869)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

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Enzymes

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