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Identification
- Summary
Acetazolamide is a carbonic anhydrase inhibitor used to treat edema from heart failure or medications, certain types of epilepsy, and glaucoma.
- Generic Name
- Acetazolamide
- DrugBank Accession Number
- DB00819
- Background
One of the carbonic anhydrase inhibitors that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Acetazolamide (DB00819)
- Weight
- Average: 222.245
Monoisotopic: 221.988131458 - Chemical Formula
- C4H6N4O3S2
- Synonyms
- 2-acetylamino-1,3,4-thiadiazole-5-sulfonamide
- 5-acetamido-1,3,4-thiadiazole-2-sulfonamide
- 5-acetylamino-1,3,4-thiadiazole-2-sulfonamide
- Acetazolamid
- Acetazolamida
- Acétazolamide
- Acetazolamide
- Acetazolamidum
- N-[5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamide
- N-[5-(aminosulfonyl)-1,3,5-thiadiazol-2-yl]acetamide
- External IDs
- L 579486
- NSC-145177
- RP 5172
Pharmacology
- Indication
For adjunctive treatment of: edema due to congestive heart failure; drug-induced edema; centrencephalic epilepsies; chronic simple (open-angle) glaucoma
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute mountain sickness •••••••••••• Adjunct therapy in treatment of Edema •••••••••••• ••••••••• Treatment of Familial periodic paralysis ••• ••••• Treatment of Metabolic alkalosis ••• ••••• Adjunct therapy in treatment of Open angle glaucoma •••••••••••• •••••••• •••••••• •••••••• ••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Acetazolamide is a potent carbonic anhydrase inhibitor, effective in the control of fluid secretion, in the treatment of certain convulsive disorders and in the promotion of diuresis in instances of abnormal fluid retention. Acetazolamide is not a mercurial diuretic. Rather, it is a nonbacteriostatic sulfonamide possessing a chemical structure and pharmacological activity distinctly different from the bacteriostatic sulfonamides.
- Mechanism of action
The anticonvulsant activity of Acetazolamide may depend on a direct inhibition of carbonic anhydrase in the CNS, which decreases carbon dioxide tension in the pulmonary alveoli, thus increasing arterial oxygen tension. The diuretic effect depends on the inhibition of carbonic anhydrase, causing a reduction in the availability of hydrogen ions for active transport in the renal tubule lumen. This leads to alkaline urine and an increase in the excretion of bicarbonate, sodium, potassium, and water.
Target Actions Organism ACarbonic anhydrase 1 inhibitorHumans ACarbonic anhydrase 2 inhibitorHumans ACarbonic anhydrase 4 inhibitorHumans ACarbonic anhydrase 12 inhibitorHumans ACarbonic anhydrase 14 inhibitorHumans ACarbonic anhydrase 3 inhibitorHumans ACarbonic anhydrase 7 inhibitorHumans UAquaporin-1 inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
98%
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
3 to 9 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Acetazolamide is combined with 1,2-Benzodiazepine. Abacavir Acetazolamide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Acetazolamide. Acalabrutinib The serum concentration of Acalabrutinib can be increased when it is combined with Acetazolamide. Acamprosate The excretion of Acamprosate can be decreased when combined with Acetazolamide. - Food Interactions
- Drink plenty of fluids.
- Take with food. Take at least 6 hours before bedtime.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Acetazolamide sodium 429ZT169UH 1424-27-7 MRSXAJAOWWFZJJ-UHFFFAOYSA-M - Product Images
- International/Other Brands
- Acemit (Medphano) / Acemox (Acme) / Acetak (Akorn) / Acetamide (Micro Vision) / Acetazolamax (Pfoshen) / Azm (Ethical) / Azol (New Chemical) / Azomid (Adcock Ingram Pharmaceuticals) / Carbinib (Edol) / Défiltran (CSP) / Diabo (Raymos) / Diacarb (Polpharma) / Diamox (Sanofi Aventis) / Diamox Depot (Goldshield) / Diazomid (Sanofi-Aventis) / Diluran (Zentiva) / Diuramid (Polpharma) / Edemox (Chiesi) / Glaumox (Phebra) / Glaupax (Omnivision) / Glupax (Phebra) / Huma-Zolamide (Teva) / Iopar-SR (FDC) / Medene (Pharmaland) / Oculten (Acromax) / Ödemin (Santen) / Uramox (Taro) / Zolmide (Vista Pharma)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Acetazolam Tablet 250 mg Oral Valeant Canada Lp Valeant Canada S.E.C. 1974-12-31 2014-07-30 Canada 
Acetazolamide Tablet 250 mg Oral Aa Pharma Inc 1982-12-31 Not applicable Canada Acetazolamide for Injection USP Powder, for solution 500 mg / vial Intravenous Marcan Pharmaceuticals Inc 2023-07-26 Not applicable Canada Acetazolamide for Injection, USP Powder, for solution 500 mg / vial Intravenous Sterimax Inc 2010-12-03 Not applicable Canada Diamox IV 500mg Powder, for solution 500 mg / vial Intravenous Wyeth Ayerst Canada Inc. 1998-12-02 2001-05-07 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image AcetaZOLAMIDE Tablet 250 mg/1 Oral Breckenridge Pharmaceutical, Inc. 2020-09-01 2022-08-31 US 
Acetazolamide Tablet 250 mg/1 Oral bryant ranch prepack 2020-11-13 Not applicable US Acetazolamide Capsule, extended release 500 mg/1 Oral Heritage Pharmaceuticals Inc. d/b/a Avet Pharmaceuticals Inc. 2012-09-24 2022-12-31 US 
Acetazolamide Tablet 250 mg/1 Oral Marlex Pharmaceuticals Inc 2022-12-01 Not applicable US AcetaZOLAMIDE Tablet 250 mg/1 Oral Marlex Pharmaceuticals Inc 2014-10-01 Not applicable US
Categories
- ATC Codes
- G01AE10 — Combinations of sulfonamides
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Anticonvulsants
- Antiglaucoma Agents
- Antiglaucoma Preparations and Miotics
- Carbonic Anhydrase Inhibitors
- Cardiovascular Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Diuretics
- Drugs causing inadvertant photosensitivity
- Enzyme Inhibitors
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Natriuretic Agents
- OAT1/SLC22A6 inhibitors
- Ophthalmologicals
- Photosensitizing Agents
- Sensory Organs
- Sulfonamides
- Sulfur Compounds
- Thiadiazoles
- Thiazoles
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as thiadiazole sulfonamides. These are heterocyclic compounds containing a thiazole ring substituted by at least one sulfonamide group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azoles
- Sub Class
- Thiadiazoles
- Direct Parent
- Thiadiazole sulfonamides
- Alternative Parents
- N-acetylarylamines / Organosulfonamides / Heteroaromatic compounds / Aminosulfonyl compounds / Acetamides / Secondary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- 1,3,4-thiadiazole-2-sulfonamide / Acetamide / Aminosulfonyl compound / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative show 14 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- monocarboxylic acid amide, sulfonamide, thiadiazoles (CHEBI:27690) / a small molecule (CPD0-1626)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- O3FX965V0I
- CAS number
- 59-66-5
- InChI Key
- BZKPWHYZMXOIDC-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H6N4O3S2/c1-2(9)6-3-7-8-4(12-3)13(5,10)11/h1H3,(H2,5,10,11)(H,6,7,9)
- IUPAC Name
- N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide
- SMILES
- CC(=O)NC1=NN=C(S1)S(N)(=O)=O
References
- Synthesis Reference
Angela C. Potts, Mark Gibson, "Stable ophthalmic preparations containing acetazolamide." U.S. Patent US4888168, issued August, 1981.
US4888168- General References
- External Links
- Human Metabolome Database
- HMDB0014957
- KEGG Drug
- D00218
- KEGG Compound
- C06805
- PubChem Compound
- 1986
- PubChem Substance
- 46504493
- ChemSpider
- 1909
- BindingDB
- 10880
- 167
- ChEBI
- 27690
- ChEMBL
- CHEMBL20
- ZINC
- ZINC000003813042
- Therapeutic Targets Database
- DAP000600
- PharmGKB
- PA448018
- PDBe Ligand
- AZM
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Acetazolamide
- PDB Entries
- 1azm / 1dmy / 1jd0 / 1rj6 / 1yda / 1ydb / 1ydd / 1zsb / 2h4n / 2uy4 … show 26 more
- FDA label
- Download (149 KB)
- MSDS
- Download (73.4 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Control of Elevated Eye Pressure by Local and Systemic Therapy 1 somestatus stop reason just information to hide Not Available Completed Not Available Healthy (Controls) / Sickle Cell Disease (SCD) / Thalassemia 1 somestatus stop reason just information to hide Not Available Completed Basic Science Headache / Migraine 1 somestatus stop reason just information to hide Not Available Completed Basic Science Heart Failure 1 somestatus stop reason just information to hide Not Available Completed Basic Science High Altitude Headache 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Zydus pharmaceuticals usa inc
- Duramed pharmaceuticals inc sub barr laboratories inc
- Alra laboratories inc
- Ascot hosp pharmaceuticals inc div travenol laboratories inc
- Lannett co inc
- Mutual pharmaceutical co inc
- Taro pharmaceutical industries ltd
- Vangard laboratories inc div midway medical co
- Watson laboratories inc
- Bedford laboratories div ben venue laboratories inc
- Hospira inc
- X gen pharmaceuticals inc
- Packagers
- American Cyanamid Co.
- Amerisource Health Services Corp.
- A-S Medication Solutions LLC
- Barr Pharmaceuticals
- Bedford Labs
- Ben Venue Laboratories Inc.
- Cardinal Health
- Direct Dispensing Inc.
- Dispensing Solutions
- DSM Corp.
- Duramed
- Emcure Pharmaceuticals Ltd.
- Heartland Repack Services LLC
- Innovative Manufacturing and Distribution Services Inc.
- Kaiser Foundation Hospital
- Lannett Co. Inc.
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mutual Pharmaceutical Co.
- Nucare Pharmaceuticals Inc.
- PD-Rx Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Prescript Pharmaceuticals
- Resource Optimization and Innovation LLC
- Taro Pharmaceuticals USA
- United Research Laboratories Inc.
- Watson Pharmaceuticals
- X-Gen Pharmaceuticals
- Zydus Pharmaceuticals
- Dosage Forms
Form Route Strength Tablet Oral 250.000 mg Tablet Oral 250.00 mg Capsule Oral 500 mg/1 Injection, powder, lyophilized, for solution Intravenous 500 mg/1 Injection, powder, lyophilized, for solution Intravenous 500 mg/5mL Tablet Oral 125 mg/1 Tablet Oral 250 1/1 Tablet Oral 250 mg/1 Powder, for solution Intravenous 500 mg Tablet Oral Injection, powder, for solution Parenteral 500 mg Powder, for solution Intravenous 500 mg / vial Capsule, extended release Oral 500 mg Capsule, extended release Oral 500 mg/1 Powder 500 mg Capsule, extended release Oral 500 mg / src Tablet Oral 250 mg - Prices
Unit description Cost Unit Acetazolamide sod 500 mg vial 51.75USD vial Diamox Sequels 500 mg 12 Hour Capsule 5.49USD capsule Diamox sequels er 500 mg capsule 5.24USD capsule Acetazolamide powder 4.53USD g AcetaZOLAMIDE 500 mg 12 Hour Capsule 4.46USD capsule Acetazolamide 125 mg tablet 0.37USD tablet Acetazolamide 250 mg tablet 0.35USD tablet Apo-Acetazolamide 250 mg Tablet 0.13USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 260.5 °C PhysProp water solubility 980 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -0.26 HANSCH,C ET AL. (1995) logS -2.36 ADME Research, USCD pKa 7.2 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 2.79 mg/mL ALOGPS logP -0.39 ALOGPS logP -1 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 6.55 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 115.04 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 47.36 m3·mol-1 Chemaxon Polarizability 19.16 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9156 Blood Brain Barrier + 0.9382 Caco-2 permeable - 0.7761 P-glycoprotein substrate Non-substrate 0.8369 P-glycoprotein inhibitor I Non-inhibitor 0.9267 P-glycoprotein inhibitor II Non-inhibitor 0.9507 Renal organic cation transporter Non-inhibitor 0.9365 CYP450 2C9 substrate Non-substrate 0.7316 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7817 CYP450 1A2 substrate Non-inhibitor 0.9259 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9625 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9037 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8798 Ames test Non AMES toxic 0.8445 Carcinogenicity Non-carcinogens 0.802 Biodegradation Not ready biodegradable 0.9301 Rat acute toxicity 1.8939 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9926 hERG inhibition (predictor II) Non-inhibitor 0.9449
Spectra
- Mass Spec (NIST)
- Download (8.82 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 147.7881833 predictedDarkChem Lite v0.1.0 [M-H]- 148.6649833 predictedDarkChem Lite v0.1.0 [M-H]- 148.5945833 predictedDarkChem Lite v0.1.0 [M-H]- 133.99387 predictedDeepCCS 1.0 (2019) [M+H]+ 148.3011833 predictedDarkChem Lite v0.1.0 [M+H]+ 149.2596833 predictedDarkChem Lite v0.1.0 [M+H]+ 148.9179833 predictedDarkChem Lite v0.1.0 [M+H]+ 137.21367 predictedDeepCCS 1.0 (2019) [M+Na]+ 148.0920833 predictedDarkChem Lite v0.1.0 [M+Na]+ 148.6443833 predictedDarkChem Lite v0.1.0 [M+Na]+ 146.47661 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the reversible hydration of carbon dioxide (PubMed:10550681, PubMed:16506782, PubMed:16686544, PubMed:16807956, PubMed:17127057, PubMed:17314045, PubMed:17407288, PubMed:18618712, PubMed:19186056, PubMed:19206230). Can hydrate cyanamide to urea (PubMed:10550681)
- Specific Function
- arylesterase activity
- Gene Name
- CA1
- Uniprot ID
- P00915
- Uniprot Name
- Carbonic anhydrase 1
- Molecular Weight
- 28870.0 Da
References
- Puscas I, Coltau M, Pasca R: Nonsteroidal anti-inflammatory drugs activate carbonic anhydrase by a direct mechanism of action. J Pharmacol Exp Ther. 1996 Jun;277(3):1464-6. [Article]
- Meierkord H, Grunig F, Gutschmidt U, Gutierrez R, Pfeiffer M, Draguhn A, Bruckner C, Heinemann U: Sodium bromide: effects on different patterns of epileptiform activity, extracellular pH changes and GABAergic inhibition. Naunyn Schmiedebergs Arch Pharmacol. 2000 Jan;361(1):25-32. [Article]
- Puscas I, Ifrim M, Maghiar T, Coltau M, Domuta G, Baican M, Hecht A: Indomethacin activates carbonic anhydrase and antagonizes the effect of the specific carbonic anhydrase inhibitor acetazolamide, by a direct mechanism of action. Int J Clin Pharmacol Ther. 2001 Jun;39(6):265-70. [Article]
- Puscas I, Coltau M, Baican M, Domuta G, Hecht A: Vasodilatory effect of diuretics is dependent on inhibition of vascular smooth muscle carbonic anhydrase by a direct mechanism of action. Drugs Exp Clin Res. 1999;25(6):271-9. [Article]
- Perez Velazquez JL: Bicarbonate-dependent depolarizing potentials in pyramidal cells and interneurons during epileptiform activity. Eur J Neurosci. 2003 Sep;18(5):1337-42. [Article]
- Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the reversible hydration of carbon dioxide (PubMed:11327835, PubMed:11802772, PubMed:11831900, PubMed:12056894, PubMed:12171926, PubMed:1336460, PubMed:14736236, PubMed:15300855, PubMed:15453828, PubMed:15667203, PubMed:15865431, PubMed:16106378, PubMed:16214338, PubMed:16290146, PubMed:16686544, PubMed:16759856, PubMed:16807956, PubMed:17127057, PubMed:17251017, PubMed:17314045, PubMed:17330962, PubMed:17346964, PubMed:17540563, PubMed:17588751, PubMed:17705204, PubMed:18024029, PubMed:18162396, PubMed:18266323, PubMed:18374572, PubMed:18481843, PubMed:18618712, PubMed:18640037, PubMed:18942852, PubMed:1909891, PubMed:1910042, PubMed:19170619, PubMed:19186056, PubMed:19206230, PubMed:19520834, PubMed:19778001, PubMed:7761440, PubMed:7901850, PubMed:8218160, PubMed:8262987, PubMed:8399159, PubMed:8451242, PubMed:8485129, PubMed:8639494, PubMed:9265618, PubMed:9398308). Can also hydrate cyanamide to urea (PubMed:10550681, PubMed:11015219). Stimulates the chloride-bicarbonate exchange activity of SLC26A6 (PubMed:15990874). Essential for bone resorption and osteoclast differentiation (PubMed:15300855). Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption
- Specific Function
- arylesterase activity
- Gene Name
- CA2
- Uniprot ID
- P00918
- Uniprot Name
- Carbonic anhydrase 2
- Molecular Weight
- 29245.895 Da
References
- Avvaru BS, Wagner JM, Maresca A, Scozzafava A, Robbins AH, Supuran CT, McKenna R: Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors. Bioorg Med Chem Lett. 2010 Aug 1;20(15):4376-81. doi: 10.1016/j.bmcl.2010.06.082. Epub 2010 Jun 17. [Article]
- Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the reversible hydration of carbon dioxide into bicarbonate and protons and thus is essential to maintaining intracellular and extracellular pH (PubMed:15563508, PubMed:16686544, PubMed:16807956, PubMed:17127057, PubMed:17314045, PubMed:17652713, PubMed:17705204, PubMed:18618712, PubMed:19186056, PubMed:19206230, PubMed:7625839). May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis (PubMed:15563508). It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid (PubMed:15563508)
- Specific Function
- carbonate dehydratase activity
- Gene Name
- CA4
- Uniprot ID
- P22748
- Uniprot Name
- Carbonic anhydrase 4
- Molecular Weight
- 35032.075 Da
References
- Avvaru BS, Wagner JM, Maresca A, Scozzafava A, Robbins AH, Supuran CT, McKenna R: Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors. Bioorg Med Chem Lett. 2010 Aug 1;20(15):4376-81. doi: 10.1016/j.bmcl.2010.06.082. Epub 2010 Jun 17. [Article]
- Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Reversible hydration of carbon dioxide
- Specific Function
- carbonate dehydratase activity
- Gene Name
- CA12
- Uniprot ID
- O43570
- Uniprot Name
- Carbonic anhydrase 12
- Molecular Weight
- 39450.615 Da
References
- Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Reversible hydration of carbon dioxide
- Specific Function
- carbonate dehydratase activity
- Gene Name
- CA14
- Uniprot ID
- Q9ULX7
- Uniprot Name
- Carbonic anhydrase 14
- Molecular Weight
- 37667.37 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Reversible hydration of carbon dioxide
- Specific Function
- carbonate dehydratase activity
- Gene Name
- CA3
- Uniprot ID
- P07451
- Uniprot Name
- Carbonic anhydrase 3
- Molecular Weight
- 29557.215 Da
References
- Avvaru BS, Wagner JM, Maresca A, Scozzafava A, Robbins AH, Supuran CT, McKenna R: Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors. Bioorg Med Chem Lett. 2010 Aug 1;20(15):4376-81. doi: 10.1016/j.bmcl.2010.06.082. Epub 2010 Jun 17. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Reversible hydration of carbon dioxide
- Specific Function
- carbonate dehydratase activity
- Gene Name
- CA7
- Uniprot ID
- P43166
- Uniprot Name
- Carbonic anhydrase 7
- Molecular Weight
- 29658.235 Da
References
- Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Forms a water-specific channel that provides the plasma membranes of red cells and kidney proximal tubules with high permeability to water, thereby permitting water to move in the direction of an osmotic gradient (PubMed:1373524). Component of the ankyrin-1 complex, a multiprotein complex involved in the stability and shape of the erythrocyte membrane (PubMed:35835865)
- Specific Function
- ammonium channel activity
- Gene Name
- AQP1
- Uniprot ID
- P29972
- Uniprot Name
- Aquaporin-1
- Molecular Weight
- 28525.68 Da
References
- Xiang Y, Ma B, Li T, Yu HM, Li XJ: Acetazolamide suppresses tumor metastasis and related protein expression in mice bearing Lewis lung carcinoma. Acta Pharmacol Sin. 2002 Aug;23(8):745-51. [Article]
- Mu SM, Ji XH, Ma B, Yu HM, Li XJ: [Differential protein analysis in rat renal proximal tubule epithelial cells in response to acetazolamide and its relation with the inhibition of AQP1]. Yao Xue Xue Bao. 2003 Mar;38(3):169-72. [Article]
- Ma B, Xiang Y, Mu SM, Li T, Yu HM, Li XJ: Effects of acetazolamide and anordiol on osmotic water permeability in AQP1-cRNA injected Xenopus oocyte. Acta Pharmacol Sin. 2004 Jan;25(1):90-7. [Article]
- Oshio K, Song Y, Verkman AS, Manley GT: Aquaporin-1 deletion reduces osmotic water permeability and cerebrospinal fluid production. Acta Neurochir Suppl. 2003;86:525-8. [Article]
- Xiang Y, Ma B, Li T, Gao JW, Yu HM, Li XJ: Acetazolamide inhibits aquaporin-1 protein expression and angiogenesis. Acta Pharmacol Sin. 2004 Jun;25(6):812-6. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Spina E, Pisani F, Perucca E: Clinically significant pharmacokinetic drug interactions with carbamazepine. An update. Clin Pharmacokinet. 1996 Sep;31(3):198-214. doi: 10.2165/00003088-199631030-00004. [Article]
- American Academy of Ophthalmology: Acetazolamide - Considerations for Systemic Administration [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- alpha-ketoglutarate transmembrane transporter activity
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Uwai Y, Saito H, Hashimoto Y, Inui KI: Interaction and transport of thiazide diuretics, loop diuretics, and acetazolamide via rat renal organic anion transporter rOAT1. J Pharmacol Exp Ther. 2000 Oct;295(1):261-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 11, 2024 18:19