Acetazolamide
Identification
- Name
- Acetazolamide
- Accession Number
- DB00819
- Description
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
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Indication
For adjunctive treatment of: edema due to congestive heart failure; drug-induced edema; centrencephalic epilepsies; chronic simple (open-angle) glaucoma
- Associated Conditions
- Associated Therapies
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- 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 softwareAbacavir Acetazolamide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Acetazolamide. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Acetazolamide. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Acetazolamide. Aceclofenac Acetazolamide may increase the excretion rate of Aceclofenac which could result in a lower serum level and potentially a reduction in efficacy. Acemetacin The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Acemetacin. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Acetazolamide. Acetaminophen Acetazolamide may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Acetazolamide. Acetophenazine The risk or severity of adverse effects can be increased when Acetazolamide is combined with Acetophenazine. 
Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- Drink plenty of fluids.
- Take with food. Take at least 6 hours before bedtime.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- 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 Oral Valeant Canada Lp Valeant Canada S.E.C. 1974-12-31 2014-07-30 Canada 
Acetazolamide Tablet Oral Aa Pharma Inc 1982-12-31 Not applicable Canada Acetazolamide for Injection, USP Powder, for solution Intravenous Sterimax Inc 2010-12-03 Not applicable Canada Diamox IV 500mg Powder, for solution Intravenous Wyeth Ayerst Canada Inc. 1998-12-02 2001-05-07 Canada Diamox Pws 500mg/vial Powder, for solution Intravenous Storz, Division Of Wyeth Ayerst Canada Inc. 1994-12-31 1999-08-12 Canada Diamox Sequels Capsule, extended release 500 mg/1 Oral Teva Women's Health, Inc. 2000-02-22 2019-05-31 US 
Diamox Sequels Capsule, extended release 500 mg/1 Oral Remedy Repack 2012-07-20 2013-10-30 US 
Diamox Sequels Capsule, extended release 500 mg Oral Wyeth Ltd. 1998-12-23 2006-03-22 Canada Diamox Src 500mg Capsule, extended release Oral Storz, Division Of Wyeth Ayerst Canada Inc. 1994-12-31 1999-08-12 Canada Diamox Tab 250mg Tablet Oral Storz, Division Of Wyeth Ayerst Canada Inc. 1994-12-31 2000-08-02 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Acetazolamide Injection, powder, lyophilized, for solution 500 mg/5mL Intravenous Zydus Pharmaceuticals (USA) Inc. 2020-01-09 Not applicable US 
Acetazolamide Tablet 250 mg/1 Oral Av Kare, Inc. 2017-05-18 Not applicable US Acetazolamide Capsule 500 mg/1 Oral Zydus Pharmaceuticals (USA) Inc. 2019-05-08 Not applicable US Acetazolamide Tablet 125 mg/1 Oral Mutual Pharmaceutical 1998-06-22 2007-10-01 US Acetazolamide Tablet 125 mg/1 Oral Avera McKennan Hospital 2015-07-20 2017-05-24 US 
Acetazolamide Tablet 250 mg/1 Oral Novitium Pharma Llc 2019-10-17 Not applicable US Acetazolamide Capsule, extended release 500 mg/1 Oral American Health Packaging 2010-02-15 2020-08-31 US AcetaZOLAMIDE Tablet 250 1/1 Oral Red Pharm Drug, Inc. 1978-03-31 Not applicable US 
Acetazolamide Tablet 125 mg/1 Oral bryant ranch prepack 2020-11-13 Not applicable US Acetazolamide Injection, powder, lyophilized, for solution 500 mg/5mL Intravenous Heritage Pharmaceuticals Inc. d/b/a Avet Pharmaceuticals Inc. 2014-12-19 2014-12-20 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)
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
- Farzam K, Abdullah M: Acetazolamide . [PubMed:30335315]
- FDA Approved Drug Products: DIAMOX SEQUELS (acetazolamide extended release) oral capsules [Link]
- AA Pharma Inc.: ACETAZOLAMIDE Product Monograph [Link]
- FDA Approved Drug Products: Acetazolamide (for injection) [Link]
- 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
- AHFS Codes
- 52:40.00 — Antiglaucoma Agents
- 52:40.12 — Carbonic Anhydrase Inhibitors
- PDB Entries
- 1azm / 1dmy / 1jd0 / 1rj6 / 1yda / 1ydb / 1ydd / 1zsb / 2h4n / 2uy4 … show 25 more
- FDA label
- Download (149 KB)
- MSDS
- Download (73.4 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Prevention Altitude Hypoxia 7 4 Active Not Recruiting Prevention Chronic Obstructive Pulmonary Disease (COPD) 2 4 Active Not Recruiting Prevention Other and unspecified effects of high altitude 1 4 Completed Not Available Chronic Heart Failure (CHF) 1 4 Completed Not Available Other and unspecified effects of high altitude 1 4 Completed Basic Science Altitude Sickness / Pulmonary Hypertension (PH) 1 4 Completed Basic Science Hypoxia 1 4 Completed Prevention Chronic Obstructive Pulmonary Disease (COPD) 6 4 Completed Prevention Hyperalgesia / Opioid-Related Disorders 1 4 Completed Treatment Alkalosis / Respiratory Insufficiency 1
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 Capsule Oral 500 mg/1 Injection, powder, lyophilized, for solution Intravenous 500 mg/5mL Injection, powder, lyophilized, for solution Intravenous 500 mg/1 Tablet Oral 125 mg/1 Tablet Oral 250 1/1 Tablet Oral 250 mg/1 Powder, for solution Intravenous Capsule, extended release Oral Injection, powder, for solution Parenteral Capsule, extended release Oral 500 mg/1 Capsule, extended release Oral 500 mg 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) 6.93 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
Targets
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with our fully connected ADMET & drug target dataset.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- 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
- 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. [PubMed:8667211]
- 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. [PubMed:10651143]
- 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. [PubMed:11430635]
- 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. [PubMed:10713865]
- Perez Velazquez JL: Bicarbonate-dependent depolarizing potentials in pyramidal cells and interneurons during epileptiform activity. Eur J Neurosci. 2003 Sep;18(5):1337-42. [PubMed:12956733]
- 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. [PubMed:18336310]
- 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
- 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. [PubMed:20605094]
- 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. [PubMed:18336310]
- 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
- 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. [PubMed:20605094]
- 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. [PubMed:18336310]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Reversible hydration of carbon dioxide.
- 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. [PubMed:18336310]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Reversible hydration of carbon dioxide.
- 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. [PubMed:10592235]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- 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
- 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. [PubMed:20605094]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Reversible hydration of carbon dioxide.
- 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. [PubMed:18336310]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Water transmembrane transporter activity
- Specific 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 o...
- 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. [PubMed:12147198]
- 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. [PubMed:12830709]
- 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. [PubMed:14704128]
- 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. [PubMed:14753499]
- 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. [PubMed:15169637]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- 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. [PubMed:8877250]
- American Academy of Ophthalmology: Acetazolamide - Considerations for Systemic Administration [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- 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. [PubMed:10991988]
Drug created on June 13, 2005 13:24 / Updated on April 11, 2021 00:58