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Showing metabocard for Acetazolamide (HMDB0014957)

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enzymes (8)transporters (1) Show 9 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:42 UTC
HMDB IDHMDB0014957
Secondary Accession Numbers
  • HMDB14957
Metabolite Identification
Common NameAcetazolamide
DescriptionOne 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)
Structure
Data?1582753242
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Acetylamino-1,3,4-thiadiazole-5-sulfonamideChEBI
5-ACETAMIDO-1,3,4-thiadiazole-2-sulfonamideChEBI
5-Acetylamino-1,3,4-thiadiazole-2-sulfonamideChEBI
AcetazolamidaChEBI
AcetazolamidumChEBI
DefiltranChEBI
DiacarbChEBI
DiamoxChEBI
DiluranChEBI
GlaupaxChEBI
N-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamideChEBI
N-[5-(Aminosulfonyl)-1,3,5-thiadiazol-2-yl]acetamideChEBI
2-Acetylamino-1,3,4-thiadiazole-5-sulphonamideGenerator
5-ACETAMIDO-1,3,4-thiadiazole-2-sulphonamideGenerator
5-Acetylamino-1,3,4-thiadiazole-2-sulphonamideGenerator
N-[5-(Aminosulphonyl)-1,3,4-thiadiazol-2-yl]acetamideGenerator
N-[5-(Aminosulphonyl)-1,3,5-thiadiazol-2-yl]acetamideGenerator
AcetamidothiadiazolesulfonamideHMDB
AcetazolamidHMDB
AcetazolamineHMDB
AcetazoleamideHMDB
AcetozalamideHMDB
Carbonic anhydrase inhibitor 6063HMDB
Acetazolamide llorens brandHMDB
Acetazolamide medphano brandHMDB
Acetazolamide novopharm brandHMDB
Acetazolamide wassermann brandHMDB
Ak-zolHMDB
Apo acetazolamideHMDB
Apo-acetazolamideHMDB
Cyanamid brand OF acetazolamide preparationHMDB
EdemoxHMDB
Huma zolamideHMDB
HumaZolamideHMDB
Lederle brand OF acetazolamide preparationHMDB
Llorens brand OF acetazolamideHMDB
Monosodium salt acetazolamideHMDB
Wassermann brand OF acetazolamideHMDB
Acetazolamide chiesi brandHMDB
Acetazolamide dioptic brandHMDB
Acetazolamide grin brandHMDB
Acetazolamide sodium, (sterile)HMDB
Acetazolamide, monosodium saltHMDB
Grin brand OF acetazolamideHMDB
Medphano brand OF acetazolamideHMDB
Orion brand OF acetazolamideHMDB
Théraplix brand OF acetazolamide preparationHMDB
Whelehan brand OF acetazolamide preparationHMDB
Wyeth brand OF acetazolamide preparationHMDB
AcetadiazolHMDB
AcetazolamHMDB
Acetazolamide icn brandHMDB
Acetazolamide jumer brandHMDB
Ak zolHMDB
Ciba vision brand OF acetazolamideHMDB
DiuramideHMDB
DéfiltranHMDB
GlauconoxHMDB
Jumer brand OF acetazolamideHMDB
Storz brand OF acetazolamide preparationHMDB
Acetazolamide apotex brandHMDB
Acetazolamide orion brandHMDB
AkZolHMDB
ApoAcetazolamideHMDB
Apotex brand OF acetazolamideHMDB
Chiesi brand OF acetazolamideHMDB
Dioptic brand OF acetazolamideHMDB
Huma-zolamideHMDB
ICN brand OF acetazolamideHMDB
Novopharm brand OF acetazolamideHMDB
Chemical FormulaC4H6N4O3S2
Average Molecular Weight222.245
Monoisotopic Molecular Weight221.988131458
IUPAC NameN-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide
Traditional Nameacetazolamide
CAS Registry Number59-66-5
SMILES
CC(=O)NC1=NN=C(S1)S(N)(=O)=O
InChI Identifier
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)
InChI KeyBZKPWHYZMXOIDC-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassThiadiazoles
Direct ParentThiadiazole sulfonamides
Alternative Parents
Substituents
  • N-acetylarylamine
  • 1,3,4-thiadiazole-2-sulfonamide
  • N-arylamide
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Heteroaromatic compound
  • Acetamide
  • Aminosulfonyl compound
  • Sulfonyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point260.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.79 g/LNot Available
LogP-0.26HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.79 g/LALOGPS
logP-0.39ALOGPS
logP-1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)6.93ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area115.04 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.36 m³·mol⁻¹ChemAxon
Polarizability19.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-3900000000-d066d2601c8f3d625916Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00e9-9070000000-e2f68ded4939412340f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-9020000000-59775cde1cab229764b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-9000000000-1ee1fd41bb44b523dd8eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-9000000000-de6c64393f3dc86c15b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-9000000000-7158c10cba32f3b3896bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-06si-9000000000-32cc006b3850024fd5b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00e9-0890000000-f407810fc44461e62ecbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0920000000-6dd62d0ae588814e0cf2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0900000000-6b6d74d2f34efd5f876aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-1900000000-05fedd43edecd53593c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-5900000000-76456c439130c5477d45Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00e9-9300000000-5ca7214eb79224d3dc21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-b9d984e83e00c2e23943Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01x0-1950000000-c5bb42824cbdfdaae48dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-2890000000-5f098f8e1576ee3ffaa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fu-7890000000-3e47220ae52b55be57f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-9400000000-78f160649efa3b627e2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9300000000-6ecab458fac9db3ee404Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00819 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00819 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00819
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1909
KEGG Compound IDC06805
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetazolamide
METLIN IDNot Available
PubChem Compound1986
PDB IDAZM
ChEBI ID27690
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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 ]
Enzyme Details
2. Carbonic anhydrase 1
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular weight:
28870.0
References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
Enzyme Details
3. Carbonic anhydrase 2
General function:
Involved in carbonate dehydratase activity
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 into the anterior chamber of the eye.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular weight:
29245.895
References
  1. 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 ]
  2. 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 ]
Enzyme Details
4. Carbonic anhydrase 3
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide.
Gene Name:
CA3
Uniprot ID:
P07451
Molecular weight:
29557.215
References
  1. 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 ]
Enzyme Details
5. Carbonic anhydrase 4
General function:
Involved in carbonate dehydratase activity
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 and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:
CA4
Uniprot ID:
P22748
Molecular weight:
35032.075
References
  1. 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 ]
  2. 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 ]
Enzyme Details
6. Carbonic anhydrase 14
General function:
Inorganic ion transport and metabolism
Specific function:
Reversible hydration of carbon dioxide.
Gene Name:
CA14
Uniprot ID:
Q9ULX7
Molecular weight:
37667.37
References
  1. 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 ]
Enzyme Details
7. Carbonic anhydrase 7
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide.
Gene Name:
CA7
Uniprot ID:
P43166
Molecular weight:
23451.435
References
  1. 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 ]
Enzyme Details
8. Aquaporin-1
General function:
Involved in 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 osmotic gradient
Gene Name:
AQP1
Uniprot ID:
P29972
Molecular weight:
28525.7
References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]

Transporters

Enzyme Details
1. Solute carrier family 22 member 6
General function:
Involved in ion 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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. 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 ]