Identification

Name
Acetazolamide
Accession Number
DB00819  (APRD00119, EXPT00604)
Type
Small Molecule
Groups
Approved, Vet approved
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)

Structure
Thumb
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
  • 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
Product Ingredients
IngredientUNIICASInChI Key
Acetazolamide sodium429ZT169UH1424-27-7MRSXAJAOWWFZJJ-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AcetazolamTablet250 mgOralValeant Canada Lp Valeant Canada S.E.C.1974-12-312014-07-30Canada
AcetazolamideTablet250 mgOralAa Pharma Inc1982-12-31Not applicableCanada
Acetazolamide for Injection, USPPowder, for solution500 mgIntravenousSterimax Inc2010-12-03Not applicableCanada
Diamox IV 500mgPowder, for solution500 mgIntravenousWyeth Ayerst Canada Inc.1998-12-022001-05-07Canada
Diamox Pws 500mg/vialPowder, for solution500 mgIntravenousStorz, Division Of Wyeth Ayerst Canada Inc.1994-12-311999-08-12Canada
Diamox SequelsCapsule, extended release500 mg/1OralTeva Women's Health, Inc.2000-02-222019-05-31Us
Diamox SequelsCapsule, extended release500 mg/1OralRemedy Repack2012-07-202013-10-30Us51285 0754 02 nlmimage10 122f892c
Diamox SequelsCapsule, extended release500 mgOralWyeth Ltd.1998-12-232006-03-22Canada
Diamox Src 500mgCapsule, extended release500 mgOralStorz, Division Of Wyeth Ayerst Canada Inc.1994-12-311999-08-12Canada
Diamox Tab 250mgTablet250 mgOralStorz, Division Of Wyeth Ayerst Canada Inc.1994-12-312000-08-02Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AcetazolamideInjection, powder, lyophilized, for solution500 mg/5mLIntravenousMylan Institutional LLC2018-09-13Not applicableUs
AcetaZOLAMIDETablet250 1/1OralRed Pharm Drug, Inc.1978-03-31Not applicableUs67296 080120180907 15195 wrnf8j
AcetazolamideTablet125 mg/1OralTaro Pharmaceuticals U.S.A., Inc.1997-05-28Not applicableUs51672 402220180907 15195 y3l0la
AcetaZOLAMIDETablet250 mg/1OralLannett Company, Inc.1978-03-31Not applicableUs0527 105020180913 8702 2pkykx
AcetaZOLAMIDETablet250 mg/1OralMarlex Pharmaceuticals Inc2014-10-01Not applicableUs
AcetazolamideTablet250 mg/1OralRemedy Repack2012-08-102013-11-14Us
AcetazolamideTablet250 mg/1OralPd Rx Pharmaceuticals, Inc.1997-05-28Not applicableUs
AcetazolamideTablet250 mg/1OralStrides Shasun Limited2017-11-21Not applicableUs
AcetazolamideCapsule, extended release500 mg/1OralHeritage2012-09-24Not applicableUs23155 0120 01 nlmimage10 0a45855c
AcetazolamideTablet125 mg/1OralAvera McKennan Hospital2015-07-202018-05-25Us69189 402220180907 15195 1on8wqf
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) / Defiltran / 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)
Categories
UNII
O3FX965V0I
CAS number
59-66-5
Weight
Average: 222.245
Monoisotopic: 221.988131458
Chemical Formula
C4H6N4O3S2
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

Pharmacology

Indication

For adjunctive treatment of: edema due to congestive heart failure; drug-induced edema; centrencephalic epilepsies; chronic simple (open-angle) glaucoma

Associated Conditions
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.

TargetActionsOrganism
ACarbonic anhydrase 1
inhibitor
Human
ACarbonic anhydrase 2
inhibitor
Human
ACarbonic anhydrase 4
inhibitor
Human
ACarbonic anhydrase 12
inhibitor
Human
ACarbonic anhydrase 14
inhibitor
Human
ACarbonic anhydrase 3
inhibitor
Human
ACarbonic anhydrase 7
inhibitor
Human
UAquaporin-1
inhibitor
Human
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Acetazolamide.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Acetazolamide.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Acetazolamide.
2,5-Dimethoxy-4-ethylamphetamineAcetazolamide may decrease the excretion rate of 2,5-Dimethoxy-4-ethylamphetamine which could result in a higher serum level.
2,5-Dimethoxy-4-ethylthioamphetamineAcetazolamide may decrease the excretion rate of 2,5-Dimethoxy-4-ethylthioamphetamine which could result in a higher serum level.
3-isobutyl-1-methyl-7H-xanthineAcetazolamide may increase the excretion rate of 3-isobutyl-1-methyl-7H-xanthine which could result in a lower serum level and potentially a reduction in efficacy.
3,4-MethylenedioxyamphetamineAcetazolamide may decrease the excretion rate of 3,4-Methylenedioxyamphetamine which could result in a higher serum level.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Acetazolamide.
4-Bromo-2,5-dimethoxyamphetamineAcetazolamide may decrease the excretion rate of 4-Bromo-2,5-dimethoxyamphetamine which could result in a higher serum level.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Acetazolamide.
Food Interactions
  • Drink plenty of liquids.
  • Take with food; at least 6 hours before bedtime.

References

Synthesis Reference

Angela C. Potts, Mark Gibson, "Stable ophthalmic preparations containing acetazolamide." U.S. Patent US4888168, issued August, 1981.

US4888168
General References
Not Available
External Links
Human Metabolome Database
HMDB0014957
KEGG Drug
D00218
KEGG Compound
C06805
PubChem Compound
1986
PubChem Substance
46504493
ChemSpider
1909
BindingDB
10880
ChEBI
27690
ChEMBL
CHEMBL20
Therapeutic Targets Database
DAP000600
PharmGKB
PA448018
HET
AZM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Acetazolamide
ATC Codes
S01EC01 — AcetazolamideG01AE10 — Combinations of sulfonamides
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 20 more
FDA label
Download (149 KB)
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingBasic ScienceArterial hypoxia / Cognitive Function / Dexterity / Exercise Performance1
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1CompletedDiagnosticCocaine Use / Pharmacokinetics1
1CompletedPreventionOther and unspecified effects of high altitude1
1Not Yet RecruitingTreatmentMalignant Glioma of Brain1
1RecruitingPreventionOther and unspecified effects of high altitude1
1TerminatedTreatmentAndersen-Tawil Syndrome1
1TerminatedTreatmentHealthy Volunteers1
1, 2Active Not RecruitingTreatmentChronic Orthostatic Intolerance / Tachycardia1
1, 2CompletedTreatmentErythrocytosis / Mountain Sickness1
1, 2RecruitingTreatmentHematopoietic Stem Cell Transplantation (HSCT) / Lung Diseases, Interstitial / Obliterative Bronchiolitis1
2CompletedNot AvailableMacular Degeneration / Macular Edema (ME) / Retinopathy, Diabetic1
2CompletedPreventionCisplatin Nephrotoxicity1
2CompletedPreventionContrast Induced Nephropathy (CIN)1
2CompletedTreatmentAge Related Macular Degeneration (ARMD) / Retinopathy, Diabetic1
2CompletedTreatmentBlood Pressures / High Blood Pressure (Hypertension) / Obstructive Sleep Apnea (OSA) / Sleep-Disordered Breathing1
2CompletedTreatmentBreathing-Related Sleep Disorder / Pulmonary Hypertension (PH)1
2CompletedTreatmentCerebrovascular Accident, Acute / Edema of the cerebrum1
2CompletedTreatmentMacular Edema, Cystoid1
2Not Yet RecruitingTreatmentDisseminated Sclerosis1
2RecruitingPreventionDermal Sinus / Fibrolipoma of Filum Terminale / Lipomyelomeningocele / Split Cord Malformation / Tethered Cord Syndrome / Tumors1
2WithdrawnOtherCompliance / Pain, Chronic1
2WithdrawnTreatmentCerebrovascular Accident, Acute / Vasospasm1
2, 3CompletedTreatmentIdiopathic Intracranial Hypertension (IIH)1
2, 3Enrolling by InvitationTreatmentLandau-Kleffner Syndrome / Status Epilepticus, Electrographic1
2, 3RecruitingTreatmentNeurocysticercosis1
2, 3RecruitingTreatmentPulmonary Hypertension (PH)2
3CompletedPreventionOther and unspecified effects of high altitude1
3CompletedTreatmentMetabolic Alkalosis / Obesity Hypoventilation Syndrome / Pulmonary Disease, Chronic Obstructive1
3RecruitingPreventionGlaucoma1
3RecruitingTreatmentAcute Heart Failure (AHF) / Heart Failure, Unspecified1
3RecruitingTreatmentHigh Blood Pressure (Hypertension)1
3RecruitingTreatmentIdiopathic Intracranial Hypertension (IIH)1
3TerminatedBasic ScienceCentral Apnea / Heart Failure, Unspecified1
3TerminatedTreatmentCognitive Investigation / Motor Condition / Motor Condition as Measured by Quantified Scale1
3TerminatedTreatmentFibrinolysis / Hemodilution / Retinal Artery Occlusions / Strokes / Visual Acuity1
4CompletedNot AvailableChronic Heart Failure (CHF)1
4CompletedNot AvailableOther and unspecified effects of high altitude1
4CompletedBasic ScienceAltitude Sickness / Pulmonary Hypertension (PH)1
4CompletedBasic ScienceArterial hypoxia1
4CompletedTreatmentAlkalosis / Respiratory Insufficiency1
4CompletedTreatmentDecompensated Chronic Obstructive Pulmonary Disease1
4CompletedTreatmentEdema / Glomerulonephritis minimal lesion1
4CompletedTreatmentHeart Failure, Unspecified1
4CompletedTreatmentHigh Altitude Polycythemia1
4CompletedTreatmentObstructive Sleep Apnea Syndrome (OSAS)2
4CompletedTreatmentProphylaxis of Acute Mountain Sickness1
4Not Yet RecruitingTreatmentAcute Decompensated Heart Failure (ADHF) / Volume Overload1
4RecruitingOtherElderly Adults / Sleep Apnea Syndrome1
4RecruitingPreventionAltitude Hypoxia7
4RecruitingPreventionChronic Obstructive Pulmonary Disease (COPD)8
4RecruitingPreventionHyperalgesia / Opioid-Related Disorders1
4RecruitingPreventionOther and unspecified effects of high altitude1
4RecruitingTreatmentGlaucoma1
4TerminatedTreatmentHigh Altitude Pulmonary Edema1
4Unknown StatusTreatmentGlaucoma1
4Unknown StatusTreatmentThoracic Aneurysm1
Not AvailableCompletedBasic ScienceControls Without Heart Failure / Heart Failure, Unspecified1
Not AvailableCompletedBasic ScienceHeadaches / Migraines1
Not AvailableCompletedBasic ScienceHigh Altitude Headache1
Not AvailableCompletedDiagnosticRenal Stones1
Not AvailableCompletedPreventionEdema of the cerebrum / Pulmonary Edemas1
Not AvailableCompletedPreventionIntracranial Pressure Increase1
Not AvailableCompletedPreventionIntraocular Pressure Change in Intravitreal Injection1
Not AvailableCompletedTreatmentGlaucoma, Angle-Closure1
Not AvailableCompletedTreatmentHigh-altitude Sleep Disturbance1
Not AvailableRecruitingNot AvailableHealthy Controls / Sickle Cell Disorders / Thalassaemic disorders1
Not AvailableRecruitingNot AvailableSickle Cell Disorders1
Not AvailableRecruitingPreventionAltitude Sickness1
Not AvailableUnknown StatusEducational/Counseling/TrainingMigraines1
Not AvailableUnknown StatusTreatmentMetabolic Alkalosis / Ventilator Weaning1
Not AvailableUnknown StatusTreatmentSleep Apnea Syndrome1
Not AvailableWithdrawnDiagnosticSleep Apnea, Obstructive / Strokes1
Not AvailableWithdrawnTreatmentCerebrospinal Fluid Leaks1
Not AvailableWithdrawnTreatmentSleep Apnea Syndrome1

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
FormRouteStrength
Capsule, extended releaseOral500 mg/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/5mL
TabletOral125 mg/1
TabletOral250 mg
TabletOral250 1/1
TabletOral250 mg/1
Powder, for solutionIntravenous500 mg
Capsule, extended releaseOral500 mg
Prices
Unit descriptionCostUnit
Acetazolamide sod 500 mg vial51.75USD vial
Diamox Sequels 500 mg 12 Hour Capsule5.49USD capsule
Diamox sequels er 500 mg capsule5.24USD capsule
Acetazolamide powder4.53USD g
AcetaZOLAMIDE 500 mg 12 Hour Capsule4.46USD capsule
Acetazolamide 125 mg tablet0.37USD tablet
Acetazolamide 250 mg tablet0.35USD tablet
Apo-Acetazolamide 250 mg Tablet0.13USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)260.5 °CPhysProp
water solubility980 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.26HANSCH,C ET AL. (1995)
logS-2.36ADME Research, USCD
pKa7.2MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility2.79 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.36 m3·mol-1ChemAxon
Polarizability19.16 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier+0.9382
Caco-2 permeable-0.7761
P-glycoprotein substrateNon-substrate0.8369
P-glycoprotein inhibitor INon-inhibitor0.9267
P-glycoprotein inhibitor IINon-inhibitor0.9507
Renal organic cation transporterNon-inhibitor0.9365
CYP450 2C9 substrateNon-substrate0.7316
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7817
CYP450 1A2 substrateNon-inhibitor0.9259
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9625
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9037
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8798
Ames testNon AMES toxic0.8445
CarcinogenicityNon-carcinogens0.802
BiodegradationNot ready biodegradable0.9301
Rat acute toxicity1.8939 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9926
hERG inhibition (predictor II)Non-inhibitor0.9449
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.82 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00e9-9070000000-e2f68ded4939412340f7
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-9020000000-59775cde1cab229764b9
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-9000000000-1ee1fd41bb44b523dd8e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-9000000000-de6c64393f3dc86c15b1
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-9000000000-7158c10cba32f3b3896b
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-06si-9000000000-32cc006b3850024fd5b7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00e9-0890000000-f407810fc44461e62ecb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0920000000-6dd62d0ae588814e0cf2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-6b6d74d2f34efd5f876a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-1900000000-05fedd43edecd53593c2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-5900000000-76456c439130c5477d45
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00e9-9300000000-5ca7214eb79224d3dc21

Taxonomy

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
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
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid amide, sulfonamide, thiadiazoles (CHEBI:27690) / a small molecule (CPD0-1626)

Targets

Details
1. Carbonic anhydrase 1
Kind
Protein
Organism
Human
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
  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]
Details
2. Carbonic anhydrase 2
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 Da
References
  1. 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]
Details
3. Carbonic anhydrase 4
Kind
Protein
Organism
Human
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
  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]
Details
4. Carbonic anhydrase 12
Kind
Protein
Organism
Human
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
  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]
Details
5. Carbonic anhydrase 14
Kind
Protein
Organism
Human
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
  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]
Details
6. Carbonic anhydrase 3
Kind
Protein
Organism
Human
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
  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]
Details
7. Carbonic anhydrase 7
Kind
Protein
Organism
Human
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
  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]
Kind
Protein
Organism
Human
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
  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]

Enzymes

Kind
Protein
Organism
Human
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
  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]
  2. 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]

Transporters

Kind
Protein
Organism
Human
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
  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]

Drug created on June 13, 2005 07:24 / Updated on November 14, 2018 12:46