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Identification
NameAcetazolamide
Accession NumberDB00819  (APRD00119, EXPT00604)
TypeSmall Molecule
GroupsApproved, Vet Approved
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
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
Defiltran
Diacarb
Diamox
Diluran
Glaupax
N-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamide
N-[5-(Aminosulfonyl)-1,3,5-thiadiazol-2-yl]acetamide
External Identifiers
  • RP 5172
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acetazolamtablet250 mgoralValeant Canada Lp Valeant Canada S.E.C.1974-12-312014-07-30Canada
Acetazolamidecapsule, extended release500 mg/1oralBarr Laboratories Inc.2000-02-22Not applicableUs
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.1962-03-01Not applicableUs
Diamox Sequelscapsule, extended release500 mg/1oralREMEDYREPACK INC.2013-02-21Not applicableUs
Diamox Sequelscapsule (sustained-release)500 mgoralWyeth Canada1998-12-232006-03-22Canada
Diamox Src 500mgcapsule (sustained-release)500 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
Diamox Tablets 250mgtablet250 mgoralWyeth Ayerst Canada Inc.1999-10-272002-12-03Canada
Novo-zolamide Tab 250mgtablet250 mgoralNovopharm Limited1981-12-312005-08-10Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acetazolamideinjection, powder, lyophilized, for solution500 mg/5mLintravenousX Gen Pharmaceuticals, Inc.2013-12-10Not applicableUs
Acetazolamidecapsule, extended release500 mg/1oralAmerican Health Packaging2010-04-14Not applicableUs
Acetazolamidecapsule, extended release500 mg/1oralKAISER FOUNDATION HOSPITALS2010-02-09Not applicableUs
Acetazolamidetablet250 mg/1oralPhysicians Total Care, Inc.2010-02-09Not applicableUs
Acetazolamidetablet250 mg/1oralREMEDYREPACK INC.2013-03-11Not applicableUs
Acetazolamideinjection, powder, lyophilized, for solution500 mg/5mLintravenousHeritage Pharmaceuticals Inc.2014-12-19Not applicableUs
Acetazolamidecapsule, extended release500 mg/1oralHeritage Pharmaceuticals Inc.2012-09-24Not applicableUs
Acetazolamidetablet125 mg/1oralGolden State Medical Supply, Inc.1997-05-28Not applicableUs
Acetazolamidetablet250 mg/1oralAv Kare, Inc.2012-07-02Not applicableUs
Acetazolamidetablet250 mg/1oralAmerican Health Packaging2011-11-01Not applicableUs
Acetazolamidetablet250 mg/1oralLannett Company, Inc.1978-03-31Not applicableUs
Acetazolamidetablet250 mg/1oralCardinal Health1997-05-28Not applicableUs
Acetazolamidetablet250 mg/1oralREMEDYREPACK INC.2013-03-27Not applicableUs
Acetazolamidecapsule, extended release500 mg/1oralNostrum Laboratories, Inc.2016-03-30Not applicableUs
Acetazolamideinjection, powder, lyophilized, for solution500 mg/5mLintravenousSagent Pharmaceuticals2012-06-15Not applicableUs
Acetazolamidetablet250 mg/1oralGolden State Medical Supply, Inc.1997-05-28Not applicableUs
Acetazolamidetablet125 mg/1oralTaro Pharmaceuticals U.S.A., Inc.1997-05-28Not applicableUs
Acetazolamidecapsule, extended release500 mg/1oralZydus Pharmaceuticals USA Inc.2008-12-15Not applicableUs
Acetazolamidetablet250 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1997-05-28Not applicableUs
Acetazolamidetablet250 mg/1oralPd Rx Pharmaceuticals, Inc.1997-05-28Not applicableUs
Acetazolamidetablet250 mg/1oralA S Medication Solutions Llc1997-05-28Not applicableUs
Acetazolamidetablet250 1/1oralRed Pharm Drug Inc.1978-03-31Not applicableUs
Acetazolamideinjection, powder, lyophilized, for solution500 mg/5mLintravenousX Gen Pharmaceuticals, Inc.2008-12-10Not applicableUs
Acetazolamidetablet250 mg/1oralTaro Pharmaceuticals U.S.A., Inc.1997-05-28Not applicableUs
Acetazolamidetablet125 mg/1oralAvera Mc Kennan Hospital2015-07-20Not applicableUs
Acetazolamidetablet250 mg/1oralMarlex Pharmaceuticals Inc2014-10-01Not applicableUs
Acetazolamidetablet125 mg/1oralPd Rx Pharmaceuticals, Inc.1997-05-28Not applicableUs
Acetazolamidetablet125 mg/1oralA S Medication Solutions Llc1997-05-28Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AcemitMedphano
AcemoxAcme
AcetakAkorn
AcetamideMicro Vision
AcetazolamaxPfoshen
AzmEthical
AzolNew Chemical
AzomidAdcock Ingram Pharmaceuticals
CarbinibEdol
DéfiltranCSP
DefiltranNot Available
DiaboRaymos
DiacarbPolpharma
DiamoxSanofi Aventis
Diamox DepotGoldshield
DiazomidSanofi-Aventis
DiluranZentiva
DiuramidPolpharma
EdemoxChiesi
GlaumoxPhebra
GlaupaxOmnivision
GlupaxPhebra
Huma-ZolamideTeva
Iopar-SRFDC
MedenePharmaland
OcultenAcromax
ÖdeminSanten
UramoxTaro
ZolmideVista Pharma
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Acetazolamide Sodium
1424-27-7
Thumb
  • InChI Key:
  • Monoisotopic Mass:
  • Average Mass:
DBSALT000539
Categories
UNIIO3FX965V0I
CAS number59-66-5
WeightAverage: 222.245
Monoisotopic: 221.988131458
Chemical FormulaC4H6N4O3S2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-arylamides. These are organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R')H, R = organyl group and R'= aryl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassN-arylamides
Sub ClassNot Available
Direct ParentN-arylamides
Alternative Parents
Substituents
  • N-arylamide
  • 1,3,4-thiadiazole-2-sulfonamide
  • 2-amino-5-substituted-1,3,4-thiadiazole
  • 2-amino-1,3,4-thiadiazole
  • Heteroaromatic compound
  • Acetamide
  • Aminosulfonyl compound
  • Thiadiazole
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Azole
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor adjunctive treatment of: edema due to congestive heart failure; drug-induced edema; centrencephalic epilepsies; chronic simple (open-angle) glaucoma
PharmacodynamicsAcetazolamide 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 actionThe 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding98%
MetabolismNot Available
Route of eliminationNot Available
Half life3 to 9 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
Capsule, extended releaseoral500 mg/1
Injection, powder, lyophilized, for solutionintravenous500 mg/5mL
Tabletoral125 mg/1
Tabletoral250 mg
Tabletoral250 mg/1
Tabletoral250 1/1
Powder for solutionintravenous500 mg
Capsule (sustained-release)oral500 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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point260.5 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.82 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

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

US4888168
General ReferencesNot Available
External Links
ATC CodesS01EC01
AHFS Codes
  • 52:10.00
PDB Entries
FDA labelDownload (149 KB)
MSDSDownload (73.4 KB)
Interactions
Drug Interactions
Drug
3,4-MethylenedioxyamphetamineAcetazolamide may decrease the excretion rate of 3,4-Methylenedioxyamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
3,4-MethylenedioxymethamphetamineAcetazolamide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
AcebutololThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Acebutolol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Acetazolamide.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Acetazolamide.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Acetazolamide.
AliskirenThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Aliskiren.
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Acetazolamide.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Acetazolamide.
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Acetazolamide.
AmlodipineThe risk or severity of adverse effects can be increased when Amlodipine is combined with Acetazolamide.
AmobarbitalAmobarbital may increase the hypotensive activities of Acetazolamide.
AmphetamineAcetazolamide may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Amyl NitriteThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Amyl Nitrite.
ApraclonidineThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Apraclonidine.
AripiprazoleAripiprazole may increase the hypotensive activities of Acetazolamide.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Acetazolamide.
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Azilsartan medoxomil.
BarbitalBarbital may increase the hypotensive activities of Acetazolamide.
BenazeprilThe risk or severity of adverse effects can be increased when Benazepril is combined with Acetazolamide.
BendroflumethiazideThe risk or severity of adverse effects can be increased when Bendroflumethiazide is combined with Acetazolamide.
BenzphetamineAcetazolamide may decrease the excretion rate of Benzphetamine which could result in a lower serum level and potentially a reduction in efficacy.
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Acetazolamide.
BezitramideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Acetazolamide.
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Acetazolamide.
BretyliumThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Bretylium.
BrimonidineThe risk or severity of adverse effects can be increased when Brimonidine is combined with Acetazolamide.
BrinzolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Brinzolamide.
BumetanideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Bumetanide.
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Acetazolamide.
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Acetazolamide.
CanagliflozinThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Canagliflozin.
CandesartanThe risk or severity of adverse effects can be increased when Candesartan is combined with Acetazolamide.
CaptoprilThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Captopril.
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Acetazolamide.
CarfentanilThe risk or severity of adverse effects can be increased when Carfentanil is combined with Acetazolamide.
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Acetazolamide.
CarvedilolThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Carvedilol.
ChlorothiazideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Chlorothiazide.
ChlorphentermineAcetazolamide may decrease the excretion rate of Chlorphentermine which could result in a lower serum level and potentially a reduction in efficacy.
ChlorthalidoneThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Acetazolamide.
CilazaprilThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Cilazapril.
ClevidipineThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Clevidipine.
ClonidineThe risk or severity of adverse effects can be increased when Clonidine is combined with Acetazolamide.
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Acetazolamide.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Acetazolamide.
DapagliflozinThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Dapagliflozin.
DexmedetomidineThe risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Acetazolamide.
DextroamphetamineAcetazolamide may decrease the excretion rate of Dextroamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
DextromoramideThe risk or severity of adverse effects can be increased when Dextromoramide is combined with Acetazolamide.
DextropropoxypheneThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Acetazolamide.
DezocineThe risk or severity of adverse effects can be increased when Dezocine is combined with Acetazolamide.
DiclofenamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Diclofenamide.
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Acetazolamide.
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Acetazolamide.
DihydroetorphineThe risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Acetazolamide.
DihydromorphineThe risk or severity of adverse effects can be increased when Dihydromorphine is combined with Acetazolamide.
DiltiazemThe risk or severity of adverse effects can be increased when Diltiazem is combined with Acetazolamide.
DinutuximabThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Dinutuximab.
DiphenoxylateThe risk or severity of adverse effects can be increased when Diphenoxylate is combined with Acetazolamide.
DipyridamoleThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Dipyridamole.
DorzolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Dorzolamide.
DoxazosinThe risk or severity of adverse effects can be increased when Doxazosin is combined with Acetazolamide.
DPDPEThe risk or severity of adverse effects can be increased when DPDPE is combined with Acetazolamide.
DuloxetineAcetazolamide may increase the orthostatic hypotensive activities of Duloxetine.
EmpagliflozinThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Empagliflozin.
EnalaprilThe risk or severity of adverse effects can be increased when Enalapril is combined with Acetazolamide.
EplerenoneThe risk or severity of adverse effects can be increased when Eplerenone is combined with Acetazolamide.
EprosartanThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Eprosartan.
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Acetazolamide.
Etacrynic acidThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Etacrynic acid.
EthoxzolamideThe risk or severity of adverse effects can be increased when Ethoxzolamide is combined with Acetazolamide.
EthylmorphineThe risk or severity of adverse effects can be increased when Ethylmorphine is combined with Acetazolamide.
EtorphineThe risk or severity of adverse effects can be increased when Etorphine is combined with Acetazolamide.
FelodipineThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Felodipine.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Acetazolamide.
FlecainideThe serum concentration of Flecainide can be increased when it is combined with Acetazolamide.
FosinoprilThe risk or severity of adverse effects can be increased when Fosinopril is combined with Acetazolamide.
FosphenytoinThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Fosphenytoin.
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Acetazolamide.
GuanfacineThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Guanfacine.
HeroinThe risk or severity of adverse effects can be increased when Heroin is combined with Acetazolamide.
HexamethylenetetramineThe therapeutic efficacy of Hexamethylenetetramine can be decreased when used in combination with Acetazolamide.
HexobarbitalHexobarbital may increase the hypotensive activities of Acetazolamide.
HydralazineThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Hydralazine.
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Hydrochlorothiazide.
HydrocodoneThe risk or severity of adverse effects can be increased when Hydrocodone is combined with Acetazolamide.
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Acetazolamide.
Hydroxyamphetamine hydrobromideAcetazolamide may decrease the excretion rate of Hydroxyamphetamine hydrobromide which could result in a lower serum level and potentially a reduction in efficacy.
IndapamideThe risk or severity of adverse effects can be increased when Indapamide is combined with Acetazolamide.
IrbesartanThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Irbesartan.
Isosorbide DinitrateThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Isosorbide Dinitrate.
Isosorbide MononitrateThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Isosorbide Mononitrate.
IsoxsuprineThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Isoxsuprine.
IsradipineThe risk or severity of adverse effects can be increased when Isradipine is combined with Acetazolamide.
KetobemidoneThe risk or severity of adverse effects can be increased when Ketobemidone is combined with Acetazolamide.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Acetazolamide.
LevobunololThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Levobunolol.
LevodopaAcetazolamide may increase the orthostatic hypotensive activities of Levodopa.
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Acetazolamide.
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Acetazolamide.
LisdexamfetamineAcetazolamide may decrease the excretion rate of Lisdexamfetamine which could result in a lower serum level and potentially a reduction in efficacy.
LisinoprilThe risk or severity of adverse effects can be increased when Lisinopril is combined with Acetazolamide.
LithiumThe serum concentration of Lithium can be decreased when it is combined with Acetazolamide.
LofentanilThe risk or severity of adverse effects can be increased when Lofentanil is combined with Acetazolamide.
LosartanThe risk or severity of adverse effects can be increased when Losartan is combined with Acetazolamide.
MannitolThe risk or severity of adverse effects can be increased when Mannitol is combined with Acetazolamide.
MecamylamineThe risk or severity of adverse effects can be increased when Mecamylamine is combined with Acetazolamide.
MefloquineThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Mefloquine.
MemantineAcetazolamide may decrease the excretion rate of Memantine which could result in a lower serum level and potentially a reduction in efficacy.
MephentermineAcetazolamide may decrease the excretion rate of Mephentermine which could result in a lower serum level and potentially a reduction in efficacy.
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Acetazolamide.
MetforminThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Metformin.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Acetazolamide.
Methadyl AcetateThe risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Acetazolamide.
MethamphetamineAcetazolamide may decrease the excretion rate of Methamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
MethazolamideThe risk or severity of adverse effects can be increased when Methazolamide is combined with Acetazolamide.
MethohexitalMethohexital may increase the hypotensive activities of Acetazolamide.
MethyclothiazideThe risk or severity of adverse effects can be increased when Methyclothiazide is combined with Acetazolamide.
MethyldopaThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Methyldopa.
MethylphenobarbitalMethylphenobarbital may increase the hypotensive activities of Acetazolamide.
MetipranololThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Metipranolol.
MetolazoneThe risk or severity of adverse effects can be increased when Metolazone is combined with Acetazolamide.
MetoprololThe risk or severity of adverse effects can be increased when Metoprolol is combined with Acetazolamide.
MianserinThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Mianserin.
MinoxidilThe risk or severity of adverse effects can be increased when Minoxidil is combined with Acetazolamide.
MoexiprilThe risk or severity of adverse effects can be increased when Moexipril is combined with Acetazolamide.
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Acetazolamide.
NadololThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Nadolol.
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Acetazolamide.
NebivololThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Nebivolol.
NesiritideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Nesiritide.
NicardipineThe risk or severity of adverse effects can be increased when Nicardipine is combined with Acetazolamide.
NicorandilNicorandil may increase the hypotensive activities of Acetazolamide.
NifedipineThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Nifedipine.
NimodipineThe risk or severity of adverse effects can be increased when Nimodipine is combined with Acetazolamide.
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Acetazolamide.
NisoldipineThe risk or severity of adverse effects can be increased when Nisoldipine is combined with Acetazolamide.
NitroglycerinThe risk or severity of adverse effects can be increased when Nitroglycerin is combined with Acetazolamide.
NitroprussideThe risk or severity of adverse effects can be increased when Nitroprusside is combined with Acetazolamide.
NormethadoneThe risk or severity of adverse effects can be increased when Normethadone is combined with Acetazolamide.
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Acetazolamide.
OpiumThe risk or severity of adverse effects can be increased when Opium is combined with Acetazolamide.
OrlistatThe serum concentration of Acetazolamide can be decreased when it is combined with Orlistat.
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Acetazolamide.
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Acetazolamide.
PapaverineThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Papaverine.
PenbutololThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Penbutolol.
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Acetazolamide.
PentobarbitalPentobarbital may increase the hypotensive activities of Acetazolamide.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Acetazolamide.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Acetazolamide.
PhenobarbitalPhenobarbital may increase the hypotensive activities of Acetazolamide.
PhentermineAcetazolamide may decrease the excretion rate of Phentermine which could result in a lower serum level and potentially a reduction in efficacy.
PhenytoinThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Phenytoin.
PindololThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Pindolol.
PrazosinThe risk or severity of adverse effects can be increased when Prazosin is combined with Acetazolamide.
PrimidoneThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Primidone.
PrimidonePrimidone may increase the hypotensive activities of Acetazolamide.
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Acetazolamide.
QuetiapineThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Quetiapine.
QuinaprilThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Quinapril.
QuinidineAcetazolamide may decrease the excretion rate of Quinidine which could result in a lower serum level and potentially a reduction in efficacy.
RamiprilThe risk or severity of adverse effects can be increased when Ramipril is combined with Acetazolamide.
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Acetazolamide.
ReserpineThe risk or severity of adverse effects can be increased when Reserpine is combined with Acetazolamide.
RiociguatThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Riociguat.
RisperidoneAcetazolamide may increase the hypotensive activities of Risperidone.
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Acetazolamide.
SecobarbitalSecobarbital may increase the hypotensive activities of Acetazolamide.
Sodium bicarbonateThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Sodium bicarbonate.
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Acetazolamide.
SpironolactoneThe risk or severity of adverse effects can be increased when Spironolactone is combined with Acetazolamide.
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Acetazolamide.
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Acetazolamide.
TelmisartanThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Telmisartan.
TerazosinThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Terazosin.
ThiamylalThiamylal may increase the hypotensive activities of Acetazolamide.
ThiopentalThiopental may increase the hypotensive activities of Acetazolamide.
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Acetazolamide.
TizanidineThe risk or severity of adverse effects can be increased when Tizanidine is combined with Acetazolamide.
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Acetazolamide.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Acetazolamide.
TrandolaprilThe risk or severity of adverse effects can be increased when Trandolapril is combined with Acetazolamide.
TriamtereneThe risk or severity of adverse effects can be increased when Triamterene is combined with Acetazolamide.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Acetazolamide.
VerapamilThe risk or severity of adverse effects can be increased when Verapamil is combined with Acetazolamide.
Food Interactions
  • Drink plenty of liquids.
  • Take with food; at least 6 hours before bedtime.

Targets

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
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 ]
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
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 ]
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 into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate ex...
Gene Name:
CA2
Uniprot ID:
P00918
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 ]
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
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 ]
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 and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:
CA4
Uniprot ID:
P22748
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 ]
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
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 osmotic gradient.
Gene Name:
AQP1
Uniprot ID:
P29972
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 ]

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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23