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Identification
NameAcetazolamide
Accession NumberDB00819  (APRD00119, EXPT00604)
TypeSmall Molecule
GroupsApproved, 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
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 (sustained-release)500 mgoralWyeth Canada1998-12-232006-03-22Canada
Diamox Sequelscapsule, extended release500 mg/1oralREMEDYREPACK INC.2013-02-21Not applicableUs
Diamox Sequelscapsule, extended release500 mg/1oralTeva Women's Health, Inc.1962-03-01Not applicableUs
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
Acetazolamidetablet250 mg/1oralCardinal Health1997-05-28Not applicableUs
Acetazolamidetablet250 mg/1oralAv Kare, Inc.2012-07-02Not applicableUs
Acetazolamidecapsule, extended release500 mg/1oralKAISER FOUNDATION HOSPITALS2010-02-09Not applicableUs
Acetazolamidetablet125 mg/1oralAvera Mc Kennan Hospital2015-07-20Not applicableUs
Acetazolamidetablet250 mg/1oralPd Rx Pharmaceuticals, Inc.1997-05-28Not applicableUs
Acetazolamideinjection, powder, lyophilized, for solution500 mg/5mLintravenousX Gen Pharmaceuticals, Inc.2013-12-10Not applicableUs
Acetazolamidecapsule, extended release500 mg/1oralZydus Pharmaceuticals USA Inc.2008-12-15Not applicableUs
Acetazolamidetablet250 mg/1oralPhysicians Total Care, Inc.2010-02-09Not applicableUs
Acetazolamidetablet250 mg/1oralAmerican Health Packaging2011-11-01Not applicableUs
Acetazolamidetablet125 mg/1oralA S Medication Solutions Llc1997-05-28Not applicableUs
Acetazolamideinjection, powder, lyophilized, for solution500 mg/5mLintravenousX Gen Pharmaceuticals, Inc.2008-12-10Not applicableUs
Acetazolamidecapsule, extended release500 mg/1oralAmerican Health Packaging2010-04-14Not applicableUs
Acetazolamidetablet250 mg/1oralA S Medication Solutions Llc1997-05-28Not applicableUs
Acetazolamideinjection, powder, lyophilized, for solution500 mg/5mLintravenousSagent Pharmaceuticals2012-06-15Not applicableUs
Acetazolamidetablet250 1/1oralRed Pharm Drug Inc.1978-03-31Not applicableUs
Acetazolamidetablet250 mg/1oralREMEDYREPACK INC.2013-03-27Not applicableUs
Acetazolamidecapsule, extended release500 mg/1oralHeritage Pharmaceuticals Inc.2012-09-24Not applicableUs
Acetazolamidetablet250 mg/1oralGolden State Medical Supply, Inc.1997-05-28Not applicableUs
Acetazolamidetablet250 mg/1oralREMEDYREPACK INC.2013-03-11Not applicableUs
Acetazolamidetablet250 mg/1oralMarlex Pharmaceuticals Inc2014-10-01Not applicableUs
Acetazolamidecapsule, extended release500 mg/1oralNostrum Laboratories, Inc.2016-03-30Not applicableUs
Acetazolamidetablet125 mg/1oralGolden State Medical Supply, Inc.1997-05-28Not applicableUs
Acetazolamidetablet250 mg/1oralTaro Pharmaceuticals U.S.A., Inc.1997-05-28Not applicableUs
Acetazolamidetablet250 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1997-05-28Not applicableUs
Acetazolamideinjection, powder, lyophilized, for solution500 mg/5mLintravenousHeritage Pharmaceuticals Inc.2014-12-19Not applicableUs
Acetazolamidetablet125 mg/1oralPd Rx Pharmaceuticals, Inc.1997-05-28Not applicableUs
Acetazolamidetablet125 mg/1oralTaro Pharmaceuticals U.S.A., Inc.1997-05-28Not applicableUs
Acetazolamidetablet250 mg/1oralLannett Company, Inc.1978-03-31Not 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
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
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.
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Acetazolamide.
AmphetamineAcetazolamide may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
BenzphetamineAcetazolamide may decrease the excretion rate of Benzphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Bismuth SubsalicylateThe risk or severity of adverse effects can be increased when Bismuth Subsalicylate is combined with Acetazolamide.
BrinzolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Brinzolamide.
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Acetazolamide.
ButabarbitalButabarbital may increase the hypotensive activities of Acetazolamide.
ButethalButethal may increase the hypotensive activities of Acetazolamide.
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Acetazolamide.
CaffeineThe risk or severity of adverse effects can be increased when Caffeine is combined with Acetazolamide.
CanagliflozinThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Canagliflozin.
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Acetazolamide.
CathinoneAcetazolamide may decrease the excretion rate of Cathinone which could result in a lower serum level and potentially a reduction in efficacy.
ChlorphenamineThe risk or severity of adverse effects can be increased when Chlorphenamine 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.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen 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.
DiclofenamideThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Acetazolamide.
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Acetazolamide.
DorzolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Dorzolamide.
DuloxetineAcetazolamide may increase the orthostatic hypotensive activities of Duloxetine.
EphedrineThe serum concentration of Ephedrine can be increased when it is combined with Acetazolamide.
EthoxzolamideThe risk or severity of adverse effects can be increased when Ethoxzolamide is combined with Acetazolamide.
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.
FosphenytoinThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Fosphenytoin.
HeptabarbitalHeptabarbital may increase the hypotensive activities of Acetazolamide.
HexamethylenetetramineThe therapeutic efficacy of Hexamethylenetetramine can be decreased when used in combination with Acetazolamide.
HexobarbitalHexobarbital may increase the hypotensive activities of Acetazolamide.
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.
LevodopaAcetazolamide may increase the orthostatic hypotensive activities of Levodopa.
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.
LithiumThe serum concentration of Lithium can be decreased when it is combined with Acetazolamide.
Magnesium salicylateThe risk or severity of adverse effects can be increased when Magnesium salicylate is combined with Acetazolamide.
MecamylamineThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Mecamylamine.
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.
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.
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 Acetazolamide is combined with Methazolamide.
MethohexitalMethohexital may increase the hypotensive activities of Acetazolamide.
MianserinThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Mianserin.
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Acetazolamide.
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Acetazolamide.
NicorandilNicorandil may increase the hypotensive activities of 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.
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Acetazolamide.
PentobarbitalPentobarbital may increase the hypotensive activities of Acetazolamide.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Acetazolamide.
PhendimetrazineAcetazolamide may decrease the excretion rate of Phendimetrazine which could result in a lower serum level and potentially a reduction in efficacy.
PhenelzinePhenelzine may increase the orthostatic 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.
PrimidoneThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Primidone.
PseudoephedrineThe serum concentration of Pseudoephedrine can be increased when it is combined with Acetazolamide.
QuinidineAcetazolamide may decrease the excretion rate of Quinidine which could result in a lower serum level and potentially a reduction in efficacy.
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Acetazolamide.
RisperidoneAcetazolamide may increase the hypotensive activities of Risperidone.
SalsalateThe risk or severity of adverse effects can be increased when Salsalate 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.
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.
TopiramateThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Topiramate.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Acetazolamide.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Acetazolamide.
TriethylenetetramineThe serum concentration of Triethylenetetramine can be decreased when it is combined with Acetazolamide.
TriprolidineThe serum concentration of Triprolidine can be increased when it is combined with Acetazolamide.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Acetazolamide.
ZonisamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Zonisamide.
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 November 08, 2013 13:31