acetazolamide Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
56 59-66-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • acetazolamide
  • acetamox
  • acetazolamid
  • cidamex
  • nephramide
  • acetazolamide sodium
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)
  • Molecular weight: 222.24
  • Formula: C4H6N4O3S2
  • CLOGP: -0.98
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 115.04
  • ALOGS: -1.90
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.75 g O
0.75 g P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 75.14 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.64 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 90 % Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.37 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.65 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.04 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 13 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 27, 1953 FDA TEVA BRANDED PHARM

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug ineffective 142.58 56.83 58 288 101566 2256173
Intraocular pressure increased 123.51 56.83 22 324 1487 2356252
Off label use 112.75 56.83 45 301 73553 2284186
Angle closure glaucoma 110.05 56.83 18 328 726 2357013
Metabolic acidosis 72.58 56.83 18 328 5980 2351759
Intellectual disability 70.95 56.83 10 336 143 2357596

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Choroidal detachment 154.41 79.49 19 178 95 1746489
Intraocular pressure increased 116.88 79.49 20 177 1161 1745423
Angle closure glaucoma 105.55 79.49 15 182 250 1746334
Drug ineffective 97.73 79.49 38 159 63763 1682821
Choroidal effusion 86.51 79.49 11 186 73 1746511

Pharmacologic Action:

SourceCodeDescription
ATC S01EC01 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Carbonic anhydrase inhibitors
FDA EPC N0000175517 Carbonic Anhydrase Inhibitor
FDA CS M0020790 Sulfonamides
MeSH PA D000927 Anticonvulsants
MeSH PA D002257 Carbonic Anhydrase Inhibitors
MeSH PA D002491 Central Nervous System Agents
MeSH PA D004232 Diuretics
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D045283 Natriuretic Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Malignant glaucoma indication 10100008
Anoxia due to high altitude indication 42883007
Absence seizure indication 79631006
Open-angle glaucoma indication 84494001 DOID:1067
Secondary glaucoma indication 95717004
Edema indication 267038008
Peripheral edema indication 271809000
Angle-closure glaucoma indication 392291006 DOID:13550
Peripheral Edema due to Chronic Heart Failure indication
Metabolic alkalosis off-label use 1388004
Myoclonic seizure off-label use 37356005
Benign intracranial hypertension off-label use 68267002 DOID:11459
Epilepsy off-label use 84757009 DOID:1826
Obstructive hydrocephalus off-label use 230746009 DOID:14159
Familial periodic paralysis off-label use 267607008 DOID:1029
Tonic-clonic epilepsy off-label use 352818000 DOID:7725
Simple partial seizure off-label use 117891000119100
Hydrocephalus due to Intraventricular Hemorrhage off-label use
Mixed Epilepsy off-label use
Urine Alkalinization off-label use
Renal tubular acidosis contraindication 1776003 DOID:14219
Respiratory acidosis contraindication 12326000
Hyperkalemia contraindication 14140009
Metabolic acidosis, normal anion gap, acidifying salts contraindication 18104000
Diabetes mellitus type 2 contraindication 44054006 DOID:9352
Diabetes mellitus type 1 contraindication 46635009 DOID:9744
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Decreased respiratory function contraindication 80954004
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Disease of blood AND/OR blood-forming organ contraindication 191124002 DOID:74
Disease of liver contraindication 235856003 DOID:409
Disorder of electrolytes contraindication 237840007
Primary adrenocortical insufficiency contraindication 373662000
Recurrent Calcium Renal Calculi contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.04 acidic
pKa2 9.21 acidic
pKa3 1.84 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Carbonic anhydrase 12 Enzyme INHIBITOR Ki 8.60 CHEMBL CHEMBL
Carbonic anhydrase 4 Enzyme INHIBITOR Ki 7.96 CHEMBL CHEMBL
Carbonic anhydrase 1 Enzyme INHIBITOR Ki 7.92 CHEMBL CHEMBL
Carbonic anhydrase 2 Enzyme INHIBITOR Ki 8.48 CHEMBL CHEMBL
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 7.22 CHEMBL
Carbonic anhydrase Enzyme Ki 9.10 CHEMBL
Carbonic anhydrase 14 Enzyme Ki 7.39 CHEMBL
Carbonic anhydrase 7 Enzyme Ki 8.60 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 8.05 CHEMBL
Carbonic anhydrase V Enzyme Ki 8.74 CHEMBL
Carbonic anhydrase 5B, mitochondrial Enzyme Ki 7.27 CHEMBL
Carbonic anhydrase 3 Enzyme Ki 8.51 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 8.24 CHEMBL
Carbonic anhydrase 6 Enzyme Ki 7.96 CHEMBL
Aquaporin-1 Transporter WOMBAT-PK
Carbonic anhydrase 2 Unclassified Ki 8 CHEMBL
Carbonic anhydrase Enzyme Ki 7.09 CHEMBL
Carbonic anhydrase Unclassified Ki 5.24 CHEMBL
Carbonic anhydrase 2 Enzyme IC50 6.02 CHEMBL
Carbonic anhydrase Enzyme Ki 4.92 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 7.77 CHEMBL
Carbonic anhydrase Enzyme Ki 7.70 CHEMBL
Carbonic anhydrase 15 Enzyme Ki 7.14 CHEMBL
Alpha carbonic anhydrase Unclassified Ki 7.80 CHEMBL
Carbonic anhydrase 7 Enzyme Ki 7.80 CHEMBL
Probable transmembrane carbonic anhydrase (Carbonate dehydratase) (Carbonic dehydratase); Transmembrane carbonic anhydrase Enzyme Ki 7.92 CHEMBL
Carbonic anhydrase Enzyme IC50 7.80 CHEMBL
Endochitinase Enzyme Ki 4.68 CHEMBL
Carbonic anhydrase 3 Enzyme Ki 4.08 CHEMBL
Astrosclerin-3 Unclassified Ki 7.29 CHEMBL
Carbonic anhydrase Enzyme Ki 7.40 CHEMBL
Carbonic anhydrase Enzyme Ki 7.22 CHEMBL
Beta-carbonic anhydrase 1 Enzyme Ki 6.60 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 8.05 CHEMBL
Carbonic anhydrase Enzyme Ki 7.96 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 7.15 CHEMBL
Carbonic anhydrase Enzyme Ki 7.57 CHEMBL
Carbonic anhydrase Unclassified Ki 7.56 CHEMBL
Carbonic anhydrase 1; GH09688p Enzyme Ki 6.97 CHEMBL
Carbonic anhydrase Unclassified Ki 7.12 CHEMBL
Carbonic anhydrase 2, isoform A; LD26647p Enzyme Ki 7.11 CHEMBL
Carbonic anhydrase Unclassified Ki 7.13 CHEMBL
Delta carbonic anhydrase Unclassified Ki 7.08 CHEMBL

External reference:

IDSource
D000086 MESH_DESCRIPTOR_UI
4017898 VUID
N0000146250 NUI
C0000981 UMLSCUI
D00218 KEGG_DRUG
429ZT169UH UNII
1424-27-7 SECONDARY_CAS_RN
33664007 SNOMEDCT_US
4017898 VANDF
814 MMSL
167 RXNORM
372709008 SNOMEDCT_US
4121 MMSL
d00161 MMSL
002286 NDDF
1986 PUBCHEM_CID
CHEBI:50634 CHEBI
CHEMBL20 ChEMBL_ID
DB00819 DRUGBANK_ID
CHEMBL1200814 ChEMBL_ID
481 INN_ID
6792 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 0143-9503 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS ANDA 12 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 0527-1050 TABLET 250 mg ORAL ANDA 11 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 0615-1511 TABLET 250 mg ORAL ANDA 12 sections
acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 0904-6663 TABLET 250 mg ORAL ANDA 11 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 10135-567 TABLET 250 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 23155-120 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 11 sections
acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 23155-287 TABLET 125 mg ORAL ANDA 11 sections
acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 23155-288 TABLET 250 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 29033-030 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 12 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 39822-0190 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS ANDA 11 sections
acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 42291-089 TABLET 125 mg ORAL ANDA 11 sections
acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 42291-090 TABLET 250 mg ORAL ANDA 11 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 42291-103 TABLET 250 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 46708-349 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 11 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 50090-3003 TABLET 250 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 50090-3132 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 50090-4511 TABLET 125 mg ORAL ANDA 12 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 50742-233 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 12 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 51672-4022 TABLET 125 mg ORAL ANDA 12 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 51672-4023 TABLET 250 mg ORAL ANDA 12 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 54868-1195 TABLET 250 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 55289-720 TABLET 125 mg ORAL ANDA 12 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 60429-033 TABLET 125 mg ORAL ANDA 12 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 60429-034 TABLET 250 mg ORAL ANDA 12 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 62332-349 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 11 sections
acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 63629-7889 TABLET 250 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 64380-833 TABLET 125 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 64380-834 TABLET 250 mg ORAL ANDA 11 sections
acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 65841-762 CAPSULE 500 mg ORAL ANDA 11 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 67296-0801 TABLET 250 1 ORAL ANDA 11 sections