acetazolamide indications/contra

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

Drug dosage:

DoseUnitRoute
0.75 g O
0.75 g P

Approvals:

DateAgencyCompanyOrphan
July 27, 1953 FDA TEVA BRANDED PHARM

FDA Adverse Event Reporting System

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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
Intraocular pressure increased 189.26 46.58 33 352 2389 3383085
Drug ineffective 151.68 46.58 60 325 116030 3269444
Congenital intestinal malformation 103.14 46.58 12 373 37 3385437
Metabolic acidosis 88.71 46.58 22 363 8756 3376718
Angle closure glaucoma 82.10 46.58 14 371 866 3384608
Death neonatal 69.61 46.58 11 374 422 3385052
Drug hypersensitivity 65.69 46.58 24 361 35656 3349818
Vision blurred 62.82 46.58 20 365 19569 3365905
Photophobia 59.69 46.58 13 372 2909 3382565
Anterior chamber disorder 52.57 46.58 7 378 77 3385397
Foetal exposure during pregnancy 50.29 46.58 16 369 15535 3369939
Hyphaema 48.61 46.58 7 378 141 3385333
Visual impairment 47.58 46.58 15 370 14131 3371343
Headache 46.67 46.58 25 360 91955 3293519

Pharmacologic Action:

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SourceCodeDescription
ATC S01EC01 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Carbonic anhydrase inhibitors
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
FDA EPC N0000175517 Carbonic Anhydrase Inhibitor
FDA Chemical/Ingredient N0000008048 Sulfonamides

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Malignant glaucoma indication 10100008
Anoxia due to high altitude indication 42883007
Absence seizure indication 79631006 DOID:1825
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
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:2527
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 DOID:13774
Recurrent Calcium Renal Calculi contraindication
Metabolic alkalosis off-label use 1388004
Myoclonic seizure off-label use 37356005 DOID:308
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
Urine Alkalinization off-label use
Mixed Epilepsy off-label use
Hydrocephalus due to Intraventricular Hemorrhage off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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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:

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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 Unclassified 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:

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IDSource
4017898 VUID
N0000146250 NUI
C0000981 UMLSCUI
6792 IUPHAR_LIGAND_ID
D00218 KEGG_DRUG
CHEMBL20 ChEMBL_ID
429ZT169UH UNII
1424-27-7 SECONDARY_CAS_RN
DB00819 DRUGBANK_ID
1986 PUBCHEM_CID
4017898 VANDF
814 MMSL
N0000146250 NDFRT
N0000007364 NDFRT
167 RXNORM
33664007 SNOMEDCT_US
372709008 SNOMEDCT_US
4121 MMSL
d00161 MMSL
002286 NDDF
CHEBI:50634 CHEBI
CHEMBL1200814 ChEMBL_ID
481 INN_ID
D000086 MESH_DESCRIPTOR_UI
AZM PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
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 0179-0050 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 12 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 0527-1050 TABLET 250 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 0555-0513 CAPSULE, EXTENDED RELEASE 500 mg ORAL NDA authorized generic 11 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 0615-1511 TABLET 250 mg ORAL ANDA 12 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 23155-288 TABLET 250 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 23155-313 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 25021-817 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS ANDA 12 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 39822-0191 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 50090-0279 TABLET 250 mg ORAL ANDA 12 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 50090-0577 TABLET 125 mg ORAL ANDA 12 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 50090-3003 TABLET 250 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 50742-233 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 12 sections
Diamox Sequels HUMAN PRESCRIPTION DRUG LABEL 1 51285-754 CAPSULE, EXTENDED RELEASE 500 mg ORAL NDA 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 55289-221 TABLET 250 mg ORAL ANDA 12 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 64380-833 TABLET 125 mg ORAL ANDA 11 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 64380-834 TABLET 250 mg ORAL ANDA 11 sections