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
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
MRTD (Maximum Recommended Therapeutic Daily Dose) 75.14 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
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
Idiopathic intracranial hypertension 163.99 17.35 42 5815 2467 46677738
Hair follicle tumour benign 131.53 17.35 25 5832 357 46679848
Intraocular pressure increased 116.11 17.35 39 5818 5918 46674287
Angle closure glaucoma 107.14 17.35 29 5828 2110 46678095
Intracranial pressure increased 103.99 17.35 33 5824 4187 46676018
Metabolic acidosis 103.50 17.35 63 5794 38717 46641488
Papilloedema 92.41 17.35 29 5828 3548 46676657
Off label use 64.83 17.35 145 5712 379696 46300509
Complications of bone marrow transplant 57.53 17.35 13 5844 446 46679759
Hepatosplenic T-cell lymphoma 53.47 17.35 13 5844 615 46679590
Retinal detachment 49.52 17.35 20 5837 5080 46675125
Macular detachment 46.09 17.35 8 5849 66 46680139
Flat anterior chamber of eye 40.30 17.35 7 5850 58 46680147
Acute generalised exanthematous pustulosis 37.82 17.35 20 5837 9385 46670820
Intellectual disability 37.71 17.35 10 5847 672 46679533
Hypercapnia 37.67 17.35 16 5841 4610 46675595
Choroidal effusion 37.03 17.35 9 5848 425 46679780
Aggression 36.58 17.35 27 5830 22717 46657488
Hypotony of eye 34.55 17.35 7 5850 141 46680064
Choroidal detachment 33.03 17.35 7 5850 177 46680028
Corneal oedema 32.95 17.35 11 5846 1635 46678570
Psychiatric decompensation 28.56 17.35 9 5848 1114 46679091
Persecutory delusion 28.22 17.35 11 5846 2544 46677661
Iridocyclitis 27.11 17.35 10 5847 1990 46678215
Myasthenic syndrome 26.19 17.35 6 5851 219 46679986
Glaucoma 25.82 17.35 19 5838 15902 46664303
Product use in unapproved indication 25.78 17.35 43 5814 90230 46589975
Photophobia 25.05 17.35 18 5839 14526 46665679
Retinopathy haemorrhagic 24.94 17.35 4 5853 19 46680186
Lens dislocation 24.61 17.35 4 5853 21 46680184
Retroperitoneal oedema 24.45 17.35 4 5853 22 46680183
Cerebral venous sinus thrombosis 24.28 17.35 9 5848 1816 46678389
CSF pressure increased 23.65 17.35 5 5852 125 46680080
Visual impairment 23.52 17.35 35 5822 66654 46613551
Ocular pemphigoid 23.50 17.35 4 5853 29 46680176
Sickle cell anaemia with crisis 23.49 17.35 11 5846 3981 46676224
Optic disc haemorrhage 22.54 17.35 4 5853 38 46680167
Ocular surface disease 22.44 17.35 4 5853 39 46680166
Visual field defect 21.84 17.35 12 5845 6071 46674134
Metabolic alkalosis 20.99 17.35 9 5848 2651 46677554
Foetal exposure during pregnancy 20.19 17.35 22 5835 30725 46649480
Vision blurred 20.17 17.35 36 5821 79672 46600533
Conjunctival hyperaemia 20.00 17.35 8 5849 1981 46678224
Acidosis 19.63 17.35 14 5843 11160 46669045
Vitreous disorder 19.58 17.35 4 5853 84 46680121
Drug ineffective 19.39 17.35 148 5709 677690 46002515
Splenomegaly 19.04 17.35 13 5844 9675 46670530
Retinal vascular occlusion 18.60 17.35 5 5852 354 46679851
Diplopia 18.49 17.35 17 5840 19388 46660817
Dropped head syndrome 18.28 17.35 4 5853 118 46680087
Serous retinal detachment 17.91 17.35 4 5853 130 46680075
Single umbilical artery 17.68 17.35 4 5853 138 46680067
Nasal flaring 17.36 17.35 3 5854 24 46680181

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
Intraocular pressure increased 194.13 21.94 53 2928 5067 29944430
Choroidal detachment 125.30 21.94 23 2958 345 29949152
Metabolic acidosis 108.18 21.94 59 2922 37402 29912095
Angle closure glaucoma 103.72 21.94 22 2959 712 29948785
Choroidal effusion 80.36 21.94 14 2967 153 29949344
Toxic epidermal necrolysis 53.75 21.94 29 2952 17911 29931586
Congenital emphysema 49.30 21.94 6 2975 0 29949497
Glaucoma 44.22 21.94 18 2963 5890 29943607
Visual acuity reduced 40.29 21.94 23 2958 15823 29933674
Hyphaema 39.66 21.94 9 2972 399 29949098
Ocular surface disease 39.65 21.94 7 2974 83 29949414
Idiopathic intracranial hypertension 36.55 21.94 9 2972 569 29948928
Open angle glaucoma 32.85 21.94 7 2974 231 29949266
Anterior chamber disorder 31.00 21.94 6 2975 121 29949376
Hypochloraemia 30.80 21.94 8 2973 627 29948870
Photocoagulation 26.43 21.94 4 2977 16 29949481
Acidosis hyperchloraemic 26.06 21.94 6 2975 284 29949213
Hypocapnia 25.82 21.94 5 2976 101 29949396
Trabeculectomy 25.23 21.94 4 2977 23 29949474
Corneal oedema 25.06 21.94 8 2973 1304 29948193
Dysmetria 24.68 21.94 6 2975 359 29949138
Intracranial pressure increased 23.96 21.94 10 2971 3480 29946017
Hypercapnia 23.08 21.94 10 2971 3814 29945683
Visual acuity tests abnormal 22.04 21.94 4 2977 56 29949441
Corneal opacity 21.94 21.94 6 2975 573 29948924

Pharmacologic Action:

SourceCodeDescription
ATC S01EC01 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Carbonic anhydrase inhibitors
FDA CS M0020790 Sulfonamides
FDA MoA N0000000235 Carbonic Anhydrase Inhibitors
FDA EPC N0000175517 Carbonic Anhydrase Inhibitor
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
CHEBI has role CHEBI:23018 carbonate dehydratase inhibitor
CHEBI has role CHEBI:35498 diuretics
CHEBI has role CHEBI:35623 antiepileptic

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
Idiopathic intracranial hypertension off-label use 68267002 DOID:11459
Benign intracranial hypertension off-label use 68267002 DOID:11459
Familial hypokalemic periodic paralysis off-label use 82732003 DOID:14452
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
Hydrocephalus due to Intraventricular Hemorrhage off-label use
Mixed Epilepsy 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
O3FX965V0I UNII
4017898 VUID
N0000146250 NUI
D00218 KEGG_DRUG
1424-27-7 SECONDARY_CAS_RN
C0000981 UMLSCUI
CHEBI:27690 CHEBI
AZM PDB_CHEM_ID
CHEMBL20 ChEMBL_ID
CHEMBL1200814 ChEMBL_ID
1986 PUBCHEM_CID
DB00819 DRUGBANK_ID
D000086 MESH_DESCRIPTOR_UI
481 INN_ID
6792 IUPHAR_LIGAND_ID
167 RXNORM
2596 MMSL
4121 MMSL
814 MMSL
d00161 MMSL
002286 NDDF
002287 NDDF
33664007 SNOMEDCT_US
372709008 SNOMEDCT_US
72469007 SNOMEDCT_US
4017898 VANDF
4017899 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 0143-9503 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS ANDA 20 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 0527-1050 TABLET 250 mg ORAL ANDA 19 sections
acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 0904-6663 TABLET 250 mg ORAL ANDA 18 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 10135-567 TABLET 250 mg ORAL ANDA 18 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 18 sections
acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 23155-288 TABLET 250 mg ORAL ANDA 18 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 23155-787 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 12 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 29033-030 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 22 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 39822-0190 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS ANDA 13 sections
acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 42291-089 TABLET 125 mg ORAL ANDA 18 sections
acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 42291-090 TABLET 250 mg ORAL ANDA 18 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 42291-103 TABLET 250 mg ORAL ANDA 19 sections
ACETAZOLAMIDE EXTENDED-RELEASE HUMAN PRESCRIPTION DRUG LABEL 1 42571-243 CAPSULE 500 mg ORAL ANDA 21 sections
Acetazolamide Human Prescription Drug Label 1 46708-349 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 21 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 50090-3003 TABLET 250 mg ORAL ANDA 19 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 50090-3003 TABLET 250 mg ORAL ANDA 19 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 18 sections
Acetazolamide Human Prescription Drug Label 1 50090-5217 TABLET 125 mg ORAL ANDA 18 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 50268-054 TABLET 250 mg ORAL ANDA 17 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 50742-233 CAPSULE, EXTENDED RELEASE 500 mg ORAL ANDA 18 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 51672-4022 TABLET 125 mg ORAL ANDA 20 sections
Acetazolamide HUMAN PRESCRIPTION DRUG LABEL 1 51672-4023 TABLET 250 mg ORAL ANDA 20 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 51991-884 TABLET 125 mg ORAL ANDA 20 sections
AcetaZOLAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 51991-885 TABLET 250 mg ORAL ANDA 20 sections
ACETAZOLAMIDE Human Prescription Drug Label 1 52817-200 TABLET 125 mg ORAL ANDA 18 sections
ACETAZOLAMIDE Human Prescription Drug Label 1 52817-201 TABLET 250 mg ORAL ANDA 18 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 20 sections