Details of the Drug

General Information of Drug (ID: DM1AF5U)

Drug Name

Acetazolamide

Synonyms

Acetadiazol; Acetamidothiadiazolesulfonamide; Acetamox; Acetazolam; Acetazolamid; Acetazolamida; Acetazolamidum; Acetazolamine; Acetazoleamide; Acetozalamide; AkZol; ApoAcetazolamide; Atenezol; Cidamex; Dazamide; Defiltran; Dehydratin; Diacarb; Diakarb; Diamox; Didoc; Diluran; Diuramid; Diuramide; Diuriwas; Diutazol; Donmox; Duiramid; Edemox; Eumicton; Fonurit; Glauconox; Glaumox; Glaupax; Glupax; HumaZolamide; Natrionex; Nephramid; Nephramide; Phonurit; Storzolamide; Vetamox; Acetazolamide Apotex Brand; Acetazolamide Chiesi Brand; Acetazolamide Dioptic Brand; Acetazolamide Grin Brand; Acetazolamide ICN Brand; Acetazolamide Jumer Brand; Acetazolamide Llorens Brand; Acetazolamide Medphano Brand; Acetazolamide Novopharm Brand; Acetazolamide Orion Brand; Acetazolamide Wassermann Brand; Ak Zol; Apo Acetazolamide; Apotex Brand of Acetazolamide; Chiesi Brand of Acetazolamide; Ciba Vision Brand of Acetazolamide; DiamoxSequels; Dioptic Brand of Acetazolamide; Grin Brand of Acetazolamide; Huma Zolamide; ICN Brand of Acetazolamide; Jumer Brand of Acetazolamide; Llorens Brand of Acetazolamide; Medphano Brand of Acetazolamide; Monosodium Salt Acetazolamide; Novopharm Brand of Acetazolamide; Orion Brand of Acetazolamide; Storz Brand of Acetazolamide Preparation; Wassermann Brand of Acetazolamide; Wyeth Brand of Acetazolamide Preparation; A 6011; Carbonic anhydrase inhibitor 6063; Acetazolamida [INN-Spanish]; Acetazolamide (AAZ); Acetazolamide, Monosodium Salt; Acetazolamidum [INN-Latin]; Ak-Zol; Apo-Acetazolamide; Carbonic Anhydrase Inhibitor No. 6063; Diamox (TN); Diureticum-holzinger; Huma-Zolamide; SK-acetazolamide; Acetazolamide Sodium, (Sterile); Acetazolamide [INN:BAN:JAN]; Acetazolamide (JP15/USP/INN); 4-Diamox

Indication

Disease Entry	ICD 11	Status	REF
Glaucoma/ocular hypertension	9C61	Approved	[1], [2]

Therapeutic Class

Anticonvulsants

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

222.3

Topological Polar Surface Area (xlogp)

-0.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [3]
Bioavailability: 99% of drug becomes completely available to its intended biological destination(s) [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 0.65 mL/min/kg [5]
Elimination: 90% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 3 - 9 hours [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 75.14216 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.04% [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.37 L/kg [5]
Water Solubility: The ability of drug to dissolve in water is measured as 0.64 mg/mL [3]

Chemical Identifiers

Formula: C4H6N4O3S2
IUPAC Name: N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide
Canonical SMILES: CC(=O)NC1=NN=C(S1)S(=O)(=O)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)
InChIKey: BZKPWHYZMXOIDC-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 1986
ChEBI ID: CHEBI:27690
CAS Number: 59-66-5
DrugBank ID: DB00819
TTD ID: D0E1SW
VARIDT ID: DR00606
ACDINA ID: D00010

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Carbonic anhydrase I (CA-I)	TTHQPL7	CAH1_HUMAN	Modulator	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Glaucoma/ocular hypertension

ICD Disease Classification

9C61

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Carbonic anhydrase I (CA-I)	DTT	CA1	5.23E-14	-0.11	-0.41

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Acetazolamide (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Dronedarone	DMA8FS5	Major	Increased risk of ventricular arrhythmias by the combination of Acetazolamide and Dronedarone.	Angina pectoris [BA40]	[15]
Desipramine	DMT2FDC	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Acetazolamide caused by Desipramine mediated altered urine pH.	Attention deficit hyperactivity disorder [6A05]	[16]
Levomilnacipran	DMV26S8	Moderate	Increased risk of hyponatremia by the combination of Acetazolamide and Levomilnacipran.	Chronic pain [MG30]	[17]
Sertraline	DM0FB1J	Moderate	Increased risk of hyponatremia by the combination of Acetazolamide and Sertraline.	Depression [6A70-6A7Z]	[17]
Vilazodone	DM4LECQ	Moderate	Increased risk of hyponatremia by the combination of Acetazolamide and Vilazodone.	Depression [6A70-6A7Z]	[17]
Vortioxetine	DM6F1PU	Moderate	Increased risk of hyponatremia by the combination of Acetazolamide and Vortioxetine.	Depression [6A70-6A7Z]	[17]
Milnacipran	DMBFE74	Moderate	Increased risk of hyponatremia by the combination of Acetazolamide and Milnacipran.	Depression [6A70-6A7Z]	[17]
Escitalopram	DMFK9HG	Moderate	Increased risk of hyponatremia by the combination of Acetazolamide and Escitalopram.	Depression [6A70-6A7Z]	[17]
Desvenlafaxine	DMHD4PE	Moderate	Increased risk of hyponatremia by the combination of Acetazolamide and Desvenlafaxine.	Depression [6A70-6A7Z]	[17]
Clomipramine	DMINRKW	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Acetazolamide caused by Clomipramine mediated altered urine pH.	Depression [6A70-6A7Z]	[16]
Doxepin	DMPI98T	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Acetazolamide caused by Doxepin mediated altered urine pH.	Depression [6A70-6A7Z]	[16]
Eslicarbazepine	DMZREFQ	Moderate	Increased risk of hyponatremia by the combination of Acetazolamide and Eslicarbazepine.	Epilepsy/seizure [8A61-8A6Z]	[18]
Digitoxin	DMWVIGP	Moderate	Increased risk of hypomagnesemia by the combination of Acetazolamide and Digitoxin.	Heart failure [BD10-BD1Z]	[19]
Captopril	DM458UM	Moderate	Additive hypotensive effects by the combination of Acetazolamide and Captopril.	Hypertension [BA00-BA04]	[20]
Quinapril	DMR8H31	Moderate	Additive hypotensive effects by the combination of Acetazolamide and Quinapril.	Hypertension [BA00-BA04]	[20]
Hydroxychloroquine	DMSIVND	Moderate	Antagonize the effect of Acetazolamide when combined with Hydroxychloroquine.	Malaria [1F40-1F45]	[21]
Arsenic trioxide	DM61TA4	Major	Increased risk of ventricular arrhythmias by the combination of Acetazolamide and Arsenic trioxide.	Mature B-cell lymphoma [2A85]	[22]
Sibutramine	DMFJTDI	Moderate	Increased risk of hyponatremia by the combination of Acetazolamide and Sibutramine.	Obesity [5B80-5B81]	[17]
Levomethadyl Acetate	DM06HG5	Major	Increased risk of ventricular arrhythmias by the combination of Acetazolamide and Levomethadyl Acetate.	Opioid use disorder [6C43]	[23]
Aspirin	DM672AH	Major	Increased plasma concentration of Acetazolamide and Aspirin due to competitive binding of plasma proteins.	Pain [MG30-MG3Z]	[24]
Choline salicylate	DM8P137	Major	Increased plasma concentration of Acetazolamide and Choline salicylate due to competitive binding of plasma proteins.	Postoperative inflammation [1A00-CA43]	[25]
Salsalate	DM13P4C	Major	Increased plasma concentration of Acetazolamide and Salsalate due to competitive binding of plasma proteins.	Rheumatoid arthritis [FA20]	[25]
Paliperidone	DM7NPJS	Moderate	Increased risk of ventricular arrhythmias by the combination of Acetazolamide and Paliperidone.	Schizophrenia [6A20]	[21]
Trifluoperazine	DMKBYWI	Moderate	Increased risk of ventricular arrhythmias by the combination of Acetazolamide and Trifluoperazine.	Schizophrenia [6A20]	[21]
Amisulpride	DMSJVAM	Moderate	Increased risk of ventricular arrhythmias by the combination of Acetazolamide and Amisulpride.	Schizophrenia [6A20]	[21]
Pimozide	DMW83TP	Major	Increased risk of ventricular arrhythmias by the combination of Acetazolamide and Pimozide.	Schizophrenia [6A20]	[26]
Salicyclic acid	DM2F8XZ	Major	Increased plasma concentration of Acetazolamide and Salicyclic acid due to competitive binding of plasma proteins.	Seborrhoeic dermatitis [EA81]	[24]
Amiodarone	DMUTEX3	Major	Increased risk of ventricular arrhythmias by the combination of Acetazolamide and Amiodarone.	Ventricular tachyarrhythmia [BC71]	[27]
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⏷ Show the Full List of 28 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
D&C red no. 28	E00491	6097185	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Oleic acid	E00421	445639	Emulsifying agent; Penetration agent; Solubilizing agent
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Ammonia	E00007	222	Alkalizing agent
Calcium stearate	E00244	15324	lubricant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Gelatin	E00630	Not Available	Other agent
Glycerin	E00026	753	Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Medium-chain triglyceride	E00640	Not Available	Emollient; Lubricant; Surfactant
Potassium hydroxide	E00233	14797	Alkalizing agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Propylene glycol distearate	E00395	110800	Emollient; Opacifying agent; Surfactant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent
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⏷ Show the Full List of 25 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Acetazolamide 500 mg capsule	500 mg	12 HR Extended Release Oral Capsule	Oral
Acetazolamide 125 mg tablet	125 mg	Oral Tablet	Oral
Acetazolamide 250 mg tablet	250 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6792).
2	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 040195.
3	BDDCS applied to over 900 drugs
4	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
8	Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8.
9	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 2597).
10	Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5050-3.
11	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-2164.
12	Understanding the Dual Inhibition of COX-2 and Carbonic Anhydrase-II by Celecoxib and CG100649 Using Density Functional Theory Calculations and other Molecular Modelling Approaches. Protein Pept Lett. 2015;22(10):903-12.
13	Carbonic anhydrase inhibitors. Interaction of the antitumor sulfamate EMD 486019 with twelve mammalian carbonic anhydrase isoforms: Kinetic and X-r... Bioorg Med Chem Lett. 2008 Aug 1;18(15):4282-6.
14	Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1;14(21):5435-9.
15	Product Information. Multaq (dronedarone). sanofi-aventis , Bridgewater, NJ.
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17	Product Information. Savella (milnacipran). Forest Pharmaceuticals, St. Louis, MO.
18	Product Information. Aptiom (eslicarbazepine). Sunovion Pharmaceuticals Inc, Marlborough, MA.
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24	Cowan RA, Hartnell GG, Lowdell CP, Baird IM, Leak AM "Metabolic acidosis induced by carbonic anhydrase inhibitors and salicylates in patients with normal renal function." Br Med J (Clin Res Ed) 289 (1984): 347-8. [PMID: 6432091]
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26	Product Information. Orap Tablets (pimozide). Gate Pharmaceuticals, Sellersville, PA.
27	Antonelli D, Atar S, Freedberg NA, Rosenfeld T "Torsade de pointes in patients on chronic amiodarone treatment: contributing factors and drug interactions." Isr Med Assoc J 7 (2005): 163-5. [PMID: 15792261]