Details of the Drug

General Information of Drug (ID: DMH7IDQ)

Drug Name
Dichlorphenamide
Synonyms
dichlorphenamide; Diclofenamide; 120-97-8; 4,5-dichlorobenzene-1,3-disulfonamide; Dichlofenamide; Dichlorophenamide; Daranide; Dichlorphenamid; Glauconide; Antidrasi; Glaucol; Oratrol; Diclofenamidum; Diclofenamida; Diclofenamid; Barastonin; Glaumid; Glafco; Glajust; 4,5-Dichloro-m-benzenedisulfonamide; 1,3-Benzenedisulfonamide, 4,5-dichloro-; Diclofenamidum [INN-Latin]; 4,5-Dichloro-1,3-disulfamoylbenzene; 1,3-Disulfamoyl-4,5-dichlorobenzene; Diclofenamida [INN-Spanish]; 1,3-Disulfamyl-4,5-dichlorobenzene; Dasanide; Keveyis; Antidrasi; Dichlorphenamide [BAN]; Llorens Brand of Dichlorphenamide; Merck Brand of Dichlorphenamide; CB 8000; I7A; Daranide (TN); Dichlorophenamide (DCP); Dichlorphenamide (USP); Diclofenamide (JP15/INN); 3,4-Dichloro-5-sulfamylbenzenesulfonamide; 4,5-Dichloro-1,3-benzenedisulfonamide; 4,5-Dichloro-benzene-1,3-disulfonic acid diamide; 4,5-DICHLOROBENZENE-1,3-DISULFONAMIDE
Indication
Disease Entry ICD 11 Status REF
Chronic glaucoma 9C61.0Z Approved [1], [2]
Therapeutic Class
Antiglaucomic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 305.2
Topological Polar Surface Area (xlogp) 0.3
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 9.3628 micromolar/kg/day [3]
Chemical Identifiers
Formula
C6H6Cl2N2O4S2
IUPAC Name
4,5-dichlorobenzene-1,3-disulfonamide
Canonical SMILES
C1=C(C=C(C(=C1S(=O)(=O)N)Cl)Cl)S(=O)(=O)N
InChI
InChI=1S/C6H6Cl2N2O4S2/c7-4-1-3(15(9,11)12)2-5(6(4)8)16(10,13)14/h1-2H,(H2,9,11,12)(H2,10,13,14)
InChIKey
GJQPMPFPNINLKP-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3038
ChEBI ID
CHEBI:101085
CAS Number
120-97-8
DrugBank ID
DB01144
TTD ID
D0J4GO
ACDINA ID
D00191

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 [4]
Carbonic anhydrase II (CA-II) TTANPDJ CAH2_HUMAN Inhibitor [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Chronic glaucoma
ICD Disease Classification 9C61.0Z
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
Carbonic anhydrase II (CA-II) DTT CA2 7.95E-08 0.52 0.33
Molecular Expression Atlas (MEA) 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 Dichlorphenamide (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Dronedarone DMA8FS5 Major Increased risk of ventricular arrhythmias by the combination of Dichlorphenamide and Dronedarone. Angina pectoris [BA40] [19]
Levomilnacipran DMV26S8 Moderate Increased risk of hyponatremia by the combination of Dichlorphenamide and Levomilnacipran. Chronic pain [MG30] [20]
Vilazodone DM4LECQ Moderate Increased risk of hyponatremia by the combination of Dichlorphenamide and Vilazodone. Depression [6A70-6A7Z] [20]
Vortioxetine DM6F1PU Moderate Increased risk of hyponatremia by the combination of Dichlorphenamide and Vortioxetine. Depression [6A70-6A7Z] [20]
Milnacipran DMBFE74 Moderate Increased risk of hyponatremia by the combination of Dichlorphenamide and Milnacipran. Depression [6A70-6A7Z] [20]
Escitalopram DMFK9HG Moderate Increased risk of hyponatremia by the combination of Dichlorphenamide and Escitalopram. Depression [6A70-6A7Z] [20]
Desvenlafaxine DMHD4PE Moderate Increased risk of hyponatremia by the combination of Dichlorphenamide and Desvenlafaxine. Depression [6A70-6A7Z] [20]
Eslicarbazepine DMZREFQ Moderate Increased risk of hyponatremia by the combination of Dichlorphenamide and Eslicarbazepine. Epilepsy/seizure [8A61-8A6Z] [21]
Digitoxin DMWVIGP Moderate Increased risk of hypomagnesemia by the combination of Dichlorphenamide and Digitoxin. Heart failure [BD10-BD1Z] [22]
Captopril DM458UM Moderate Additive hypotensive effects by the combination of Dichlorphenamide and Captopril. Hypertension [BA00-BA04] [23]
Arsenic trioxide DM61TA4 Major Increased risk of ventricular arrhythmias by the combination of Dichlorphenamide and Arsenic trioxide. Mature B-cell lymphoma [2A85] [24]
Levomethadyl Acetate DM06HG5 Major Increased risk of ventricular arrhythmias by the combination of Dichlorphenamide and Levomethadyl Acetate. Opioid use disorder [6C43] [25]
Choline salicylate DM8P137 Major Increased risk of metabolic acidosis by the combination of Dichlorphenamide and Choline salicylate. Postoperative inflammation [1A00-CA43] [26]
Salsalate DM13P4C Major Increased plasma concentration of Dichlorphenamide and Salsalate due to competitive binding of plasma proteins. Rheumatoid arthritis [FA20] [26]
⏷ Show the Full List of 14 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
Quinoline yellow WS E00309 24671 Colorant
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Dichlorphenamide 50 mg tablet 50 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: 6807).
2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 011366.
3 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
4 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
5 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
6 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.
7 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).
8 Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5050-3.
9 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.
10 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.
11 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.
12 Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1;14(21):5435-9.
13 Sulfonamide linked neoglycoconjugates--a new class of inhibitors for cancer-associated carbonic anhydrases. J Med Chem. 2010 Apr 8;53(7):2913-26.
14 Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorg Med Chem. 2009 Jul 15;17(14):5054-8.
15 Localization of diuretic effects along the loop of Henle: an in vivo microperfusion study in rats. Clin Sci (Lond). 2000 Apr;98(4):481-8.
16 Selective effect of thiazides on the human osteoblast-like cell line MG-63. Kidney Int. 1996 Nov;50(5):1476-82.
17 Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50.
18 Nature of the inhibition of carbonic anhydrase by acetazolamide and benzthiazide. J Pharmacol Exp Ther. 1961 Mar;131:271-4.
19 Product Information. Multaq (dronedarone). sanofi-aventis , Bridgewater, NJ.
20 Product Information. Savella (milnacipran). Forest Pharmaceuticals, St. Louis, MO.
21 Product Information. Aptiom (eslicarbazepine). Sunovion Pharmaceuticals Inc, Marlborough, MA.
22 Semple P, Tilstone WJ, Lawson DH "Furosemide and urinary digoxin clearance." N Engl J Med 293 (1975): 612-3. [PMID: 902451]
23 Murphy BF, Whitworth JA, Kincaid-Smith P "Renal insufficiency with combinations of angiotensin converting enzyme inhibitors and diuretics." Br Med J 288 (1984): 844-5. [PMID: 6322905]
24 Ohnishi K, Yoshida H, Shigeno K, et al. "Prolongation of the QT interval and ventricular tachycardia in patients treated with arsenic trioxide for acute promyelocytic leukemia." Ann Intern Med 133 (2000): 881-5. [PMID: 11103058]
25 Cohen J "Long-term efficacy and safety of terazosin alone and in combination with other antihypertensive agents." Am Heart J 122 (1991): 919-25. [PMID: 1678923]
26 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]