Identification

Name
Diclofenamide
Accession Number
DB01144  (APRD00131, DB07948)
Type
Small Molecule
Groups
Approved
Description

A carbonic anhydrase inhibitor that is used in the treatment of glaucoma. [PubChem]

Structure
Thumb
Synonyms
  • 1,3-disulfamoyl-4,5-dichlorobenzene
  • 1,3-Disulfamyl-4,5-dichlorobenzene
  • 3,4-Dichloro-5-sulfamylbenzenesulfonamide
  • 4,5-Dichloro-1,3-benzenedisulfonamide
  • 4,5-dichloro-1,3-disulfamoylbenzene
  • 4,5-Dichloro-benzene-1,3-disulfonic acid diamide
  • 4,5-dichloro-m-benzenedisulfonamide
  • 4,5-DICHLOROBENZENE-1,3-disulfonamide
  • Dichlofenamide
  • Dichlorophenamide
  • Dichlorphenamide
  • Diclofenamida
  • Diclofenamide
  • Diclofenamidum
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DaranideTablet50 mg/1OralTaro Pharmaceuticals U.S.A., Inc.2012-03-16Not applicableUs
KeveyisTablet50 mg/1OralTaro Pharmaceuticals U.S.A., Inc.2015-08-07Not applicableUs
KeveyisTablet50 mg/1OralStrongbridge Us Inc.2015-08-07Not applicableUs
International/Other Brands
Oratrol (Alcon)
Categories
UNII
VVJ6673MHY
CAS number
120-97-8
Weight
Average: 305.159
Monoisotopic: 303.914603484
Chemical Formula
C6H6Cl2N2O4S2
InChI Key
GJQPMPFPNINLKP-UHFFFAOYSA-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)
IUPAC Name
4,5-dichlorobenzene-1,3-disulfonamide
SMILES
NS(=O)(=O)C1=CC(=C(Cl)C(Cl)=C1)S(N)(=O)=O

Pharmacology

Indication

For adjunctive treatment of: chronic simple (open-angle) glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where delay of surgery is desired in order to lower intraocular pressure

Structured Indications
Pharmacodynamics

Dichlorphenamide is an oral carbonic anhydrase inhibitor indicated for adjunctive treatment of: chronic simple (open-angle) glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where delay of surgery is desired in order to lower intraocular pressure. Carbonic anhydrase inhibitors reduce intraocular pressure by partially suppressing the secretion of aqueous humor (inflow).

Mechanism of action

Carbonic anhydrase inhibitors reduce intraocular pressure by partially suppressing the secretion of aqueous humor (inflow), although the mechanism by which they do this is not fully understood. Evidence suggests that HCO3- ions are produced in the ciliary body by hydration of carbon dioxide under the influence of carbonic anhydrase and diffuse into the posterior chamber which contains more Na+ and HCO3- ions than does plasma and consequently is hypertonic. Water is then attracted to the posterior chamber by osmosis, resulting in a drop in pressure.

TargetActionsOrganism
ACarbonic anhydrase 1
inhibitor
Human
ACarbonic anhydrase 2
inhibitor
Human
ACarbonic anhydrase 4
inhibitor
Human
ACarbonic anhydrase 7
inhibitor
Human
UCarbonic anhydrase 3
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

55%

Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamineDiclofenamide may decrease the excretion rate of 2,5-Dimethoxy-4-ethylamphetamine which could result in a higher serum level.Experimental, Illicit
3,4-MethylenedioxyamphetamineDiclofenamide may decrease the excretion rate of 3,4-Methylenedioxyamphetamine which could result in a higher serum level.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamineDiclofenamide may decrease the excretion rate of 4-Bromo-2,5-dimethoxyamphetamine which could result in a higher serum level.Experimental, Illicit
AcebutololThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Acebutolol.Approved
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Diclofenamide.Approved, Vet Approved
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Diclofenamide.Approved, Vet Approved
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Diclofenamide.Approved
AliskirenThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Aliskiren.Approved, Investigational
AloxiprinThe risk or severity of adverse effects can be increased when Aloxiprin is combined with Diclofenamide.Experimental
AmifostineThe risk or severity of adverse effects can be increased when Amifostine is combined with Diclofenamide.Approved, Investigational
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Diclofenamide.Approved
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Diclofenamide.Approved
AmiodaroneThe risk or severity of adverse effects can be increased when Amiodarone is combined with Diclofenamide.Approved, Investigational
AmlodipineThe risk or severity of adverse effects can be increased when Amlodipine is combined with Diclofenamide.Approved
AmobarbitalAmobarbital may increase the hypotensive activities of Diclofenamide.Approved, Illicit
AmphetamineDiclofenamide may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved, Illicit
Amphotericin BThe risk or severity of adverse effects can be increased when Amphotericin B is combined with Diclofenamide.Approved, Investigational
Amyl NitriteThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Amyl Nitrite.Approved
ApomorphineThe risk or severity of adverse effects can be increased when Apomorphine is combined with Diclofenamide.Approved, Investigational
ApraclonidineThe risk or severity of adverse effects can be increased when Apraclonidine is combined with Diclofenamide.Approved
AripiprazoleAripiprazole may increase the hypotensive activities of Diclofenamide.Approved, Investigational
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Diclofenamide.Approved, Investigational
Arsenic trioxideThe risk or severity of adverse effects can be increased when Arsenic trioxide is combined with Diclofenamide.Approved, Investigational
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Diclofenamide.Approved
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Azilsartan medoxomil.Approved
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Diclofenamide.Approved, Investigational
BarbexacloneBarbexaclone may increase the hypotensive activities of Diclofenamide.Experimental
BarbitalBarbital may increase the hypotensive activities of Diclofenamide.Illicit
BarnidipineThe risk or severity of adverse effects can be increased when Barnidipine is combined with Diclofenamide.Approved
BenazeprilThe risk or severity of adverse effects can be increased when Benazepril is combined with Diclofenamide.Approved, Investigational
BendroflumethiazideThe risk or severity of adverse effects can be increased when Bendroflumethiazide is combined with Diclofenamide.Approved
BenzphetamineDiclofenamide may decrease the excretion rate of Benzphetamine which could result in a higher serum level.Approved, Illicit
BepridilThe risk or severity of adverse effects can be increased when Bepridil is combined with Diclofenamide.Approved, Withdrawn
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Diclofenamide.Approved
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Diclofenamide.Approved
BortezomibThe risk or severity of adverse effects can be increased when Bortezomib is combined with Diclofenamide.Approved, Investigational
BretyliumThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Bretylium.Approved
BrimonidineThe risk or severity of adverse effects can be increased when Brimonidine is combined with Diclofenamide.Approved
BrinzolamideThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Brinzolamide.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Diclofenamide.Approved, Investigational
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Diclofenamide.Approved
BupivacaineThe risk or severity of adverse effects can be increased when Bupivacaine is combined with Diclofenamide.Approved, Investigational
CanagliflozinThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Canagliflozin.Approved
Candesartan cilexetilThe risk or severity of adverse effects can be increased when Candesartan is combined with Diclofenamide.Approved
CaptoprilThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Captopril.Approved
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Diclofenamide.Approved, Investigational
Carbaspirin calciumThe risk or severity of adverse effects can be increased when Carbaspirin calcium is combined with Diclofenamide.Experimental, Investigational
CarbetocinThe risk or severity of adverse effects can be increased when Carbetocin is combined with Diclofenamide.Approved
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Diclofenamide.Approved
CarvedilolThe risk or severity of adverse effects can be increased when Carvedilol is combined with Diclofenamide.Approved, Investigational
ChlorothiazideThe risk or severity of adverse effects can be increased when Chlorothiazide is combined with Diclofenamide.Approved, Vet Approved
ChlorphentermineDiclofenamide may decrease the excretion rate of Chlorphentermine which could result in a higher serum level.Illicit, Withdrawn
ChlorpromazineThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Diclofenamide.Approved, Vet Approved
ChlorthalidoneThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Diclofenamide.Approved
CilazaprilThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Cilazapril.Approved
CilnidipineThe risk or severity of adverse effects can be increased when Cilnidipine is combined with Diclofenamide.Approved, Investigational
ClevidipineThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Clevidipine.Approved
ClofarabineThe risk or severity of adverse effects can be increased when Clofarabine is combined with Diclofenamide.Approved, Investigational
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Diclofenamide.Approved, Vet Approved
ClonidineThe risk or severity of adverse effects can be increased when Clonidine is combined with Diclofenamide.Approved
ClozapineThe risk or severity of adverse effects can be increased when Clozapine is combined with Diclofenamide.Approved
ConivaptanThe risk or severity of adverse effects can be increased when Conivaptan is combined with Diclofenamide.Approved, Investigational
DapagliflozinThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Dapagliflozin.Approved
dersalazineThe risk or severity of adverse effects can be increased when dersalazine is combined with Diclofenamide.Investigational
DesfluraneThe risk or severity of adverse effects can be increased when Desflurane is combined with Diclofenamide.Approved
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Diclofenamide.Approved, Investigational
DexmedetomidineThe risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Diclofenamide.Approved, Vet Approved
DextroamphetamineDiclofenamide may decrease the excretion rate of Dextroamphetamine which could result in a higher serum level.Approved, Illicit
DiethylpropionDiclofenamide may decrease the excretion rate of Diethylpropion which could result in a higher serum level.Approved, Illicit
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Diclofenamide.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Diltiazem is combined with Diclofenamide.Approved
DinutuximabThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Dinutuximab.Approved
DipyridamoleThe risk or severity of adverse effects can be increased when Dipyridamole is combined with Diclofenamide.Approved
DorzolamideThe risk or severity of adverse effects can be increased when Dorzolamide is combined with Diclofenamide.Approved
DoxazosinThe risk or severity of adverse effects can be increased when Doxazosin is combined with Diclofenamide.Approved
DuloxetineDiclofenamide may increase the orthostatic hypotensive activities of Duloxetine.Approved
EfonidipineThe risk or severity of adverse effects can be increased when Efonidipine is combined with Diclofenamide.Approved
EmpagliflozinThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Empagliflozin.Approved
EnalaprilThe risk or severity of adverse effects can be increased when Enalapril is combined with Diclofenamide.Approved, Vet Approved
EnalaprilatThe risk or severity of adverse effects can be increased when Enalaprilat is combined with Diclofenamide.Approved
EplerenoneThe risk or severity of adverse effects can be increased when Eplerenone is combined with Diclofenamide.Approved
EpoprostenolThe risk or severity of adverse effects can be increased when Epoprostenol is combined with Diclofenamide.Approved
EprosartanThe risk or severity of adverse effects can be increased when Eprosartan is combined with Diclofenamide.Approved
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Diclofenamide.Approved
Etacrynic acidThe risk or severity of adverse effects can be increased when Etacrynic acid is combined with Diclofenamide.Approved
EthoxzolamideThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Ethoxzolamide.Withdrawn
FelodipineThe risk or severity of adverse effects can be increased when Felodipine is combined with Diclofenamide.Approved, Investigational
FenoldopamThe risk or severity of adverse effects can be increased when Fenoldopam is combined with Diclofenamide.Approved
FimasartanThe risk or severity of adverse effects can be increased when Fimasartan is combined with Diclofenamide.Approved, Investigational
FlecainideThe serum concentration of Flecainide can be increased when it is combined with Diclofenamide.Approved, Withdrawn
FosinoprilThe risk or severity of adverse effects can be increased when Fosinopril is combined with Diclofenamide.Approved
FosphenytoinThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Fosphenytoin.Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Diclofenamide.Approved, Vet Approved
GepefrineDiclofenamide may decrease the excretion rate of Gepefrine which could result in a higher serum level.Experimental
GuacetisalThe risk or severity of adverse effects can be increased when Guacetisal is combined with Diclofenamide.Experimental
GuanfacineThe risk or severity of adverse effects can be increased when Guanfacine is combined with Diclofenamide.Approved, Investigational
HalothaneThe risk or severity of adverse effects can be increased when Halothane is combined with Diclofenamide.Approved, Vet Approved
Hemoglobin crosfumarilThe risk or severity of adverse effects can be increased when Hemoglobin crosfumaril is combined with Diclofenamide.Experimental
HexobarbitalHexobarbital may increase the hypotensive activities of Diclofenamide.Approved
HydralazineThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Hydralazine.Approved
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Hydrochlorothiazide is combined with Diclofenamide.Approved, Vet Approved
HydroflumethiazideThe risk or severity of adverse effects can be increased when Hydroflumethiazide is combined with Diclofenamide.Approved, Investigational
HydroxyamphetamineDiclofenamide may decrease the excretion rate of Hydroxyamphetamine which could result in a higher serum level.Approved
IloprostThe risk or severity of adverse effects can be increased when Iloprost is combined with Diclofenamide.Approved, Investigational
ImidaprilThe risk or severity of adverse effects can be increased when Imidapril is combined with Diclofenamide.Investigational
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Diclofenamide.Approved
IndapamideThe risk or severity of adverse effects can be increased when Indapamide is combined with Diclofenamide.Approved
IndoraminThe risk or severity of adverse effects can be increased when Indoramin is combined with Diclofenamide.Withdrawn
Iofetamine I-123Diclofenamide may decrease the excretion rate of Iofetamine I-123 which could result in a higher serum level.Approved
IrbesartanThe risk or severity of adverse effects can be increased when Irbesartan is combined with Diclofenamide.Approved, Investigational
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Diclofenamide.Approved
IsofluraneThe risk or severity of adverse effects can be increased when Isoflurane is combined with Diclofenamide.Approved, Vet Approved
Isosorbide DinitrateThe risk or severity of adverse effects can be increased when Isosorbide Dinitrate is combined with Diclofenamide.Approved
Isosorbide MononitrateThe risk or severity of adverse effects can be increased when Isosorbide Mononitrate is combined with Diclofenamide.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Isoxsuprine.Approved, Withdrawn
IsradipineThe risk or severity of adverse effects can be increased when Isradipine is combined with Diclofenamide.Approved
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Diclofenamide.Approved
LacidipineThe risk or severity of adverse effects can be increased when Lacidipine is combined with Diclofenamide.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Lercanidipine is combined with Diclofenamide.Approved, Investigational
LevobunololThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Levobunolol.Approved
LevobupivacaineThe risk or severity of adverse effects can be increased when Levobupivacaine is combined with Diclofenamide.Approved, Investigational
LevodopaDiclofenamide may increase the orthostatic hypotensive activities of Levodopa.Approved
LevosimendanThe risk or severity of adverse effects can be increased when Levosimendan is combined with Diclofenamide.Approved, Investigational
LisdexamfetamineDiclofenamide may decrease the excretion rate of Lisdexamfetamine which could result in a higher serum level.Approved, Investigational
LisinoprilThe risk or severity of adverse effects can be increased when Lisinopril is combined with Diclofenamide.Approved, Investigational
LithiumThe serum concentration of Lithium can be decreased when it is combined with Diclofenamide.Approved
LofexidineThe risk or severity of adverse effects can be increased when Lofexidine is combined with Diclofenamide.Approved, Investigational
LosartanThe risk or severity of adverse effects can be increased when Losartan is combined with Diclofenamide.Approved
MannitolThe risk or severity of adverse effects can be increased when Mannitol is combined with Diclofenamide.Approved, Investigational
MecamylamineThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Mecamylamine.Approved
MemantineDiclofenamide may decrease the excretion rate of Memantine which could result in a higher serum level.Approved, Investigational
MephedroneDiclofenamide may decrease the excretion rate of Mephedrone which could result in a higher serum level.Investigational
MephentermineDiclofenamide may decrease the excretion rate of Mephentermine which could result in a higher serum level.Approved
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Diclofenamide.Approved
MetforminThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Metformin.Approved
MethamphetamineDiclofenamide may decrease the excretion rate of Methamphetamine which could result in a higher serum level.Approved, Illicit
MethenamineThe therapeutic efficacy of Methenamine can be decreased when used in combination with Diclofenamide.Approved, Vet Approved
MethohexitalMethohexital may increase the hypotensive activities of Diclofenamide.Approved
MethoxyphenamineDiclofenamide may decrease the excretion rate of Methoxyphenamine which could result in a higher serum level.Experimental
MethyclothiazideThe risk or severity of adverse effects can be increased when Methyclothiazide is combined with Diclofenamide.Approved
MethyldopaThe risk or severity of adverse effects can be increased when Methyldopa is combined with Diclofenamide.Approved
MethylphenobarbitalMethylphenobarbital may increase the hypotensive activities of Diclofenamide.Approved
MetipranololThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Metipranolol.Approved
MetolazoneThe risk or severity of adverse effects can be increased when Metolazone is combined with Diclofenamide.Approved
MetoprololThe risk or severity of adverse effects can be increased when Metoprolol is combined with Diclofenamide.Approved, Investigational
MidomafetamineDiclofenamide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Experimental, Illicit, Investigational
MinoxidilThe risk or severity of adverse effects can be increased when Minoxidil is combined with Diclofenamide.Approved
MMDADiclofenamide may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental, Illicit
MoexiprilThe risk or severity of adverse effects can be increased when Moexipril is combined with Diclofenamide.Approved
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Diclofenamide.Approved, Investigational
MoxonidineThe risk or severity of adverse effects can be increased when Moxonidine is combined with Diclofenamide.Approved, Investigational
NabiloneThe risk or severity of adverse effects can be increased when Nabilone is combined with Diclofenamide.Approved, Investigational
NadololThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Nadolol.Approved
NebivololThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Nebivolol.Approved, Investigational
NesiritideThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Nesiritide.Approved, Investigational
NicardipineThe risk or severity of adverse effects can be increased when Nicardipine is combined with Diclofenamide.Approved
NicorandilNicorandil may increase the hypotensive activities of Diclofenamide.Approved, Investigational
NifedipineThe risk or severity of adverse effects can be increased when Nifedipine is combined with Diclofenamide.Approved
NilvadipineThe risk or severity of adverse effects can be increased when Nilvadipine is combined with Diclofenamide.Approved, Investigational
NimodipineThe risk or severity of adverse effects can be increased when Nimodipine is combined with Diclofenamide.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Nisoldipine is combined with Diclofenamide.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Nitrendipine is combined with Diclofenamide.Approved, Investigational
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Diclofenamide.Approved
NitroaspirinThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with Diclofenamide.Investigational
NitroglycerinThe risk or severity of adverse effects can be increased when Nitroglycerin is combined with Diclofenamide.Approved, Investigational
NitroprussideThe risk or severity of adverse effects can be increased when Nitroprusside is combined with Diclofenamide.Approved
ObinutuzumabThe risk or severity of adverse effects can be increased when Obinutuzumab is combined with Diclofenamide.Approved
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Diclofenamide.Approved, Investigational
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Diclofenamide.Approved
OxprenololThe risk or severity of adverse effects can be increased when Oxprenolol is combined with Diclofenamide.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Diclofenamide.Approved, Vet Approved
PapaverineThe risk or severity of adverse effects can be increased when Papaverine is combined with Diclofenamide.Approved
PenbutololThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Penbutolol.Approved, Investigational
PentobarbitalPentobarbital may increase the hypotensive activities of Diclofenamide.Approved, Vet Approved
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Diclofenamide.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Diclofenamide.Approved
PhenobarbitalPhenobarbital may increase the hypotensive activities of Diclofenamide.Approved
PhenoxybenzamineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Diclofenamide.Approved
PhentermineDiclofenamide may decrease the excretion rate of Phentermine which could result in a higher serum level.Approved, Illicit
PhentolamineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Diclofenamide.Approved
PhenytoinThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Phenytoin.Approved, Vet Approved
PindololThe risk or severity of adverse effects can be increased when Pindolol is combined with Diclofenamide.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Pipamperone is combined with Diclofenamide.Approved, Investigational
PramipexoleThe risk or severity of adverse effects can be increased when Pramipexole is combined with Diclofenamide.Approved, Investigational
PrazosinThe risk or severity of adverse effects can be increased when Prazosin is combined with Diclofenamide.Approved
PrimidoneThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Primidone.Approved, Vet Approved
PropofolThe risk or severity of adverse effects can be increased when Propofol is combined with Diclofenamide.Approved, Investigational, Vet Approved
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Diclofenamide.Approved, Investigational
PseudoephedrineDiclofenamide may decrease the excretion rate of Pseudoephedrine which could result in a higher serum level.Approved
QuetiapineThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Quetiapine.Approved
QuinaprilThe risk or severity of adverse effects can be increased when Quinapril is combined with Diclofenamide.Approved, Investigational
QuinidineDiclofenamide may decrease the excretion rate of Quinidine which could result in a higher serum level.Approved
RamiprilThe risk or severity of adverse effects can be increased when Ramipril is combined with Diclofenamide.Approved
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Diclofenamide.Approved
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Diclofenamide.Approved
ReserpineThe risk or severity of adverse effects can be increased when Reserpine is combined with Diclofenamide.Approved, Investigational
RiociguatThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Riociguat.Approved
RisperidoneDiclofenamide may increase the hypotensive activities of Risperidone.Approved, Investigational
RitobegronDiclofenamide may decrease the excretion rate of Ritobegron which could result in a higher serum level.Investigational
RopiniroleThe risk or severity of adverse effects can be increased when Ropinirole is combined with Diclofenamide.Approved, Investigational
RopivacaineThe risk or severity of adverse effects can be increased when Ropivacaine is combined with Diclofenamide.Approved
RotigotineThe risk or severity of adverse effects can be increased when Rotigotine is combined with Diclofenamide.Approved
SacubitrilThe risk or severity of adverse effects can be increased when Sacubitril is combined with Diclofenamide.Approved
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Diclofenamide.Approved, Vet Approved
SecobarbitalSecobarbital may increase the hypotensive activities of Diclofenamide.Approved, Vet Approved
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Diclofenamide.Approved, Investigational, Vet Approved
SevofluraneThe risk or severity of adverse effects can be increased when Sevoflurane is combined with Diclofenamide.Approved, Vet Approved
Sodium NitriteThe risk or severity of adverse effects can be increased when Sodium Nitrite is combined with Diclofenamide.Approved
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Diclofenamide.Approved
SpironolactoneThe risk or severity of adverse effects can be increased when Spironolactone is combined with Diclofenamide.Approved
StreptokinaseThe risk or severity of adverse effects can be increased when Streptokinase is combined with Diclofenamide.Approved, Investigational
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Diclofenamide.Approved, Investigational
TamsulosinThe risk or severity of adverse effects can be increased when Tamsulosin is combined with Diclofenamide.Approved, Investigational
TelmisartanThe risk or severity of adverse effects can be increased when Telmisartan is combined with Diclofenamide.Approved, Investigational
TerazosinThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Terazosin.Approved
ThalidomideThe risk or severity of adverse effects can be increased when Thalidomide is combined with Diclofenamide.Approved, Investigational, Withdrawn
ThiamylalThiamylal may increase the hypotensive activities of Diclofenamide.Approved, Vet Approved
ThiopentalThiopental may increase the hypotensive activities of Diclofenamide.Approved, Vet Approved
ThioridazineThe risk or severity of adverse effects can be increased when Thioridazine is combined with Diclofenamide.Approved, Withdrawn
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Diclofenamide.Approved
TizanidineThe risk or severity of adverse effects can be increased when Tizanidine is combined with Diclofenamide.Approved
TolazolineThe risk or severity of adverse effects can be increased when Tolazoline is combined with Diclofenamide.Approved, Vet Approved
TolcaponeThe risk or severity of adverse effects can be increased when Tolcapone is combined with Diclofenamide.Approved, Withdrawn
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Diclofenamide.Approved
TrandolaprilThe risk or severity of adverse effects can be increased when Trandolapril is combined with Diclofenamide.Approved
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Diclofenamide.Approved
TretinoinThe risk or severity of adverse effects can be increased when Tretinoin is combined with Diclofenamide.Approved, Investigational, Nutraceutical
TriamtereneThe risk or severity of adverse effects can be increased when Triamterene is combined with Diclofenamide.Approved
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Diclofenamide.Approved, Investigational
VerapamilThe risk or severity of adverse effects can be increased when Verapamil is combined with Diclofenamide.Approved
Food Interactions
Not Available

References

Synthesis Reference

Schultz,E.M.; U.S.Patent 2,835,702; May 20, 1958; assigned to Merck & Co.,Inc.

General References
  1. Tawil R, McDermott MP, Brown R Jr, Shapiro BC, Ptacek LJ, McManis PG, Dalakas MC, Spector SA, Mendell JR, Hahn AF, Griggs RC: Randomized trials of dichlorphenamide in the periodic paralyses. Working Group on Periodic Paralysis. Ann Neurol. 2000 Jan;47(1):46-53. [PubMed:10632100]
  2. Okada S, Izumi W, Murai M, Komatsu H, Ishimitsu S: [Diclofenamide Reference Standard (Control 891) of National Institute of Hygienic Sciences]. Eisei Shikenjo Hokoku. 1991;(109):148-50. [PubMed:1364383]
External Links
Human Metabolome Database
HMDB15275
KEGG Drug
D00518
KEGG Compound
C07459
PubChem Compound
3038
PubChem Substance
46505039
ChemSpider
2930
BindingDB
10883
ChEBI
101085
ChEMBL
CHEMBL17
Therapeutic Targets Database
DAP000601
PharmGKB
PA164745512
HET
I7A
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Dichlorphenamide
ATC Codes
S01EC02 — DiclofenamideG01AE10 — Combinations of sulfonamides
PDB Entries
2pou

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentHypokalemic Periodic Paralysis / Paralysis, Hyperkalemic Periodic1
3CompletedTreatmentHypokalemic Periodic Paralysis / Paralysis, Hyperkalemic Periodic / Paramyotonia Congenita1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral50 mg/1
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)228.5Schultz,E.M.; U.S.Patent 2,835,702; May 20, 1958; assigned to Merck & Co.,Inc.
logP0.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.398 mg/mLALOGPS
logP0.92ALOGPS
logP0.39ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.98 m3·mol-1ChemAxon
Polarizability25.04 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9913
Blood Brain Barrier+0.8167
Caco-2 permeable-0.54
P-glycoprotein substrateNon-substrate0.8835
P-glycoprotein inhibitor INon-inhibitor0.9593
P-glycoprotein inhibitor IINon-inhibitor0.9922
Renal organic cation transporterNon-inhibitor0.9254
CYP450 2C9 substrateNon-substrate0.8101
CYP450 2D6 substrateNon-substrate0.9085
CYP450 3A4 substrateNon-substrate0.7198
CYP450 1A2 substrateNon-inhibitor0.9044
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.957
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9691
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8017
Ames testNon AMES toxic0.7954
CarcinogenicityNon-carcinogens0.7986
BiodegradationNot ready biodegradable0.9872
Rat acute toxicity2.1828 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9697
hERG inhibition (predictor II)Non-inhibitor0.9558
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Benzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Dichlorobenzenes / Organosulfonamides / Aryl chlorides / Aminosulfonyl compounds / Organochlorides / Organic oxides / Organic nitrogen compounds / Hydrocarbon derivatives
Substituents
Benzenesulfonamide / Benzenesulfonyl group / 1,2-dichlorobenzene / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Organosulfonic acid amide / Aminosulfonyl compound / Sulfonyl
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
sulfonamide, dichlorobenzene (CHEBI:101085)

Targets

Details
1. Carbonic anhydrase 1
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name
CA1
Uniprot ID
P00915
Uniprot Name
Carbonic anhydrase 1
Molecular Weight
28870.0 Da
References
  1. Winum JY, Casini A, Mincione F, Starnotti M, Montero JL, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits. Bioorg Med Chem Lett. 2004 Jan 5;14(1):225-9. [PubMed:14684332]
  2. Lindskog S: Structure and mechanism of carbonic anhydrase. Pharmacol Ther. 1997;74(1):1-20. [PubMed:9336012]
  3. Nishimori I, Minakuchi T, Onishi S, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. J Med Chem. 2007 Jan 25;50(2):381-8. [PubMed:17228881]
  4. Giacomotto J, Pertl C, Borrel C, Walter MC, Bulst S, Johnsen B, Baillie DL, Lochmuller H, Thirion C, Segalat L: Evaluation of the therapeutic potential of carbonic anhydrase inhibitors in two animal models of dystrophin deficient muscular dystrophy. Hum Mol Genet. 2009 Nov 1;18(21):4089-101. doi: 10.1093/hmg/ddp358. Epub 2009 Jul 31. [PubMed:19648295]
  5. Cleland JC, Griggs RC: Treatment of neuromuscular channelopathies: current concepts and future prospects. Neurotherapeutics. 2008 Oct;5(4):607-12. doi: 10.1016/j.nurt.2008.09.001. [PubMed:19019313]
Details
2. Carbonic anhydrase 2
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 Da
References
  1. Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [PubMed:18336310]
Details
3. Carbonic anhydrase 4
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina an...
Gene Name
CA4
Uniprot ID
P22748
Uniprot Name
Carbonic anhydrase 4
Molecular Weight
35032.075 Da
References
  1. Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [PubMed:18336310]
Details
4. Carbonic anhydrase 7
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide.
Gene Name
CA7
Uniprot ID
P43166
Uniprot Name
Carbonic anhydrase 7
Molecular Weight
29658.235 Da
References
  1. Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [PubMed:18336310]
Details
5. Carbonic anhydrase 3
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide.
Gene Name
CA3
Uniprot ID
P07451
Uniprot Name
Carbonic anhydrase 3
Molecular Weight
29557.215 Da
References
  1. Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25. [PubMed:17826101]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 02:56