Dichlorphenamide
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Dichlorphenamide
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CAS No:
120-97-8
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Formula:
C6H6Cl2N2O4S2
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Chemical Name:
Dichlorphenamide
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Synonyms:
1,3-Benzenedisulfonamide,4,5-dichloro-;m-Benzenedisulfonamide,4,5-dichloro-;4,5-Dichloro-1,3-benzenedisulfonamide;Daranide;Dichlofenamide;4,5-Dichloro-m-benzenedisulfonamide;4,5-Dichloro-1,3-disulfamoylbenzene;Dichlorophenamide;3,4-Dichloro-5-sulfamylbenzenesulfonamide;Dichlorphenamide;Oratrol;1,3-Disulfamyl-4,5-dichlorobenzene;Antidrasi;1,3-Disulfamoyl-4,5-dichlorobenzene;Daramide;Diclofenamid;Glaucol;Diclofenamide;CB 8000;Keveyis;179044-03-2
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CAS No:
Description
Off-White SolidChEBI: A sulfonamide that is benzene-1,3-disulfonamide in which the hydrogens at positions 4 and 5 are substituted by chlorine. An oral carbonic anhydrase inhibitor, it partially suppresses the secretion (inflow) of aqueous humor in the eye and so reduces intraoc lar pressure. It is used for the treatment of glaucoma.
Solid
Diclofenamide is a sulfonamide that is benzene-1,3-disulfonamide in which the hydrogens at positions 4 and 5 are substituted by chlorine. An oral carbonic anhydrase inhibitor, it partially suppresses the secretion (inflow) of aqueous humor in the eye and so reduces intraocular pressure. It is used for the treatment of glaucoma. It has a role as an EC 4.2.1.1 (carbonic anhydrase) inhibitor, an antiglaucoma drug and an ophthalmology drug. It is a sulfonamide and a dichlorobenzene.|A carbonic anhydrase inhibitor that is used in the treatment of glaucoma.|Dichlorphenamide is a Carbonic Anhydrase Inhibitor. The mechanism of action of dichlorphenamide is as a Carbonic Anhydrase Inhibitor.
Dichlorphenamide Basic Attributes
305.16
305.16
204-440-6
VVJ6673MHY
DTXSID1022922
NEEDLES FROM DIMETHYLSULFOXIDE + WATER|WHITE OR NEARLY WHITE, CRYSTALLINE POWDER
S - Sensory organs
2935904000
Characteristics
137
0.3
Solid
1.7263 (rough estimate)
239-241 °C
590.5±60.0 °C(Predicted)
310.9±32.9 °C
1.6000 (estimate)
3.98e-01 g/L
0.0079mmHg at 25°C
SLIGHT CHARACTERISTIC ODOR
PKA: 7.4, KA: 8.6
Safety Information
NONH for all modes of transport
63
36
CZ9200000
Xn
|Warning|H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Drug Information
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|...USED IN TREATMENT OF PRIMARY GLAUCOMA, ACUTE PHASE OF SECONDARY GLAUCOMA, & IN PREOPERATIVE CONTROL OF INTRAOCULAR TENSION. ... ALTHOUGH IT HAS DIURETIC PROPERTIES, IT IS NOT PROMOTED FOR THIS PURPOSE.|...DRUG HAS BEEN FOUND TO INHIBIT EPILEPTIC SEIZURES & TO DECR RATE OF SPINAL FLUID FORMATION. /ACETAZOLAMIDE/|...REDUCES RATE OF AQ HUMOR FORMATION; INTRAOCULAR PRESSURE IN PT WITH GLAUCOMA IS CORRESPONDINGLY REDUCED. THIS ACTION OF DRUG APPEARS TO BE INDEPENDENT OF SYSTEMIC ACID-BASE BALANCE. /ACETAZOLAMIDE/|For more Therapeutic Uses (Complete) data for DICHLORPHENAMIDE (11 total), please visit the HSDB record page.
IT HAS BEEN SUGGESTED THAT POSTOPERATIVE USE /AFTER IRIDECTOMY/...MAY ADVERSELY AFFECT OUTCOME OF FILTERING OPERATIONS BY REDUCING SIZE OF RESULTANT DRAINAGE BLEB & DELAYING REFORMATION OF ANTERIOR CHAMBER. /CARBONIC ANHYDRASE INHIBITORS/|...SHOULD BE USED CAUTIOUSLY IN PT WITH OBSTRUCTIVE PULMONARY DISEASE BECAUSE THEY MAY PPT ACUTE RESPIRATORY FAILURE. /CARBONIC ANHYDRASE INHIBITORS/|DIURESIS MAY BE TROUBLESOME INITIALLY BUT SUBSIDES DURING CONTINUED THERAPY BECAUSE OF PERSISTENT METABOLIC ACIDOSIS. /CARBONIC ANHYDRASE INHIBITORS/|...BE GIVEN CAUTIOUSLY TO PT...WITH DISEASES ASSOC WITH INCR MINERALOCORTICOID ACTIVITY (EG, PRIMARY HYPERALDOSTERONISM, CUSHING'S SYNDROME) & THOSE RECEIVING POTASSIUM-WASTING DRUGS (EG, THIAZIDES, LOOP DIURETICS, CORTICOSTEROIDS). /CARBONIC ANHYDRASE INHIBITORS/|For more Drug Warnings (Complete) data for DICHLORPHENAMIDE (7 total), please visit the HSDB record page.
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).
A class of compounds that reduces the secretion of H+ ions by the proximal kidney tubule through inhibition of CARBONIC ANHYDRASES. (See all compounds classified as Carbonic Anhydrase Inhibitors.)
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.|PHOSPHATURIA MAY BE RELATED TO DIRECT STIMULATION...OF CYCLIC ADENOSINE 3',5'-MONOPHOSPHATE...PRODN BY KIDNEY. ...DRUG ACTS SIMILARLY TO PARATHYROID HORMONE IN ENHANCING URINARY EXCRETION OF PHOSPHATE & CYCLIC AMP, IN CONTRAST TO ITS ANTAGONISM OF ACTION OF HORMONE ON BONE. /ACETAZOLAMIDE/|...INHIBITION OF...CARBONIC ANHYDRASE. ...IS NONCOMPETITIVE. ...ENZYME IS NORMALLY PRESENT IN TISSUES IN HUGE EXCESS. MORE THAN 99% OF ENZYME ACTIVITY IN KIDNEY MUST BE INHIBITED BEFORE PHYSIOLOGICAL EFFECTS BECOME APPARENT. ENZYME...IS DOMINANT TISSUE COMPONENT TO WHICH INHIBITORS BECOME BOUND. /ACETAZOLAMIDE/|/CHANGES IN URINE/...MAY BE ATTRIBUTED TO INHIBITION OF (+)H SECRETION BY RENAL TUBULE. ... CURRENT EVIDENCE INDICATES GREATER EFFECT ON PROXIMAL THAN ON DISTAL TUBULE, WITH LITTLE OR NO EFFECT ON ASCENDING LIMB. ...PHOSPHATURIA...USED AS INDEX OF LOCALIZING DIURETIC ACTION... /ACETAZOLAMIDE/|...INCR URINARY EXCRETION OF BICARBONATE & FIXED CATION, MOSTLY SODIUM. AS RESULT, CONCN OF BICARBONATE IN EXTRACELLULAR FLUID DECR & METABOLIC ACIDOSIS RESULTS. ...RENAL RESPONSE TO ACETAZOLAMIDE IS GREATLY REDUCED.../BUT/ DIURETIC RESPONSE IS ENHANCED. /ACETAZOLAMIDE/|DRUG LOWERS INTRAOCULAR PRESSURE BY REDUCING RATE OF SECRETION OF AQ HUMOR.
CALCULUS FORMATION & URETERAL COLIC HAVE BEEN ATTRIBUTED TO MARKED REDN IN URINARY CITRATE...ASSOC WITH EITHER NO CHANGE OR EVEN RISE IN URINARY CALCIUM. ...DEPRESSES UPTAKE OF IODINE BY THYROID GLAND. /ACETAZOLAMIDE/|WITH LARGE DOSES, MANY PT EXHIBIT DROWSINESS & PARESTHESIAS. IN HEPATIC CIRRHOSIS, EPISODES OF DISORIENTATION MAY BE INDUCED. ... HYPERSENSITIVITY REACTIONS ARE RELATIVELY RARE. THEY CONSIST IN FEVER, SKIN REACTIONS, BONE-MARROW DEPRESSION, & SULFONAMIDE-LIKE RENAL LESIONS. /CARBONIC ANHYDRASE INHIBITORS/|LESS FREQUENT UNTOWARD REACTIONS INCL FATIGUE, EXCITEMENT, & GI REACTIONS. /CARBONIC ANHYDRASE INHIBITORS/|GI DISTURBANCES...ANOREXIA, NAUSEA, VOMITING, DIARRHEA, WT LOSS, ALTERED TASTE & SMELL, CONSTIPATION, DRYNESS OF MOUTH, EXCESSIVE THIRST...ABDOMINAL DISTENTION...PARESTHESIA...NUMBNESS & TINGLING SENSATION...IN EXTREMITIES, TONGUE, &/OR MUCOCUTANEOUS JUNCTIONS OF LIPS OR ANUS /ADVERSE EFFECT, ORAL/|For more Human Toxicity Excerpts (Complete) data for DICHLORPHENAMIDE (6 total), please visit the HSDB record page.
Daranide
Dichlorphenamide Use and Manufacturing
SCHULTZ, US PATENT 2,835,702 (1958 TO MERCK & CO).
Diclofenamide is a potent carbonic anhydrase inhibitor. Diclofenamide may provide a therapeutic strategy in the inhibition of the human cytosolic isoforms I and II and transmembrane tumor-associated isoenzymes IX and XII. Diclofenamide has been shown to be is effective in the prevention of episodic weakness in both hypokalemic periodic paralysis (HypoPP) and potassium-sensitive periodic paralysis (PSPP).
DICHLORPHENAMIDE, USP (DARANIDE), IS AVAIL AS OFFICIAL 50-MG TABLETS.
GAS LIQUID CHROMATOGRAPHY (3% OV-17 ON 100-120 MESH GAS CHROM Q, COLUMN TEMP 265 DEG) WITH ELECTRON-CAPTURE DETECTION WAS APPLIED TO ASSAY OF DICHLORPHENAMIDE & DEMONSTRATED SENSITIVITY OF 10 NG IN 0.5 ML OF RABBIT SERUM OR WHOLE AQUEOUS HUMOR FROM 1 RABBIT EYE.
Human drugs -> Rare disease (orphan)|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals
Computed Properties
Molecular Weight:305.2
XLogP3:0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:303.9146044
Monoisotopic Mass:303.9146044
Topological Polar Surface Area:137
Heavy Atom Count:16
Complexity:452
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Containing two sulfonamide groups in its molecule, it has a strong carbonic anhydrase inhibitory function. In addition to inhibiting the reabsorption of Na and K, it also increases the discharge of CI-, so the occurrence of metabolic acidosis is slow. The efficacy of 50 mg of this product is equivalent to that of 250 mg of acetazolamide. This product can reduce the amount of aqueous humor produced by 39%, thereby reducing intraocular pressure. It can reduce intraocular pressure in both normal eyes and glaucoma, with an average decrease of 0.32 kPa (2.4 mmHg) in normal eyes and 1.08 kPa (8.1 mmHg) in glaucoma. However, the ease of aqueous humor outflow remains unchanged, that is, this product does not have the function of increasing the discharge of aqueous humor.
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