Basic information
- Standard SMILES
NS(=O)(=O)c1cc(Cl)c(Cl)c(S(N)(=O)=O)c1- InChIKey
GJQPMPFPNINLKP-UHFFFAOYSA-N- Molecular formula
- C6H6Cl2N2O4S2
- Average molar mass
- 305.2 g/mol
- Monoisotopic mass
- 303.91460403
Overview
Dichlorphenamide can cause developmental toxicity according to state or federal government labeling requirements.
Names & identifiers
- Preferred name
- Dichlorphenamide
- IUPAC
- 4,5-dichlorobenzene-1,3-disulfonamide
- English name
- Dichlorphenamide
- Molecular formula
- C6H6Cl2N2O4S2
- Molecular weight
- 305.16
Names & synonyms
Show more names
Database identifiers
- CAS
120-97-8- PubChem CID
- 3038
- DTXSID
DTXSID1022922- ChEMBL
CHEMBL17- ChEBI
CHEBI:101085- UNII
- VVJ6673MHY
- EC Number
- 204-440-6
- Nikkaji
- J8.589H
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 137 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 452
Experimental & physicochemical properties
LogP
0.2
0.92
Color/Form
NEEDLES FROM DIMETHYLSULFOXIDE + WATER
WHITE OR NEARLY WHITE, CRYSTALLINE POWDER
Solubility
PRACTICALLY INSOL IN WATER; SOL IN ALKALINE SOLN
FREELY SOL IN PYRIDINE & IN 1 N NAOH; SOL IN ALCOHOL; SOL IN 2 N SODIUM CARBONATE; SLIGHTLY SOL IN ETHER
3.98e-01 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Melting Point
239-241 °C
228.7 °C
Physicochemical properties
- Melting point
- 239 · 239-241° (patent, mp 228.5-229°)
- Boiling point
- 590.5 · 590.5±60.0 °C(Predicted)
- Density
- 1.7263 · 1.7263 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Acetonitrile (Slightly), Chloroform, DMSO (Slightly), Methanol
- form
- Solid
- pka
- 7.4 · pKa 7.4 (Uncertain);8.6 (Uncertain)
- color
- White to Off-White
- Major Application
- pharmaceutical (small molecule)
- 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
- SMILES
- C1(S(N)(=O)=O)=CC(Cl)=C(Cl)C(S(N)(=O)=O)=C1
- CAS DataBase Reference
- 120 · 120-97-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6673 MHY · VVJ6673MHY
- Proposition 65 List
- Dichlorphenamide
- ATC code
- 1 EC02 · S01EC02
- NIST Chemistry Reference
- 4 · 4,5-Dichloro-m-benzenedisulfonamide(120-97-8)
- EPA Substance Registry System
- 1 · 1,3-Benzenedisulfonamide, 4,5-dichloro- (120-97-8)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 361 · H361
- Precautionary statements
- 201 · P201-P202-P281-P308+P313-P405-P501
- Hazard Codes
- Xn
- Risk Statements
- 63 · 63
- Safety Statements
- 36 · 36
- WGK Germany
- 3 · WGK 3
- RTECS
- 9200000 · CZ9200000
- HS Code
- 2935904000 · 2935904000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazardous Substances Data
- 120 · 120-97-8(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P264, P264+P265, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Hazard Traits - Developmental Toxicity
1,3-Benzenedisulfonamide, 4,5-dichloro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Toxicology
Human Toxicity Excerpts
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.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Dichlorphenamide
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- WGK 3
- rtecs
- CZ9200000
- hs_code
- 2935904000
- risk_code
- 63
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H361
- Precautionary statements
- P201-P202-P281-P308+P313-P405-P501
- Hazardous Substances Data
- 120-97-8(Hazardous Substances Data)
Chemistry & industry
Pharmacology
ATC Code
S - Sensory organs
QS - Sensory organs
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 HCO<sup>3-</sup> 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<sup>+</sup> and HCO<sup>3-</sup> 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.
FDA Pharmacological Classification
VVJ6673MHY
DICHLORPHENAMIDE
Established Pharmacologic Class [EPC] - Carbonic Anhydrase Inhibitor
Mechanisms of Action [MoA] - Carbonic Anhydrase Inhibitors
Chemical Structure [CS] - Sulfonamides
Dichlorphenamide is a Carbonic Anhydrase Inhibitor. The mechanism of action of dichlorphenamide is as a Carbonic Anhydrase Inhibitor.
Uses & manufacturing
Applications
UsesLike the drugs described above, dichlorphenamide is used for secreting excess water in cases of elevated intraocular pressure, and it is used for treating wide-angle and secondary glaucoma as well as in cases where it is necessary to lower intraocular pressure before surgical intervention in severe wide-angle glaucoma.
UsesDiclofenamide 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).
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: 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.
Related reactions
Linked notes
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