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Furosemide(CAS No. 54-31-9)

Furosemide C12H11ClN2O5S (cas 54-31-9) Molecular Structure

54-31-9 Structure

Identification and Related Records

【Name】
Furosemide
【Iupac name】
4-chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoic acid
【CAS Registry number】
54-31-9
【Synonyms】
5-(aminosulfonyl)-4-chloro-2-((2-furanylmethyl)amino)benzoic acid
4-chloro-n-furfuryl-5-sulfamoylanthranilic acid
2-furfurylamino-4-chloro-5-sulfamoylbenzoic acid
【EINECS(EC#)】
200-203-6
【Molecular Formula】
C12H11ClN2O5S (Products with the same molecular formula)
【Molecular Weight】
330.74414
【Inchi】
InChI=1S/C12H11ClN2O5S/c13-9-5-10(15-6-7-2-1-3-20-7)8(12(16)17)4-11(9)21(14,18)19/h1-5,15H,6H2,(H,16,17)(H2,14,18,19)
【InChIKey】
ZZUFCTLCJUWOSV-UHFFFAOYSA-N
【Canonical SMILES】
C1=COC(=C1)CNC2=CC(=C(C=C2C(=O)O)S(=O)(=O)N)Cl
【MOL File】
54-31-9.mol

Chemical and Physical Properties

【Appearance】
white powder
【Density】
1.606
【Melting Point】
220℃
【Boiling Point】
582.1 °C at 760 mmHg
【Flash Point】
305.9 °C
【Water】
Slightly soluble in water
【Solubilities】
Slightly soluble in water
【Color/Form】
Crystals from aqueous ethanol
Yellow powder
FINE, WHITE TO SLIGHTLY YELLOW, CRYSTALLINE POWDER
【Stability】
Stable, but light sensitive, air sensitive and hygroscopic. Incompatible with strong oxidizing agents.
【Storage temp】
2-8°C
【Spectral properties】
UV Max (95% ethanol): 288, 276, 336 nm (E(1%)(1 cm): 945, 588, 144); (0.1N NaOH): 226, 273, 336 (E(1%)(1 cm): 1147, 557, 133).
【Computed Properties】
Molecular Weight:330.74414 [g/mol]
Molecular Formula:C12H11ClN2O5S
XLogP3:2
H-Bond Donor:3
H-Bond Acceptor:7
Rotatable Bond Count:5
Tautomer Count:4
Exact Mass:330.00772
MonoIsotopic Mass:330.00772
Topological Polar Surface Area:131
Heavy Atom Count:21
Formal Charge:0
Complexity:481
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:2
Feature 3D Anion Count:1
Feature 3D Cation Count:1
Feature 3D Ring Count:2
Effective Rotor Count:5
Conformer Sampling RMSD:0.8
CID Conformer Count:21

Safety and Handling

【Hazard Codes】
T:Toxic;
【Risk Statements】
R61
【Safety Statements 】
S22;S36/37/39;S53;S45
【Safety】

Hazard Codes of Furosemide (CAS NO.54-31-9): TF
Risk Statements: 61-39/23/24/25-11
61: May cause harm to the unborn child
39/23/24/25: Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed 
11: Highly Flammable
Safety Statements: 7-16-45-53-36/37/39-22
7: Keep container tightly closed 
16: Keep away from sources of ignition - No smoking 
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
53: Avoid exposure - obtain special instruction before use 
36/37/39: Wear suitable protective clothing, gloves and eye/face protection 
22: Do not breathe dust
RIDADR: UN 1230 3/PG 2
WGK Germany: 3
RTECS: CB2625000

【Transport】
UN 1230 3/PG 2
【Formulations/Preparations】
FUROSEMIDE, USP (LASIX), IS AVAILABLE AS 20-, 40- and & 80-MG TABLETS. ... PREPN IS ALSO AVAILABLE FOR PARENTERAL ADMIN, EITHER IV OR IM.
Oral solution, 40 mg/5 ml furosemide solution (with alcohol 0.2% and sorbitol), Roxane; Lasix (with alcohol 11.5%, parabens, and sorbitol), Hoechst-Roussel; Tablets, 20 mg, Lasix, Hoechst-Roussel; 40 mg, Lasix (scored), Hoechst-Roussel; 80 mg, Lasix, Hoechst-Roussel.
Parenteral Injection, 10 mg/ml, Furomide, Hyrex; Lasix (with benzyl alcohol 0.9%), Hoechst-Rousel.
Tablets, 20, 40, and 80 mg. Oral solution, 10 mg/ml. Ampules, vials, and syringes, 10 mg/ml.
Grade: National Formulary grade
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl furosemide, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act.
Furosemide: (a) Each tablet contains 12.5 or 50 mg furosemide. Each tablet contains 2 g furosemide. Each bolus contains 2 g furosemide. Each milliliter of syrup contains 10 mg furosemide. ... (d) Indications for use: In cattle for treatment of physiological parturient edema of the mammary gland and associated sturctures. Limitations: Treatment not to exceed 48 hours post-parturition. Milk taken during treatment and for 48 hours after the last treatment must not be used for food. Cattle must not be slaughtered for food within 48 hours following last treatment. In dogs for treatment of edema (pulmonary congestion, ascites) associated with cardiac insufficiency and acute noninflammatory tissue edema. For treatment of edema (pulmonary congestion, ascites) associated with cardiac insufficiency. In cats for treatment of edema (pulmonary congestion, ascites) associated with cardiac insufficiency and acute noninflammatory tissue edema.
Furosemide: (a) Each milliliter of solution contains 50 mg of furosemide diethanolamine. ... (d) In dogs and cats for treatment of edema (pulmonary congestion, ascites) associated with cardiac insufficiency and acute noninflammatory tissue edema. In horses for treatment of edema (pulmonary congestion, ascites) associated with cardiac insufficiency and acute noninflammatory tissue edema. Do not use in horses intended for food. In cattle for treatment of physiological parturient edema of the mammary gland and associated structures. Treatment not to exceed 48 hours post-parturition. Milk taken during treatment and for 48 hours after the last treatment must not be used for food. Cattle must not be slaughtered for food within 48 hours following last treatment.
【Reactivities and Incompatibilities】
Furosemide is soluble in alkaline soln that is prepared as a mildly buffered alkaline product. It should not be mixed with acidic solns have a pH below 5.5. Furosemide may precipitate if combined with ascorbic acid, epinephrine, norepinephrine, or tetracycline. The acidic pH of aminoglycoside admixtures may cause transient cloudiness or frank precipitation if furosemide is added, depending on which aminoglycoside is used & the concn of the additives. Avoiding the admixture of furosemide & aminoglycosides has been recommended.
Furosemide may precipitate if mixed with milrinone lactate infusions.
【Specification】

 Furosemide may undergo hydrolysis at sufficiently low pH. The pH of aqueous solutions should be maintained in the basic range to prevent hydrolysis. Alcohol has been shown to improve the stability of Furosemide. Incompatible with strong oxidizing agents .

【Octanol/Water Partition Coefficient】
log Kow = 2.03
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

2,4-DICHLOROBENZOIC ACID IS REACTED WITH CHLOROSULFONIC ACID, TREATED WITH AMMONIA, THEN REFLUXED WITH EXCESS FURFURYLAMINE.
2,4-DICHLOROBENZOIC ACID IS HEATED WITH CHLOROSULFONIC ACID & RESULTING 5-CHLOROSULFONYL DERIV IS REACTED WITH CONCN AMMONIA TO CONVERT IT TO 5-SULFAMOYL ANALOG. REFLUXING WITH FURFURYLAMINE ... YIELDS CRUDE FUROSEMIDE WHICH IS RECRYSTALLIZED FROM AQ ETHANOL.
Prepn: K. Sturm et al., DE 1122541; eidem US 3058882 (both 1962 to Hoechst)
Production: 2,4-dichloro-5-sulphamoylbenzoic acid + chlorosulphonic acid + ammonia + furfurylamine (amide formation)
Synthetically from furfural, hydroxyethylhydrazine, and diethyl carbonate
Produced by conversion of 2,4-dichloro-5-sulfamoylbenzoic acid with excess furfurylamine, in the absence of solvent, at 120-130 deg C.
Prepared in 85% yield from 2-fluoro-4-chloro-5-sulfamoylbenzoic acid and furfurylamine at 95 deg C for 2 hr
U.S. Imports

(1976) 1.82X10+3 GRAMS (PRINCPL CUSTMS DISTS)
(1978) 1.25X10+6 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production

(1976) NOT PRODUCED COMMERCIALLY IN US
(1978) NOT PRODUCED COMMERCIALLY IN US
【Usage】
Used as a diuretic

Biomedical Effects and Toxicity

【Biological Activity】
Loop diuretic that inhibits the Na + /2Cl - /K + (NKCC) cotransporter. Also acts as a non-competitive antagonist at GABA A receptors with ~ 100-fold greater selectivity for α 6-containing receptors than α 1-containing receptors.
【Pharmacological Action】
- Agents that promote the excretion of urine through their effects on kidney function.
- Agents that inhibit SODIUM-POTASSIUM-CHLORIDE SYMPORTERS which are concentrated in the thick ascending limb at the junction of the LOOP OF HENLE and KIDNEY TUBULES, DISTAL. They act as DIURETICS. Excess use is associated with HYPOKALEMIA and HYPERGLYCEMIA.
【Therapeutic Uses】
Diuretics, Sulfamyl
Furosemide augments radionucide renography and renal scintigraphy by stimulating the flow of urine and thereby aiding in the differentiation of mechanical obstruction from nonobstructive dilatation in patients with hydroureteronephrosis. /NOT included in US product labeling/
Furosemide /is/ used in the treatment of hypercalcemia. /NOT included in US product labeling/
Furosemide /is/ not considered to be primary agents in the treatment of essential hypertension. However, they may be indicated in combination with other antihypertensives in the treatment of hypertension associated with impaired renal function. In the stepped-care approach to antihypertensive treatment, ... furosemide may be substituted for a thiazide diuretic in patients with renal function impairment. /Included in US product labeling/
Furosemide /is/ indicated in the treatment of mild to moderate hypertension, usually in combination with other antihypertensive agents, and as adjuncts in the treatment of hypertensive crisis. /Included in US product labeling/
Furosemide /is/ especially useful in patients refractory to other diuretics or with existing acid-base disorders, congestive heart failure, or renal disease. /Included in US product labeling/
Furosemide /is/ indicated as adjunct in the treatment of acute pulmonary edema. /Included in US product labeling/
... Furosemide are indicated in the treatment of edema associated with congestive heart failure, hepatic cirrhosis, and renal disease (including nephrotic syndrome). /Included in US product labeling/
... HIGH CEILING ... DIURETICS ... HAVE DISTINCTIVE ACTION ON RENAL TUBULAR FUNCTION. ... (1) PROMPT ONSET OF ACTION, (2) INHIBITION OF SODIUM & CHLORIDE TRANSPORT IN ASCENDING LIMB OF LOOP OF HENLE, & (3) INDEPENDENCE OF THEIR ACTION FROM ACID-BASE BALANCE CHANGES. /HIGH CEILING DIURETICS/
A major use of loop diuretics is in the treatment of acute pulmonary edema. A rapid incr in venous capacitance in conjunction with a brisk natriuresis reduced left ventricular filling pressures & thereby rapidly relieves pulmonary edema. Loop diuretics also are widely used for the treatment of chronic congestive heart failure when diminution of extracellular fluid volume is desirable to minimize venous & pulmonary congestion. Diuretics are widely used for the treatment of hypertension ... . The edema of nephrotic syndrome often is refractory to other classes of diuretics, & loop diuretics often are the only drugs capable of reducing the massive edema associated with this renal disease. Loop diuretics also are employed in the treatment of edema & ascites of liver cirrhosis; however, car must be taken not to induce encephalopathy or hepatorenal syndrome. In patients with a drug overdose, loop diuretics can be used to induce a forced diuresis to facilitate more rapid renal elimination of the offending drug. Loop diuretics- combined with isotonic saline admin to prevent volume depletion- are used to treat hypercalcemia. Loop diuretics interfere with the kidney's ability to produce a concentrated urine. Consequently, loop diuretics combined with hypertonic saline are useful for the treatment of life-threatening hyponatremia. Loop diuretics also are used to treat edema associated with chronic renal insufficiency. /Loop diuretics/
IN SYMPTOMATIC HYPERCALCEMIA HIGH CEILING DIURETICS MAY LOWER PLASMA CALCIUM CONCN BY INCR URINARY EXCRETION. /HIGH CEILING DIURETICS/
PATIENTS WITH SEVERE ANEMIA ... SHOULD RECEIVE LOOP DIURETIC (FUROSEMIDE ...) SEVERAL HR BEFORE BLOOD TRANSFUSION IS BEGUN.
FUROSEMIDE IS INDICATED FOR TREATMENT OF EDEMA ASSOC WITH CONGESTIVE HEART FAILURE, CIRRHOSIS OF LIVER, & RENAL DISEASE, INCL NEPHROTIC SYNDROME. ... IT IS ALSO USEFUL IN MGMNT OF HYPERTENSION.
VET: TO HELP REDUCE MAMMARY EDEMA IN CATTLE; IN LAMINITIS & LOCALIZED CONGESTIVE EDEMAS ("STOCKING UP") OF LIMBS IN HORSES; IN CONGESTIVE CARDIAC EDEMAS, ASCITES, & HYPERTENSIVE SYNDROMES IN DOGS.
Furosemide is useful in the management of edema associated with congestive heart failure. ...
Furosemide may be used orally for the management of hypertension, especially when complicated by congestive heart failure or renal disease.
Furosemide has been used iv alone or with 0.9% sodium chloride injection or sodium sulfate to increase renal excretion of calcium in patients with hypercalcemia.
/It/ is a loop diuretic indicated for the treatment of edema associated with congestive heart failure, cirrhosis of the liver, and renal diseases and hypertension. Is also indicated via intravenous use as adjunctive therapy in acute pulmonary edema.
Treatment of magnesium excess. ... If renal functionis normal, iv furosemide ... may be admin as alternate therapy with replacement of urine volume by 0.90% saline.
Furosemide is one of the most effective & least toxic diuretics used in pediatric practice. Experimental & clinical data suggest that adrenocorticosteroids &/or endogenous ouabain-like substances may play an important role in its diuretic effect. Also, the drug appears to have anti-inflammatory properties. In children with different diseases who received orally or iv 1-2 mg/kg doses of furosemide, a statistically significant positive linear relationship was found between the drug urinary excretion rate & the urine flow rate, but log dose-response curves to the drug were found to vary depending on the disease & the route of the drug admin. No sigmoid-shaped log dose-response curve (ie, one approaching a zero response at very low furosemide urinary excretion rates & a max response at very high excretion rates) was attained, which may suggest that the capacity of the kidney tubules to respond diuretically to the aforementioned doses of furosemide was not exceeded in these patients. However, in infants with different diseases & reasonably normal renal function who required admin of this diuretic, a very steep log dose-response curve to a 1 mg/kg iv dose of furosemide was found, which may suggest that higher doses may not result in a significant incr in diuretic response. The lowest mean furosemide urinary excretion rate & its concn in urine associated with a significant diuresis were found to be 0.58 +/- 0.33 microg/kg/min & 24.2 +/- 10.5 microg/ml, respectively. Also, a significant correlation was found between the amount (in milligrams) of furosemide excreted in the urine during the first 6 hr after admin & the urine volume collected during that time. Patients with cystic fibrosis appeared to have a markedly more pronounced diuretic response to the average oral dose of 0.835 +/- 0.18 mg/kg than that reported in control children given 2 mg/kg. In children with acute renal failure caused by acute gastroenterocolitis or glomerulonephritis, a broad relationship was observed between a single iv dose & diuretic response after admin of furosemide (1.2 to 30.8 mg/kg). It was suggested that the total daily dose of the drug should not exceed 100 mg in these patients. Furosemide was found to be effective in management of bronchoconstriction accompanying chronic lung disease & narrowing of the upper respiratory airways; in hydrocephalus in infancy to avoid cerebrospinal fluid shunts; in some diagnostic procedures, such as an assessment of fetal & neonatal hydronephrosis; & in evaluation of different types of renal tubular acidosis. Among side effects accompanying clinical use of this drug were cholelithiasis in premature infants receiving total parenteral nutrition concomitantly with the diuretic; secondary hyperparathyroidism & bone disease in infants obtaining long-term furosemide treatment; & drug-induced fever.
【Biomedical Effects and Toxicity】
WITH ORAL INGESTION, DIURETIC RESPONSE MAY BE ANTICIPATED WITHIN HR; WITH IV INJECTION, WITHIN 2-10 MIN. ... FUROSEMIDE IS STRONGLY BOUND TO PLASMA PROTEINS. ALTHOUGH URINARY EXCRETION IS ACCOMPLISHED BOTH BY GLOMERULAR FILTRATION & PROXIMAL TUBULAR SECRETION ... ACCOUNTS FOR ... 2/3 OF INGESTED DOSE. REMAINDER ... IN FECES.
The oral bioavailability, plasma half life, & route of elimination of /furosemide are as follows: ~60%, ~1.5 hours, & ~65% renal excretion of intact drug, ~35% metabolism. /from table//. Because furosemide ... /is/ extensively bound to plasma proteins, delivery ... to the tubules by filtration is limited. However, /it is/ efficiently secreted by the organic acid transport system in the proximal tubule & thereby gains access to /its/ binding sites on the Na+_K+_2Cl- symport in the luminal membrane of the thick ascending limb. Probenecid shifts the plasma concn-response curve to furosemide to the right by competitively inhibiting furosemide secretion by the organic acid transport system.
PLACENTAL TRANSFER STUDIED IN 18 PREGNANT WOMEN AFTER ORAL DOSES OF 25-40 MG ON DAY OF DELIVERY. SUBSTANTIAL CONCN OF DRUG DETECTED IN UMBILICAL CORD VEIN PLASMA & AMNIOTIC FLUID. PENETRATES PLACENTAL MEMBRANE & REACHES FETUS. [BEERMANN B ET AL; CLIN PHARMACOL THER 24 (NOV): 560-2 (1978)] PubMed Abstract
In one study in patients with normal renal function, approx 60% of a single 80 mg oral dose of furosemide was absorbed from the Gl tract. When admin to fasting adults in this dosage, the drug appeared in the serum within 10 min, reached a peak concn of 2.3 ug/mL in 60-70 min, & was almost completely cleared from the serum in 4 hr. When the same dose was given after a meal, the serum concn of furosemide increased slowly to a peak of about 1 ug/ml after 2 hr & similar concns were present 4 hr after ingestion. However, a similar diuretic response occurred regardless of whether the drug was given with food or to fasting patients. In another study, the rate & extent of absorption varied considerably when 1 g of furosemide was given orally to uremic patients. An avg of 76% of a dose was absorbed, & peak plasma concns were achieved within 2-9 hr (avg 4.4 hr). Serum concns required to produce max diuresis are not known, & it has been reported that the magnitude of response does not correlate with either the peak or the mean serum concns.
The diuretic effect of orally administered furosemide is apparent within 30 minutes to 1 hr and is maximal in the first or second hour. The duration of action is usually 6-8 hr. The maximum hypotensive effect may not be apparent until several days after furosemide therapy is begun. After iv administration of furosemide, diuresis occurs within 5 min, reaches a maximum within 20-60 min, and persists for approximately 2 hr. After im administration, peak plasma concentrations are attained within 30 min; onset of diuresis occurs somewhat later than after iv administration. In patients with severely impaired renal function, the diuretic response may be prolonged.
Furosemide is approximately 95% bound to plasma proteins in both normal & azotemic patients.
In patients with normal renal function, a small amount of furosemide is metabolized in the liver to the defurfurylated derivative, 4-chloro-5-sulfamoylanthranilic acid. Furosemide & its metabolite are rapidly excreted in urine by glomerular filtration & by secretion from the proximal tubule. In patients with normal renal function, approx 50% of an oral dose & 80% of an iv or im dose are excreted in urine within 24 hr; 69-97% of these amounts is excreted in the first 4 hr. The remainder of the drug is eliminated by nonrenal mechanisms including degradation in the liver & excretion of unchanged drug in the feces. In patients with marked renal impairment without liver disease, nonrenal clearance of furosemide is increased so that up to 98% of the drug is removed from the plasma within 24 hr. One patient with uremia & hepatic cirrhosis eliminated only 58% of an iv dose in 24 hr. Furosemide is not removed by hemodialysis.
It has been claimed that the absorption, & therefore effectiveness, of furosemide will be further diminished in patients with /congestive heart failure/ due to edema of the bowel & decreased splanchnic blood flow. The has been partially refuted by /a study that/ showed an average bioavailability of 61% in CHF patients, the same as in normal patients. However, total absorption in patients with CHF varies widely (34-80%) and there is a delay in both rate of absorption & time to peak urinary excretion for both furosemide & bumetanide.
Not only are there interindividual differences in the rate & extent of absorption, but large intraindividual variability also exists. Ingestion of the same brand of furosemide by the same individual on multiple occasions can show up to a threefold difference in bioavailability. These differences are evident whether considering the innovator's brand (Lasix) or one of several generic brands. One might infer that iv therapy would be the preferred route, giving a better response for any given dose. Surprisingly, this is not always the case. In both normal volunteers & patients with CHF, total daily fluid & electrolyte loss after oral therapy & parenteral therapy are comparable. The major difference is in the time course of response. During the first 2 hr, diuresis from the iv dose far exceeds that from the oral therapy, but by 4-6 hr, the total urinary output is equivalent.
In neonates ... a decreased clearance is seen for drugs that are eliminated by proximal tubular secretion (e.g., furosemide ...).

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 302(SRC), determined from a log Kow of 2.03(2), indicates that furosemide is expected to have moderate mobility in soil(SRC). Volatilization of furosemide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.9X10-16 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Furosemide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.2X10-10 mm Hg(SRC), determined from a fragment constant method(5).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 302(SRC), determined from a log Kow of 2.03(2) and a regression-derived equation(3), indicates that furosemide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.9X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The pKa1 and pKa2 of furosemide are 3.9 and 7.5, respectively(5), indicating that this compound will partially exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(6). According to a classification scheme(7), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), furosemide, which has an estimated vapor pressure of 3.2X10-10 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase furosemide may be removed from the air by wet and dry deposition(SRC).

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