Fosinopril sodium
Hypotensive drug- Product Name
- Fosinopril sodium
- CAS No.
- 88889-14-9
- Chemical Name
- Fosinopril sodium
- Synonyms
- MONOPRIL;DYNACIL;ELIDIUR;FOSINORM;Acecor-d5;Staril-d5;TENSOZIDE;Eosinopril;SQ 28555-d5;Secorvas-d5
- CBNumber
- CB5110597
- Molecular Formula
- C30H46NNaO7P
- Formula Weight
- 586.65
- MOL File
- 88889-14-9.mol
Fosinopril sodium Property
- Melting point:
- 196-198°C
- storage temp.
- Inert atmosphere,Store in freezer, under -20°C
- solubility
- H2O: >20mg/mL
- form
- powder
- color
- white to off-white
- CAS DataBase Reference
- 88889-14-9(CAS DataBase Reference)
Safety
- WGK Germany
- 3
- HS Code
- 2933995300
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H319Causes serious eye irritation
- Precautionary statements
-
P202Do not handle until all safety precautions have been read and understood.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P308+P313IF exposed or concerned: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- F1308
- Product name
- Fosinopril sodium
- Purity
- ≥98% (HPLC), powder
- Packaging
- 5mg
- Price
- $129
- Updated
- 2024/03/01
- Product number
- PHR3356
- Product name
- Fosinopril sodium
- Purity
- certified reference material, pharmaceutical secondary standard
- Packaging
- 500MG
- Price
- $253
- Updated
- 2024/03/01
- Product number
- BP1091
- Product name
- Fosinopril sodium
- Purity
- British Pharmacopoeia (BP) Reference Standard
- Packaging
- 100MG
- Price
- $257
- Updated
- 2024/03/01
- Product number
- 1283404
- Product name
- Fosinopril sodium
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 200mg
- Price
- $174.4
- Updated
- 2024/03/01
- Product number
- H37120
- Product name
- Fosinopril (sodium)
- Purity
- 98%
- Packaging
- 250mg
- Price
- $202
- Updated
- 2023/06/20
Fosinopril sodium Chemical Properties,Usage,Production
Hypotensive drug
Fosinopril sodium is a unique novel angiotensin converting enzyme inhibitor containing phosphono,it is a sodium of fosinopril , belonging to lowering blood pressure drugs in the cardiovascular system drugs , it is originally and successfully developed by the US Bristol-Myers Squibb company , the trade name is Monopril, it was first listed in the UK in 1991, followed by a number of countries including the United States and European countries,it is used for the treatment of hypertension ,and for treatment of heart failure in combination with a diuretic. Fosinopril is a prodrug, after oral absorption,it is hydrolyzed in the gastrointestinal tract and liver to become a diacids complex complex, fosinopril sodium which has pharmacological activity and to play its role. It can competitively bind with ACE active ligand zinc ion , blocking angiotensin Ⅰ becoming into angiotensin Ⅱ, so that the blood vessels are dilate, aldosterone secretion is decreased, and blood pressure is decreased. Its ACE inhibition strength is similar to enalapril. Hypertension patients are treated with fosinopril ,the drug plays its role one hour after administration ,after 2 to 6 hours .it is up to maximum antihypertensive effect, it can hold effect for 24 hours, 1 times/day administration. Fosinopril can reduce peripheral vascular resistance, so that systemic vascular resistance is decreased, the cardiovascular output, left ventricular ejection fraction and left ventricular filling increase, thereby cardiac function is improved . The product also allows renal blood flow, glomerular filtration, plasma volume maintained or improved, renal vascular resistance is decreased, it does not affect cerebral blood flow. Oral bioavailability 36%, the concentration of blood Fosinoprilat reaches the peak 3 hours after the administration, t1/2 is 11.5 hours, and for hypertension associated with reduced renal function patients, when they take the drug, there is compensatory increase in hepatic metabolism, and when hypertension associated reduced liver function, renal function increases the elimination of the drug, due to the elimination of this compensatory mechanism, fosinopril treatment for high blood pressure,when it comes to that liver and kidney function is reduced, it is generally not necessary to adjust the dosage. First treatment of hypertension with the drug is an oral dose of 10mg/times, 1 time/day, general therapeutic dose range is 20~40mg/d. It can"in a lasting time and stably decrease blood pressure to protect heart and kidney , the dual elimination of kidney and liver is safer" because fosinopril sodium-does not have free thiol group, clinically, skin rashes and other allergic reactions caused by mercapto are less generated,it is the based medication for hypertension combined crown heart disease and chronic heart failure patients, it is also the preferred treatment of hypertension and diabetes patients , it is suitable for all strong indications of high blood pressure. Especially for the elderly and patients with liver and kidney dysfunction, the use of the product is more safe and convenient.
The above information is edited by the chemicalbook of Tian Ye.
Description
Fosinopril sodium, an ester prodrug of fosinoprilat, is the first of a new generation of phosphinic acid ACE inhibitors indicated for the once-daily treatment of hypertension. Unlike captopril and lisinopril, it is reportedly effective in increasing the left ventricular peak filling rates and peak ejection rates in hypertensive patients at rest. Another advantage is that fosinopril sodium is metabolized equally by renal and hepatic routes, thereby avoiding the requirement to modify dosage in patients with renal insufficiency.
Chemical Properties
White to Off-White Crystalline Solid
Originator
Bristol-Myers Squibb (U.S.A.)
Uses
A phosphinic acid containing angiotensin converting enzyme (ACE) inhibitor. Antihypertensive.
Uses
A labelled phosphinic acid containing angiotensin converting enzyme (ACE) inhibitor.
Uses
Fosinopril sodium is the ester prodrug of an angiotensin-converting enzyme (ACE) inhibitor, used for the treatment of hypertension and some types of chronic heart failure.
Definition
ChEBI: The sodium salt of fosinopril. It is used for the treatment of hypertension and heart failure. A pro-drug, its phosphinate ester group is hydrolysed in vivo to give the corresponding phosphininc acid, fosinoprilat, which is the active metaboli e.
Manufacturing Process
To a solution of 4-phenylbutyl phosphinic acid (2.0 g, 0.01 mole) in
chloroform (40 ml) was added triethylamine (3.2 ml, 0.022 mole) and the
mixture was cooled in an ice bath to 0°C. Trimethylsilyl chloride (2.8 ml,
0.022 mole) was added to the above solution dropwise, followed by benzyl
bromoacetate (1.6 ml, 0.011 mole). The ice bath was removed and the
mixture stirred at room temperature for 5 hours and poured into 10%
aqueous HCl (30 ml) and crushed ice (20 g). After shaking the mixture in a
separatory funnel, the chloroform layer was separated and the aqueous layer
was extracted with dichloromethane. The combined organic phase was washed
with brine, dried over anhydrous sodium sulfate and the solvents removed in
vacuum. The resulting crude thick oil (3.5 g) was dissolved in 30 ml ether,
hexane was added dropwise to get a turbid solution and the mixture was left
at room temperature overnight to complete the crystallization. It was cooled
in the freezer for 2 hours, filtered and the solid was washed very thoroughly
with hexane (50 ml), ether (50 ml) and again hexane (50 ml), ether (50 ml)
in that order. The solid was vacuum dried to get 2.48 g (71%) of [hydroxy-(4-phenylbutyl)-phosphinyl]acetic acid, phenylmethyl ester, m.p. 68-70°C. TLC
(Silica gel, CH2Cl2:MeOH:HOAc (20:1:1)) shows a single spot.
A solution of 50 g (0.14 mole) of [hydroxy-(4-phenylbutyl)-phosphinyl]acetic
acid, phenylmethyl ester in 300 ml of dry CHCl3 was treated with 28.6 g (0.28
mole) of Et3N, 35.6 g (0.21 mole) of 1-chloroisobutyl propionate, 12.0 g
(0.035 mole) of (n-Bu)4NHSO4 and 5.3 g (0.035 mole) of NaI. The above
mixture was stirred and heated to mild reflux for 20 hours, then cooled and
the solvent evaporated in vacuo. The oil residue was dissolved in 150 ml of
ether and washed with 150 ml of water. The aqueous wash was extracted with
150 ml of ether. The combined ether solutions were washed with 5% NaHCO3,
10% NaHSO3 and brine. After drying (MgSO4) the ether was evaporated in
vacuo to give 57.0 g (83%) of crude [[2-methyl-1-(1-oxopropoxy)propoxy](4-
phenylbutyl)phosphinyl]acetic acid, phenyl methyl ester as an oil product.
A solution of 57.0 g (0.12 mole) of [[2-methyl-1-(1-oxopropoxy)propoxy](4-
phenylbutyl)phosphinyl]acetic acid, phenyl methyl ester in 300 ml of ethyl
acetate was treated with 3.0 g of 10% Pd/C and hydrogenated on the Parr
apparatus (45 psi) for 4 hours. The mixture was filtered through Hyflo and the
solution was extracted with 5% NaHCO3. The aqueous extracts were washed
with ether, cooled to 5°C and treated with 36 ml of HOAc. The product was
extracted into ethyl acetate, dried (MgSO4) and the solvent was evaporated in
vacuo. The residue was dissolved in 300 ml of toluene and the solvent was
evaporated in vacuo to remove last traces of acetic acid. The oil residue
became semi-solid on standing at room temperature. The yield of the product
of debenzoylation - 2-[carboxymethyl)-(4-phenylbutyl)-phosphinoyloxy]-2-
methylpropionic acid ethyl ester (racemic mixtures) was 39.8 g (72%).
A suspension of 10.0 g (0.026 mole) of [[2-methyl-1-(1-oxopropoxy)propoxy]
(4-phenylbutyl)phosphinyl]acetic acid in 50 ml of isopropyl ether was stirred
vigorously for 15 min, then kept at 5°C for 20 hours. The colorless product
was filtered, washed with a small amount of cold isopropyl ether to give 5.0 g
of [[2-methyl-1-(1-oxopropoxy)propoxy](4-phenylbutyl)phosphinyl]acetic acid
(A/B isomer, racemic mixture) , m.p. 87-89°C. The filtrate was evaporated in
vacuo and retained for isolation of isomer C/D. A solution of the above
material in 110 ml of hot isopropyl ether was filtered through a hot glass
funnel (glass wool). The cooled solution gave 4.6 g (92%) of desired product,
m.p. 90-92°C.
To a vigorously stirred suspension of 980 g (3.33 mol) of l-cinchonidine in 6 L
of ethyl acetate maintained at 45°C was gradually added 1275.5 g (3.33 mol)
of A/B isomer mixture and stirring then continued for an additional 2.5 hours
while the resulting suspension of salt was gradually heated to 70°C when
complete solution was obtained. After filtration (Hyflo) from a small amount of
insoluble material, the solution was seeded and cooled. The crystalline product
which separated was then filtered, washed with 1200 ml of 1:1 ethyl
acetate/isopropyl ether, and dried in vacuo to give 1897.2 g of cinchonidine
salt enriched in the B-isomer, m.p. 106-109°C, [α]D = -59.3° (c = 1,
methanol). This material was combined with 136.8 g of similarly prepared
material (from 0.412 mol of A/B isomer) and the total quantity (2014 g)
recrystallized from 10.18 L of boiling ethyl acetate to afford after filtration,
washing with 1500 ml of the same solvent mixture used before, and drying in
vacuo 1162 g (92%) of [[2-methyl-1-(1-oxopropoxy)propoxy](4-phenylbutyl) phosphinyl]acetic acid (Resolution; isomer B), cinchonidine salt (1:1), m.p.
120-122°C (dec.), [α]D= -45° (c = 1, methanol), [α]365 = -185.5° (c = 1,
methanol). A sample (10 g) was recrystallized twice from acetonitirle and
three times from ethyl acetate additionally to give salt of m.p. 125-126°C
(dec.), [α]D= -42.2°.
A slurry of methyl-1-(1-oxopropoxy)propoxy](4-phenylbutyl)phosphinyl]acetic
acid (B-isomer), dried in vacuo at room temperature for 72 hours, (230.4 g,
0.6 moles) and hydroxybenzotriazole hydrate, dried, in vacuo at 80°C for 24
hours, (101.1 g, 0.66 mole) dichloromethane (sieved dried) (6 L) was chilled
in an ice/acetone bath and treated with N,N-dicyclohexylcarbodiimide (136 g,
0.66 mole). The mixture was warmed to room temperature and stirred for 3
hours. The mixture was then chilled in ice/acetone and treated with (trans)-4-
cyclohexyl-L-proline, hydrochloride (154.2 g, 0.66 mole) followed by
diisopropylethylamine (170.7 g, 1.32 mole). The reaction mixture was stirred
at room temperature for 18 hours. The mixture was then chilled, treated with
water (1 L) and concentrated in vacuo to remove dichloromethane. The
residue was diluted with ether (3600 ml) and water (3600 ml) and filtered.
The filtrate was brought to pH = 1.8 with 10% hydrochloric acid. The ether
layer was separated and the aqueous layer washed with ethyl acetate (3 x 2
L). The combined organic layers were washed with 5% KHSO4 (3 x 1 L), water
(3 x 1 L) and brine (1 L), dried over magnesium sulfate and concentrated in
vacuo to yield 398.9 g of crude [R,1S,4S]-4-Cyclohexyl-1-[[[2-methyl-1-(1-
oxopropoxy)propoxy](4-phenylbutyl)phosphinyl]acetyl]-L-proline, monosodium
salt (isomer B). The crude product was dissolved in acetone (4393 ml),
treated with a solution of 2-ethyl hexanoic acid, sodium salt (117.3 g) in
acetone (1468 ml), then stirred at room temperature overnight. The resultant
precipitate was collected by filtration, washed with acetone (3 x 400 ml) and
hexane (1 L) then dried in vacuo. Yield 277 g, m.p. 195-196°C, [α]D= -5.1°
(MeOH, c = 2), HI = 99.8%. Isomer "A" was not detectable.
brand name
Monopril (Bristol-Myers Squibb);Staril.
Therapeutic Function
Antihypertensive
General Description
Fosinopril sodium, (4S)-4-cyclohexyl-1-[[[(RS)-1-hydroxy-2-methylpropoxy](4-phenylbutyl)phosphinyl]acetyl]-L-proline sodium salt (Monopril),is a phosphorus-containing ACE inhibitor. It is inactive butserves as a prodrug, being completely hydrolyzed by intestinaland liver enzymes to the active diacid fosinoprilat.
Clinical Use
Angiotensin-converting enzyme inhibitor:
Hypertension
Heart failure
Drug interactions
Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: antagonism of hypotensive effect and
increased risk of renal impairment with NSAIDs;
hyperkalaemia with ketorolac and other NSAIDs.
Antihypertensives: increased risk of hyperkalaemia,
hypotension and renal failure with ARBs and
aliskiren.
Bee venom extract: possible severe anaphylactoid
reactions when used together.
Ciclosporin: increased risk of hyperkalaemia and
nephrotoxicity.
Cytotoxics: increased risk of angioedema with
everolimus.
Diuretics: enhanced hypotensive effect;
hyperkalaemia with potassium-sparing diuretics.
ESAs: increased risk of hyperkalaemia; antagonism
of hypotensive effect.
Gold: flushing and hypotension with sodium
aurothiomalate.
Lithium: reduced excretion, possibility of enhanced
lithium toxicity.
Potassium salts: increased risk of hyperkalaemia.
Tacrolimus: increased risk of hyperkalaemia and
nephrotoxicity.
Metabolism
Fosinopril acts as a prodrug of the diacid fosinoprilat, its
active metabolite. Fosinopril is rapidly and completely
hydrolysed to fosinoprilat in both gastrointestinal mucosa
and liver.
Fosinoprilat is excreted both in urine and in the faeces via
the bile.
References
[1] shionoiri h, naruse m, minamisawa k, ueda s, himeno h, hiroto s, takasaki i. fosinopril. clinical pharmacokinetics and clinical potential. clin pharmacokinet. 1997 jun;32(6):460-80.
Fosinopril sodium Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Fosinopril sodium manufacturers
- Product
- Fosinopril sodium 88889-14-9
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-10
- Product
- Fosinopril sodium 88889-14-9
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-09
- Product
- Fosinopril sodium 88889-14-9
- Price
- US $0.00-0.00/Kg
- Min. Order
- 1KG
- Purity
- 99.0%
- Supply Ability
- 500 MT
- Release date
- 2020-05-09