ChemicalBook > CAS DataBase List > Enalapril maleate

Enalapril maleate

Product Name
Enalapril maleate
CAS No.
76095-16-4
Chemical Name
Enalapril maleate
Synonyms
Olivin;Renitek;Renivace;Enalapril Maleate Salt;(S)-1-((S)-2-((S)-1-ETHOXY-1-OXO-4-PHENYLBUTAN-2-YLAMINO)PROPANOYL)PYRROLIDINE-2-CARBOXYLIC ACID MALEATE;BQL;Pres;Ednyt;Envas;Nuril
CBNumber
CB1467853
Molecular Formula
C24H32N2O9
Formula Weight
492.52
MOL File
76095-16-4.mol
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Enalapril maleate Property

Melting point:
143-144,5°C
alpha 
D25 -42.2° (c = 1 in methanol)
Boiling point:
0°C
Flash point:
0°C
storage temp. 
2-8°C
solubility 
methanol: ≥50 mg/mL, clear, colorless to yellow
form 
powder
pka
pKa1 3.0; pKa2 (25°) 5.4
color 
white to off-white
Water Solubility 
Soluble in water, methanol, and ethanol.
λmax
208nm(MeOH)(lit.)
Merck 
14,3567
BCS Class
1 (LogP), 3 (CLogP)
InChIKey
OYFJQPXVCSSHAI-QFPUQLAESA-N
CAS DataBase Reference
76095-16-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-62-63
Safety Statements 
22-24/25-36/37-26
RIDADR 
3077
WGK Germany 
2
RTECS 
TW3666000
HS Code 
29339900
Toxicity
LD50 oral in rat: 2973mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
BP741
Product name
Enalapril maleate
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$229
Updated
2024/03/01
Sigma-Aldrich
Product number
1235300
Product name
Enalapril maleate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
16616
Product name
Enalapril maleate salt
Purity
analytical standard
Packaging
50mg
Price
$71.7
Updated
2022/05/15
TCI Chemical
Product number
E1010
Product name
Enalapril Maleate
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$51
Updated
2024/03/01
TCI Chemical
Product number
E1010
Product name
Enalapril Maleate
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$197
Updated
2024/03/01
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Enalapril maleate Chemical Properties,Usage,Production

Description

Enalapril maleate is the second angiotensin converting enzyme inhibitor to reach the marketplace. Like captopril, the first entry in this area, enalapril is useful in the treatment of hypertension and congestive heart failure. It has a longer effective half-life than captopril, allowing once or twice-daily dosing, and appears to have a somewhat lower incidence of side effects.

Chemical Properties

White to Off-White Crystalline Powder

Originator

Merck (USA)

Uses

sunscreen

Uses

Enalapril maleate salt is used as a long-acting ACE inhibitor and antihypertensive, used to study diabetic angiopathy in diabetic rats and inhibition of ACE in hog plasma (I50=1.2nM). ACE inhibitors disturb the enin-angiotensin- aldosterone system. Additional ACE inhibitors include: Enalapril, Enalaprilat dihydrate, Enalaprilat, and Enalapril-d5 Maleate Salt, among others.

Uses

An antihypertensive. An angiotensin-converting enzyme (ACE) inhibitor.

Definition

ChEBI: The maleic acid salt of enalapril. It contains one molecule of maleic acid for each molecule of enalapril. Following oral administration, the ethyl ester group of enalapril is hydrolysed to afford the corresponding carboxylic acid, enalaprilat, an angioten in-converting enzyme (ACE) inhibitor. Enalapril is thus a prodrug for enalaprilat (which, unlike enalapril, is not absorbed by mouth), and its maleate is used in the treatment of hypertension and heart failure, for reduction of proteinuria and renal diseas in patients with nephropathies, and for the prevention of stroke, myocardial infarction, and cardiac death in high-risk patients.

Manufacturing Process

N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanyl-L-proline maleic acid salt
A mixture of 3 g of L-alanyl-L-proline, 5 g of ethyl 2-oxo-4-phenyl-butanoate, 13 g of 3A molecular sieves, and 3.6 g of Raney nickel in 85 ml of ethanol is hydrogenated at 25°C and at 40 psig of hydrogen until uptake of hydrogen ceases. The solids are filtered, washed with 80 ml of ethanol and the filtrates are combined. Assay by high pressure liquid chromatography shows an 87:13 ratio of diastereoisomers in favor of the desired product. Ethanol is removed under vacuum to afford an oil which is dissolved in 60 ml of water and 20 ml of ethyl acetate. The pH of the stirred two-phase mixture is adjusted to 8.6 with 50% NaOH. The layers are separated and the water phase is extracted with 2x20 ml of ethyl acetate. The water phase is adjusted to pH 4.25 with hydrochloric acid, 12 g of NaCl is dissolved in the water, and product is extracted with 5x12 ml of ethyl acetate. The extracts are combined and dried with Na2SO4. The desired product, N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]- L-alanyl-L-proline, is crystallized as its maleate salt by addition of 1.86 g of maleic acid. After stirring for 4 hours, the salt is filtered, washed with ethyl acetate and dried to afford 5.2 g of pure product, melting point 150°-151°C.

brand name

RENITEN

Therapeutic Function

Antihypertensive

General Description

Enalapril maleate, 1-[N[(S)-1-carboxy-3-phenylpropyl]-L-alanyl]-L-proline 1 -ethyl estermaleate (Vasotec), is a long-acting ACE inhibitor. It requiresactivation by hydrolysis of its ethyl ester to form thediacid enalaprilat. Enalapril is devoid of the side effects ofrash and loss of taste seen with captopril. These side effectsare similar to those of the mercapto-containing drugpenicillamine. The absence of the thiol group in enalaprilmaleate may free it from these side effects. The half-life is11 hours.

Biochem/physiol Actions

A long-acting angiotensin-converting enzyme inhibitor.

Clinical Use

Angiotensin converting enzyme inhibitor:
Hypertension
Heart failure

Veterinary Drugs and Treatments

The principle use of enalapril/enalaprilat in veterinary medicine at present is as a vasodilator in the treatment of heart failure. Recent studies have demonstrated that enalapril, particularly when used in conjunction with furosemide, does improve the quality of life in dogs with heart failure. It is not clear, however, whether it has any significant effect on survival times. It may also be of benefit in treating the effects associated with valvular heart disease (mitral regurgitation) and left to right shunts. It is being explored as adjunctive treatment in chronic renal failure and protein losing nephropathies.
While ACE inhibitors are a mainstay for treating hypertension in humans, they have not been particularly useful in treating hypertension in dogs or cats.

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

Following absorption, oral enalapril is rapidly and extensively hydrolysed to enalaprilat, a potent angiotensin converting enzyme inhibitor. Peak serum concentrations of enalaprilat occur about 4 hours after an oral dose of enalapril tablet, and the effective half-life is 11 hours. Excretion of enalaprilat is primarily renal. The principal components in urine are enalaprilat, accounting for about 40% of the dose, and intact enalapril.

Enalapril maleate Preparation Products And Raw materials

Raw materials

Preparation Products

Enalapril
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View Lastest Price from Enalapril maleate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Enalapril maleate 76095-16-4
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98.5%-101.5% Titration
Supply Ability
1000KGS
Release date
2021-07-21
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Enalapril maleate 76095-16-4
Price
US $100.00-70.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-16
Hebei Weibang Biotechnology Co., Ltd
Product
Enalapril maleate 76095-16-4
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-01

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