Aliskiren hemifumarate

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Aliskiren hemifumarate

Product Name: Aliskiren hemifumarate
CAS No.: 173334-58-2
Chemical Name: Aliskiren hemifumarate
Synonyms: HSDB 7272;CCRIS 9267;Unii-C8A0p8G029;ALISKIREN FUMARATE;skiren heMifuMarate;Rasilez HeMifuMarate;SPP 100 hemifumarate;Tekturna HeMifuMarate;Aliskiren hemifumarate;Aliskiren hemifumerate
CBNumber: CB21471023
Molecular Formula: C30H53N3O6
Formula Weight: 551.75832
MOL File: 173334-58-2.mol

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Aliskiren hemifumarate Property

Melting point:: 72-75?C
storage temp.: Sealed in dry,Store in freezer, under -20°C
solubility: Methanol (Slightly), Water (Slightly)
form: Solid
color: White

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H360May damage fertility or the unborn child

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML2077
Product name: Aliskiren hemifumarate
Purity: ≥95% (HPLC)
Packaging: 10MG
Price: $64.9
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML2077
Product name: Aliskiren hemifumarate
Purity: ≥95% (HPLC)
Packaging: 50MG
Price: $211
Updated: 2024/03/01

Cayman Chemical

Product number: 19640
Product name: Aliskiren (hemifumarate)
Purity: ≥95%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 19640
Product name: Aliskiren (hemifumarate)
Purity: ≥95%
Packaging: 5mg
Price: $116
Updated: 2024/03/01

Cayman Chemical

Product number: 19640
Product name: Aliskiren (hemifumarate)
Purity: ≥95%
Packaging: 10mg
Price: $214
Updated: 2024/03/01

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Aliskiren hemifumarate Chemical Properties,Usage,Production

Description

Aliskiren hemifumarate (Tekturna(R)) was the first renin inhibitor approved by FDA in March 2007, and genomic analysis validated that Pgx-based dosing guidelines are not required for this drug. The once-daily, oral, direct renin inhibitor received FDA approval for treatment of high blood pressure as mono therapy or in combination with other antihypertensive medications. Furthermore, aliskiren demonstrated increased efficacy when used in combination with other commonly used blood pressure-lowering medications. Novartis is conducting a large outcome trial program to evaluate the long-term effects of aliskiren and of direct renin inhibition in general.

Chemical Properties

white to slightly yellowish crystalline powder. It is soluble in phosphate buffer, n-Octanol, and highly soluble in water.

Uses

Aliskiren hemifumarate is a potent renin inhibitor (IC50 = 0.6 and 80 nM for human and rat respectively). It has antihypertensive activity, decreasing plasma renin activity and inhibiting the conversion of angiotensinogen to Angiotensin I by binding to the S3 sub-pocket of renin. Exhibits selectivity for renin over a range of other aspartic proteinases (>5000 nM). Lowers blood pressure in a hypertensive rodent model. Orally active.
Aliskiren hemifumarate (ALS) has been used to treat hypertension, alone or with other antihypertensive medications. It is suitable for oral administration. ALS regulates baseline systolic and diastolic blood pressure by blocking the catalytic activity of renin system at its rate-limiting step.

Uses

An orally active, synthetic nonpeptide renin inhibitor. Antihypertensive.

Definition

ChEBI: Aliskiren fumarate is the hemifumarate salt of aliskiren. It has a role as an antihypertensive agent. It contains an aliskiren.

Clinical Use

Renin inhibitor:
Hypertension

Synthesis

The synthesis of aliskiren by Novartis is depicted in the scheme.Aliskiren (I) was synthesized through a convergent synthetic strategy by coupling key intermediate chloride 5 with aldehyde 10. Hydrogenation of cinnamic acid 1, followed by generation of the acid chloride of the corresponding acid and reaction with (+)-pseudoephedrine provided amide 2 in 91% yield. Deprotonation of amide 2 with LDA followed by alkylation with 2-iodopropane in refluxing THF gave 3 as a single diastereomer in 52% yield. Reduction of the amide functionality in 3 using n-butyl lithium boron trifluoride ammonium complex proceeded without epimerization of the chiral center to give alcohol 4 in 66% yield. Chlorination of 4 using phosphorus oxychloride gave chloride 5, in 78% yield as the organometallic precursor for the eventual coupling to aldehyde 10. Synthesis of fragment 10 commenced with (+)-pseudoephedrine isovaleramide 6, which was efficiently deprotonated with LDA and alkylated using allyl bromide; diastereomerically pure 7 was obtained upon crystallization of the crude reaction mixture in 78% yield. Bromolactonization of 7, using n-bromosuccinimide in the absence of acetic acid gave amide acetal 8 with a single configuration at the spirocenter and a 6:1 mixture of trans:cis ring substituents. Displacement of the bromide using tetrabutylammonium acetate followed by basic hydrolysis provided alcohol 9 in 85% yield. Oxidation of 9 using dimethyl sulfoxide-sulfur trioxide/pyridine proceeded without epimerization to furnish the masked lactone aldehyde 10 in 60% yield. Coupling of fragments 5 and 10 was achieved by treatment of 10 with the organocerium reagent of the corresponding Grignard reagent prepared from 5. Hydrolysis of the crude spirocyclic addition product revealed that the hydroxylactone 11 was formed in 51% overall yield as an inseparable epimeric mixture with a Felkin-Anh selectivity of 85:15. The requisite nitrogen functionality was installed via the brosylate to give azido lactone 12 in 68% yield. Aminolysis with 3-amino-2,2-dimethylpropionamide led to formation of the open chain azido alcohol 13 in 76% yield. The synthesis of aliskiren was completed by azide hydrogenolysis and formation of the hemifumarate salt. Generation of pure aliskiren was achieved via crystallization which removed the residual minor (R)-epimer carried through from the Grignard addition step to afford aliskiren (I) in 43% yield.

Drug interactions

Potentially hazardous interactions with other drugs
Other antihypertensive agents: enhanced antihypertensive effect; concentration possibly reduced by irbesartan; increased risk of hyperkalaemia and hypotension with ACE-Is and ARBs.
Antifungals: concentration increased by itraconazole and ketoconazole, avoid with itraconazole.
Ciclosporin: concentration of aliskiren increased - avoid.
Diuretics: may reduce concentration of furosemide; hyperkalaemia with potassium-sparing diuretics.
Grapefruit juice: concentration of aliskiren reduced - avoid.
Heparins: increased risk of hyperkalaemia.
Potassium salts: increased risk of hyperkalaemia.

Metabolism

Approximately 1.4% of the total oral dose is metabolised by CYP3A4. Approximately 0.6% of the dose is recovered in urine following oral administration. Aliskiren is mainly eliminated as unchanged compound in the faeces (78%).

storage

Store at -20°C

Aliskiren hemifumarate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Aliskiren hemifumarate manufacturers

Ouhuang Engineering Materials (Hubei) Co., Ltd

Product: Aliskiren hemifumarate 173334-58-2
Price: US $50.00/kg
Min. Order: 1kg
Purity: 99.10%
Supply Ability: 50000kg
Release date: 2024-04-25

Hebei Duling International Trade Co. LTD

Product: Aliskiren hemifumarate 173334-58-2
Price: US $50.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 50 tons
Release date: 2023-04-17

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Aliskiren hemifumarate 173334-58-2
Price: US $0.00/g
Min. Order: 1g
Purity: 98%min
Supply Ability: 1000g
Release date: 2021-08-13

173334-58-2, Aliskiren hemifumarateRelated Search:

Bisoprolol fumarate Fumaric acid Glycine Anisole Aliskiren POLY(ETHYLENE GLYCOL) METHYL ETHER ACRYLATE Ketotifen fumarate (Trifluoromethoxy)benzene (2S,4S,5S,7S)-7-(3-(3-Methoxypropoxy)-4-methoxybenzyl)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-2-isopropyl-8-methylnonanamide hydrochloride 4-Methoxyphenol CHLOROPHOSPHONAZO III p-Anisaldehyde Dimethyl fumarate Ferrous fumarate ISOPROPYL LAURATE ALTRENOGEST p-Anisidine 6-Aminocaproic acid

(2S,4S,5S,7S)-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-2-isopropyl-8-methylnonanamide hemifumarate

Aliskiren hemifumarate (2S,4S,5S,7S)-5-Amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnonanamide hemifumarate

ALISKIREN FUMARATE

(2S,4S,5S,7S)-5-Amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnonanamide hemifumarate

Benzeneoctanamide, delta-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-gamma-hydroxy-4-methoxy-3-(3-methoxypropoxy)-alpha,zeta-bis(1-methylethyl)-, (alphas,gammas,deltas,zetas)-, (2E)-2-butenedioate (2:1) (salt)

Aliskiren hemifumarate

(αS,γS,δS,ζS)-δ-Amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-γ-hydroxy-4-methoxy-3-(3-methoxypropoxy)-α,ζ-bis(1-methylethyl)benzeneoctanamide hemifumarate

Unii-C8A0p8G029

Aliskiren-D6 HeMifuMarate

(αS,γS,δS,zS)-δ-AMino-N-(3-aMino-2,2-diMethyl-3-oxopropyl)-γ-hydroxy-4-Methoxy-3-(3-Methoxypropoxy)-α,z-bis(1-Methylethyl)benzeneoctanaMide HeMifuMarate

Rasilez HeMifuMarate

Tekturna HeMifuMarate

skiren heMifuMarate

Benzeneoctanamide, δ-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-γ-hydroxy-4-methoxy-3-(3-methoxypropoxy)-α,ζ-bis(1-methylethyl)-, (αS,γS,δS,ζS)-, (2E)-2-butenedioate (2:1)

Aliskiren hemifumerate

Aliskiren hemifumarate USP/EP/BP

Aliskiren Hemifumarate (CGP 60536)

Aliskiren D6 hemifumarateQ: What is Aliskiren D6 hemifumarate Q: What is the CAS Number of Aliskiren D6 hemifumarate Q: What is the storage condition of Aliskiren D6 hemifumarate Q: What are the applications of Aliskiren D6 hemifumarate

Aliskiren HemifumarateQ: What is Aliskiren Hemifumarate Q: What is the CAS Number of Aliskiren Hemifumarate Q: What is the storage condition of Aliskiren Hemifumarate

CCRIS 9267

HSDB 7272

Aliskiren CAS 173334-58-2

(2S,4S,5S,7S)-5-Amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonanamide hemifumarate

Aliskiren hemifumarate CAS NO.173334-58-2

CGP 60536 hemifumarate

CGP60536B hemifumarate

SPP 100 hemifumarate

173334-58-2

17334-58-2

C30H53N3O612C4H4O4

2C30H53N3O6C4H4O4

C32H55N3O8

C64H110N6O16

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