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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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Aliskiren hemifumarate Suppliers

Changzhou Kangte Pharmtech Co.,Ltd
Tel
0519-82813797 18994752886
Fax
0519-82813703
Email
czkangte@hotmail.com
Country
China
ProdList
45
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62
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
ZHIWE CHEMTECH CO LTD
Tel
021-20221225 13917446399
Fax
QQ:115820162
Email
sales@zhiwe.net
Country
China
ProdList
604
Advantage
61
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
Beijing Ouhe Technology Co., Ltd
Tel
010-82967028 13552068683
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12438
Advantage
60
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
19172
Advantage
64
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
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View Lastest Price from Aliskiren hemifumarate manufacturers

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
Hebei Weibang Biotechnology Co., Ltd
Product
Aliskiren hemifumarate 173334-58-2
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2023-04-14
Henan Bao Enluo International TradeCo.,LTD
Product
Aliskiren hemifumarate 173334-58-2
Price
US $30.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000tons
Release date
2023-08-03

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