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Telmisartan

A novel blood pressure-lowering drug Irbesartan Patent and administrative protection Appearance and solubility properties Telmisartan intermediates Advances in the treatment of hypertension Side Effects Uses

CAS No.144701-48-4
Chemical Name:Telmisartan
Synonyms:TU-199;PRITOR;BIBR 277;MICARDIS;Telmisaran;TIMISHATAN;BIBR 277SE;TELMISARTAN;TIMETAZIDINE;TelMisartan API
CBNumber:CB4266172
Molecular Formula:C33H30N4O2
Formula Weight:514.63
MOL File:144701-48-4.mol
Telmisartan Property
Melting point : 261-263°C
density : 1.16
RTECS : DV2037500
storage temp. : Hygroscopic, -20°C Freezer, Under Inert Atmosphere
solubility : DMSO: >5 mg/mL at 60 °C
form : solid
color : white
Water Solubility : insoluble
CAS DataBase Reference: 144701-48-4(CAS DataBase Reference)
Safety
Hazard Codes : Xi
Risk Statements : 36/37/38
Safety Statements : 22-24/25-36-26
WGK Germany : 2
Hazardous Substances Data: 144701-48-4(Hazardous Substances Data)

Telmisartan Chemical Properties,Usage,Production

A novel blood pressure-lowering drug
Telmisartan is a novel type of blood pressure lowering drug and is a kind of specific antagonist for the angiotensin II receptor (AT I type) antagonist for the treatment of essential hypertension, replacing the angiotensin II receptor for binding with the AT I receptor subtypes (known action sites of angiotensin II) with high affinity. Telmisartan has no site agonist effect on the AT I receptor and selectively binds with the AT I receptors with a long-lasting binding effect. It has no affinity to other receptors (including AT2 and other less characterized AT receptors). The function of other receptors remains unknown. Since telmisartan resulting in increased levels of angiotensin II, it is also possible to cause excessive stimulating effect on the receptor. Telmisartan does not inhibit human plasma renin, nor block the ion channel. It does not inhibit the angiotensin-converting enzyme II that can alleviate the adverse reaction of the enhanced effect of bradykinin. Administration of 80 mg of Telmisartan to the human body can almost completely inhibit the increase in blood pressure caused by angiotensin II. The inhibitory effect can last for 24 hours and is still detectable at 48 hours. Within three hours after the initial dose, the antihypertensive effect became significant gradually. At the first 4 weeks after the start of treatment, we can obtain the maximum antihypertensive effect and the efficacy can be maintained during long-term therapy. If the treatment gets sudden interruption, the blood pressure will gradually return back to the pre-treatment level after a few days without the emergence of the rebound hypertension. In a clinical trials for direct comparison between these two kinds hypertension drugs, the incidence of dry cough in treatment group was significantly lower than that in the treatment group via angiotensin-converting enzyme inhibitor.
Clinical efficacy and characteristics:
1, Pharmacokinetic exhibits that: fast-action (0.3h), long duration (35.4h), small effect on the heart rate during blood pressure lowering.
2 Comparison with enalapril: its antihypertensive effect is better than enalapril; even when both of them are used in combination with diuretics, Telmisartan still has a better effect with a lower incidence of cough.
3. Comparison with lisinopril: the antihypertensive (systolic and diastolic) effect is more significant; the incidence of cough in the telmisartan group (16%) was significantly lower than that in the lisinopril group (60%)
4, Comparison with atenolol: it has a comparable antihypertensive with the incidence of the adverse reaction (impotence and fatigue) being lower.
5, compared with amlodipine: telmisartan group can significantly reduce the heart rate within four hours after taking the drugs and from 6’ clock to 12’ clock in the morning.In short, compared with other classes of antihypertensive drugs, telmisartan has the following characteristics: having specificity of the receptors action; significant antihypertensive effect; remarkable diuretic effect; can improve cardiac stenosis disorder; safe drug; excellent tolerability; Take one time per day; it is easy to take.
Irbesartan
Irbesartan is a kind of inhibitors of the angiotensin II (Ang II) receptor. The angiotensin II receptors are divided into two kinds, AT1 and AT2. Irbesartan, through selectively blocking the AT1 receptor of AnglI, can inhibit the conversion from Ang I to Ang II and specifically antagonizing the angiotensin converting enzyme 1 receptor (AT1) with its antagonism effect on AT1 being 8500 times as high as AT2. Through selectively blocking the binding between Ang II with AT1 receptor, it can inhibit the vasoconstriction and the release of aldosterone, resulting in the antihypertensive effect. This product does not inhibit the angiotensin converting enzyme (ACE), renin, other hormone receptors as well as the ion channels involved in the blood pressure regulation and the sodium balance. Irbesartan can also reduce the electrical remodeling of the myocardium, thereby reducing the mortality rate of patients with hypertension. It is the most effective drugs in treatment of hypertension and cardiovascular disease.
Angiotensin antagonists (abbreviated ARB) are frequently applied to the clinical treatment of hypertension and diabetic nephropathy. Currently drugs for the treatment of high blood pressure, according to the site of action, are divided into angiotensin converting enzyme inhibitor (referred to ACEI), calcium antagonists, and β-blockers. According to the comparison, ARB has good antihypertensive efficacy while irbesartan is a novel angiotensin antagonists in lowering blood pressure as well as inhibiting the left ventricular hypertrophy and protecting the kidney.
According to foreign information, oral administration of irbesartan can lead to rapid absorption with the bioavailability being 60-80% and will not be affected by food. The time for the plasma concentration to reach peak is about 1 to 1.5 hours with the plasma protein-binding rate being 90%, and the elimination half-life of 11-15 hours. The plasma concentration will reach steady state within three days. It can be metabolized through glucuronide acidifying and oxidation. In vitro studies have shown that it can subject to oxidation by cytochrome P450 and 2C9. The product and its metabolites can be excreted through biliary and renal.
On March 8, 2007, the irbesartan developed by the Hangzhou Sanofi Minsheng Pharmaceutical Co. (Aprovel) has received SFDA approval for the treatment of type 2 diabetic nephropathy (together with hypertension), thus becoming the first antihypertensive drug with related indication in China.
The above information is edited by the chemicalbook of Dai Xiongfeng.
Patent and administrative protection
1, Telmisartan was originally developed and invented by the German pharmaceutical company Boehringer Ingelheim. In 1991, it has the approved in German in the patent EP502, 314. In 1998, it was first approved for marketing in the United States. Later, it had been also successively approved for marketing in Germany, the Philippines, Australia, Belgium, Britain and other countries.
2, It has not received patent and administrative protection in China.
3, there is no intellectual property issue regarding the development of this product.
Appearance and solubility properties
It is white to white-like crystalline powder. It is odorless and tasteless. It is soluble in chloroform, slightly soluble in methanol, very slightly soluble in acetone but almost insoluble in water. It is also slight soluble in 0.1mol/L hydrochloric acid and is also soluble in 0.1mol/L sodium hydroxide.
Absorption coefficient (E1% 1cm): 509~541
Telmisartan intermediates
Telmisartan methyl ester
2-n-propyl-4-methyl-6-(1-methyl-benzimidazol-2-yl) benzimidazole (152628-02-9)
2-n-propyl-4-methyl-benzimidazole-6-carboxylic acid (152628-03-0)
4'-methyl-biphenyl-2-carboxylate (114772-34-8)
Advances in the treatment of hypertension
The common property of ARB lie in its specific blockage of the angiotensin II AT1 receptor while having almost no effect on the AT2 receptor and ACE, thereby avoiding the escape phenomenon of the ACEI angiotensin II as well as having no inhibitory effect on the degradation of bradykinin, which further avoids side effects such as the cough and angioedema. Many large-scale clinical studies have shown that ARB has a good heart and kidney protection effect. Compared with other antihypertensive drugs, the greatest advantages of ARB include the good safety, mild adverse events and transient effect. The patients also have good compliance towards it.
ARB is divided into three categories: diphenyl tetra-imidazole (losartan, telmisartan, candesartan, irbesartan, etc.), non-diphenyl tetra-imidazole (eprosartan) and a non-heterocyclic (valsartan). ARB class has benzimidazole ring with the modifications in imidazole ring of each drug varying and therefore having varied physical and chemical properties. Telmisartan (Micardis) has specific aromatic group modification so that the drug is highly fat-soluble with good tissue penetration. At the same time, the aromatic groups make telmisartan be with higher AT1 receptor affinity and thereby having stronger antagonism against angiotensin II.
The property of the action of ARB on the AT1 receptors is classified into unsurpassable type and surpassable type. The former means that, after the application of ARB, even increasing the angiotensin II to a maximum concentration can still not reach the contraction peak of blood before treatment. The non-competitive binding strength of the drug with AT1 receptors is very strong. Telmisartan belongs to this type of medication, and therefore having a better antihypertensive effect. Figure 1 shows, the active drugs, the reaction rate of angiotensin II in the telmisartan group at 1400 minutes (about 24 hours), compared with the variation at 30 minutes has the smallest scale of change and can still maintain a very low reaction rate, which fully demonstrates the efficient, compact, persistent antagonism effect with AT1 receptor.
The half-life of telmisartan is around 18 to 24 hours with the onset starting at 1 to 4 hours after administration and the efficacy duration period being up to 35 hours. It has a high trough to peak ratio (T/P) with significant efficacy in controlling the blood pressure in early morning. Therefore, the drug can effectively control blood pressure for 24 hours that is consistent with the medication standard of once per day (40~80 mg, qd).
Side Effects
In the placebo-controlled trial, the overall incidence of the adverse events in telmisartan (41.4%) is similar with that of placebo (43.9%). The occurrence of adverse events has no correlation with the dose as well as no correlation with gender, age and ethnicity.
The adverse reactions listed below are obtained from the clinical trials where a total of 5788 patients of hypertension had received telmisartan treatment.
Adverse reactions, according to the frequency of occurrence, are divided into:
Very common (> 1/10); common (> 1/100, <1/10); uncommon (> 1/1000, <1/100); rare (> 1/10000, <1/1000); very rare (<1/10000) systemic reactions: common symptoms: back pain (e.g. sciatica), chest pain, flu-like symptoms, symptoms of infection (such as urinary tract infections including cystitis) uncommon: abnormal vision, sweating
Central and peripheral nervous system: Common: vertigo
Gastrointestinal system: Common symptoms: abdominal pain, diarrhea, dyspepsia, gastrointestinal disorders; rare: dry mouth, flatulence
Musculoskeletal System: common: joint pain, leg cramps or leg pain, myalgia; uncommon symptoms: tenosynovitis-like symptoms
Nervous system: rare: Anxiety
Respiratory system: Common: upper respiratory tract infection including pharyngitis and rhinitis
Skin and accessory system: Common: skin abnormalities such as eczema
In addition, since the listing of telmisartan, in some individual cases it has been reported of erythema, pruritus, syncope, insomnia, depression, upset stomach, vomiting, hypotension, bradycardia, tachycardia, dyspnea, eosinophilia syndrome, thrombocytopenia, weakness, and reduced working efficiency. Similar as other kinds of angiotensin II antagonist, there has been reported of the occurrence of a few cases of angioedema, nettle and other disease-related adverse reactions.
The labs have found: compared with placebo, in the telmisartan group, it has been found occasionally of drop in hemoglobin or increase in uric acid. Regarding the effect of the elevated serum creatinine or liver enzymes, telmisartan has similar or lower effect as/than placebo.
Uses
It can be used as anti-hypertensive drugs and vasodilator hormone antagonist.
Chemical Properties
White or off white crystalline powder
Usage
cardiotonic
Usage
Telmisartan is an angiotensin II receptor antagonist.
Usage
anti-cancer agent
Usage
Used alone or in combination with other classes of antihypertensives for the treatment of hypertension. Also used in the treatment of diabetic nephropathy in hypertensive patients with type 2 diabetes mellitus, as well as the treatment of congestive heart
Definition
ChEBI: A member of the class of benzimidazoles used widely in the treatment of hypertension.
Telmisartan Preparation Products And Raw materials
Raw materials
N-Methyl-1,2-benzenediamine dihydrochloride
Preparation Products
Telmisartan Suppliers      Global( 384)Suppliers     
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Hubei Xinyuanshun Pharmaceutical Chemical Co., Ltd. 027-50664929 / 13971561712027-50664927 / QQ: 3452835437hubxys2001@163.comChina 2014 55
Zhuhai Beri Medical Technology Co., Ltd 0756-86994560756-8699456sales@zhberi.comChina 121 58
J & K SCIENTIFIC LTD. 400-666-7788 +86-10-82848833+86-10-82849933jkinfo@jkchemical.com;market6@jkchemical.comChina 96832 76
Meryer (Shanghai) Chemical Technology Co., Ltd. +86-(0)21-61259100(Shanghai) +86-(0)755-86170099(ShenZhen) +86-(0)10-59487313(Beijing)+86-(0)21-61259102(Shanghai) +86-(0)755-86170066(ShenZhen) +86-(0)10-88580358(Beijing)sh@meryer.comChina 40403 62
INTATRADE GmbH +49 3493/605464+49 3493/605470sales@intatrade.deGermany 3589 66
3B Pharmachem (Wuhan) International Co.,Ltd. 86-21-50328103 * 801、802、803、804 Mobile:1893055203786-21-503281093bsc@sina.comChina 15950 69
Arden pharmaceutical &chemical Co., Ltd +86-(0)533-3595900 13793319233+86-(0)533-3595900info@chems.com.cnChina 670 61
TCI (Shanghai) Development Co., Ltd. 800-988-0390021-67121385sales@tcishanghai.com.cnChina 22833 81
Energy Chemical 021-58432009 / 400-005-6266021-58436166-800info@energy-chemical.comChina 44198 61
Wuhan Chemwish Technology Co., Ltd 86-027-6784991286-027-87531808sales@chemwish.comChina 35930 56
 
144701-48-4(Telmisartan)Related Search:
3-Methyl-2-[pentanoyl-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]amino]-butanoic acid Telmisartan-d3 Acyl--D-glucuronide 4-Methyl Biphenyl-2-Carboxylate [Telmisartan Intermediates] Telmisartan acyl glucuronide 4-butanamide-3-methyl-5-nitrobenzene carboxylate acid cas:(intermediate of telmisartan) 3-methyl-4-n-butyramide-5-amino-benzoic acid methyl ester (intermediate of telmisartan) Telmisartan Methyl Ester TERT-BUTHYL 4'-(METHYL)BIPHENYL-2-CARBOXYLATE(FOR TELMISARTAN) N-METHYL-O-PHENLENEDIAMINE DIHYDROCHLORIDE/INTERMEDIATE OF TELMISARTAN METHYL4/-(BROMOMETHYL)-BIPHENYL2-CARBOXLATE/INTERMEDIATE OF TELMISARTAN Intermediate of Telmisartan A 2-N-PROPYL-4-METHYL-6-(1-METHYLBENZIMIDAZOLE-2-YL)BENZIMIDAZOLE(INTERMEDIATE OF TELMISARTAN) 2-N-PROPY1-4-METHYL-6-(1-METHYL BENZIMIDAZOLE-2-YL) BENZIMIDAZOLE/INTERMEDIATE OF TELMISARTAN TELMISARTAN-D3 ACYL-B-D-GLUCURONIDE TELMISARTAN SODIUM 4'-[[1,4'-Dimethyl-2'-propyl(2,6'-bi-1H-benzimidazol)-1'-yl]-methyl]-1,1'-biphenyl-2-carboxylic acid 1,1-dimethylethyl ester METHYL 4'-[[2-N-PROPYL-4-METHYL-6-(1-METHYLBENZIMIDAZOL-2-YL)-BENZIMIDAZOL-1-YL]METHYL]BIPHENYL-2-CARBOXYLATE Telmisartan Acyl--D-glucuronide
TU-199 TELMISARTAN PRITOR MICARDIS BIBR 277 144701-48-4 4'[(1,4'-DIMETHYL-2'-PROPYL[2,6'-BI-1H-BENZIMIDAZOL]-1'-YL)METHYL][1,1'-BIPHENYL]-2-CARBOXYLIC ACID 4'-[(1,4'-DIMETHYL-2'-PROPYL[2,6'-BI-H-BENZIMIDAZOL]-1'-YL)METHYL][1,1'-BIPHENYL]-2-CARBOXYLIC ACID 3-methoxy-8-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl sulfinyl]-2,7,9-triazabicyclo[4.3.0]nona-2,4,8,10-tetraene [1,1'-Biphenyl]-2-carboxylic acid, 4'-[(1,4'-dimethyl-2'-propyl[2,6'-bi-1H-benzimidazol]-1'-yl)methyl]- 4'-[[1,4'-Dimethyl-2'-propyl[2,6'-bi-1H-benzimidazol]-1'-yl]-methyl]-1,1'-biphenyl-2carboxylic acid,dimethylethyl ester Telmisaran Telmisartan99.5% TelmisartanC33H30N402 C16H18N4O3S C33H30N4O2 Micardis, Pritor, 4[(1,4Dimethyl-2propyl[2,6bi-H-benzimidazol]-1yl)methyl][1,1biphenyl]-2-carboxylic Acid, TIMETAZIDINE TIMISHATAN 4′-((2-n-Propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl)methyl)biphenyl-2-carbonsure 1447014-48-4 Pharmaceutical material and intermeidates Active Pharmaceutical Ingredients C37H38N4O2 4'-[{1,4'-Dimethyl-2'-Propyl[2,6'-Bi-1H-Benzimiaszol]-1'yl}-Methyl}-1,1'-Biphenyl-2-Caroxylic Acid INTERMEDIATESOF Antihypertensive 4'-[{1,4'-Dimethyl-2'-Propyl[2,6'-Bi-1H-Benzimiaszol]-1'yl}-Methyl}-1,1'-Biphenyl-2-Caroxylic Acid Dimethyl Ethyl Ester Imidazoles (intermediates of telmisartan) 4''-(1,7''-DIMETHYL-2''-PROPYL-1H-[2,5'']BIBENZOIMIDAZOLYL-3''-YLMETHYL)-BIPHENYL-2-CARBOXYLIC ACID 4-chloromethyl-5-methyl-1,3-dioxol-2-tone Telmisartan 4'-(1,7'-Dimethyl-2'-propyl-1H- Hypertension Intermediates & Fine Chemicals Pharmaceuticals API's BIBR 277, 4μ[(1,4μ-Dimethyl-2μ-propyl[2,6μ-bi-1H-benzimidazol]-1μ-yl)methyl][1,1μ-biphenyl]-2-carboxylic acid C20H24N2O5SD4 C33H27N4O2D3 4'-[[4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl]methyl]-2-biphenylcarboxylic acid Telmisartan,4′[(1,4′-Dimethyl-2′-propyl[2,6′-bi-1H-benzimidazol]-1′-yl)methyl][1,1′-biphenyl]-2-carboxylic acid, BIBR 277 4'-[[1,4'-Dimethyl-2 Other Products Telmisartan (150 mg) 2-(4-{[4-Methyl-6-(1-Methyl-1H-1,3-benzodiazol-2-yl)-2-propyl-1H-1,3-benzodiazol-1-yl]Methyl}phenyl)benzoic acid TelMisartan (Micardis) BIBR 277SE TelMisartan API Hypertension. 4'-[[4-Methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-propyl-1H-benzimidazol-1-yl]methyl]biphenyl-2-carboxylic Acid 4'-((1,7'-DiMethyl-2'-propyl-1H,3'H-[2,5'-bibenzo[d]iMidazol]-3'-yl)Methyl)-[1,1'-biphenyl]-2-carboxylic acid 4'-((1,7'-Dimethyl-2'-propyl-1H,3'H-[2,5'-bibenzo[d]imidazol]-3'-yl)methyl)-[1,1'-biphenyl]-2-car CARADRIN Telmisartan Synonyms 4'[(1,4'-Dimethyl-2'-propyl[2,6'-bi-1H-benzimidazol]-1'-yl)methyl][1,1'-biphenyl]-2-carboxylic acid (1,1'-Biphenyl)-2-carboxylic acid, 4'-((1,4'-dimethyl-2'-propyl(2,6'-bi-1H-b 2-[4-[[4-methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl]methyl]phenyl]benzoic acid
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