Chemical Properties Mechanisms of Action Side Effects Patent
ChemicalBook > CAS DataBase List > Telmisartan

Telmisartan

Chemical Properties Mechanisms of Action Side Effects Patent
Product Name
Telmisartan
CAS No.
144701-48-4
Chemical Name
Telmisartan
Synonyms
TU-199;PRITOR;BIBR 277;MICARDIS;misartan;BIBR 277SE;Telmisaran;TIMISHATAN;Telmisattan;timishatyan
CBNumber
CB4266172
Molecular Formula
C33H30N4O2
Formula Weight
514.62
MOL File
144701-48-4.mol
More
Less

Telmisartan Property

Melting point:
261-263°C
Boiling point:
771.9±70.0 °C(Predicted)
Density 
1.16
RTECS 
DV2037500
storage temp. 
Hygroscopic, -20°C Freezer, Under Inert Atmosphere
solubility 
DMSO: >5 mg/mL at 60 °C
form 
solid
pka
3.86±0.36(Predicted)
color 
white
Water Solubility 
insoluble
Merck 
14,9129
InChIKey
RMMXLENWKUUMAY-UHFFFAOYSA-N
CAS DataBase Reference
144701-48-4(CAS DataBase Reference)
More
Less

Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-36-26
WGK Germany 
2
HS Code 
2933995300
Hazardous Substances Data
144701-48-4(Hazardous Substances Data)
More
Less

Hazard and Precautionary Statements (GHS)

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1855
Product name
Telmisartan
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
500mg
Price
$160
Updated
2021/03/22
Sigma-Aldrich
Product number
1643419
Product name
Telmisartan
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$366
Updated
2021/03/22
TCI Chemical
Product number
T2861
Product name
Telmisartan
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$116
Updated
2021/03/22
TCI Chemical
Product number
T2861
Product name
Telmisartan
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$290
Updated
2021/03/22
Alfa Aesar
Product number
J61441
Product name
Telmisartan, 99%
Packaging
250mg
Price
$61.5
Updated
2021/03/22
More
Less

Telmisartan Chemical Properties,Usage,Production

Chemical Properties

White or off-white crystalline powder, odorless and tasteless. Soluble in chloroform, slightly soluble in methanol, very slightly soluble in acetone, practically insoluble in water. Slightly soluble in 0.1mol/L hydrochloric acid, soluble in 0.1mol/L sodium hydroxide.
Absorption coefficient(E1%1cm):509~541

Mechanisms of Action

80mg of telmisartan for the human body will practically completely counter the high blood pressure caused by angiotension II. Effects will last for 24 and can still be detected within 48 hours. Blood pressure-lowering effects should gradually become apparent within 3 hours after the initial dose. If treatment is suddenly interrupted, blood pressure will return to the same level as before treatment in a matter of days, and there will be no rebound high blood pressure. In a clinical trial that compared two kinds of antihypertensive drugs, patients in the treatment group experienced lower rates of coughing than those in the group treated by angiotensin converting enzyme inhibitors.
Telmisartan has a half-life of 18~24 hours, and will take effect 1~4 hours after taken. Medicinal effects can last for as long as 35 hours, with a high (T/P) ratio and outstanding effects in controlling morning blood pressure. Thus, this medicine can effectively control blood pressure for 24 hours, and it meets the once-daily medicinal standard (40~80mg, qd).
Clinical effects and characteristics:

  • Pharmacokinetics show: Rapid effects (0.3h), long duration (35.4h), little effect on heart rate when lowering blood pressure.
  • Compared to Enalapril: Stronger antihypertensive effects than Enalapril; when both are used in combination with diuretics, Telmisartan still appears to be superior and results in a lower coughing rate.
  • Compared to Lisinopril: More apparent antihypertensive effects (for both systolic and diastolic blood pressure), coughing rate for Telmisartan (16%) is drastically lower than that of Lisinopril (60%).
  • Compared to Atenolol: Similar antihypertensive effects, lower rate of side effects (impotence and fatigue).
  • Compared to Amlodipine: The Telmisartan group experienced noticeably lower heart rates four hours after ingestion and from six a.m. to twelve p.m.
Overall, Telmisartan has the following characteristics in comparison with other antihypertensive medicine: specific receptor effects, noticeable hypertensive effects, good diuretic effects, improvement of myocardial stenosis, safe usage, good tolerance, and convenient daily dosage.

Side Effects

In the placebo control experiment, the incidence rate of negative events for the Telmisartan group (41.4%) was similar to that of the placebo group (43.9%). Negative events were unrelated to dosage, sex, age, or race.
The following lists negative reactions were accumulated via the 5788 hypertensive patients that were treated with Telmisartan in the clinical trial.
Negative effects are categorized by incident rate as:
Very common (>1/10); common (>1/100, <1/10=); uncommon (>1/1000, <1/100=); rare (>1/10000, <1/1000=); very rare (<1/100000=)
Bodily reaction: Common: Back pain (e.g. sciatica), chest pain, flu-like symptoms, infection symptoms (e.g. urinary tract infection including cystitis). Uncommon: sight abnormality, sweating.
Central and peripheral nervous system: Common: vertigo.
Digestive system: Common: stomach pain, diarrhea, indigestion, gastrointestinal disorders. Rare: dry mouth, bloating.
Muscle skeletal system: Common: joint pain, leg cramps or leg pain, muscle pain. Rare: Tenosensitis 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.
Additionally, since Telmisartan entered the market, there have been individual cases of erythema, itching, syncope, insomnia, depression, stomach discomfort, vomiting, hypotension, bradycardia, tachycardia, dyspnea, eosinophilia, thrombocytopenia, weakness, and reduced work efficiency. Similar to other angiotensin II receptor blockers, very few cases have reported vascular edema, nettles, and other negative reactions.
The laboratory found: compared to the placebo, the Telmisartan group occasionally exhibited lowered hemoglobin or raised uric acid. Any increase in serum creatinine or liver enzymes in the Telmisartan group was similar or lower than that of the placebo group.

Patent

Telmisartan was originally formulated by the German pharmaceutical company Boehringer Ingelheim; it earned the German patent EP502,314 in 1991, was first approved to enter the American market in November 1998, and then entered German, Philippines, Australian, Belgium, British, and other markets.

Description

Telmisartan was launched in the US for the treatment of hypertension. It can be prepared in eight steps starting with methyl 4-amino-3-methyl benzoate; the first and second cyclization into a benzimidazole ring occur at steps 4 and 6 respectively. Telmisartan blocks the action of angiotensin II (Ang II), the primary effector molecule of the renin-angiotensin-aldosterone system (RAAS). It is the sixth of this class of 《sartans》 to be marketed after the lead compound Losartan. Its long lasting effect (24h half-life) could be the main difference with other angiotensin II antagonists. Unlike several other agents in this category, its activity does not depend upon transformation into an active metabolite, the 1-O-acylglucuronide being the principal metabolite found in humans. Telmisartan is a potent competitive antagonist of AT1 receptors that mediate most of the important effects of angiotensin II while lacking affinity for the AT2 subtypes or other receptors involved in cardiovascular regulation. In several clinical studies, Telmisartan, at a once daily dosage, produced effective and sustained blood-pressure lowering effects with a low incidence of side effects (particularly treatment-related cough associated with ACE inhibitors in elderly patients).

Chemical Properties

White or off white crystalline powder

Originator

Boehringer Ingelheim (Germany)

Uses

cardiotonic

Uses

Telmisartan is an angiotensin II receptor antagonist.

Uses

anti-cancer agent

Uses

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.

Manufacturing Process

A solution of 23.9 g (100 mMol) of methyl 3,4-diaminobenzoate dihydrochloride and 11.7 g (110 mMol) of butyric acid chloride in 100 ml of phosphorus oxychloride is refluxed for 2 h. Then about 80 ml of phosphorus oxychloride are distilled off and the residue is mixed with about 150 ml of water. The oily crude product precipitated is extracted three times with 50 ml of ethyl acetate and after evaporation purified by column chromatography (600 g of silica gel; eluant:methylene chloride/methanol (30:1)). Yield of methyl-2-n-propyl-benzimidazole-5-carboxylate: 15.0 g of oil (69%).
A solution of 15.0 g (73 mmol) of methyl 2-n-propyl-benzimidazole-5- carboxylate and 8 g (200 mMol) of sodium hydroxide in 200 ml of water and 400 ml of ethanol is refluxed for 2 h. Then the alcohol is distilled off, the aqueous solution is acidified with dilute sulphuric acid (pH 4-5) and evaporated using a rotary evaporator. The product crystallising out is suction filtered, washed with 50 ml of acetone and 50 ml of diethylether and dried. Yield of 2-n-propyl-benzimidazole-5-carboxylic acid-hemisulphate: 9.1 g (61%), melting point: >220°C.
A solution of 6.7 g (25 mMol) of 2-n-propyl-benzimidazole-5-carboxylic acidhemisulphate and 4.9 g (25 mMol) of 2-methylaminoaniline dihydrochloride in 200 g of polyphosphoric acid is stirred for 5 h at 150°C, then poured onto 600 ml of water and made alkaline with concentrated ammonia whilst cooling with ice. The resulting solution is extracted three times with 200 ml of ethyl acetate, the crude product thus obtained is purified by column chromatography (300 g of silica gel; eluant:methylene chloride/methanol = 15:1). Yield of 2-n-propy1-5-(1-methylbenzimidazol-2-yl)-benzimidazole: 2.8 g of oil (39%).
A solution of 2.0 g (6.9 mMol) of 2-n-propyl-5-(1-methylbenzimidazol-2-yl)- benzimidazole and 0.91 g (7.5 mmol) of potassium tert-butoxide in 50 ml of dimethylsulfoxide is stirred for 90 min at room temperature, then 2.6 g (7.5 mMol) of tert-butyl 4'-bromomethyl-biphenyl-2-carboxylate are added and the mixture is stirred for a further 15 h at room temperature. The mixture is then poured onto 300 ml of water and extracted three times with 50 ml of ethyl acetate. The crude product obtained after evaporation of the organic phase is purified by column chromatography (300 g silica gel; eluant:methylene chloride/methanol = 30:1). In this way, 2.7 g (70%) of an isomer mixture are obtained (by NMR spectroscopy), contains about 1.18 g of tert-butyl-4'-[(2-npropyl- 5-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl)-methyl]biphenyl-2- carboxylate and about 1.52 g of tert-butyl 4'-[(2-n-propyl-6-(1- methylbenzimidazol-2-yl)-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylate).
2.70 g of the isomer mixture obtained above are dissolved in 100 ml of methylene chloride, mixed with 40 ml of trifluoroacetic acid and stirred for 4 h at room temperature. The mixture is then evaporated to dryness in vacuo, the residue is dissolved in 100 ml of 2 N sodium hydroxide solution, the solution is washed with 50 ml of diethylether and the product mixture is precipitated by acidifying the aqueous phase with acetic acid. By column chromatography (400 g of silica gel, eluant:methylene chloride/methanol = 15:1) of the solid thus obtained 0.9 g (74%) of 4'-[[2-n-propyl-6-(1-methylbenzimidazol-2-yl)- benzimidazol-1-yl]methyl]biphenyl-2-carboxylate, melting point 217°-218°C.

brand name

Micardis (Boehringer Ingelheim).

Therapeutic Function

Antihypertensive

General Description

Telmisartan, 4'-[(1,4'-dimethyl-2'-propyl[2,6'-bi-1H-benzimidazol]-1'-yl)methyl]-[1,1'-biphenyl]-2-carboxylic acid (Micardis), does not appear to bear any structuralrelationship to this class, but there is actually a great dealof overlap in the chemical architecture with other agents. Thefirst, and most significant, difference is the replacement of theacidic tetrazole system with a simple carboxylic acid. Thisacid, like the tetrazole, plays a role in receptor binding. Thesecond difference is the lack of a carboxylic acid near the imidazolenitrogen that also contributes to receptor binding.As with irbesartan, however, there is not a need for this groupto be acidic but, rather, to be one that participates in receptorbinding. The second imidazole ring, much like a purine basein deoxyribonucleic acid (DNA), can hydrogen bond with theangiotensin II receptor.

Telmisartan Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Telmisartan Suppliers

Changzhou Yabang Pharmaceutical Co., Ltd.
Tel
0519-86388158-
Email
sales@yabangpharma.com
Country
China
ProdList
1
Advantage
58
Beri Pharma Co., Ltd.
Tel
0756-8699456-
Fax
+86-756-8699456
Email
sales@zhberi.com
Country
China
ProdList
211
Advantage
58
Jiangsu United-value International Trading Co., Ltd.
Tel
0519-89885611 89885616 15312500313
Fax
+86(519)89885615
Email
luke.li@uvcs.cn.com
Country
China
ProdList
476
Advantage
58
Jiangsu Zhongbang Pharmaceutical Co., Ltd
Tel
025-87151129
Fax
0086-25- 87151120
Email
sales@chinaredsun.com
Country
China
ProdList
142
Advantage
58
Suzhou Langen Biotechnology Co., Ltd.
Fax
+86-512-58875450
Email
380766406@QQ.COM
Country
China
ProdList
110
Advantage
58
Absin Bioscience Inc.
Tel
021-38015121-
Email
info@absin.cn
Country
China
ProdList
12787
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96500
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40264
Advantage
62
INTATRADE GmbH
Tel
+49 3493/605464
Fax
+49 3493/605470
Email
sales@intatrade.de
Country
Germany
ProdList
3579
Advantage
66
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15877
Advantage
69
More
Less

View Lastest Price from Telmisartan manufacturers

Wuhan wingroup Pharmaceutical Co., Ltd
Product
Telmisartan 144701-48-4
Price
US $5.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100 Tons
Release date
2021-07-14
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Telmisartan 144701-48-4
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-09-26
Hebei Lingding Biological Technology Co., Ltd
Product
Telmisartan 144701-48-4
Price
US $95.00-46.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
9000kg/per week
Release date
2021-07-23

144701-48-4, TelmisartanRelated Search:


  • 4'-[{1,4'-Dimethyl-2'-Propyl[2,6'-Bi-1H-Benzimiaszol]-1'yl}-Methyl}-1,1'-Biphenyl-2-Caroxylic Acid Dimethyl Ethyl Ester
  • 4'-[{1,4'-Dimethyl-2'-Propyl[2,6'-Bi-1H-Benzimiaszol]-1'yl}-Methyl}-1,1'-Biphenyl-2-Caroxylic Acid
  • 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
  • 4'-(1,7'-Dimethyl-2'-propyl-1H-
  • BIBR 277, 4μ[(1,4μ-Dimethyl-2μ-propyl[2,6μ-bi-1H-benzimidazol]-1μ-yl)methyl][1,1μ-biphenyl]-2-carboxylic acid
  • 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
  • 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
  • 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
  • Telmisattan
  • timishatyan
  • BIBR 277
  • 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
  • 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
  • TU-199
  • TELMISARTAN
  • PRITOR
  • MICARDIS
  • 4'-((1,7'-Dimethyl-2'-propyl-1H,3'H-[2,5'-bibenzo[d]imidazol]-3'-yl)methyl)-[1,1'-biphenyl]-2-car
  • (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
  • 2-[4-[[4-methyl-6-(1-methylbenzimidazol-2-yl)-2-propyl-benzimidazol-1-yl]methyl]phenyl]benzoic acid
  • 2-[4-[[4-methyl-6-(1-methylbenzimidazol-2-yl)-2-propylbenzimidazol-1-yl]methyl]phenyl]benzoic acid
  • 4'-[(1,7'-dimethyl-2'-propyl-1H,3'H-2,5'-bibenzimidazol-3'-yl)methyl]biphenyl-2-carboxylic acid
  • Telmisartan Synonyms 4'[(1,4'-Dimethyl-2'-propyl[2,6'-bi-1H-benzimidazol]-1'-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-
  • Telmisartan for system suitability CRS
  • Telmisartan for peak identification CRS
  • Telmisartan CRS
  • misartan
  • Telmisartan USP/EP/BP
  • Telmisartan (10mM in DMSO)
  • 144701-48-4
  • 144704-48-4
  • 1447014-48-4
  • C16H18N4O3S
  • C33H30N4O2
  • C20H24N2O5SD4
  • C33H27N4O2D3
  • C37H38N4O2
  • CARADRIN