Chemical Properties Mechanisms of Action Side Effects Patent
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Telmisartan

Chemical Properties Mechanisms of Action Side Effects Patent
Product Name
Telmisartan
CAS No.
144701-48-4
Chemical Name
Telmisartan
Synonyms
MICARDIS;TU-199;Telmisaran;TIMISHATAN;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,4′[(1,4′-Dimethyl-2′-propyl[2,6′-bi-1H-benzimidazol]-1′-yl)methyl][1,1′-biphenyl]-2-carboxylic acid, BIBR 277;PRITOR;BIBR 277;misartan;BIBR 277SE
CBNumber
CB4266172
Molecular Formula
C33H30N4O2
Formula Weight
514.62
MOL File
144701-48-4.mol
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Telmisartan Property

Melting point:
261-263°C
Boiling point:
771.9±70.0 °C(Predicted)
Density 
1.16
RTECS 
DV2037500
storage temp. 
2-8°C
solubility 
DMSO: >5 mg/mL at 60 °C
form 
solid
pka
3.86±0.36(Predicted)
color 
white
Water Solubility 
insoluble
Merck 
14,9129
BCS Class
2
Stability:
Hygroscopic
InChI
InChI=1S/C33H30N4O2/c1-4-9-30-35-31-21(2)18-24(32-34-27-12-7-8-13-28(27)36(32)3)19-29(31)37(30)20-22-14-16-23(17-15-22)25-10-5-6-11-26(25)33(38)39/h5-8,10-19H,4,9,20H2,1-3H3,(H,38,39)
InChIKey
RMMXLENWKUUMAY-UHFFFAOYSA-N
SMILES
C1(C2=CC=C(CN3C(CCC)=NC4=C(C)C=C(C5N(C)C6=CC=CC=C6N=5)C=C43)C=C2)=CC=CC=C1C(O)=O
CAS DataBase Reference
144701-48-4(CAS DataBase Reference)
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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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

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

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1855
Product name
Telmisartan
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
500mg
Price
$214
Updated
2024/03/01
Sigma-Aldrich
Product number
1643419
Product name
Telmisartan
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
T2861
Product name
Telmisartan
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$144
Updated
2024/03/01
TCI Chemical
Product number
T2861
Product name
Telmisartan
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$358
Updated
2024/03/01
Alfa Aesar
Product number
J61441
Product name
Telmisartan, 99%
Packaging
250mg
Price
$69.8
Updated
2023/06/20
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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 is an angiotensin receptor blocker (ARB), It is used in the treatment of hypertension also effective in cardiovascular risk reduction.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.

Chemical Properties

White or off white crystalline powder

Originator

Boehringer Ingelheim (Germany)

Uses

Telmisartan, an angiotensin II receptor antagonist, is an effective medication for the treatment of hypertension. It can be used alone or in combination with other antihypertensive drugs. Additionally, it is beneficial in the treatment of diabetic nephropathy in hypertensive individuals with type 2 diabetes mellitus. Telmisartan is also used to address congestive heart issues.

Definition

ChEBI: Telmisartan is a member of the class of benzimidazoles used widely in the treatment of hypertension. It has a role as an antihypertensive agent, an angiotensin receptor antagonist, an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, a xenobiotic and an environmental contaminant. It is a member of biphenyls, a member of benzimidazoles and a carboxybiphenyl.

Manufacturing Process

Telmisartan was synthesized through the reaction of methyl 3,4-diaminobenzoate dihydrochloride and butyric acid chloride in the presence of phosphorous oxychloride, with subsequent purification steps:
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 Telmisartan, 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.

Biochem/physiol Actions

Telmisartan is a non-peptide AT1 angiotensin receptor antagonist.

Clinical Use

Angiotensin-II antagonist:
Hypertension
Prevention of cardiovascular events

Synthesis

Telmisartan 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.

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 impairment with ACE-Is and aliskiren.
Cardiac glycosides: concentration of digoxin increased.
Ciclosporin: increased risk of hyperkalaemia and nephrotoxicity.
Diuretics: enhanced hypotensive effect; hyperkalaemia with potassium-sparing diuretics.
ESAs: increased risk of hyperkalaemia; antagonism of hypotensive effect.
Lithium: reduced excretion (possibility of enhanced lithium toxicity).
Potassium salts: increased risk of hyperkalaemia.
Tacrolimus: increased risk of hyperkalaemia and nephrotoxicity.

Metabolism

Telmisartan is metabolised by conjugation to the glucuronide of the parent compound. No pharmacological activity has been shown for the conjugate.
Telmisartan is excreted almost entirely in the faeces via bile, mainly as unchanged drug.

Clinical claims and research

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).

Telmisartan Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Telmisartan manufacturers

Hebei Dangtong Import and export Co LTD
Product
Telmisartan 144701-48-4
Price
US $100.00-92.00/kilograms
Min. Order
10kilograms
Purity
99%
Supply Ability
100tons
Release date
2023-02-15
Sinoway Industrial co., ltd.
Product
Telmisartan 144701-48-4
Price
US $0.00/Kg/Bag
Min. Order
2Kg/Bag
Purity
EP / USP
Supply Ability
20 tons
Release date
2022-07-19
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

144701-48-4, TelmisartanRelated Search:


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  • 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
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  • TIMISHATAN
  • 4′-((2-n-Propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl)methyl)biphenyl-2-carbonsure
  • TU-199
  • TELMISARTAN
  • PRITOR
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  • 2-[4-[[4-methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl]methyl]phenyl]benzoic acid
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  • 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-
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