Telmisartan
- CAS No.
- 144701-48-4
- Chemical Name:
- Telmisartan
- Synonyms
- MICARDIS;TU-199;TIMISHATAN;Telmisaran;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
- Molecular Weight:
- 514.62
- MOL File:
- 144701-48-4.mol
- MSDS File:
- SDS
- Modify Date:
- 2025/1/27 9:38:02
| 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 |
| pka | 3.86±0.36(Predicted) |
| form | solid |
| color | white |
| Water Solubility | insoluble |
| Merck | 14,9129 |
| BCS Class | 2 |
| Stability | Hygroscopic |
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H315-H319-H335 |
| Precautionary statements | P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501c |
| 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) |
Telmisartan price More Price(5)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | T8949 | Telmisartan ≥98% (HPLC), solid | 144701-48-4 | 10MG | ₹18759.73 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | T8949 | Telmisartan ≥98% (HPLC), solid | 144701-48-4 | 50MG | ₹73945.58 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1855 | Telmisartan Pharmaceutical Secondary Standard; Certified Reference Material | 144701-48-4 | 500MG | ₹18954.58 | 2022-06-14 | Buy |
| TCI Chemicals (India) | T2861 | Telmisartan | 144701-48-4 | 1G | ₹7600 | 2022-05-26 | Buy |
| TCI Chemicals (India) | T2861 | Telmisartan | 144701-48-4 | 5G | ₹19600 | 2022-05-26 | Buy |
Telmisartan Chemical Properties,Uses,Production
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
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.
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.
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.
Telmisartan Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| GLR Innovations | +91 9891111994 | New Delhi, India | 4535 | 58 | Inquiry |
| Jigs Chemical ltd | +919099003427 | Gujarat, India | 239 | 58 | Inquiry |
| Cadila Pharmaceuticals Ltd | +91-7069076657 +91-7069076657 | Ahmedabad, India | 53 | 58 | Inquiry |
| HEMA PHARMACEUTICALS PVT LTD | +91-9537936912 +91-9537936912 | Gujarat, India | 48 | 58 | Inquiry |
| SURYA LIFE SCIENCES LIMITED | +91-2646226290 +91-9428511112 | Gujarat, India | 61 | 58 | Inquiry |
| SGMR PHARMACEUTICALS PVT LTD | +91-9032001889 +91-9032001889 | Telangana, India | 83 | 58 | Inquiry |
| ANWITA APIS | +919000311012 | Hyderabad, India | 195 | 58 | Inquiry |
| J S LABS | +91-7330612784 +91-7330612784 | Tamil Nadu, India | 159 | 58 | Inquiry |
| SEUTIC | +91-8309787199 +91-8309787199 | Hyderabad, India | 124 | 58 | Inquiry |
| Prajna generics pvt ltd | +91-9441174873 +91-9441174873 | Hyderabad, India | 24 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| GLR Innovations | 58 |
| Jigs Chemical ltd | 58 |
| Cadila Pharmaceuticals Ltd | 58 |
| HEMA PHARMACEUTICALS PVT LTD | 58 |
| SURYA LIFE SCIENCES LIMITED | 58 |
| SGMR PHARMACEUTICALS PVT LTD | 58 |
| ANWITA APIS | 58 |
| J S LABS | 58 |
| SEUTIC | 58 |
| Prajna generics pvt ltd | 58 |
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Related Qustion
- Q:Is telmisartan the same as losartan?
- A:The most often prescribed ARBs are telmisartan and losartan. Both drugs are ARBs. However, they are different.
- Jun 11，2024
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