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Telmisartan(CAS No. 144701-48-4)

Telmisartan C33H30N4O2 (cas 144701-48-4) Molecular Structure

144701-48-4 Structure

Identification and Related Records

【Name】
Telmisartan
【Iupac name】
2-[4-[[4-methyl-6-(1-methylbenzimidazol-2-yl)-2-propylbenzimidazol-1-yl]
methyl]phenyl]benzoic acid
【CAS Registry number】
144701-48-4
【Synonyms】
(1,1-Biphenyl)-2-carboxylic acid, 4-((1,4-dimethyl-2-propyl(2,6-bi-1H-benzimidazol)-1-yl)methyl)-
Micardis
4-((4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl)methyl)-2-biphenylcarboxylic acid
Timetazidine
4'-[(1,4'-dimethyl-2'-propyl[2,6'-bi-1H-benzimidazol]-1'-yl)methyl]- [1,1'-biphenyl]-2-carboxylic acid
【Molecular Formula】
C33H30N4O2 (Products with the same molecular formula)
【Molecular Weight】
514.62
【Inchi】
InChI=1/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)
【Canonical SMILES】
CCCC1=NC2=C(C=C(C=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C(=O)O)C5=NC6=CC=CC=C6N5C)C
【MOL File】
144701-48-4.mol

Chemical and Physical Properties

【Appearance】
White or off white crystalline powder
【Density】
1.24g/cm3
【Melting Point】
261-263°C
【Boiling Point】
771.9°Cat760mmHg
【Vapour】
0mmHg at 25°C
【Refractive Index】
1.624
【Flash Point】
420.6°C
【Water】
insoluble
【Solubilities】
insoluble in water
【Color/Form】
white
【Stability】
Stable at normal temperatures and pressures.
【Storage temp】
Store in a cool, dry place (25 C). The bottles should be kept tightly closed.
【Computed Properties】
Molecular Weight:514.6169 [g/mol]
Molecular Formula:C33H30N4O2
XLogP3-AA:6.9
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:7
Tautomer Count:4
Exact Mass:514.236876
MonoIsotopic Mass:514.236876
Topological Polar Surface Area:72.9
Heavy Atom Count:39
Formal Charge:0
Complexity:831
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Anion Count:1
Feature 3D Cation Count:2
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:6
Effective Rotor Count:7
Conformer Sampling RMSD:1
CID Conformer Count:62

Safety and Handling

【Hazard Codes】
Xi: Irritant;
【Risk Statements】
R36/37/38
【Safety Statements 】
S22;S24/25
【Safety】

Safety Information about?Telmisartan (CAS NO.144701-48-4):
Hazard Codes:?IrritantXi
Risk Statements: 36/37/38?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36-26?
S22: Do not breathe dust.?
S24/25: Avoid contact with skin and eyes.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36: Wear suitable protective clothing.
WGK Germany: 2

【Formulations/Preparations】
Oral: Tablets: 20 mg Micardis (with povidone), (Boehringer Ingelheim (also promoted by Abbott)); 40 mg Micardis (with povidone), (Boehringer Ingelheim (also promoted by Abbott)); 80 mg Micardis (with povidone), (Boehringer Ingelheim (also promoted by Abbott)).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl telmisartan, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Octanol/Water Partition Coefficient】
log Kow = 8.42 (est)
【Report】

It is believed that telmisartan’s dual mode of action may provide protective benefits against the vascular and renal damage caused by diabetes and cardiovascular disease (CVD).

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation: N. Hauel et al, EP 502314 (1992 to Thomae)
【Usage】

An angiotensin II receptor antagonist

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents that antagonize ANGIOTENSIN II TYPE 1 RECEPTOR. Included are ANGIOTENSIN II analogs such as SARALASIN and biphenylimidazoles such as LOSARTAN. Some are used as ANTIHYPERTENSIVE AGENTS.
- A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility.
【Therapeutic Uses】
Telmisartan is indicated for the treatment of hypertension when diuretic or beta-adrenergic blocker therapy has failed, or is contraindicated, or in the event that side effects of these agents are too severe. It may be used alone or in combination with other antihypertensive medications. /Included in US product labeling/
/EXPL THER/: The term nonalcoholic steatohepatitis (NASH) has recently been proposed to identify a fatty liver disease accompanied by diffuse fatty infiltration and inflammation. However, no drug therapy has been established for NASH as yet. In the present study, ... the effect of the angiotensin II type 1 receptor antagonist telmisartan on the development of NASH in a rat model /is examined/. Telmisartan, but not the angiotensin receptor antagonist valsartan, markedly attenuated hepatic steatosis, inflammation, and fibrosis in these rats. The quantitative parameters of steatosis, inflammation, and fibrosis were also ameliorated by treatment with telmisartan. Compared with telmisartan, the peroxisome proliferator-activated receptor-gamma agonist pioglitazone attenuated hepatic steatosis and fibrosis of the liver to a similar degree. However, telmisartan, but not pioglitazone, dramatically decreased both subcutaneous and visceral fat. In conclusion, these results indicated that telmisartan should be the drug of first choice for the treatment of patients with NASH. [Fujita K et al; Dig Dis Sci 52 (12): 3455-64 (2007)]
【Biomedical Effects and Toxicity】
Following either intravenous or oral administration of (14)C-labeled telmisartan, most of the administered dose (>97%) was eliminated unchanged in feces via biliary excretion; only minute amounts were found in the urine (0.91% and 0.49% of total radioactivity, respectively).
Following oral administration, peak concentrations (Cmax) of telmisartan are reached in 0.5-1 hour after dosing. Food slightly reduces the bioavailability of telmisartan, with a reduction in the area under the plasma concentration-time curve (AUC) of about 6% with the 40 mg tablet and about 20% after a 160 mg dose. The absolute bioavailability of telmisartan is dose dependent. At 40 and 160 mg the bioavailability was 42% and 58%, respectively. The pharmacokinetics of orally administered telmisartan are nonlinear over the dose range 20-160 mg, with greater than proportional increases of plasma concentrations (Cmax and AUC) with increasing doses. Telmisartan shows bi-exponential decay kinetics with a terminal elimination half life of approximately 24 hours. Trough plasma concentrations of telmisartan with once daily dosing are about 10-25% of peak plasma concentrations. Telmisartan has an accumulation index in plasma of 1.5 to 2.0 upon repeated once daily dosing.
Telmisartan is highly bound to plasma proteins (>99.5%), mainly albumin and alpha 1-acid glycoprotein. Plasma protein binding is constant over the concentration range achieved with recommended doses. The volume of distribution for telmisartan is approximately 500 liters indicating additional tissue binding.
It is not known whether telmisartan is excreted in human milk, but telmisartan was shown to be present in the milk of lactating rats.
Telmisartan has been shown to be present in rat fetuses during late gestation and in rat milk.
To study the pharmacolkinetics of telmisartan in healthy Chinese male subjects after oral administration of two dosage levels, 36 healthy subjects were divided into two groups and given a single oral dose of 40 or 80 mg telmisartan (CAS 144701-48-4, MicardisPlus). A sensitive liquid chromatography-tandem mass spectrometry method (LC-MS-MS) was used for the determination of telmisartan in plasma. Both, a non-compartmental and compartmental method were used for analysis of parameters of kinetics. The main pharmacokinetic parameters of the 40 mg and 80 mg regimen group were as follows: t(max) (1.76 +/- 1.75) h, (1.56 +/- 1.09) h, C(max) (163.2 +/- 128.4) ng/mL, (905.7 +/- 583.4) ng/mL, t1/2 (23.6 +/- 10.8) h, (23.0 +/- 6.4) h, AUC(o-t) (1456 +/- 1072) ng x h/mL, (6759 +/- 3754) ng x h/mL, AUC(o-infinity (1611 +/- 1180) ng x h/mL, (7588 +/- 4661) ng x h/mL, respectively. After dose normalization, there was significant difference for main pharmacokinetic parameters C(max) AUC(o-t) and AUC(o-infinity) between two dosage level groups. The plasma concentration-time profile of telmisartan was characterized by a high degree of inter-individual variability and the disposition of telmisartan in healthy Chinese subjects was dose-dependent. The pharmacokinetic parameters C(max) and AUC(o-inifinity) of the 80 mg regimen group increased to about 5-fold compared to that of the 40 mg regimen group, but there was no significant difference for t(max) and t1/2 between the two dose groups. [Zhang P et al; Arzneimittelforschung 56 (8): 569-73 (2006)] PubMed Abstract

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