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Valsartan(CAS No. 137862-53-4)

Valsartan C24H29N5O3 (cas 137862-53-4) Molecular Structure

137862-53-4 Structure

Identification and Related Records

【Name】
Valsartan
【Iupac name】
(2S)-3-methyl-2-[pentanoyl-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]
methyl]amino]butanoic acid
【CAS Registry number】
137862-53-4
【Synonyms】
L-Valine,N-(1-oxopentyl)-N-[[2'-(1H-tetrazol- 5-yl)[1,1'-biphenyl]-4-yl]methyl]-
Diovan
Diovan (TN)
L-Valine, N-(1-oxopentyl)-N-((2-(1H-tetrazol-5-yl)(1,1-biphenyl)-4-yl)methyl)-
N-(p-(o-1H-Tetrazol-5-ylphenyl)benzyl)-N-valeryl-L-valine
Valsartan [USAN:INN]
N-(1-n.Pentanoyl)-N-[[2'-(1H-tetrazol-5-yl)[1',1- biphenyl]-4-yl]methyl]-L-valine
Dihydrotachystero
Valsartan USP30
【Molecular Formula】
C24H29N5O3 (Products with the same molecular formula)
【Molecular Weight】
435.52 .
【Inchi】
InChI=1S/C24H29N5O3/c1-4-5-10-21(30)29(22(16(2)3)24(31)32)15-17-11-13-18(14-12-17)19-8-6-7-9-20(19)23-25-27-28-26-23/h6-9,11-14,16,22H,4-5,10,15H2,1-3H3,(H,31,32)(H,25,26,27,28)/t22-/m0/s1
【Canonical SMILES】
CCCCC(=O)N(CC1=CC=C(C=C1)C2=CC=CC=C2C3=NNN=N3)C(C(C)C)C(=O)O
【Isomers smiles】
CCCCC(=O)N(CC1=CC=C(C=C1)C2=CC=CC=C2C3=NNN=N3)[C@@H](C(C)C)C(=O)O
【MOL File】
137862-53-4.mol

Chemical and Physical Properties

【Appearance】
white crystalline powder
【Density】
1.212 g/cm3
【Melting Point】
116-117 °C
【Boiling Point】
684.9 °C at 760 mmHg
【Flash Point】
368 °C
【Solubilities】
Soluble
【Color/Form】
White to practically white fine powder
Crystals from diisopropyl ether
【Storage temp】
Store in original container in a cool dark place.
【Computed Properties】
Molecular Weight:435.51876 [g/mol]
Molecular Formula:C24H29N5O3
XLogP3-AA:4.4
H-Bond Donor:2
H-Bond Acceptor:4
Rotatable Bond Count:10
Tautomer Count:2
Exact Mass:435.22704
MonoIsotopic Mass:435.22704
Topological Polar Surface Area:112
Heavy Atom Count:32
Formal Charge:0
Complexity:608
Isotope Atom Count:0
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Anion Count:1
Feature 3D Cation Count:1
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:3
Effective Rotor Count:11
Conformer Sampling RMSD:1
CID Conformer Count:50

Safety and Handling

【Hazard Codes】
Xi: Irritant;
【Risk Statements】
R36/37/38
【Safety Statements 】
26-37/39
【Safety】

Hazard Codes:?IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S37/39:Wear suitable gloves and eye/face protection.

【Transport】
10kgs
【Formulations/Preparations】
Oral: Tablets: 40 mg Diovan, (Novartis), 80 mg Diovan, (Novartis), 160 mg Diovan, (Novartis), 320 mg Diovan, (Novartis).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl valsartan, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Specification】

?Valsartan (CAS NO.137862-53-4) is also named as?CGP 48933 ; Diovan ; HSDB 7519 ; UNII-80M03YXJ7I ; Valtan ; Valzaar?; L-Valine, N-(1-oxopentyl)-N-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)- ; N-(p-(o-1H-Tetrazol-5-ylphenyl)benzyl)-N-valeryl-L-valine?.?It is an angiotensin II receptor antagonist (more commonly called an "ARB", which stands for angiotensin receptor blocker), with particularly high affinity for the type I (AT1) angiotensin receptor.

【Octanol/Water Partition Coefficient】
log Kow = 3.65 (est)
【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

【Usage】

A nonpeptide angiotensin II AT1-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.
- Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
【Therapeutic Uses】
In clinically stable patients with left ventricular failure or left ventricular dysfunction following myocardial infarction, valsartan is indicated to reduce cardiovascular mortality. /Included in US product labeling/
Valsartan is indicated for the treatment of hypertension. It may be used alone or in combination with other antihypertensive medications. Valsartan is normally used in those patients in whom treatment with a diuretic or beta-blocker was ineffective or associated with unacceptable side effects. Valsartan may be used as an initial agent in those patients in whom the use of diuretics and/or beta-blockers is contraindicated or in patients with medical conditions in which these drugs frequently cause serious side effects. /Included in US product labeling/
Valsartan is indicated for the treatment of heart failure (NYHA class II-IV). In a controlled clinical trial, valsartan significantly reduced hospitalizations for heart failure. There is not evidence that valsartan provides added benefits when it is used with an adequate dose of an ACE inhibitor. /Included in US product labeling/
/EXPL THER:/ In order to investigate the effect of angiotensin receptor blockage for the treatment on diabetic erectile dysfunction, we used male Sprague-Dawley rats injected with 65 mg/kg streptozotocin to induce diabetes mellitus. The diabetic rats with erectile dysfunction were selected by hypodermic injection of apomorphine after 8 weeks of model setting. All rats were divided into four groups: G1 (normal control rats), G2 (diabetic rats treated with normal saline), G3 (diabetic rats treated with valsartan) and G4 (diabetic rats treated with spironolactone). After treatment with drugs for 8 weeks, the rate of erection for each group was evaluated after the injection of apomorphine. The intracavernous pressure of each rat was then recorded before and after the electrostimulation of the major pelvic ganglion. The rates of erection and the intracavernous pressure after electrostimulation for diabetic rats treated with valsartan were significantly higher than that in diabetic rats treated with normal saline and spironolactone. The angiotensin receptor blockage may be an effective therapy for diabetics with erectile dysfunction. [Chen Y et al; Int J Impot Res (2006)]
【Biomedical Effects and Toxicity】
Valsartan, when administered as an oral solution, is primarily recovered in feces (about 83% of dose) and urine (about 13% of dose). The recovery is mainly as unchanged drug, with only about 20% of dose recovered as metabolites. ... Following intravenous administration, plasma clearance of valsartan is about 2 L/hr and its renal clearance is 0.62 L/hr (about 30% of total clearance).
Absolute bioavailability for the capsule formulation is approximately 25% (range, 10-35%). Food decreases the area under the plasma concentration-time curve (AUC) and peak plasma concentration by approximately 40 and 50%, respectively.
Valsartan peak plasma concentration is reached 2 to 4 hours after dosing. Valsartan shows biexponential decay kinetics following intravenous administration, with an average elimination half-life of about 6 hours. Absolute bioavailability for the capsule formulation is about 25% (range 10%-35%). Food decreases the exposure (as measured by AUC) to valsartan by about 40% and peak plasma concentration (Cmax) by about 50%. AUC and Cmax values of valsartan increase approximately linearly with increasing dose over the clinical dosing range. Valsartan does not accumulate appreciably in plasma following repeated administration.
The steady state volume of distribution of valsartan after intravenous administration is small (17 L), indicating that valsartan does not distribute into tissues extensively. Valsartan is highly bound to serum proteins (95%), mainly serum albumin.
It is not known whether valsartan is excreted in human milk, but valsartan was excreted in the milk of lactating rats. ...
... In an investigation of pharmacokinetics and pharmacodynamics in normotensive male volunteers, valsartan was rapidly absorbed with the maximal plasma concentration occurring 2-3 hr after oral administration. The elimination half-life was about 4-6 hr, valsartan was poorly metabolized, and most of the drug was excreted via feces. ... [Kimura M et al; Nippon Yakurigaku Zasshi 120 (5): 353-60 (2002)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.0X10+6(SRC), determined from a structure estimation method(2), indicates that valsartan is expected to be immobile in soil(SRC). Volatilization of valsartan from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.1X10-18 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Valsartan is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.2X10-16 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2007).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.0X10+6(SRC), determined from a structure estimation method(2), indicates that valsartan is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.1X10-18 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 3.65(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation date were not available(SRC, 2007).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), valsartan, which has an estimated vapor pressure of 8.2X10-16 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase valsartan may be removed from the air by wet or dry deposition(SRC). Valsartan contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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