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137862-53-4 molecular structure
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(2S)-3-methyl-2-[N-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)pentanamido]butanoic acid

ChemBase ID: 62
Molecular Formular: C24H29N5O3
Molecular Mass: 435.51876
Monoisotopic Mass: 435.22703981
SMILES and InChIs

SMILES:
OC(=O)[C@@H](N(Cc1ccc(cc1)c1c(cccc1)c1n[nH]nn1)C(=O)CCCC)C(C)C
Canonical SMILES:
CCCCC(=O)N([C@H](C(=O)O)C(C)C)Cc1ccc(cc1)c1ccccc1c1n[nH]nn1
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
InChIKey:
ACWBQPMHZXGDFX-QFIPXVFZSA-N

Cite this record

CBID:62 http://www.chembase.cn/molecule-62.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-3-methyl-2-[N-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)pentanamido]butanoic acid
(2S)-3-methyl-2-[N-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)pentanamido]butanoic acid
IUPAC Traditional name
valsartan
diovan
(2S)-3-methyl-2-[N-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)pentanamido]butanoic acid
Brand Name
Diovan
Valsarran
Synonyms
valsartan
Valsartan
(S)-2-(N-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid
N-(1-Oxopentyl)-N-[[2′-(2H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl]-L-valine
Diovan
Valtan
L-Valsartan
Valsartan
CAS Number
137862-53-4
MDL Number
MFCD00865840
PubChem SID
160963525
46509000
PubChem CID
60846

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.3663416  H Acceptors
H Donor LogD (pH = 5.5) 4.1015096 
LogD (pH = 7.4) 2.052606  Log P 5.269379 
Molar Refractivity 134.7733 cm3 Polarizability 48.579018 Å3
Polar Surface Area 112.07 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five false 
Log P 3.68  LOG S -4.27 
Solubility (Water) 2.34e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO: ≥20 mg/mL expand Show data source
Apperance
white to tan powder expand Show data source
Optical Rotation
[α]/D -55 to -70°, c = 1 in methanol expand Show data source
Hydrophobicity(logP)
5.8 expand Show data source
Storage Condition
-20°C expand Show data source
desiccated expand Show data source
Storage Warning
IRRITANT expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
TSCA Listed
false expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
Angiotensin recep expand Show data source
Mechanism of Action
Angiotensin 2 receptor antagonist expand Show data source
Purity
≥98% (HPLC) expand Show data source
95+% expand Show data source
Salt Data
Free Base expand Show data source
Application(s)
Antihypertensive agent expand Show data source
Empirical Formula (Hill Notation)
C24H29N5O3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals
DrugBank - DB00177 external link
Item Information
Drug Groups approved; investigational
Description Valsartan is an angiotensin-receptor blocker (ARB) that may be used to treat a variety of cardiac conditions including hypertension, diabetic nephropathy and heart failure. Valsartan lowers blood pressure by antagonizing the renin-angiotensin-aldosterone system (RAAS); it competes with angiotensin II for binding to the type-1 angiotensin II receptor (AT1) subtype and prevents the blood pressure increasing effects of angiotensin II. Unlike angiotensin-converting enzyme (ACE) inhibitors, ARBs do not have the adverse effect of dry cough. Valsartan may be used to treat hypertension, isolated systolic hypertension, left ventricular hypertrophy and diabetic nephropathy. It may also be used as an alternative agent for the treatment of heart failure, systolic dysfunction, myocardial infarction and coronary artery disease.
Indication May be used as a first line agent to treat uncomplicated hypertension, isolated systolic hypertension and left ventricular hypertrophy. May be used as a first line agent to delay progression of diabetic nephropathy. Losartan may be also used as a second line agent in the treatment of congestive heart failure, systolic dysfunction, myocardial infarction and coronary artery disease in those intolerant of ACE inhibitors.
Pharmacology Valsartan belongs to a class of antihypertensive agents called angiotensin II receptor blockers (ARBs). Valsartan is a specific and selective type-1 angiotensin II receptor (AT1) antagonist which blocks the blood pressure increasing effects angiotensin II via the renin-angiotensin-aldosterone system (RAAS). RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from granular cells of the juxtaglomerular apparatus in the kidneys. Renin cleaves circulating angiotensinogen to angiotensin I, which is cleaved by angiotensin converting enzyme (ACE) to angiotensin II. Angiotensin II increases blood pressure by increasing total peripheral resistance, increasing sodium and water reabsorption in the kidneys via aldosterone secretion, and altering cardiovascular structure. Angiotensin II binds to two receptors: AT1 and type-2 angiotensin II receptor (AT2). AT1 is a G-protein coupled receptor (GPCR) that mediates the vasoconstrictive and aldosterone-secreting effects of angiotensin II. Studies performed in recent years suggest that AT2 antagonizes AT1-mediated effects and directly affects long-term blood pressure control by inducing vasorelaxation and increasing urinary sodium excretion. Angiotensin receptor blockers (ARBs) are non-peptide competitive inhibitors of AT1. ARBs block the ability of angiotensin II to stimulate pressor and cell proliferative effects. Unlike ACE inhibitors, ARBs do not affect bradykinin-induced vasodilation. The overall effect of ARBs is a decrease in blood pressure.
Affected Organisms
Humans and other mammals
Biotransformation Valsartan is excreted largely as unchanged drug (80%) and is minimally metabolized in humans. The primary circulating metabolite, 4-OH-valsartan, is pharmacologically inactive and produced CYP2C9. 4-OH-valsartan accounts for approximately 9% of the circulating dose of valsartan. Although valsartan is metabolized by CYP2C9, CYP-mediated drug-drug interactions between valsartan and other drugs is unlikely.
Absorption Absolute bioavailability = 23% with high variability
Half Life The initial phase t1/2 α is < 1 hour while the terminal phase t1/2 β is 5-9 hours.
Protein Binding 94 - 97% bound to serum proteins, primarily serum albumin
Elimination 83% of absorbed valsartan is excreted in feces and 13% is excreted in urine, primarily as unchanged drug
Distribution * 17 L (low tissue distribution)
Clearance * 2 L/h [IV administration]
* 4.5 L/h [heart Failure patients receiving oral administration 40 to 160 mg twice a day]
References
Bader, M. (2004). Renin-angiotensin-aldosterone system. In S. Offermanns, & W. Rosenthal (Eds.). _Encyclopedic reference of molecular pharmacology_ (pp. 810-814). Berlin, Germany: Springer.
Diovan. (2009). [Electronic version]. e-CPS. Retrieved December 28, 2009.
Stanfield, C.L., & Germann, W.J. (2008). _Principles of human physiology_ (3 ^rd^ ed.). San Francisco, CA: Pearson Education, Inc.
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1894 external link
Research Area: Cardiovascular Disease
Biological Activity:
Valsartan (Diovan) is an angiotensin II receptor antagonist with IC50 of ranging from 39.5 to116 µM. By blocking the action of angiotensin, valsartan dilates blood vessels and reduces blood pressure. In the Value trial, the angiotensin II receptor blocker valsartan produced a statistically significant 19% (p=0.02) relative increase in the prespecified secondary end point of myocardial infarction (fatal and non-fatal) compared with amlodipine. The CHARM-alternative trial showed a significant +52% (p=0.025) increase in myocardial infarction with candesartan (versus placebo) despite a reduction in blood pressure. [1]

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Diovan. (2009). [Electronic version]. e-CPS. Retrieved December 28, 2009.
  • • Stanfield, C.L., & Germann, W.J. (2008). _Principles of human physiology_ (3 ^rd^ ed.). San Francisco, CA: Pearson Education, Inc.
  • • Bader, M. (2004). Renin-angiotensin-aldosterone system. In S. Offermanns, & W. Rosenthal (Eds.). _Encyclopedic reference of molecular pharmacology_ (pp. 810-814). Berlin, Germany: Springer.
  • •  http://en.wikipedia.org/wiki/Valsartan
  • • Eur. Pat., 1991, Ciba-Geigy, 443 983; CA, 116, 151772t, (synth, pharmacol)
  • • Criscione, L. et al., Br. J. Pharmacol., 1993, 110, 761, (pharmacol)
  • • Wood, J.M. et al., Hypertension (Dallas), 1993, 21, 1056, (pharmacol)
  • • Buhlmayer, P. et al., Bioorg. Med. Chem. Lett., 1994, 4, 29, (synth)
  • • Markham, A. et al., Drugs, 1997, 54, 299-311, (rev)
  • • Langley, H.D. et al., Drugs, 1999, 57, 751-755, (rev)
  • • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 960
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PATENTS

PATENTS

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INTERNET

INTERNET

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