Home > Compound List > Compound details
144689-63-4 molecular structure
click picture or here to close

(5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate

ChemBase ID: 160
Molecular Formular: C29H30N6O6
Molecular Mass: 558.5851
Monoisotopic Mass: 558.22268271
SMILES and InChIs

SMILES:
OC(c1nc(n(c1C(=O)OCc1oc(=O)oc1C)Cc1ccc(cc1)c1c(cccc1)c1n[nH]nn1)CCC)(C)C
Canonical SMILES:
CCCc1nc(c(n1Cc1ccc(cc1)c1ccccc1c1n[nH]nn1)C(=O)OCc1oc(=O)oc1C)C(O)(C)C
InChI:
InChI=1S/C29H30N6O6/c1-5-8-23-30-25(29(3,4)38)24(27(36)39-16-22-17(2)40-28(37)41-22)35(23)15-18-11-13-19(14-12-18)20-9-6-7-10-21(20)26-31-33-34-32-26/h6-7,9-14,38H,5,8,15-16H2,1-4H3,(H,31,32,33,34)
InChIKey:
UQGKUQLKSCSZGY-UHFFFAOYSA-N

Cite this record

CBID:160 http://www.chembase.cn/molecule-160.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate
(5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate
IUPAC Traditional name
olmesartan
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)imidazole-4-carboxylate
@olmesartan
(5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate
benicar
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)imidazole-4-carboxylate
Brand Name
Benicar
Olmetec
Votum
Benicar HCT
Synonyms
Olmesartan medoximil
Olmesartan medoxomil
DE-092
Olmesartan
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl] 4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
Olmesartan medoxomil
Benicar
Olmetec
4-(1-Hydroxy-1-methylethyl)-2-propyl-1-[[2’-(1H-tetazol-5-yl)[1,1’-biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxylic Acid (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester
Olmesartan
CS-866
(5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate
CAS Number
144689-63-4
144689-24-7
MDL Number
MFCD00944911
PubChem SID
160963623
PubChem CID
130881

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 7.399751  H Acceptors
H Donor LogD (pH = 5.5) 5.5291805 
LogD (pH = 7.4) 5.25633  Log P 5.5455294 
Molar Refractivity 163.4584 cm3 Polarizability 58.660378 Å3
Polar Surface Area 154.34 Å2 Rotatable Bonds 11 
Lipinski's Rule of Five false 
Log P 4.31  LOG S -4.86 
Solubility (Water) 7.75e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Ethanol expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
180-182°C (dec.) expand Show data source
Hydrophobicity(logP)
2.66 expand Show data source
5.9 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer 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
Target
Angiotensin receptor expand Show data source
RAAS expand Show data source
Mechanism of Action
Angiotensin II receptor antagonists expand Show data source
Block the binding of angiotension II to the AT1 receptors in vascular muscle expand Show data source
Prodrug-type angiotensin II receptor antagonist expand Show data source
Purity
95% expand Show data source
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antihypertensive agent expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC Selleck Chemicals Selleck Chemicals
DrugBank - DB00275 external link
Item Information
Drug Groups approved; investigational
Description Olmesartan is an antihypertensive agent which belongs to the class of medicines called angiotensin II receptor antagonists. It acts rapidly to lower high blood pressure. It is marketed worldwide by Daiichi Sankyo, Ltd. and in the United States by Daiichi Sankyo, Inc. and Forest Laboratories.
Indication For the treatment of hypertension.
Pharmacology Olmesartan, a specific angiotensin II type 1 antagonist, is used alone or with other antihypertensive agents to treat hypertension. Unlike the angiotensin receptor antagonist losartan, olmesartan does not have an active metabolite or possess uricosuric effects. Blockade of the angiotensin II receptor inhibits the negative regulatory feedback of angiotensin II on renin secretion, but the resulting increased plasma renin activity and circulating angiotensin II levels do not overcome the effect of olmesartan on blood pressure.
Toxicity Symptoms of overdose include dehydration (dry mouth, excessive thirst, muscle pain or cramps, nausea and vomiting, weakness), dizziness, low blood pressure, and slow or irregular heartbeat.
Affected Organisms
Humans and other mammals
Biotransformation Olmesartan is rapidly and completely bioactivated by ester hydrolysis to olmesartan during absorption from the gastrointestinal tract. There is virtually no further metabolism of olmesartan.
Absorption Bioavailability is about 26%. Food does not affect the bioavailability of olmesartan.
Half Life Approximately 13 hours
Protein Binding Highly bound to plasma proteins (99%) and does not penetrate red blood cells.
Distribution * 17 L
Clearance * Total plasma cl=1.3 L/h
* Renal cl=0.6 L/h
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Toronto Research Chemicals - O550000 external link
An angiotensin II receptor antagonist. Used as an anti-hypertensive.
Selleck Chemicals - S1604 external link
Research Area: Cancer
Biological Activity:
Olmesartan medoxomil (Benicar) is a compound which is hydrolyzed to olmesartan that is a selective AT1 subtype angiotensin II receptor antagonist.Olmesartan medoxomil (Benicar) was converted to olmesartan  during absorption from the gastrointestinal tract. Olmesartan is indicated for the treatment of hypertension. It may be used alone or in combination with other antihypertensive agents. Olmesartan medoxomil (Benicar) exerts its pharmacological functions via blocking the binding of angiotensin II to the AT1 receptors in vascular muscle; it is therefore independent of angiotensin II synthesis pathways, unlike ACE inhibitors. By blocking the binding rather than the synthesis of angiotensin II, olmesartan prevents the negative regulatory feedback on renin secretion. As a result of this blockage, olmesartan attenuates vasoconstriction and the secretion of aldosterone. Olmesartan lowers blood pressure by producing vasodilation, and decreasing peripheral resistance.
Selleck Chemicals - S1587 external link
Research Area: Cardiovascular Disease
Biological Activity:
Olmesartan is an angiotensin II receptor antagonist with an IC50 of 7.7 nM. It is used to treat high blood pressure. Olmesartan works by blocking the binding of angiotensin II to the AT1 receptors in vascular muscle; it is therefore independent of angiotensin II synthesis pathways, unlike ACE inhibitors. By blocking binding rather than synthesis of angiotensin II, olmesartan inhibits the negative regulatory feedback on renin secretion. As a result of this blockage, olmesartan reduces vasoconstriction and the secretion of aldosterone. This lowers blood pressure by producing vasodilation, and decreasing peripheral resistance. [1]

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Yanagisawa, H., et al.: J. Med. Chem., 39, 323 (1996)
  • • Puchler, K., et al.: J. Hypertens., 15, 1809 (1996)
  • • Eur. Pat., 1992, Sankyo, 503 785; CA, 118, 22240k, (CS 866, RNH 6270, synth, pharmacol)
  • • Mizuno, M. et al., Eur. J. Pharmacol., 1995, 285, 181-188, (pharmacol, CS 866, RNH 6270)
  • • Yanagisawa, H. et al., J. Med. Chem., 1996, 39, 323-328, (synth, CS 866, RNH 6270, pmr, ir, pharmacol)
  • •  http://en.wikipedia.org/wiki/Olmesartan
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle