CAS 144689-63-4|CAS 144689-24-7|@olmesartan|Olmesartan|Olmetec|Benicar|(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}me...

General Information

Structure

Molecular Formula

C₂₉H₃₀N₆O₆

Molecular Mass

558.5851

Exact Mass

558.22268271

Charge

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

Canonic Smiles

CCCc1nc(c(n1Cc1ccc(cc1)c1ccccc1c1n[nH]nn1)C(=O)OCc1oc(=O)oc1C)C(O)(C)C

Isomeric Smiles

OC(c1nc(n(c1C(=O)OCc1oc(=O)oc1C)Cc1ccc(cc1)c1c(cccc1)c1n[nH]nn1)CCC)(C)C

Calculated Properties

JChem

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

Polarizability

58.660378

Polar Surface Area

154.34

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

4.31

LOG S

-4.86

Solubility (Water)

7.75e-03 g/l

Data Source

Names and Identifiers

IUPAC Traditional name

@olmesartan 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 benicar (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 (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

Synonyms

OlmesartanOlmetecBenicar(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-carboxylateOlmesartan medoxomilDE-092Olmesartan medoxomilOlmesartan medoximilCS-8664-(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 EsterOlmesartan(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 name

(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 (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

Brand Name

BenicarOlmetecVotumBenicar HCT

Names and Identifiers

Registration numbers

CAS Number

144689-63-4144689-24-7

MDL Number

MFCD00944911

PubChem CID

130881

PubChem SID

160963623

Registration numbers

Properties

Product Information

Pharmacology Properties

Target

Angiotensin receptor

RAAS

Mechanism of Action

Block the binding of angiotension II to the AT1 receptors in vascular muscle

Prodrug-type angiotensin II receptor antagonist

Angiotensin II receptor antagonists

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00275

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]

Selleck Chemicals

S1587

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]

S1604

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.

TRC

O550000

An angiotensin II receptor antagonist. Used as an anti-hypertensive.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Olmesartan

• Puchler, K., et al.: J. Hypertens., 15, 1809 (1996)

• Yanagisawa, H., et al.: J. Med. Chem., 39, 323 (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)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

Synonyms

IUPAC name

Brand Name

BenicarOlmetecVotumBenicar HCT

Registration numbers

CAS Number

144689-63-4144689-24-7

MDL Number

MFCD00944911

PubChem CID

130881

PubChem SID

160963623

Properties

Product Information

Pharmacology Properties

Target

Angiotensin receptor

RAAS

Mechanism of Action

Block the binding of angiotension II to the AT1 receptors in vascular muscle

Prodrug-type angiotensin II receptor antagonist

Angiotensin II receptor antagonists

Molecule Details

DrugBank

DB00275

Drug Groups

approved; investigational

Description

Indication

For the treatment of hypertension.

Pharmacology

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]