Compounds > angiotensin ii, sar(1)-me-tyr(4)-
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angiotensin ii, sar(1)-me-tyr(4)-

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

This modified angiotensin II analog, also known as Saralasin, is a competitive antagonist of the angiotensin II receptor. It was synthesized to block the vasoconstrictor effects of angiotensin II. Saralasin has been studied extensively for its potential to treat hypertension and other cardiovascular diseases. It has been found to lower blood pressure, reduce vascular resistance, and improve renal function. However, its clinical use has been limited due to its short half-life and the development of tolerance. Despite this, Saralasin remains an important tool for research in understanding the role of the renin-angiotensin system in cardiovascular regulation.'

angiotensin II, Sar(1)-Me-Tyr(4)-: angiotensin II antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID14585948
MeSH IDM0120372
PubMed CID122005
CHEMBL ID2371021
MeSH IDM0120372

Synonyms (11)

Synonym
angiotensin ii, sar(1)-me-tyr(4)-
sarmesin
88874-29-7
(2s)-2-[[(2s)-1-[(2s)-2-[[(2s,3s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-5-(diaminomethylideneamino)-2-[[2-(methylamino)acetyl]amino]pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-methoxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]py
angiotensin ii, 1-(n-methylglycine)-4-(o-methyl-l-tyrosine)-5-l-isoleucine-
1-sar-4-me-tyr-angiotensin ii
smt-angiotensin ii
angiotensin ii, 1-(n-methylglycine)-4-(o-methyl-l-tyrosine)-5-l-isoleucine-, (3beta)-
angiotensin ii, sarcosyl(1)-methyltyrosine(4)-
CHEMBL2371021
(sar1,tyr(me)4)-angiotensin ii

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" In the rat pressor assay, infusion of the analogue at a rate of 500ng/kg/min caused a parallel displacement of the dose-response curve to ANG II to the right."( A new approach to angiotensin antagonists: methylation of the tyrosine hydroxyl in angiotensin II.
Franklin, KJ; Matsoukas, JM; Moore, GJ; Scanlon, MN, 1984)		0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID37988Antagonistic activity against Angiotensin II receptor type 1 in rat uterus2000Bioorganic & medicinal chemistry letters, Apr-17, Volume: 10, Issue:8
Structural comparison between type I and type II antagonists: possible implications in the drug design of AT1 antagonists.
AID183442Residual ANG II-like antagonist activity, ID50 was measured in vivo, in the rat blood pressure assay1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
The role of position 4 in angiotensin II antagonism: a structure-activity study.
AID196836Compound was tested for antagonist activity in rat isolated uterus assay; pA2 is the negative logarithm of the concentration of antagonist that reduces the response to an ED50 dose of angiotensin II to the response to half the ED50 dose1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis and biological activities of analogues of angiotensins II and III containing O-methyltyrosine and D-tryptophan.
AID170474Compound was tested for agonist activity in rat isolated uterus assay1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis and biological activities of analogues of angiotensins II and III containing O-methyltyrosine and D-tryptophan.
AID173210In vivo blood pressure increase produced by a 1 ug bolus i.v.1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
The role of position 4 in angiotensin II antagonism: a structure-activity study.
AID174215Variation in mean arterial pressure, produced by angiotensin II upon administration at 30 ug/kg/min in rats1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
A carboxy-terminus truncated analogue of angiotensin II, [Sar1]angiotensin II-(1-7)-amide, provides an entry to a new class of angiotensin II antagonists.
AID166813Antagonist activity pA2, was measured in the in vitro rabbit aorta strip assay1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
The role of position 4 in angiotensin II antagonism: a structure-activity study.
AID172807In vivo activity to antagonize the effect of bolus injection of compound at 30 ug/kg in rat1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Structure-activity relationships for the carboxy-terminus truncated analogues of angiotension II, a new class of angiotensin II antagonists.
AID39334Compound was evaluated for the antagonistic activity against rat Angiotensin II receptor by using isometric bioassay system1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Structure-activity relationships for the competitive angiotensin antagonist [sarcosine,O-methyltyrosine4]angiotensin II (sarmesin).
AID174202Variation in mean arterial pressure produced by angiotensin II, 10 min after administration (dose 30 ug/kg/min) in rats; 63/31989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
A carboxy-terminus truncated analogue of angiotensin II, [Sar1]angiotensin II-(1-7)-amide, provides an entry to a new class of angiotensin II antagonists.
AID174207Variation in mean arterial pressure produced by angiotensin II, 40 min after administration (dose 30 ug/kg/min) in rats; 96/41989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
A carboxy-terminus truncated analogue of angiotensin II, [Sar1]angiotensin II-(1-7)-amide, provides an entry to a new class of angiotensin II antagonists.
AID192019Drinking water response evaluated in conscious rat at a dose of 500 pmol icv1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Structure-activity relationships for the carboxy-terminus truncated analogues of angiotension II, a new class of angiotensin II antagonists.
AID39333Angiotensin II receptor agonist activity was tested in rat isolated uterus assay using [Asp1,Ile5]ANG II (human angiotensin II) as the standard1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Structure-activity relationships for the competitive angiotensin antagonist [sarcosine,O-methyltyrosine4]angiotensin II (sarmesin).
AID172452Percentage of pressor response to antagonize the effect of bolus injection of compound at a dose of 30 ug/kg per min in rat1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Structure-activity relationships for the carboxy-terminus truncated analogues of angiotension II, a new class of angiotensin II antagonists.
AID174210Variation in mean arterial pressure produced by angiotensin II, 5 min after administration (dose 30 ug/kg/min) in rats; 35/11989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
A carboxy-terminus truncated analogue of angiotensin II, [Sar1]angiotensin II-(1-7)-amide, provides an entry to a new class of angiotensin II antagonists.
AID39348Angiotensin II receptor antagonist activity was tested in rat isolated uterus assay using [Asp1,Ile5]ANG II (human angiotensin II) as the standard1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Structure-activity relationships for the competitive angiotensin antagonist [sarcosine,O-methyltyrosine4]angiotensin II (sarmesin).
AID196419In vitro myotropic property in rat isolated uterus, expressed as pA21990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Structure-activity relationships for the carboxy-terminus truncated analogues of angiotension II, a new class of angiotensin II antagonists.
AID174204Variation in mean arterial pressure produced by angiotensin II, 20 min after administration (dose 30 ug/kg/min) in rats; 87/41989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
A carboxy-terminus truncated analogue of angiotensin II, [Sar1]angiotensin II-(1-7)-amide, provides an entry to a new class of angiotensin II antagonists.
AID174212Variation in mean arterial pressure produced by angiotensin II, 60 min after administration (dose 30 ug/kg/min) in rats; 97/31989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
A carboxy-terminus truncated analogue of angiotensin II, [Sar1]angiotensin II-(1-7)-amide, provides an entry to a new class of angiotensin II antagonists.
AID167750Angiotensin II-like agonist activity, measured in the in vitro rabbit aorta strip assay1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
The role of position 4 in angiotensin II antagonism: a structure-activity study.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (37.50)18.7374
1990's10 (41.67)18.2507
2000's5 (20.83)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.41

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.41 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews1 (4.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other24 (96.00%)84.16%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetic acid
Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.		210monocarboxylic acidantimicrobial food preservative;
Daphnia magna metabolite;
food acidity regulator;
protic solvent
sarcosine
cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis		1.9710N-alkylglycine zwitterion;
N-alkylglycine;
N-methyl-amino acid;
N-methylglycines		Escherichia coli metabolite;
glycine receptor agonist;
glycine transporter 1 inhibitor;
human metabolite;
mouse metabolite
losartan
Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position		4.680biphenylyltetrazole;
imidazoles		angiotensin receptor antagonist;
anti-arrhythmia drug;
antihypertensive agent;
endothelin receptor antagonist
pentylenetetrazole
Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.		2.4120organic heterobicyclic compound;
organonitrogen heterocyclic compound
apomorphine
Apomorphine: A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.		1.9910aporphine alkaloidalpha-adrenergic drug;
antidyskinesia agent;
antiparkinson drug;
dopamine agonist;
emetic;
serotonergic drug
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		1.9710amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
isoleucine
Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.		1.9710aspartate family amino acid;
isoleucine;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
arginine
Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.		1.9710arginine;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		biomarker;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical
azetidyl-2-carboxylic acid
azetidyl-2-carboxylic acid: a proline analog (with 4-membered ring in place of 5); a toxic non-protein amino acid that is misincorporated into protein in place of proline; induces nonfunctional heat-shock proteins; inhibits acquired thermotolerance; RN given refers to (L)-isomer; found in beets and Liliaceae. (S)-azetidine-2-carboxylic acid : The (S)-enantiomer of azetidine-2-carboxylic acid.. azetidinecarboxylic acid : A member of the class of azetidines that is azetidine substituted by at least one carboxy group at unspecified position.		1.9810azetidine-2-carboxylic acid
exp3174
losartan carboxylic acid: structure given in first source. losartan carboxylic acid : A biphenylyltetrazole that is losartan with the hydroxymethyl group at position 5 on the imidazole ring replaced with a carboxylic acid.		2.6930biphenylyltetrazole;
imidazoles;
organochlorine compound		metabolite
angiotensin ii
Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).		5.48210amino acid zwitterion;
angiotensin II		human metabolite
pd 123319
PD123319 : An imidazopyridine consisting of 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine having 4-(dimethylamino)-3-methylbenzyl, diphenylacetyl and carboxy and groups at positions 1, 5 and 6 respectively		2.4120imidazopyridineangiotensin receptor antagonist;
endothelin receptor antagonist;
vasoconstrictor agent
saralasin
Saralasin: An octapeptide analog of angiotensin II (bovine) with amino acids 1 and 8 replaced with sarcosine and alanine, respectively. It is a highly specific competitive inhibitor of angiotensin II that is used in the diagnosis of HYPERTENSION.		2.940oligopeptide
cyclohexylalanine
cyclohexylalanine: RN given refers to cpd without isomeric designation		1.9710
angiotensin i
Angiotensin I: A decapeptide that is cleaved from precursor angiotensinogen by RENIN. Angiotensin I has limited biological activity. It is converted to angiotensin II, a potent vasoconstrictor, after the removal of two amino acids at the C-terminal by ANGIOTENSIN CONVERTING ENZYME.. angiotensin I : A ten amino acid peptide formed by renin cleavage of angiotensinogen. Angiotensin I has no direct biological function except that high levels can stimulate catecholamine production. It is metabolized to its biologically active byproduct angiotensin II, a potent vasoconstrictor, by angiotensin converting enzyme (ACE) through cleavage of the two terminal amino acids.. angiotensin I dizwitterion : A peptide zwitterion that is the dizwitterionic form of angiotensin I having both carboxy groups deprotonated and the aspartyl amino group and arginine side-chain protonated. It is the major species at pH 7.3.		210angiotensin;
peptide zwitterion		human metabolite;
neurotransmitter agent
angiotensin iii
Angiotensin III: A heptapeptide formed from ANGIOTENSIN II after the removal of an amino acid at the N-terminal by AMINOPEPTIDASE A. Angiotensin III has the same efficacy as ANGIOTENSIN II in promoting ALDOSTERONE secretion and modifying renal blood flow, but less vasopressor activity (about 40%).		2.3820
angiotensin ii
Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).		1.9710amino acid zwitterion;
angiotensin II		human metabolite
angiotensin ii, 1-sar-5-ile-8-ala-
[no description available]		1.9710
saralasin
Saralasin: An octapeptide analog of angiotensin II (bovine) with amino acids 1 and 8 replaced with sarcosine and alanine, respectively. It is a highly specific competitive inhibitor of angiotensin II that is used in the diagnosis of HYPERTENSION.		1.9710oligopeptide
ConditionIndicatedRelationship StrengthStudiesTrials
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0110
Absence Seizure
[description not available]		02.0110
Seizures
Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.		02.0110
Blood Pressure, High
[description not available]		03.3320
Hypertension
Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.		03.3320
Convulsions, Grand Mal
[description not available]		01.9910
Epilepsy, Tonic-Clonic
A generalized seizure disorder characterized by recurrent major motor seizures. The initial brief tonic phase is marked by trunk flexion followed by diffuse extension of the trunk and extremities. The clonic phase features rhythmic flexor contractions of the trunk and limbs, pupillary dilation, elevations of blood pressure and pulse, urinary incontinence, and tongue biting. This is followed by a profound state of depressed consciousness (post-ictal state) which gradually improves over minutes to hours. The disorder may be cryptogenic, familial, or symptomatic (caused by an identified disease process). (From Adams et al., Principles of Neurology, 6th ed, p329)		01.9910
Abdominal Cramps
[description not available]		0210
Ache
[description not available]		0210
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		0210
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		02.3820