Page last updated: 2024-12-07

13-azaprostanoic acid

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

Description

13-Azaprostanoic acid is a synthetic analog of prostaglandin E1 (PGE1), a naturally occurring hormone-like substance. Unlike PGE1, which has a five-membered ring structure, 13-azaprostanoic acid has a nitrogen atom replacing a carbon atom in that ring. This seemingly small change has significant implications for its biological activity and makes it a valuable tool for research.

Here's why 13-azaprostanoic acid is important for research:

**1. Selective Prostaglandin Receptor Agonist:** 13-azaprostanoic acid is a selective agonist of the EP3 receptor, one of the four major subtypes of prostaglandin E receptors (EP1, EP2, EP3, and EP4). This selective action allows researchers to study the specific roles of the EP3 receptor in various physiological processes, without the confounding effects of activating other receptors.

**2. Pharmacological Studies:** 13-azaprostanoic acid has been used extensively in pharmacological studies to investigate the role of prostaglandins in various physiological processes, including:

* **Inflammation:** The EP3 receptor is known to play a role in inflammation, and 13-azaprostanoic acid has been used to study the effects of EP3 receptor activation on inflammatory responses.
* **Cardiovascular System:** PGE1 and its analogs, including 13-azaprostanoic acid, have shown potential therapeutic benefits in cardiovascular diseases. Studies have explored their use in conditions like hypertension, myocardial infarction, and heart failure.
* **Gastrointestinal System:** The EP3 receptor is also implicated in regulating gastrointestinal function. 13-azaprostanoic acid has been used to investigate the role of EP3 receptor activation in gastrointestinal motility, secretion, and inflammation.
* **Other Systems:** 13-azaprostanoic acid has been used to study the role of the EP3 receptor in other systems, including the central nervous system, respiratory system, and reproductive system.

**3. Development of New Drugs:** The selective activation of the EP3 receptor by 13-azaprostanoic acid has sparked interest in developing new drugs that target this receptor for therapeutic purposes. For example, compounds that selectively activate or block the EP3 receptor may have potential for treating inflammatory diseases, cardiovascular diseases, and other conditions.

**4. Understanding Disease Mechanisms:** By studying the effects of 13-azaprostanoic acid, researchers can gain a deeper understanding of the mechanisms by which prostaglandins and their receptors contribute to various physiological processes and diseases.

**Limitations:**

While 13-azaprostanoic acid has been a valuable tool in research, it does have some limitations:

* **Metabolic Stability:** Like many other prostaglandin analogs, 13-azaprostanoic acid has limited metabolic stability, meaning it can be rapidly broken down in the body. This can limit its in vivo efficacy.
* **Pharmacokinetic Properties:** The pharmacokinetic properties of 13-azaprostanoic acid, such as absorption, distribution, metabolism, and excretion, can vary depending on the route of administration and the specific experimental conditions.

Overall, 13-azaprostanoic acid remains an important tool for research, providing insights into the role of the EP3 receptor in various physiological processes and disease mechanisms. Its selectivity and potential therapeutic value continue to drive investigations aimed at developing novel drugs that target the EP3 receptor for clinical applications.

13-azaprostanoic acid: RN given refers to (1S-trans)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID123640
CHEMBL ID9811
SCHEMBL ID7719993
MeSH IDM0078836

Synonyms (17)

Synonym
CBIOL_001997
BIO1_000772
BIO1_001261
BIO1_000283
NCGC00161297-01
13-azaprostanoic acid
71629-07-7
CHEMBL9811
(+/-)13-azaprostanoic acid
BML1-G10
7-[(1s,2s)-2-(heptylamino)cyclopentyl]heptanoic acid
cyclopentaneheptanoic acid, 2-(heptylamino)-, (1s-trans)-
DTXSID80221872
SCHEMBL7719993
13-apa
(+-)-13-azaprostanoic acid
7-((1s,2s)-2-(heptylamino)cyclopentyl)heptanoic acid

Research Excerpts

Dosage Studied

13-azaprostanoic acid (13-APA), a TXA2/endoperoxide receptor antagonist, was pretreated with 5 X 10(-5) M and 2 X 10 (-4) M. The dose-response curve of BPS in the veins was shifted to the right.

ExcerptRelevanceReference
" Exposure to 13-azaprostanoic acid (13-APA), 5 X 10(-5) M and 2 X 10(-4) M, for 20 min caused parallel and dose-related shifts to the right of the dose-response curves generated by all three prostanoids without affecting the contractile responses to KCl, norepinephrine, or 5-hydroxytryptamine or relaxation induced by PGI2."( Antagonism of prostanoid-induced vascular contraction by 13-azaprostanoic acid (13-APA).
Horn, PT; Kohli, JD; LeBreton, GC; Venton, DL,
)
0.75
" By pretreatment with 13-azaprostanoic acid (13-APA), a TXA2/endoperoxide receptor antagonist, the dose-response curve of BPS in the veins was shifted to the right."( The contractile mechanism of beraprost sodium, a stable prostacyclin analog, in the isolated canine femoral vein.
Ishikawa, M; Namiki, A, 1994
)
0.6
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID157026Tested for effect of plasma containing platelets (PRP) against U-46,619 (1 uM) at 50 uM concentration1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
2-(6-carboxyhexyl)cyclopentanone hexylhydrazone. A potent and time-dependent inhibitor of platelet aggregation.
AID1123068Inhibition of cyclooxygenase activity in bovine seminal vesicles assessed as arachodonic acid dependent formation of adenochrome from L-epinephrine at 500 uM1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
Azaprostanoic acid derivatives. Inhibitors of arachidonic acid induced platelet aggregation.
AID1123067Inhibition of ADP-induced primary platelet aggregation in aspirin-treated human platelet-rich plasma at 100 uM after 2 mins by turbidometric method1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
Azaprostanoic acid derivatives. Inhibitors of arachidonic acid induced platelet aggregation.
AID1123066Inhibition of 300 uM arachidonate-induced platelet aggregation in human platelet-rich plasma at 10 uM by turbidometric method1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
Azaprostanoic acid derivatives. Inhibitors of arachidonic acid induced platelet aggregation.
AID157032Tested for effect of plasma containing platelets (PRP) against arachidonic acid (500 uM) at 50 uM concentration1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
2-(6-carboxyhexyl)cyclopentanone hexylhydrazone. A potent and time-dependent inhibitor of platelet aggregation.
AID1123071Inhibition of cyclooxygenase activity in bovine seminal vesicles assessed as arachodonic acid dependent formation of adenochrome from L-epinephrine at concentration of one order of magnitude greater than that necessary for 100% inhibition of platelet aggr1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
Azaprostanoic acid derivatives. Inhibitors of arachidonic acid induced platelet aggregation.
AID157031Tested for effect of plasma containing platelets (PRP) against arachidonic acid (500 uM) at 25 uM concentration1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
2-(6-carboxyhexyl)cyclopentanone hexylhydrazone. A potent and time-dependent inhibitor of platelet aggregation.
AID1123064Inhibition of 500 uM arachidonate-induced platelet aggregation in human platelet-rich plasma at 10 uM by turbidometric method1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
Azaprostanoic acid derivatives. Inhibitors of arachidonic acid induced platelet aggregation.
AID157025Tested for effect of plasma containing platelets (PRP) against U-46,619 (1 uM) at 25 uM concentration1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
2-(6-carboxyhexyl)cyclopentanone hexylhydrazone. A potent and time-dependent inhibitor of platelet aggregation.
AID1123065Inhibition of 400 uM arachidonate-induced platelet aggregation in human platelet-rich plasma at 10 uM by turbidometric method1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
Azaprostanoic acid derivatives. Inhibitors of arachidonic acid induced platelet aggregation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (37)

TimeframeStudies, This Drug (%)All Drugs %
pre-199034 (91.89)18.7374
1990's2 (5.41)18.2507
2000's1 (2.70)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: 10.51

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 Index10.51 (24.57)
Research Supply Index3.76 (2.92)
Research Growth Index4.27 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.51)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other41 (97.62%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]