Cicaprost

Modify Date: 2024-01-11 10:56:58

Cicaprost Structure
Cicaprost structure
Common Name Cicaprost
CAS Number 94079-80-8 Molecular Weight 374.471
Density 1.2±0.1 g/cm3 Boiling Point 591.1±50.0 °C at 760 mmHg
Molecular Formula C22H30O5 Melting Point N/A
MSDS N/A Flash Point 203.4±23.6 °C

 Use of Cicaprost


Cicaprost (ZK 96480) is a prostacyclin receptor (IP) agonist. Cicaprost causes a concentration-dependent relaxation of the artery with an EC50 of 5.8 nM [1]。

 Names

Name Cicaprost
Synonym More Synonyms

 Cicaprost Biological Activity

Description Cicaprost (ZK 96480) is a prostacyclin receptor (IP) agonist. Cicaprost causes a concentration-dependent relaxation of the artery with an EC50 of 5.8 nM [1]。
Related Catalog
In Vitro Cicaprost significantly reduces proliferation of human pulmonary artery smooth muscle cells (HPASMC) stimulated by fetal bovine serum (FBS). Cicaprost displays marked antiproliferative activity at 30 nM[2]. Cicaprost stimulates [3H]cyclic AMP production with EC50 values of 1.5-22 nM, and stimulates [3H]inositol phosphate production (EC50 values 49-457 nM) in all but the SK-N-SH cells[3]. Cell Proliferation Assay[2] Cell Line: HPASMC Concentration: 10 pM, 100 pM, 1 nM, 10 nM, 100 nM, 1 μM, and 10 μM Incubation Time: Result: Dose-dependently inhibited proliferation with an EC50 of 24.1 nM.
In Vivo Cicaprost alters pain perception and inflammatory response in mice lacking prostacyclin receptor. Intravenous injection of Cicaprost (1 μg/kg) causes hypotension of ∼30 mm Hg in anaesthetized wild-type mice[4]. Animal Model: Wild-type (+/+) and IP−/− mice[4] Dosage: 1 μg/kg Administration: Intravenous injection Result: Caused hypotension of ∼30 mm Hg in anaesthetized wild-type mice, whereas there was no change in blood pressure in IP-deficient mice even at 10 μg/kg.
References

[1]. Nicole Ferko, et al. NO synergism with cicaprost in the canine pulmonary artery. BioPharm Journal ONLINE 2:2 (1998).

[2]. Lucie H Clapp, et al. Differential effects of stable prostacyclin analogs on smooth muscle proliferation and cyclic AMP generation in human pulmonary artery. Am J Respir Cell Mol Biol. 2002 Feb;26(2):194-201.

[3]. Kevin B S Chow, et al. Protein kinase A-dependent coupling of mouse prostacyclin receptors to Gi is cell-type dependent. Eur J Pharmacol. 2003 Aug 1;474(1):7-13.

[4]. T Murata, et al. Altered pain perception and inflammatory response in mice lacking prostacyclin receptor. Nature. 1997 Aug 14;388(6643):678-82.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 591.1±50.0 °C at 760 mmHg
Molecular Formula C22H30O5
Molecular Weight 374.471
Flash Point 203.4±23.6 °C
Exact Mass 374.209320
PSA 86.99000
LogP 1.94
Vapour Pressure 0.0±3.8 mmHg at 25°C
Index of Refraction 1.569

 Synthetic Route

 Synonyms

({(2E)-2-[5-Hydroxy-4-(3-hydroxy-4-methyl-1,6-nonadiyn-1-yl)hexahydro-2(1H)-pentalenylidene]ethyl}oxy)acetic acid
Acetic acid, 2-[[(2E)-2-[hexahydro-5-hydroxy-4-(3-hydroxy-4-methyl-1,6-nonadiyn-1-yl)-2(1H)-pentalenylidene]ethyl]oxy]-
13,14-Didehydro-16,20-dimethyl-3-oxa-18,18,19,19-tetradehydro-6-carbaprostaglandin I2