Page last updated: 2024-12-10

cicaprost

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

Description

cicaprost: RN given refers to (3aS-(2E,3aalpha,4alpha(3R*,4R*),5beta,6aalpha))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5311044
CHEMBL ID160629
CHEBI ID135578
SCHEMBL ID61349
MeSH IDM0128650

Synonyms (26)

Synonym
2-{2-[(2e,3as,4s,5r,6as)-5-hydroxy-4-[(3s,4s)-3-hydroxy-4-methylnona-1,6-diyn-1-yl]-octahydropentalen-2-ylidene]ethoxy}acetic acid
gtpl1917
zk-96480
cicaprost
13,14-didehydro-16,20-dimethyl-3-oxa-18,18,19,19-tetradehydro-6-carbaprostaglandin i2
(2-((2e,3as,4s,5r,6as)-hexahydro-5-hydroxy-4-((3s,4s)-3-hydroxy-4-methyl-1,6-nonadiynyl)-2(1h)-pentalenylidene)ethoxy)acetic acid
zk 96480
cicaprost [inn]
5-(7-hydroxy-6-(3-hydroxy-4-methylnona-1,6-diynyl)-bicyclo(3.3.0)octan-3-yliden)-3-oxapentanoic acid
cicaprostum [latin]
PDSP2_001537
CHEBI:135578
CHEMBL160629
2-[(2e)-2-[(3as,4s,5r,6as)-5-hydroxy-4-[(3s,4s)-3-hydroxy-4-methylnona-1,6-diynyl]-3,3a,4,5,6,6a-hexahydro-1h-pentalen-2-ylidene]ethoxy]acetic acid
cicaprostum
ne94j8camd ,
94079-80-8
acetic acid, (2-(hexahydro-5-hydroxy-4-(3-hydroxy-4-methyl-1,6-nonadiynyl)-2(1h)-pentalenylidene)ethoxy)-, (3as-(2e,3aalpha,4alpha(3r*,4r*),5beta,6aalpha))-
acetic acid, ((2e)-2-((3as,4s,5r,6as)-hexahydro-5-hydroxy-4-((3s,4s)-3-hydroxy-4-methyl-1,6-nonadiynyl)-2(1h)-pentalenylidene)ethoxy)-
unii-ne94j8camd
cicaprost [mart.]
SCHEMBL61349
DTXSID00873211
Q27076013
CS-0015866
HY-19583

Research Excerpts

Overview

Cicaprost is a new synthetic prostacylin analogue which is metabolically stable and bioavailable after oral administration. In previous studies it has been shown to have vasodilator antiplatelet effects.

ExcerptReferenceRelevance
"Cicaprost is a potent, chemically and metabolically stable PGI2-mimetic. "( Development and validation of a sensitive and specific radioimmunoassay for the determination of cicaprost in biological samples.
Hildebrand, M; Nieuweboer, B; Schütt, A, 1994
)
1.95
"Cicaprost is a new synthetic prostacylin analogue which is metabolically stable and bioavailable after oral administration; in previous studies it has been shown to have vasodilator antiplatelet effects. "( A randomised, double-blind study of cicaprost, an oral prostacyclin analogue, in the treatment of Raynaud's phenomenon secondary to systemic sclerosis.
Belch, JJ; Cappell, H; Herrick, A; Jayson, M; Lau, CS; Madhok, R; Thompson, JM,
)
1.85
"Cicaprost is an orally available analogue of PGI2 and has been shown to inhibit platelet aggregation in both in vitro and animal studies."( The pharmacological effects of cicaprost, an oral prostacyclin analogue, in patients with Raynaud's syndrome secondary to systemic sclerosis--a preliminary study.
Belch, JJ; Lau, CS; McLaren, M; Saniabadi, A; Scott, N,
)
1.14

Actions

Cicaprost and iloprost inhibit DNA synthesis and proliferation to a greater extent in distal compared with proximal human PASMCs. Cicaprost failed to inhibit forskolin-stimulated [3H]cyclic AMP production in any of these cell lines.

ExcerptReferenceRelevance
"Cicaprost failed to inhibit forskolin-stimulated [3H]cyclic AMP production in any of these cell lines."( Protein kinase A-dependent coupling of mouse prostacyclin receptors to Gi is cell-type dependent.
Chow, KB; Jones, RL; Wise, H, 2003
)
1.04
"++Cicaprost and iloprost inhibit DNA synthesis and proliferation to a greater extent in distal compared with proximal human PASMCs, acting at least in part via a cAMP-dependent mechanism. "( Prostacyclin analogues differentially inhibit growth of distal and proximal human pulmonary artery smooth muscle cells.
Davie, N; Morrell, NW; Polak, JM; Upton, PD; Wharton, J; Yacoub, MH, 2000
)
1.03

Treatment

Cicaprost treatment (5 micrograms/kg x d) largely prevented the hypercholesterolemia-related impairment of coronary vasodilation and nitric oxide release.

ExcerptReferenceRelevance
"Cicaprost treatment considerably improved this endothelial function but had no effect in rabbits receiving standard diet."( Antiatherosclerotic effects of oral cicaprost in experimental hypercholesterolemia in rabbits.
Braun, M; Hohlfeld, T; Kienbaum, P; Sarbia, M; Schrör, K; Weber, AA, 1993
)
1.28
"Cicaprost treatment (5 micrograms/kg x d) largely prevented the hypercholesterolemia-related impairment of coronary vasodilation and nitric oxide release."( Oral cicaprost protects from hypercholesterolaemia-induced impairment of coronary vasodilation.
Hohlfeld, T; Schrör, K; Strobach, H; Woditsch, I, 1992
)
1.52

Pharmacokinetics

The terminal half-life in plasma of cicaprost was approx. 60 minutes. Pharmacokinetic evaluation demonstrated a similar bioavailability of the drug.

ExcerptReferenceRelevance
" Both compounds have been characterized concerning their pharmacological and pharmacokinetic profile in a number of animal species and in man."( Pharmacokinetics of iloprost and cicaprost in mice.
Hildebrand, M, 1992
)
0.56
" The terminal half-life in plasma of cicaprost was approx."( Pharmacokinetics and pharmacodynamics of cicaprost in healthy volunteers after oral administration of 5 to 20 micrograms.
Hildebrand, M; Nieuweboer, B; Staks, T, 1990
)
0.82
" The terminal half-life in the plasma was 115 +/- 30 min."( Pharmacokinetics of 3H-cicaprost in healthy volunteers.
Hildebrand, M; Matthes, H; Schütt, A; Staks, T, 1989
)
0.59
"Cica-, eptalo- and iloprost are chemically and metabolically stabilized derivatives of prostacyclin which maintain the pharmacodynamic profile of the endogenous precursor."( Inter-species extrapolation of pharmacokinetic data of three prostacyclin-mimetics.
Hildebrand, M, 1994
)
0.29
" Pharmacokinetic evaluation demonstrated a similar bioavailability of cicaprost in both groups."( Tumor metastasis inhibition with the prostacyclin analogue cicaprost depends on discontinuous plasma peak levels.
Hildebrand, M; Kraus, C; Lichtner, RB; Schirner, M; Schneider, MR, 1998
)
0.78
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Bioavailability

Cicaprost was tested for Gastro-intestinal absorption and absolute bioavailability of Cicaprost. Pharmacokinetic evaluation demonstrated a similar bioavailability in both groups.

ExcerptReferenceRelevance
" Bioavailability was 10%."( Pharmacokinetics of iloprost and cicaprost in mice.
Hildebrand, M, 1992
)
0.56
" Gastro-intestinal absorption and absolute bioavailability of Cicaprost was complete."( Pharmacokinetics of 3H-cicaprost in healthy volunteers.
Hildebrand, M; Matthes, H; Schütt, A; Staks, T, 1989
)
0.83
" On the basis of the urinary excretion of 3H-label and unchanged drug both gastro-intestinal absorption and bioavailability were complete."( Studies on the pharmacokinetics of ZK 96 480, a novel PGI2-mimetic, in rat and cynomolgus monkey.
Hildebrand, M, 1986
)
0.27
" Finally, the possibility that an impaired prostacyclin synthesis or bioavailability is involved in the pathogenesis of the diabetic nephropathy in this model underlies our results."( Effects of cicaprost and fosinopril on the progression of rat diabetic nephropathy.
García-Robles, R; Rábano, A; Ruilope, LM; Villa, E, 1997
)
0.69
" Pharmacokinetic evaluation demonstrated a similar bioavailability of cicaprost in both groups."( Tumor metastasis inhibition with the prostacyclin analogue cicaprost depends on discontinuous plasma peak levels.
Hildebrand, M; Kraus, C; Lichtner, RB; Schirner, M; Schneider, MR, 1998
)
0.78

Dosage Studied

ExcerptRelevanceReference
" dosage (7."( Pharmacokinetics of 3H-cicaprost in healthy volunteers.
Hildebrand, M; Matthes, H; Schütt, A; Staks, T, 1989
)
0.59
" In this pilot study, we investigated the clinical efficacy of and patient tolerance to two dosage levels of cicaprost (2."( A randomised, double-blind study of cicaprost, an oral prostacyclin analogue, in the treatment of Raynaud's phenomenon secondary to systemic sclerosis.
Belch, JJ; Cappell, H; Herrick, A; Jayson, M; Lau, CS; Madhok, R; Thompson, JM,
)
0.62
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
monoterpenoidAny terpenoid derived from a monoterpene. The term includes compounds in which the C10 skeleton of the parent monoterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID1346336Mouse EP3 receptor (Prostanoid receptors)1997British journal of pharmacology, Sep, Volume: 122, Issue:2
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
AID1346350Human IP receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1346431Mouse IP receptor (Prostanoid receptors)1997British journal of pharmacology, Sep, Volume: 122, Issue:2
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
AID1346427Human EP4 receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1346303Mouse EP2 receptor (Prostanoid receptors)1997British journal of pharmacology, Sep, Volume: 122, Issue:2
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
AID1346343Human EP3 receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1346408Human EP1 receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (165)

TimeframeStudies, This Drug (%)All Drugs %
pre-199013 (7.88)18.7374
1990's82 (49.70)18.2507
2000's50 (30.30)29.6817
2010's20 (12.12)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: 16.55

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index16.55 (24.57)
Research Supply Index5.18 (2.92)
Research Growth Index5.06 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index4.00 (0.95)

This Compound (16.55)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (2.91%)5.53%
Reviews5 (2.91%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other162 (94.19%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]