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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H30O5
Molecular Weight 374.4706
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CICAPROST

SMILES

[H][C@]12C[C@@H](O)[C@H](C#C[C@@H](O)[C@@H](C)CC#CCC)[C@@]1([H])C\C(C2)=C\COCC(O)=O

InChI

InChIKey=ARUGKOZUKWAXDS-SEWALLKFSA-N
InChI=1S/C22H30O5/c1-3-4-5-6-15(2)20(23)8-7-18-19-12-16(9-10-27-14-22(25)26)11-17(19)13-21(18)24/h9,15,17-21,23-24H,3,6,10-14H2,1-2H3,(H,25,26)/b16-9+/t15-,17-,18+,19-,20+,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H30O5
Molecular Weight 374.4706
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/18276980 | https://www.ncbi.nlm.nih.gov/pubmed/28072560 | https://www.ncbi.nlm.nih.gov/pubmed/8329292 | https://www.ncbi.nlm.nih.gov/pubmed/1879086 | https://www.ncbi.nlm.nih.gov/pubmed/7778316

Cicaprost is a prostacyclin receptor (IP) agonist and orally active prostacyclin analog with potent systemic and pulmonary vasodilatation and anti-inflammatory activity. In preclinical models, Cicaprost treatment largely prevented the hypercholesterolemia-related impairment of coronary vasodilation and nitric oxide release in Isolated Langendorff-hearts. Cicaprost inhibits proinflammatory chemokines production not only from lipopolysaccharides (LPS) or (tumor necrosis factor-alpha) induced primary human monocyte-derived macrophages but also from LPS-stimulated monocyte-derived dendritic cells. Besides that Cicapost strongly inhibits lymph node and organ metastases of spontaneously metastasizing mammary tumors with a mode of action different from cytostatic or antihormonal drugs. In animal models, Cicaprost prevents metastasis if given continuously from the day of tumor implantation, and is effective in reducing metastasis if treatment is begun following surgical removal of the primary tumor when micrometastases are already present. Clinical trials of Cicaprost in healthy male volunteers demonstrate significant anti-platelet and vasodilatory effects.

Approval Year

PubMed

PubMed

TitleDatePubMed
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
1997 Sep
The effect of indomethacin and prostacyclin agonists on blood pressure in a rat model of preeclampsia.
1999 May
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
2000 Jan 17
Investigation of a functional requirement for isoprenylation by the human prostacyclin receptor.
2002 Mar
Cyclooxygenase-2 acts as an endogenous brake on endothelin-1 release by human pulmonary artery smooth muscle cells: implications for pulmonary hypertension.
2002 Nov
Prostacylin receptor activation inhibits proliferation of aortic smooth muscle cells by regulating cAMP response element-binding protein- and pocket protein-dependent cyclin a gene expression.
2003 Aug
Patents

Sample Use Guides

he volunteers were given either placebo, 5 micrograms, 7.5 micrograms or 10 micrograms cicaprost (at 09.00 h, 14.00 h, 19.00 h and again at 09.00 h the following day) on four separate occasions each 14 days apart.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:32:54 UTC 2023
Edited
by admin
on Fri Dec 15 16:32:54 UTC 2023
Record UNII
NE94J8CAMD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CICAPROST
INN   MART.  
INN  
Official Name English
(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
Common Name English
cicaprost [INN]
Common Name English
CICAPROST [MART.]
Common Name English
Code System Code Type Description
ChEMBL
CHEMBL160629
Created by admin on Fri Dec 15 16:32:54 UTC 2023 , Edited by admin on Fri Dec 15 16:32:54 UTC 2023
PRIMARY
MESH
C043867
Created by admin on Fri Dec 15 16:32:54 UTC 2023 , Edited by admin on Fri Dec 15 16:32:54 UTC 2023
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SMS_ID
100000081882
Created by admin on Fri Dec 15 16:32:54 UTC 2023 , Edited by admin on Fri Dec 15 16:32:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID00873211
Created by admin on Fri Dec 15 16:32:54 UTC 2023 , Edited by admin on Fri Dec 15 16:32:54 UTC 2023
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PUBCHEM
5311044
Created by admin on Fri Dec 15 16:32:54 UTC 2023 , Edited by admin on Fri Dec 15 16:32:54 UTC 2023
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DRUG CENTRAL
631
Created by admin on Fri Dec 15 16:32:54 UTC 2023 , Edited by admin on Fri Dec 15 16:32:54 UTC 2023
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CAS
94079-80-8
Created by admin on Fri Dec 15 16:32:54 UTC 2023 , Edited by admin on Fri Dec 15 16:32:54 UTC 2023
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FDA UNII
NE94J8CAMD
Created by admin on Fri Dec 15 16:32:54 UTC 2023 , Edited by admin on Fri Dec 15 16:32:54 UTC 2023
PRIMARY
NCI_THESAURUS
C174756
Created by admin on Fri Dec 15 16:32:54 UTC 2023 , Edited by admin on Fri Dec 15 16:32:54 UTC 2023
PRIMARY
EVMPD
SUB06230MIG
Created by admin on Fri Dec 15 16:32:54 UTC 2023 , Edited by admin on Fri Dec 15 16:32:54 UTC 2023
PRIMARY
INN
5826
Created by admin on Fri Dec 15 16:32:54 UTC 2023 , Edited by admin on Fri Dec 15 16:32:54 UTC 2023
PRIMARY
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TARGET -> AGONIST
IC50
TARGET -> AGONIST
BINDING
IC50
TARGET->WEAK AGONIST
IC50
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ACTIVE MOIETY