Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H36O4 |
Molecular Weight | 364.5188 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(CCCCC(=O)OC)=C2
InChI
InChIKey=QIGRQPVOWVHYBT-KABTVRTISA-N
InChI=1S/C22H36O4/c1-3-4-5-9-18(23)11-12-19-20-14-16(13-17(20)15-21(19)24)8-6-7-10-22(25)26-2/h11-13,17-21,23-24H,3-10,14-15H2,1-2H3/b12-11+/t17-,18-,19+,20-,21+/m0/s1
DescriptionCurator's Comment: Description was created based on several sources, including https://www.jstage.jst.go.jp/article/jphs1951/71/4/71_4_351/_pdf
Curator's Comment: Description was created based on several sources, including https://www.jstage.jst.go.jp/article/jphs1951/71/4/71_4_351/_pdf
Isocarbacyclin methylester (clinprost) (isocarbacyclin methylester; methyl 5-{(1S,5S,6R,7R)-7-hydroxy-6-[(E)- (S)-3-hydroxy-1-octenyl] bicyclo[3.3.0]oct-2-en-3-yl} pentanoate) and its active metabolite, isocarbacyclin (TEI-7165), are chemically stable PGI2 analogues. TTC- 909 is a drug preparation of clinprost incorporated into lipid microspheres (LM). The hypothetical sequence of events for TTC-909 to exert pharmacological effects is as follows: the LM would deliver clinprost to most tissues including the blood and the brain, clinprost would be released gradually from the LM, and then the clinprost would be hydrolyzed to TEI-7165 by esterase action to exert pharmacological activity. Both clinprost and TEI-7165 inhibit platelet aggregation and platelet adhesion in vitro and suppress prostaglandin F2 (PGF2 )-induced contraction of isolated canine arteries. TTC-909 also has vasodilative and anti-platelet activity in vivo, similar to PGI2. TTC-909 was shown to inhibit cerebral infarction, maybe by improving cerebral blood flow and by protecting against neuronal damage.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/8953502
Curator's Comment: Known to be CNS penetrant in rats. Human data not available.
Originator
Sources: http://adisinsight.springer.com/drugs/800003132
Curator's Comment: Co-developer Taisho Pharmaceutical
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0070527 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7488316 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/2217831
2 ug of lipo-PGI2 (clinprost) daily for one week
Route of Administration:
Unknown
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/7488317
TTC-909 (clinprost) significantly inhibited platelet aggregation induced by ADP at early times after bolus i.v. injection from the dose of 0.3 ug/kg in a dose-dependent manner.
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C78568
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ACTIVE MOIETY
SUBSTANCE RECORD