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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
Structure of CLINPROST

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

HIDE SMILES / InChI

Description
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

Curator's Comment: Known to be CNS penetrant in rats. Human data not available.

Originator

Curator's Comment: Co-developer Taisho Pharmaceutical

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown

Sample Use Guides

In Vivo Use Guide
2 ug of lipo-PGI2 (clinprost) daily for one week
Route of Administration: Unknown
In Vitro Use Guide
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.
Name Type Language
CLINPROST
INN   JAN   MI  
INN  
Official Name English
TTC-909
Code English
(+)-METHYL-(3AS,5R,6R,6AS)-1,3A,4,5,6,6A-HEXAHYDRO-5-HYDROXY-6-((E)-(3S)-3-HYDROXY-1-OCTENYL)-2-PENTALENEVALERATE
Common Name English
clinprost [INN]
Common Name English
2-PENTALENEPENTANOIC ACID, 1,3A,4,5,6,6A-HEXAHYDRO-5-HYDROXY-6-((1E,3S)-3-HYDROXY-1-OCTEN-1-YL)-, METHYL ESTER, (3AS,5R,6R,6AS)-
Common Name English
ISOCARBACYCLIN METHYL ESTER
Common Name English
CLINPROST [MI]
Common Name English
TEI-9090
Code English
CLINPROST [JAN]
Common Name English
ARTERON
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
Code System Code Type Description
EVMPD
SUB06668MIG
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104163
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
PRIMARY
FDA UNII
6GRI2J11N5
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
PRIMARY
NCI_THESAURUS
C76332
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
PRIMARY
CAS
88931-51-5
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
PRIMARY
PUBCHEM
6436040
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
PRIMARY
MERCK INDEX
m1075
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
PRIMARY Merck Index
MESH
C052840
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
PRIMARY
SMS_ID
100000084297
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
PRIMARY
INN
6998
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID201107239
Created by admin on Fri Dec 15 16:09:55 GMT 2023 , Edited by admin on Fri Dec 15 16:09:55 GMT 2023
PRIMARY