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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H34O4
Molecular Weight 350.4923
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CLINPROST ACID

SMILES

[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(CCCCC(O)=O)=C2

InChI

InChIKey=JANVYOZZTKSZGN-WCAFQOMDSA-N
InChI=1S/C21H34O4/c1-2-3-4-8-17(22)10-11-18-19-13-15(7-5-6-9-21(24)25)12-16(19)14-20(18)23/h10-12,16-20,22-23H,2-9,13-14H2,1H3,(H,24,25)/b11-10+/t16-,17-,18+,19-,20+/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H34O4
Molecular Weight 350.4923
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 1
Optical Activity UNSPECIFIED

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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:12:24 GMT 2023
Edited
by admin
on Sat Dec 16 08:12:24 GMT 2023
Record UNII
J2E3T1I1U9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLINPROST ACID
Common Name English
ISOCARBACYCLIN
Common Name English
9-O-METHANOPROSTAGLANDIN I
Common Name English
CLINPROST FREE ACID [MI]
Common Name English
2-PENTALENEPENTANOIC ACID, 1,3A,4,5,6,6A-HEXAHYDRO-5-HYDROXY-6-((1E,3S)-3-HYDROXY-1-OCTENYL)-, (3AS,5R,6R,6AS)-
Systematic Name English
TEI-7165
Code English
(+)-ISOCARBACYCLIN
Common Name English
9(O)-METHANO-.DELTA.6(9)-PROSTAGLANDIN I1
Common Name English
Code System Code Type Description
CAS
99946-24-4
Created by admin on Sat Dec 16 08:12:24 GMT 2023 , Edited by admin on Sat Dec 16 08:12:24 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
CAS
88911-35-7
Created by admin on Sat Dec 16 08:12:24 GMT 2023 , Edited by admin on Sat Dec 16 08:12:24 GMT 2023
PRIMARY
FDA UNII
J2E3T1I1U9
Created by admin on Sat Dec 16 08:12:24 GMT 2023 , Edited by admin on Sat Dec 16 08:12:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID70237407
Created by admin on Sat Dec 16 08:12:24 GMT 2023 , Edited by admin on Sat Dec 16 08:12:24 GMT 2023
PRIMARY
MERCK INDEX
m1075
Created by admin on Sat Dec 16 08:12:24 GMT 2023 , Edited by admin on Sat Dec 16 08:12:24 GMT 2023
PRIMARY Merck Index
PUBCHEM
5311244
Created by admin on Sat Dec 16 08:12:24 GMT 2023 , Edited by admin on Sat Dec 16 08:12:24 GMT 2023
PRIMARY
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ACTIVE MOIETY