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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H38O5
Molecular Weight 382.5341
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SM-10906

SMILES

[H][C@@]12C[C@@H](CCOCC(O)=O)C[C@]1([H])[C@@H](\C=C\[C@@H](O)C[C@@H](C)CCCC)[C@H](O)C2

InChI

InChIKey=KCWJAXJEGXEZQC-JKVOQSHXSA-N
InChI=1S/C22H38O5/c1-3-4-5-15(2)10-18(23)6-7-19-20-12-16(8-9-27-14-22(25)26)11-17(20)13-21(19)24/h6-7,15-21,23-24H,3-5,8-14H2,1-2H3,(H,25,26)/b7-6+/t15-,16+,17-,18+,19+,20-,21+/m0/s1

HIDE SMILES / InChI
Molecular Formula C22H38O5
Molecular Weight 382.5341
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8533126 http://www.ncbi.nlm.nih.gov/pubmed/7511960 https://www.ncbi.nlm.nih.gov/pubmed/9195295

Pimilprost (SM-10902) and its free acid, SM-10906 are new stable 3-oxa-methano prostaglandin (PG) I1 analogs, SM-10902 is a prodrug of SM-10906. SM-10906, but not SM-10902 was demonstrated to be an agonist for IP receptors. SM-10906 was shown to exert its anti-platelet and vasodilatory activities through the increase of the cAMP level. Pimilprost was being developed by Dainippon Sumitomo Pharma (formerly Sumitomo Pharmaceuticals) in Japan for the treatment of skin ulcers. In Japan, an NDA was filed for pimilprost and was awaiting registration. However, development appears to have been discontinued.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Prostacyclin receptor
9
Target ID: P43252
Gene ID: 19222.0
Gene Symbol: Ptgir
Target Organism: Mus musculus (Mouse)
Agonist
2678
 100.0 nM [IC50]
Agonist
2678
 6.3 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pharmacological properties of the new stable prostacyclin analogue 3-Oxa-methano-prostaglandin I.
1994 Apr
Prostacyclin (PGI) receptor binding and cyclic AMP synthesis activities of PGI1 analogues, SM-10906 and its methyl ester, SM-10902, in mastocytoma P-815 cells.
1994 Jan
Prostaglandin I1 analogues, SM-10902 and SM-10906, affect human keratinocytes and fibroblasts in vitro in a manner similar to PGE1: therapeutic potential for wound healing.
1995
Antiplatelet functions of a stable prostacyclin analog, SM-10906 are exerted by its inhibitory effect on inositol 1,4,5-trisphosphate production and cytosolic Ca++ increase in rat platelets stimulated by thrombin.
1995 Aug 1
Effect of topical application of a stable prostacyclin analogue, SM-10902 on wound healing in diabetic mice.
1996 Apr 29
Antithrombotic effect of topically applied 3-oxa-methano-prostaglandin I1 in the microcirculation and antiplatelet functions of its active form.
1996 Feb
Affinity for [3H]iloprost binding sites and cAMP synthesis activity of a 3-oxa-methano prostaglandin I1 analog, SM-10906, in human platelets and endothelial cells.
1997 May
Patents

Patents

7790905
106
7927613
118
EP0925787A4
2

Sample Use Guides

In Vivo Use Guide
genetically diabetic mice (db/db mice) treated with Pimilprost (SM-10902) ointment (1, 10 and 100 micrograms/g) showed greater decrease in wound lesion area not covered with epidermis and fewer complete healing days than those treated with ointment base
Route of Administration: Transdermal
In Vitro Use Guide
Pimilprost (SM-10902) is a prodrug of SM-10906. SM-10906 dose-dependently stimulated GTP-dependent adenylate cyclase activity in the membrane fraction, the EC50 value being 35 nM. Furthermore, SM-10906 prevented a thrombin-induced increase in the intracellular Ca2+ concentration, the IC50 value being 300 nM. These IC50 and EC50 values are much lower than those of SM-10902.
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:11:29 GMT 2023
Edited
by admin
on Sat Dec 16 20:11:29 GMT 2023
Record UNII
NW385A9DRM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SM-10906
Code English
2-{2-[(2R,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-octahydropentalen-2-yl]ethoxy}acetic acid
Systematic Name English
SM10906
Code English
Acetic acid, [2-[(2R,3aS,4R,5R,6aS)-octahydro-5-hydroxy-4-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-2-pentalenyl]ethoxy]-
Systematic Name English
Code System Code Type Description
FDA UNII
NW385A9DRM
Created by admin on Sat Dec 16 20:11:30 GMT 2023 , Edited by admin on Sat Dec 16 20:11:30 GMT 2023
PRIMARY
CAS
157318-92-8
Created by admin on Sat Dec 16 20:11:30 GMT 2023 , Edited by admin on Sat Dec 16 20:11:30 GMT 2023
PRIMARY
PUBCHEM
6442261
Created by admin on Sat Dec 16 20:11:30 GMT 2023 , Edited by admin on Sat Dec 16 20:11:30 GMT 2023
PRIMARY
Related Record Type Details
PROSTACYCLIN RECEPTOR
TARGET -> AGONIST
Related Record Type Details
Structure of PIMILPROST
PRODRUG -> METABOLITE ACTIVE
NIH
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