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
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
DescriptionCurator'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
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P43252 Gene ID: 19222.0 Gene Symbol: Ptgir Target Organism: Mus musculus (Mouse) |
100.0 nM [IC50] | ||
Target ID: CHEMBL1995 |
6.3 null [pKi] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
Sample Use Guides
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
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.
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NW385A9DRM
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157318-92-8
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6442261
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PRODRUG (METABOLITE ACTIVE)
SUBSTANCE RECORD
