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
| 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 |
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 |
|---|---|---|
| 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 |
|
| Effect of topical application of a stable prostacyclin analogue, SM-10902 on wound healing in diabetic mice. | 1996 Apr 29 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 20:11:29 GMT 2023
by
admin
on
Sat Dec 16 20:11:29 GMT 2023
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| Record UNII |
NW385A9DRM
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| Record Status |
Validated (UNII)
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| Record Version |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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TARGET -> AGONIST |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PRODRUG -> METABOLITE ACTIVE |
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