Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H44O3 |
| Molecular Weight | 416.6365 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC[C@@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]23C)O[C@]16CC[C@@H](C)CO6
InChI
InChIKey=GMBQZIIUCVWOCD-UQHLGXRBSA-N
InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17+,18-,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
Smilagenin (also known as PYM50028 and Cogane) is a constituent of Jamaican sarsaparilla (Smilax ornata) and is a neuroprotectant that has been evaluated in Phase II clinical trials in Parkinson's disease and Alzheimer's disease. On 27 September 2011, the European Commission to Phytopharm plc, United Kingdom, granted orphan designation for smilagenin for the treatment of amyotrophic lateral sclerosis. The details of the mechanism of action of smilagenin are incomplete but involve the upregulation of neurotrophic factors including Glial cell line-derived neurotrophic factor and brain-derived neurotrophic factor.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P39905|||Q9UD33 Gene ID: 2668.0 Gene Symbol: GDNF Target Organism: Homo sapiens (Human) |
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Target ID: P23560|||Q9BYY7 Gene ID: 627.0 Gene Symbol: BDNF Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Regulation of M1-receptor mRNA stability by smilagenin and its significance in improving memory of aged rats. | 2010-06 |
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| Role of glial cell derived neurotrophic factor in the protective effect of smilagenin on rat mesencephalic dopaminergic neurons damaged by MPP+. | 2008-03-19 |
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| Anti-proliferative and pro-apoptotic effect of Smilax glabra Roxb. extract on hepatoma cell lines. | 2008-01-10 |
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| Treating senile dementia with traditional Chinese medicine. | 2007 |
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| Bioactive steroidal saponins from Smilax medica. | 2006-06 |
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| Anti-inflammatory and anti-arthritic effects of Yucca schidigera: a review. | 2006-03-29 |
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| Structure-function relationship for saponin effects on cell cycle arrest and apoptosis in the human 1547 osteosarcoma cells: a molecular modelling approach of natural molecules structurally close to diosgenin. | 2005-02-15 |
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| Investigation of spectrophotometrically determined substances in Yucca extract by GC/MS, TLC and on-column injection GC. | 2004-06 |
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| Ovine metabolism of diosgenin coated on cellulose in relation to hepatogenous photosensitization of ruminants. | 2003-02 |
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| Ruminal metabolism in sheep of saponins from Yucca schidigera. | 2002-02 |
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| Ovine metabolism of saponins: evaluation of a method for estimating the ovine uptake of steroidal saponins from Narthecium ossifragum. | 2001-04 |
Patents
Sample Use Guides
In Vitro Use Guide
Curator's Comment: Smilagenin (SMI) pretreatment significantly attenuates the neurodegenerative changes induced by beta amyloid 25-35 (Aβ(25-35)) in cultured rat cortical neurons, including decreased cholinergic neuron number, shortened neurite outgrowth length, and declined M receptor density. Brain-derived neurotrophic factor (BDNF) protein levels in the culture medium were also decreased by Aβ(25-35) and significantly elevated by SMI.
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EU-Orphan Drug |
EU/3/11/914
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NCI_THESAURUS |
C29711
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FDA ORPHAN DRUG |
345811
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C152374
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DB05450
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m9973
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93747
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126-18-1
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C046297
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ACTIVE MOIETY
