SMILAGENIN

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

Structure Search

SMILES

[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]6(CC[C@@H](C)CO6)O2

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

HIDE SMILES / InChI

Molecular Formula	C27H44O3
Molecular Weight	416.6365
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22441042 | http://www.ema.europa.eu/docs/en_GB/document_library/Orphan_designation/2011/10/WC500116523.pdf | https://clinicaltrials.gov/ct2/show/NCT00130429

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glial cell line-derived neurotrophic factor 3 Target ID: P39905\|\|\|Q9UD33 Gene ID: 2668.0 Gene Symbol: GDNF Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18298955	Agonist 2678
Brain-derived neurotrophic factor 2 Target ID: P23560\|\|\|Q9BYY7 Gene ID: 627.0 Gene Symbol: BDNF Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22441042	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Amyotrophic lateral sclerosis 41 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Orphan_designation/2011/10/WC500116523.pdf	Primary	Not Provided 504	Unknown Approved Use Unknown
Parkinson's disease 226 Sources: https://clinicaltrials.gov/ct2/show/NCT01060878	Primary	Phase II 1132	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://clinicaltrials.gov/ct2/show/NCT00130429	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
480 ng/mL OTHER https://www.kinetassist.com/images/Kinetic_modelling_poster_WPC_final.pdf	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:		SMILAGENIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY115034	https://www.001chemical.com/chem/search?q=DY115034
Alfa Chemistry	ACM82597748	http://www.alfa-chemistry.com/search.aspx?q=ACM82597748
Angene	AGN-PC-0WH8NM	http://www.angenechemical.com/productshow/AGN-PC-0WH8NM.html
BOC Sciences	126-18-1	http://www.bocsci.com/description.asp?cas=126-18-1
BOC Sciences	82597-74-8	http://www.bocsci.com/description.asp?cas=82597-74-8
Chem Scene	CS-0025639	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0025639
Frontier Scientific Services	500054392	http://orders.frontierssi.com/fssionline32/public/product.aspx?cat=500054392&type=hts
Lab Seeker	SC-82586	http://www.labseeker.com/search.php?keywords=SC-82586&category=0
LabSeeker	SC-82586	http://www.labseeker.com/search.php?keywords=SC-82586&category=0
Matrix Scientific	98157	http://www.matrixscientific.com/098157.html
MedChem Express	HY-106353	https://www.medchemexpress.com/search.html?q=HY-106353&ft=&fa=&fp=
MolPort	MolPort-006-110-813	https://www.molport.com/shop/molecule-link/MolPort-006-110-813
MolPort	MolPort-027-835-427	https://www.molport.com/shop/molecule-link/MolPort-027-835-427
Molcore	MC115034	http://www.molcore.com/CatMC115034.html
TargetMol	T3S0895	https://www.targetmol.com/search?keyword=T3S0895
Tetrahedron	TS69781	http://www.thsci.com/search.do?q=TS69781
eMolecules	36029168	https://orderbb.emolecules.com/search/#?query=36029168
eMolecules	43443763	https://orderbb.emolecules.com/search/#?query=43443763
eMolecules	44689558	https://orderbb.emolecules.com/search/#?query=44689558
eNovation Chemicals	D659560	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D659560&searchbtn.x=0&searchbtn.y=0

PubMed

Title	Date	PubMed
Ruminal metabolism in sheep of saponins from Yucca schidigera.	2002 Feb	11922485
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 Feb 15	15670922

Patents

Sample Use Guides

In Vivo Use Guide

administered once daily for up to 12 weeks

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:29:16 GMT 2023` Edited by `admin` on `Fri Dec 15 16:29:16 GMT 2023`
Record UNII	GQE3Q7YMVZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SMILAGENIN

Official Name

English

(25R)-5.BETA.-SPIROSTAN-3.BETA.-OL

Systematic Name

English

(3.BETA.,5.BETA.,25R)-SPIROSTAN-3-OL

Systematic Name

English

ESMILAGENIN

Common Name

English

smilagenin [INN]

Common Name

English

NSC-93747

Code

English

COGANE

Brand Name

English

ISOSARSASAPOGENIN

Common Name

English

SMILAGENIN [MI]

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/11/914