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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H73NO16
Molecular Weight 884.0582
Optical Activity UNSPECIFIED
Defined Stereocenters 26 / 26
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SOLASONINE

SMILES

C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@H](CC[C@]5(C)[C@H]4CC[C@]23C)O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)O[C@]19CC[C@@H](C)CN9

InChI

InChIKey=QCTMYNGDIBTNSK-XEAAVONHSA-N
InChI=1S/C45H73NO16/c1-19-8-13-45(46-16-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-36(54)34(52)31(49)21(3)56-40)38(33(51)29(18-48)59-42)60-41-37(55)35(53)32(50)28(17-47)58-41/h6,19-21,23-42,46-55H,7-18H2,1-5H3/t19-,20+,21+,23+,24-,25+,26+,27+,28-,29-,30+,31+,32-,33+,34-,35+,36-,37-,38+,39-,40+,41+,42-,43+,44+,45-/m1/s1

HIDE SMILES / InChI

Description

Solasonine, a known glycoalkaloid, is a potential anti-cancer agent. Solasonine is a component of Curaderm BEC5 indicated for the topical treatment of actinic keratosis, keratoacanthoma, basal cell carcinoma and cutaneous superficial squamous cell carcinoma. BEC is a standardized mixture of Solamargine (33%), Solasonine (33%) and di-and monoglycosides of solasodine (34%) extracted from S. sodomaeum, now reclassified as S. linnaeanum. Solasonine could inhibit cell proliferation, migration and colony formation of glioma cells. Treatment of solasonine induced apoptosis via modulating cytochrome c and caspase signaling. Besides, solasonine decreased the expression of proinflammatory mediators and nuclear translocalization of NF-κB p50/p65. Mechanistic investigation further revealed that solasonine may target anti-inflammatory signaling pathway, and more specifically p-p38 and p-JNK MAPKs.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Primary
Curaderm BEC5
Primary
Curaderm BEC5
Primary
Curaderm BEC5
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

In Vivo Use Guide
Curaderm BEC5, 0.005% BEC for topical use. BEC is a standardized mixture of Solamargine (33%), Solasonine (33%) and di-and monoglycosides of solasodine (34%) extracted from S. sodomaeum, now reclassified as S. linnaeanum. • For topical use only; not for oral, ophthalmic, or intravaginal use. (2) • Actinic Keratosis: Apply Curaderm BEC5 to the affected area with an occlusive dressing, twice daily for 3 consecutive days. (2) • Keratoacanthoma, basal cell carcinoma and cutaneous superficial squamous cell carcinoma: Apply Curaderm BEC5 only to the lesion with an occlusive dressing, twice daily until lesion is completely cleared (2)
Route of Administration: Topical
In Vitro Use Guide
Solasonine inhibited HepG2 proliferation with IC50 value of 6.01 ug/mL.
Name Type Language
SOLASONINE
MI  
Common Name English
.ALPHA.-SOLASONINE
Common Name English
PURAPURINE
Common Name English
TOMATINE SOLARADIXINE
Common Name English
.BETA.-D-GALACTOPYRANOSIDE, (3.BETA.,22.ALPHA.,25R)-SPIROSOL-5-EN-3-YL O-6- DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1-2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1-3))-
Common Name English
SOLASONIN
Common Name English
SOLASONINE [MI]
Common Name English
NSC-82149
Code English
.BETA.-D-GALACTOPYRANOSIDE, (3.BETA.,22.ALPHA.,25R)-SPIROSOL-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->3))-
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 211705
Created by admin on Tue Oct 22 12:04:15 UTC 2019 , Edited by admin on Tue Oct 22 12:04:15 UTC 2019
FDA ORPHAN DRUG 211805
Created by admin on Tue Oct 22 12:04:15 UTC 2019 , Edited by admin on Tue Oct 22 12:04:15 UTC 2019
Code System Code Type Description
CAS
19121-58-5
Created by admin on Tue Oct 22 12:04:15 UTC 2019 , Edited by admin on Tue Oct 22 12:04:15 UTC 2019
PRIMARY
MERCK INDEX
M10107
Created by admin on Tue Oct 22 12:04:15 UTC 2019 , Edited by admin on Tue Oct 22 12:04:15 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
SOLASONINE
Created by admin on Tue Oct 22 12:04:15 UTC 2019 , Edited by admin on Tue Oct 22 12:04:15 UTC 2019
PRIMARY
PUBCHEM
119247
Created by admin on Tue Oct 22 12:04:15 UTC 2019 , Edited by admin on Tue Oct 22 12:04:15 UTC 2019
PRIMARY
ECHA (EC/EINECS)
242-826-6
Created by admin on Tue Oct 22 12:04:15 UTC 2019 , Edited by admin on Tue Oct 22 12:04:15 UTC 2019
PRIMARY