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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

[H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]6(CC[C@@H](C)CN6)O2)O[C@]7([H])O[C@H](CO)[C@H](O)[C@H](O[C@]8([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@]9([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]9O

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

Molecular Formula C45H73NO16
Molecular Weight 884.0582
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 25 / 26
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Curaderm BEC5
Primary
Curaderm BEC5
Primary
Curaderm BEC5
Primary
Unknown

PubMed

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.
Substance Class Chemical
Record UNII
TR60638HXL
Record Status Validated (UNII)
Record Version