SOLASONINE

Possibly Marketed Outside US

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 Search

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	25 / 26
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.curadermbec5.com/full-prescribing-information-for-curadermbec5/ | https://www.ncbi.nlm.nih.gov/pubmed/28979674

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 Target	Pharmacology	Condition	Potency
HepG2 16 Target ID: CHEMBL395 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23475509	Inhibitor 8297
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28979674 \| https://www.ncbi.nlm.nih.gov/pubmed/26182866	Activator 1430
Hedgehog signaling pathway 11 Target ID: map04340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27754442	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Actinic keratosis 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1913614 http://www.curaderm.net/	Primary	Approved 8429	Curaderm BEC5 Approved Use Curaderm BEC5 is an inducer of cell death indicated for the topical treatment of actinic keratosis, keratoacanthoma, basal cell carcinoma and cutaneous superficial squamous cell carcinoma.
Basal cell carcinoma 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1913614 http://www.curaderm.net/	Primary	Approved 8429	Curaderm BEC5 Approved Use Curaderm BEC5 is an inducer of cell death indicated for the topical treatment of actinic keratosis, keratoacanthoma, basal cell carcinoma and cutaneous superficial squamous cell carcinoma.
Cutaneous superficial squamous cell carcinoma 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1913614 http://www.curaderm.net/	Primary	Approved 8429	Curaderm BEC5 Approved Use Curaderm BEC5 is an inducer of cell death indicated for the topical treatment of actinic keratosis, keratoacanthoma, basal cell carcinoma and cutaneous superficial squamous cell carcinoma.
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27754442 https://www.ncbi.nlm.nih.gov/pubmed/26182866 https://www.ncbi.nlm.nih.gov/pubmed/28979674	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antiproliferative activity of Solanum lycocarpum alkaloidic extract and their constituents, solamargine and solasonine, in tumor cell lines.	2014 Jan	23475509
Solasonine inhibits glioma growth through anti-inflammatory pathways.	2017	28979674

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:33:34 GMT 2023` Edited by `admin` on `Sat Dec 16 05:33:34 GMT 2023`
Record UNII	TR60638HXL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SOLASONINE

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