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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H15NO3
Molecular Weight 173.2096
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIDOLGOSIR

SMILES

[H][C@@]12[C@H](O)[C@H](O)CN1CCC[C@H]2O

InChI

InChIKey=FXUAIOOAOAVCGD-WCTZXXKLSA-N
InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1

HIDE SMILES / InChI

Molecular Formula C8H15NO3
Molecular Weight 173.2096
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Swainsonine is an indolizidine alkaloid found in Australian Swainsona canescens, North American plants of the genera Astragalus and Oxytropis and also in the fungus Rhizoctonia leguminocola. It is competitive inhibitor of Golgi alpha-mannosidase II and lysosomal alpha-mannosidases. This compound has been reported to be a potent antiproliferative and immunomodulatory agent. However, no evidence of anti-tumor activity of swainsonine was seen in phase II clinical trial, in patients with locally advanced or metastatic renal cell carcinoma. Adverse events such as fatigue, nausea and diarrhea were common but generally mild. Swainsonine is locoweed toxin. Locoweed poisoning is seen throughout the world and annually costs the livestock industry millions of dollars. Swainsonine inhibits lysosomal alpha-mannosidase and Golgi mannosidase II. Poisoned animals are lethargic, anorexic, emaciated, and have neurologic signs that range from subtle apprehension to seizures.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
37.5 ug/kg b.i.d for 3 weeks followed by one week off in each cycle
Route of Administration: Oral
In Vitro Use Guide
Tthe growth of C6 glioma cells is inhibited by swainsonine in vitro, with an IC(50) value within 24h of 0.05 ug/ml. Increases in swainsonine correlate with S phase percentages of 11.3%, 11.6% and 12.4%, respectively.
Substance Class Chemical
Record UNII
RSY4RK37KQ
Record Status Validated (UNII)
Record Version