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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Sources: DOI: 10.1071/CH9792257

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O09159
Gene ID: 17159.0
Gene Symbol: Man2b1
Target Organism: Mus musculus (Mouse)
Conditions
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Inhibition of lysosomal alpha-mannosidase by swainsonine, an indolizidine alkaloid isolated from Swainsona canescens.
1980 Nov 1
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Inhibition of AIDS virus replication by acemannan in vitro.
1991 Sep
Screening for swainsonine among South American Astragalus species.
2017 Dec 1
The Biosynthesis Pathway of Swainsonine, a New Anticancer Drug from Three Endophytic Fungi.
2017 Nov 28
Swainsonine Inhibits Invasion and the EMT Process in Esophageal Carcinoma Cells by Targeting Twist1.
2018 Sep 14
Patents

Sample Use Guides

37.5 ug/kg b.i.d for 3 weeks followed by one week off in each cycle
Route of Administration: Oral
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
Created
by admin
on Fri Dec 15 19:08:50 UTC 2023
Edited
by admin
on Fri Dec 15 19:08:50 UTC 2023
Record UNII
RSY4RK37KQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIDOLGOSIR
INN   WHO-DD  
INN  
Official Name English
SWAINSONINE
Common Name English
Tridolgosir [WHO-DD]
Common Name English
1,2,8-INDOLIZINETRIOL, OCTAHYDRO-, (1S-(1.ALPHA.,2.ALPHA.,8.BETA.,8A.BETA.))-
Common Name English
tridolgosir [INN]
Common Name English
(1S,2R,8R,8AR)-OCTAHYDRO-1,2,8-INDOLIZINETRIOL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2119
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
NCI_THESAURUS C2080
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
Code System Code Type Description
DRUG BANK
DB02034
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
WIKIPEDIA
SWAINSONINE
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
MESH
D017026
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
SMS_ID
300000036976
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
CHEBI
9367
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
PUBCHEM
51683
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
CAS
72741-87-8
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
NCI_THESAURUS
C152742
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID5046356
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
FDA UNII
RSY4RK37KQ
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
INN
8084
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
ChEMBL
CHEMBL371197
Created by admin on Fri Dec 15 19:08:51 UTC 2023 , Edited by admin on Fri Dec 15 19:08:51 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY