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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9581938 | https://www.ncbi.nlm.nih.gov/pubmed/8540223
Curator's Comment: toxic to livestock (sheeps)
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: O09159 Gene ID: 17159.0 Gene Symbol: Man2b1 Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6786280 |
|||
Target ID: CHEMBL2257 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6806288 |
|||
Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17097281 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16034517
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19427771
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C2119
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
||
|
NCI_THESAURUS |
C2080
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DB02034
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY | |||
|
SWAINSONINE
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY | |||
|
D017026
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY | |||
|
300000036976
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY | |||
|
9367
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY | |||
|
51683
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY | |||
|
72741-87-8
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY | |||
|
C152742
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY | |||
|
DTXSID5046356
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY | |||
|
RSY4RK37KQ
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY | |||
|
8084
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY | |||
|
CHEMBL371197
Created by
admin on Fri Dec 15 19:08:51 GMT 2023 , Edited by admin on Fri Dec 15 19:08:51 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)