Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H15NO3.ClH |
Molecular Weight | 209.671 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]12[C@H](O)[C@H](O)CN1CCC[C@H]2O
InChI
InChIKey=LIRVFCZWYJVKCV-XNJRRJNCSA-N
InChI=1S/C8H15NO3.ClH/c10-5-2-1-3-9-4-6(11)8(12)7(5)9;/h5-8,10-12H,1-4H2;1H/t5-,6-,7-,8-;/m1./s1
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 |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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Target ID: O09159 Gene ID: 17159.0 Gene Symbol: Man2b1 Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6786280 |
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Target ID: CHEMBL2257 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6806288 |
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Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17097281 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Inhibition of lysosomal alpha-mannosidase by swainsonine, an indolizidine alkaloid isolated from Swainsona canescens. | 1980 Nov 1 |
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Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
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Inhibition of AIDS virus replication by acemannan in vitro. | 1991 Sep |
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Screening for swainsonine among South American Astragalus species. | 2017 Dec 1 |
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The Biosynthesis Pathway of Swainsonine, a New Anticancer Drug from Three Endophytic Fungi. | 2017 Nov 28 |
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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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:48:44 GMT 2023
by
admin
on
Fri Dec 15 15:48:44 GMT 2023
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Record UNII |
78KR51ES9B
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C2119
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NCI_THESAURUS |
C2080
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78KR51ES9B
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100000184151
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DTXSID00175722
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214462-68-7
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C2065
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9837203
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DBSALT001877
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LL-55
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CHEMBL371197
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |