HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

Swainsonine

HCID 51683
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
72741-87-8
Standard SMILES
O[C@H]1[C@H]2[C@H](O)CCCN2C[C@H]1O
InChIKey
FXUAIOOAOAVCGD-WCTZXXKLSA-N
Molecular formula
C8H15NO3
Average molar mass
173.21 g/mol
Monoisotopic mass
173.10519334

Overview

Swainsonine is an indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8. It has a role as an antineoplastic agent, an immunological adjuvant, an EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor and a plant metabolite.

Names & identifiers

Preferred name
Swainsonine
IUPAC
(1S,2R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triol
English name
SWAINSONINE
Molecular formula
C8H15NO3
Molecular weight
173.21

Names & synonyms

swainsonine72741-87-8TridolgosirDTXSID5046356(1S,2R,8R,8aR)-Octahydro-1,2,8-indolizinetriolRSY4RK37KQ(1S,2R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triol1,2,8-Indolizinetriol, octahydro-, (1S-(1alpha,2alpha,8beta,8abeta))-CHEBI:9367DTXCID3026356tridolgosirumRefChem:890073
Show more names
8AR)-1SwainMoiaD-SwainsonineSWAINSONINE 98+%(-)-D-SwainsonineSwainsonine min. 99%swainsonine synthetic
(-)-SwainsonineTridolgosir [INN]Swainsonine (Synthetic)MFCD00017554(1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol1S-8AB-OCTAHYDRO-INDOLIZIDINE-1A,2A,8B-TRIOLCHEMBL371197NCGC00163481-02

Database identifiers

CAS
72741-87-8
PubChem CID
51683
DTXSID
DTXSID5046356
ChEMBL

Properties

Computed structural properties

XLogP
-1.3
Topological polar surface area
63.9 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
0
Heavy atoms
12
Formal charge
0
Complexity
176

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Melting Point143-144 °C

Physicochemical properties

Melting point
148 · 148-149°C
Boiling point
353.3 · 353.3±21.0 °C(Predicted)
Density
1.38 · 1.38±0.1 g/cm3 (20 ºC 760 Torr)
storage temp.
-20 °C · -20°C
solubility
2 O: · H2O: soluble1mg/mL
form
lyophilized powder
pka
14.01 · 14.01±0.60(Predicted)
color
white to faint yellow
biological source
synthetic
Water Solubility
50 mM · Soluble to 50 mM in water
BRN
4175740 · 4175740
Stability
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO, ethanol or distilled water may be stored at -20°C for up to 3 months.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Health Effects · 2 items

The presence of phytotoxins in plants constitutes a health risk for herbivores, particularly on ruminants who accidently consume them. Among the adverse effects produced by these exposures are reproductive alterations, represented by abortion, infertility, and morphological alterations in neonates, which are frequently attributed to other causes. While in some cases the plants that contain such metabolites are known, other times they are not, leading to alterations that are difficult to treat considering that their toxicodynamics are unknown.

Swainsonine causes a variety of neurological disorders, including locoism and "slobbers syndrome" in livestock. In man it causes a lysosomal storage disease, biochemically and morphologically similar to mannosidosis. It is also an appetite suppressant. (L1248, A3092, A3093)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 item

Swainsonine inhibits the activity of glycoside hydrolases, especially N-linked glycosylation. Inhibition of Golgi mannosidase II and other alpha-mannosidases causes the accumulation of atypical hybrid glycoproteins and oligosaccarides because the proper processing cannot occur. This also results in intracellular vacuolization. (L1248, A3092, A3093)

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

Tridolgosir competitively inhibits the alpha manosidase II (alphaMII), which processes N linked carbohydrates of newly synthesized glycoproteins passing through the Golgi apparatus to the cell surface. Highly branched carbohydrate structures are created which bind to Lectin-phytohemagglutinin (L-PHA) and are subsequently expressed in different tumor types which results in metastatic phenotype, which is correlated with an increased aggressiveness in animals and causes other human malignancies. Inhibition of alphaMII reduces carbohydrates that bind to L-PHA, reducing aggressiveness, metastatic phenotype cells, slows tumor growth, and increases“hybrid type” carbohydrates on the cell surface. Hybrid type carbohydrates may increase cytokine activation of lymphocytes, increasing tumor susceptibility to lymphokine activated and natural killer cells.

Locoweed contains the indolizidine alkaloid swainsonine. Livestock that consume locoweed can suffer from locoism. The toxic component in locoweed has been identified as swainsonine. Swainsonine inhibits lysosomal a-mannosidase and mannosidase II, resulting in altered oligosaccharide degradation and incomplete glycoprotein processing. Endophytic fungi producing swainsonine have been isolated from a variety of locoweed, and these fungi and locoweed have a close relationship, e.g., endophytic fungi can promote the growth of locoweed and increase swainsonine production. Livestock that consume locoweed exhibit several symptoms, including dispirited behavior, staggering gait, chromatopsia, trembling, ataxia, and cellular vacuolar degeneration of most tissues.

MeSH Pharmacological Classification · 3 items

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Related reactions

9 records
New reaction record
HRID 375262 reaction equation
HRID 375262As productuspto-grants-1996_01
HRID 581377 reaction equation
HRID 581377As reactantuspto-grants-1999_07
HRID 974167 reaction equation
HRID 974167As reactantuspto-grants-1991_11
HRID 981550 reaction equation
HRID 981550As reactantuspto-grants-1991_02
HRID 1494207 reaction equation
HRID 1494207As reactantuspto-grants-1991_06
HRID 1494659 reaction equation
HRID 1494659As reactantuspto-grants-1991_06
HRID 1937438 reaction equation
HRID 1937438As productuspto-grants-2002_05
HRID 1975837 reaction equation
HRID 1975837As productuspto-grants-1994_02
Page 1 of 2

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CHEMBL371197
ChEBI
CHEBI:9367
UNII
RSY4RK37KQ
EC Number
615-797-6
Nikkaji
J12.698E
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
InChIKey
FXUAIOOAOAVCGD-DCDLSZRSSA-N
SMILES
O[C@@H]1CCCN2C[C@@H](O)[C@@H](O)C12
CAS DataBase Reference
72741 · 72741-87-8
FDA UNII
4 RK37KQ · RSY4RK37KQ
UNSPSC Code
51102829 · 51102829
NACRES
85 · NA.85
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H312-H332
Precautionary statements
280 · P280
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn
Risk Statements
20 · 20/21/22
Safety Statements
36 · 36
WGK Germany
3 · 3
RTECS
2408666 · NM2408666
HS Code
29339900 · 29339900
Storage Class
11 · 11 - Combustible Solids
Signs and Symptoms · 2 items

Several plants that contain indolizidine alkaloids, including swainsonine, are toxic to livestock, causing dysfunctional lysosomes and storage disease. Swainsonine induces a neurovisceral disease, known as locoism, in sheep, goats, and cattle. Locoism occurs in several parts of the world, e.g., the western United States, China, and parts of Australia. In South America, locoism has been described in the Andean region of Argentina affecting sheep, cattle, and llamas. This publication describes the clinical course in llamas, which was about 15 days, and included moderate ataxia, incoordination of hindlimbs, and progressive loss of body condition. Swainsonine was detected in stem and leaf samples of A. punae at a concentration of 0.06%. A diagnosis of swainsonine toxicosis caused by the consumption of A. punae was made based on clinical history and signs, histologic and ultrastructural changes, and plant analysis.

Symptoms of locoism include staggering gait, depression, muscular incoordination, staring, nervousness, hyperexcitability, loss of appetite, and reproductive alterations such as abortion and birth defects. The major symptom of "slobbers syndrome" is profuse salivation. Other symptoms include diarrhea, lacrimation, stiff joints, frequent urination, tremors, spontaneous abortion, labored breathing, loss of appetite, bloat, and possibly death. Swainsonine also causes vacuolation of most tissues. (L1819, A3092, A3093)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 4 items

Swainsonine is the primary toxin in locoweeds. It causes intention tremors, reproductive dysfunction, emaciation, and death. In a mouse study, three generations were given a range of concentrations of swainsonine by intraperitoneal injection (2.50 mg/kg body weight (BW), 1.20 mg/kg BW, 0.60 mg/kg BW, and 0 mg/kg BW). The results results indicate that swainsonine may cause reproductive and developmental toxicities in mice in both parents and offspring.

Swainsonine is the principal agent in locoweed responsible for inducing locoism in animals. The toxicity of Embellisia fungi isolated from locoweed was compared with locoweed toxicity. Rats were fed diets containing locoweed, fungus and alfalfa, or alfalfa. Similar intracellular vacuolation was observed in renal, pancreatic, and hepatic tissues of rats that consumed either locoweed or fungus. Rats that ate locoweed or Embellisia fungi displayed indistinguishable toxicity symptoms. The Embellisia fungi from locoweed can induce toxicity without the plants.

Spontaneous intoxication by Astragalus arequipensis was diagnosed in a flock of 300 sheep that grazed an area heavily invaded by this plant. The main clinical signs were intention tremors, ataxia, and progressive loss of condition. The main microscopic changes were fine cytoplasmic vacuolation of cells in the cerebrum, cerebellum, thyroid and adrenal glands, kidney, liver, pancreas, urinary bladder, and lymph nodes, and swollen axons in the cerebellum. Composite leaf and stem samples of A. arequipensis analyzed by high-performance liquid chromatography contained 0.05% swainsonine. The diagnosis of intoxication by A. arequipensis was made based on the clinical history and signs, the gross, microscopic, and ultrastructural changes, and the detection of swainsonine in the plant.

Lysosomal storage diseases can causeimpaired cellular function and death. Many acquired lysosomal storage diseases are produced by toxic plants containing indolizidine alkaloids. This includes swainsonine, which inhibits lysosomal α-mannosidase and Golgi α-mannosidase II. Swainsonine-induced nervous disease associated with various plants has been reported, including species of the genus Astragalus, Sida, Oxitropis, Swainsona, and Ipomoea. The diagnosis of Astragalus spp. intoxication is established based on clinical signs, microscopic and ultrastructural findings, lectin histochemistry, the abundance of these plants in the grazing area, and the determination of swainsonine in plant specimens.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
NM2408666
hs_code
29339900
risk_code
20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
36
Storage Class
11 - Combustible Solids
Hazard statements
H302-H312-H332
Precautionary statements
P280

Uses & manufacturing

UsesSwainsonine is a plant toxin found in locoweed (families Fabaceae, Oxytropis, Astragalus and Swainsona) and some fungi (Metarhizium anisopliae, Rizoctonia leguminicola). (L1248, A3092)
Applications · 5 items

DescriptionSwainsonine (72741-87-8) is a naturally occurring alkaloidal toxin found in locoweed. Inhibits the biosynthesis of complex glycoproteins by inhibition of Golgi mannosidase II (IC50 = 0.2 mM).1 Inhibits growth and potentiates the cytotoxic effect of taxol in hepatocellular carcinoma in vivo.2 Induces apoptosis in a variety of cell types including cerebral cortical neurons.3 Impairs adult neurogenesis and spatial learning and memory.4 Abrogation of complex glycosylation by swainsonine results in strain-and cell-specific inhibition of prion replication.5 Induces lysosomal storage disease in farm animals.6

OccurrenceSwainsonia canescens yields this simple alkaloid.

UsesSwainsonine is an indolizidine alkaloid naturally found in certain plants including locoweed that inhibits N-linked glycoside hydrolases, preventing the processing of asparagine-linked glycoproteins. It reversibly inhibits lysosomal α-mannosidase and Golgi α-mannosidase II (IC50 = 0.2 μM). Swainsonine is used to study the role of N-linked glycosylation in cellular processes and has been shown to have antiproliferative and antimetastatic effects of cancer cells in culture and in mice. The inhibition of α-mannosidase activity in lysosomes produces an accumulation of partially-processed oligosaccharides and glycoproteins, giving rise to lysosomal storage disease. Swainsonine toxicity in herbivores results in a condition known as locoism, characterized by hyperactivity, aggression, stiff and clumsy gait, low head carriage, salivation, seizures, and apparent blindness, culminating in increased miscoordination, weakness and death.

UsesSwainsonine is a plant alkaloid derived from Swainsona canescens (a leguminous plant). It is a reversible, active-site directed inhibitor of a-mannosidase at concentrations of 5-10mM. At acid pH, swainsonine resembles an intermediate in the hydrolysis of mannosidases.Swainsonine completely inhibits mammalian Golgi a-mannosidase II (a-3/6-mannosidase in the glycoprotein processing pathway) and mammalian lysosomal a-mannosidase (acid mannosidase). At higher concentrations, swainsonine also inhibits mammalian cytosolic a-mannosidase. It has been shown to inhibit growth of transformed fibroblasts in soft agar and to enhance the antiproliferative effects of INF on murine lymphoreticular tumor cells in vitro. It also blocks the expression of b1-6 branched complex-type oligosaccharides and shun

General DescriptionSwainsonine is produced by endophytes, plant and insect pathogens. It is synthesized from the pipecolic acid and mevalonic acid. Swainsonine is a water-soluble indole alkaloid.

Suppliers100 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
上海纯优生物科技有限公司15921393123 18302135232 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
上海哲研生物科技有限公司021-18017610038 18017610038 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
成都普睿法药物研发有限公司82633860 18982077548 · [email protected]
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
上海颖心实验室设备有限公司021-59178156 17002132182 · [email protected]
广东方信生物科技有限公司0751-2838688 13376594225 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
湖北广奥生物科技有限公司027-02702759223056 18162699093 · [email protected]
武汉市皇臻生物化工有限公司13795480948 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
ZHEJIANG JIUZHOU CHEM CO., LTD+86-0576225566889 +86-13454675544 · [email protected];[email protected];[email protected]
上海复和化学科技有限公司0086-21-67651709 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
上海明褀化学有限公司86-21-60936353
上海遐瑞医药科技有限公司+86 21 61551611
上海贤鼎生物科技有限公司4009209199 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
安徽科迪达化工有限公司0554-2106669 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
ALB Technology Limited702-983-3769 · [email protected]
上海一研生物科技有限公司021-69985186 13611928337 · [email protected]
四川精萃天成药物科技有限公司028-87865381 18108190480 · [email protected]
上海萄普生物医药技术有限公司15900573766 18018507602 · [email protected]
上海谱振生物科技有限公司4001650900 13817534909 · [email protected]
广东翁江化学试剂有限公司0751-2815987 13927875076 · [email protected]
Wuhan ChemNorm Biotech Co.,Ltd.+86-27-8439 4403 18971486879 · [email protected]
风咏生物(AbMole)021-10000000 13000000000 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
上海西格生物科技有限公司021-57810052 18930344717 · [email protected]
常州合晶化工有限公司85528066 13775048983 · [email protected]

Additional notes

DefinitionChEBI: An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.