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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H31NO5S
Molecular Weight 421.55
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LATRUNCULIN A

SMILES

[H][C@]1(CSC(=O)N1)[C@@]2(O)C[C@@]3([H])C[C@@H](CC[C@H](C)C=C\C=C\CCC(C)=CC(=O)O3)O2

InChI

InChIKey=DDVBPZROPPMBLW-IZGXTMSKSA-N
InChI=1S/C22H31NO5S/c1-15-7-5-3-4-6-8-16(2)11-20(24)27-18-12-17(10-9-15)28-22(26,13-18)19-14-29-21(25)23-19/h3-5,7,11,15,17-19,26H,6,8-10,12-14H2,1-2H3,(H,23,25)/b4-3+,7-5-,16-11-/t15-,17-,18-,19+,22-/m1/s1

HIDE SMILES / InChI
Latrunculin A is a naturally occurring toxin that can be purified from the red sea sponge Latrunculia magnifica. It disrupts actin polymerization and prevents mitotic spindle formation; therefore preventing proper cellular replication. It was discovered that latrunculin A has strong anticancer effects, and it was investigated as a treatment candidate for peritoneal dissemination of gastric cancer.

CNS Activity

Originator

Sources: DOI: 10.1016/0040-4039(80)80255-3
Curator's Comment: Latrunculins isolation. DOI: 10.1007/BF00390634

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P68133
Gene ID: 58.0
Gene Symbol: ACTA1
Target Organism: Homo sapiens (Human)
0.2 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Microtubules, but not actin filaments, drive daughter cell budding and cell division in Toxoplasma gondii.
2000 Apr
Seizures induced by in vivo latrunculin a and jasplakinolide microperfusion in the rat hippocampus.
2006
Cocaine increases actin cycling: effects in the reinstatement model of drug seeking.
2006 Feb 1
A mutation of beta -actin that alters depolymerization dynamics is associated with autosomal dominant developmental malformations, deafness, and dystonia.
2006 Jun
Myosin light chain kinase plays a role in the regulation of epithelial cell survival.
2006 Jun 1
Azaspiracid-1 inhibits endocytosis of plasma membrane proteins in epithelial cells.
2010 Sep
Patents

Sample Use Guides

in mice: Mice bearing peritoneally disseminated MKN45 or NUGC-4 (gastric cancer cells) tumors were prepared by an i.p. inoculation of 1×107 cells in 5% DMSO/0.7 mL PBS. On day 3, 10 and 17 after tumor inoculation, each mouse was given an i.p.injection of latrunculin A. The i.p. injection group were treated with latrunculin A (0.05 mg/kg, 5% DMSO in 0.7 mL PBS, n=14, MKN45; and n=10, NUGC-4), and the control group was treated with 5% DMSO in 0.7 mL PBS (n=19, MKN45; and n=9, NUGC-4). Negative (n=10) group was given latrunculin A without tumor inoculation.
Route of Administration: Intraperitoneal
It was reported that 25 µM Latrunculin A (LatA) blocked actin polymerization in the capacitated sperm head, resulting in a marked decrease in sperm with relocated IZUMO1 during the A23187-induced acrosome reaction and cumulus layer penetration. Treated sperm also exhibited reduced zona pellucida penetration and fertilizing capacity. Interestingly, LatA-treated sperm present in the perivitelline space of eggs did not show impaired IZUMO1 relocation.
Name Type Language
LATRUNCULIN A
MI  
Common Name English
LATRUNCULIN A [MI]
Common Name English
2-THIAZOLIDINONE, 4-((1R,4Z,8E,10Z,12S,15R,17R)-17-HYDROXY-5,12-DIMETHYL-3-OXO-2,16-DIOXABICYCLO(13.3.1)NONADECA-4,8,10-TRIEN-17-YL)-, (4R)-
Systematic Name English
NSC-613011
Code English
LAT-A
Brand Name English
LATRUNCULIN
Common Name English
2-THIAZOLIDINONE, 4-(17-HYDROXY-5,12-DIMETHYL-3-OXO-2,16-DIOXABICYCLO(13.3.1)NONADECA-4,8,10-TRIEN-17-YL)-, (1R-(1R*,4Z,8E,10Z,12S*,15R*,17R*(R*)))-
Common Name English
Code System Code Type Description
WIKIPEDIA
Latrunculin
Created by admin on Fri Dec 15 17:45:14 GMT 2023 , Edited by admin on Fri Dec 15 17:45:14 GMT 2023
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DRUG BANK
DB02621
Created by admin on Fri Dec 15 17:45:14 GMT 2023 , Edited by admin on Fri Dec 15 17:45:14 GMT 2023
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MESH
C037067
Created by admin on Fri Dec 15 17:45:14 GMT 2023 , Edited by admin on Fri Dec 15 17:45:14 GMT 2023
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EPA CompTox
DTXSID90893488
Created by admin on Fri Dec 15 17:45:14 GMT 2023 , Edited by admin on Fri Dec 15 17:45:14 GMT 2023
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CAS
76343-93-6
Created by admin on Fri Dec 15 17:45:14 GMT 2023 , Edited by admin on Fri Dec 15 17:45:14 GMT 2023
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CHEBI
69136
Created by admin on Fri Dec 15 17:45:14 GMT 2023 , Edited by admin on Fri Dec 15 17:45:14 GMT 2023
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MERCK INDEX
m6703
Created by admin on Fri Dec 15 17:45:14 GMT 2023 , Edited by admin on Fri Dec 15 17:45:14 GMT 2023
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NSC
613011
Created by admin on Fri Dec 15 17:45:14 GMT 2023 , Edited by admin on Fri Dec 15 17:45:14 GMT 2023
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PUBCHEM
445420
Created by admin on Fri Dec 15 17:45:14 GMT 2023 , Edited by admin on Fri Dec 15 17:45:14 GMT 2023
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FDA UNII
SRQ9WWM084
Created by admin on Fri Dec 15 17:45:14 GMT 2023 , Edited by admin on Fri Dec 15 17:45:14 GMT 2023
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