| 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
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
| Molecular Formula | C22H31NO5S |
| Molecular Weight | 421.55 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
Approval Year
PubMed
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.