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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H37NO5
Molecular Weight 479.6078
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYTOCHALASIN B

SMILES

[H][C@]12[C@H](CC3=CC=CC=C3)NC(=O)[C@]14OC(=O)\C=C\[C@H](O)CCC[C@@H](C)C\C=C\[C@H]4[C@H](O)C(=C)[C@H]2C

InChI

InChIKey=GBOGMAARMMDZGR-TYHYBEHESA-N
InChI=1S/C29H37NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1

HIDE SMILES / InChI

Molecular Formula C29H37NO5
Molecular Weight 479.6078
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cytochalasin B is a cell-permeable alkaloid, isolated from a fungus Helminthosporium dematioideum. Cytochalasin B is an inhibitor of actin polymerization through binding to the fast-growing (barbed) end of F-actin filaments. Cytochalasin is used in studies of actin polymerization, cell division, and cell movement. The compound also inhibits glucose transporters GLUT1,3 and 4 and was investigated in a clinical trial to prevent restenosis after angioplasty surgery.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.11 µM [IC50]
0.144 µM [IC50]
0.294 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
In a clinical trial for prevention of restenosis after angioplasty, cytochalasin B was administered locally at the site of angioplasty at a concentration of 0.1-8.0 ug/mL.
Route of Administration: Intracoronary
In Vitro Use Guide
2 uM cytochalasin B reduces the maximum rate of the viscosity change during the polymerization of actin. Viscosity was measured at low shear rates at 26°C in an inclined falling ball device. The reciprocal of the ball velocity is proportional to the absolute viscosity of Newtonian fluids. For non-Newtonian fluids, the observed ball velocity is used to calculate the apparent viscosity, given in centipoise (cp) for comparison with Newtonian fluids with the same ball velocity.
Substance Class Chemical
Record UNII
3CHI920QS7
Record Status Validated (UNII)
Record Version