CYTOCHALASIN B

Investigational

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6075266
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6893016 | https://www.ncbi.nlm.nih.gov/pubmed/27078104 | https://www.ncbi.nlm.nih.gov/pubmed/10716458

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 Target	Pharmacology	Potency
Regulation of actin cytoskeleton 1 Target ID: map04810 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6893016	Inhibitor 8297
Solute carrier family 2, facilitated glucose transporter member 1 1 Target ID: P11166 Gene ID: 6513.0 Gene Symbol: SLC2A1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27078104	Inhibitor 8297	0.11 µM [IC50]
Solute carrier family 2, facilitated glucose transporter member 3 2 Target ID: P11169 Gene ID: 6515.0 Gene Symbol: SLC2A3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27078104	Inhibitor 8297	0.144 µM [IC50]
Solute carrier family 2, facilitated glucose transporter member 4 3 Target ID: P14672 Gene ID: 6517.0 Gene Symbol: SLC2A4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27078104	Inhibitor 8297	0.294 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Angioplasty 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10716458	Palliative		Phase I 428	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
8 ug/mL single, intravascular Highest studied dose Dose: 8 ug/mL Route: intravascular Route: single Dose: 8 ug/mL Sources: https://pubmed.ncbi.nlm.nih.gov/10716458 Page: p.587	unhealthy, ADULT n = 13 Health Status: unhealthy Condition: coronary artery disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 13 Sources: https://pubmed.ncbi.nlm.nih.gov/10716458 Page: p.587	Sources: https://pubmed.ncbi.nlm.nih.gov/10716458 Page: p.587

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00HY62	https://www.1pchem.com/search?query=1P00HY62
Apollo Scientific	BIC1014	http://www.apolloscientific.co.uk/chemical_results.php?qstext=BIC1014&product_group=%25&search_fieldname=header_search
BOC Sciences	14930-96-2	http://www.bocsci.com/description.asp?cas=14930-96-2
Cayman Chemical	11328	http://www.caymanchem.com/app/template/Product.vm/catalog/11328
eMolecules	313124394	https://orderbb.emolecules.com/search/#?query=313124394
eMolecules	43441899	https://orderbb.emolecules.com/search/#?query=43441899

PubMed

Title	Date	PubMed
Action of cytochalasin B on cultured human lymphocytes.	1967 Dec 16	6075266
Mechanism of action of cytochalasin B on actin.	1980 Jun	6893016
Vascular remodeling and the local delivery of cytochalasin B after coronary angioplasty in humans.	2000 Mar 1	10716458
Mechanism of inhibition of human glucose transporter GLUT1 is conserved between cytochalasin B and phenylalanine amides.	2016 Apr 26	27078104

Patents

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.

Name

Type

Language

CYTOCHALASIN B

Common Name

English

24-OXA(14)CYTOCHALASA-6(12),13,21-TRIENE-1,23-DIONE, 7,20-DIHYDROXY-16-METHYL-10-PHENYL-, (7S,13E,16R,20R,21E)-

Common Name

English

TAMM

Common Name

English

2H-OXACYCLOTETRADECINO(2,3-D)ISOINDOLE-2,18(5H)-DIONE, 6,7,8,9,10,12A,13,14,15,15A,16,17-DODECAHYDRO-5,13-DIHYDROXY-9,15-DIMETHYL-14-METHYLENE-16-(PHENYLMETHYL)-, (5R-(3E,5R*,9R*,11E,12AS*,13S*,15S*,15AS*,16S*,18AS*))-

Common Name

English

PHOMIN

Common Name

English

CYTOCHALASIN B [MI]

Common Name

English

ROTHWEILER

Common Name

English

NSC-107658

Code

English

2H-OXACYCLOTETRADECINO(2,3-D)ISOINDOLE-2,18(5H)-DIONE, 6,7,8,9,10,12A,13,14,15,15A,16,17-DODECAHYDRO-5,13-DIHYDROXY-9,15-DIMETHYL-14-METHYLENE-16-(PHENYLMETHYL)-, (3E,5R,9R,11E,12AS,13S,15S,15AS,16S,18AS)-

Common Name

English

2H-OXACYCLOTETRADECINO(2,3-D)ISOINDOLE-2,18(5H)-DIONE, 16-BENZYL-6,7,8,9,10,12A,13,14,15,15A,16,17-DODECAHYDRO-5,13-DIHYDROXY-9,15-DIMETHYL-14-METHYLENE-, (E,E)-(5R,9R,12AS,13S,15S,15AS,16S,18AS)-

Common Name

English

CYTOCHALASIN B [HSDB]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID30893482