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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
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)
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)
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)
Inhibitor
8297
 0.294 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Phase I
428
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse 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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

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

Patents

US3890435
1
US5342926
1

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
Created
by admin
on Fri Dec 15 15:36:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:36:46 GMT 2023
Record UNII
3CHI920QS7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYTOCHALASIN B
HSDB   MI  
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
Created by admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
PRIMARY
ECHA (EC/EINECS)
239-000-2
Created by admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
PRIMARY
MERCK INDEX
m4057
Created by admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
PRIMARY Merck Index
HSDB
3479
Created by admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
PRIMARY
CHEBI
23527
Created by admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
PRIMARY
FDA UNII
3CHI920QS7
Created by admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
PRIMARY
CAS
14930-96-2
Created by admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
PRIMARY
MESH
D003571
Created by admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
PRIMARY
WIKIPEDIA
CYTOCHALASIN B
Created by admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
PRIMARY
NSC
107658
Created by admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
PRIMARY
PUBCHEM
5311281
Created by admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
PRIMARY
NIH
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