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Cytochalasin B

PubChem CID
5311281
Structure
Cytochalasin B_small.png
Cytochalasin B_3D_Structure.png
Molecular Formula
Synonyms
  • CYTOCHALASIN B
  • Phomin
  • 14930-96-2
  • cytochalasin-B
  • CHEBI:23527
Molecular Weight
479.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-12-16
  • Modify:
    2025-01-18
Description
Cytochalasin B is an organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments. It has a role as a metabolite, a platelet aggregation inhibitor, a mycotoxin and an actin polymerisation inhibitor. It is a cytochalasin, an organic heterotricyclic compound, a lactam and a lactone.
Cytochalasin B has been reported in Boeremia exigua, Sonchus mauritanicus, and other organisms with data available.
A cytotoxic member of the CYTOCHALASINS.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cytochalasin B.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

GBOGMAARMMDZGR-TYHYBEHESA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@@H]1CCC[C@H](/C=C/C(=O)O[C@]23[C@@H](/C=C/C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)CC4=CC=CC=C4)C)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C29H37NO5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

11032-95-4, 11042-65-2, 16006-03-4, 21476-12-0
11042-65-2, 16006-03-4, 21476-12-0

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 KEGG ID

2.3.10 Lipid Maps ID (LM_ID)

2.3.11 Metabolomics Workbench ID

2.3.12 NSC Number

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Cytochalasin B
  • Phomin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
479.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
479.26717328 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
479.26717328 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
95.9 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
35
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
859
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
8
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid; [Merck Index] White crystalline solid; [MSDSonline]

3.2.2 Color / Form

FELTED NEEDLES FROM ACETONE
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 366

3.2.3 Melting Point

218-221 °C
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 366

3.2.4 Optical Rotation

SPECIFIC OPTICAL ROTATION: +86.7 DEG @ 21 °C/D (C= 0.9 IN METHANOL), +84 DEG @ 25 °C/D (C= 1.0 IN ETHANOL); MP: 218 °C, FROM CHLOROFORM SOLUTION; MAX ABSORPTION: 229 NM (E= 44,668), 257 NM (SHOULDER), 265 NM (SHOULDER), 269 NM (SHOULDER)
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 281

3.3 Chemical Classes

Biological Agents -> Mycotoxins

3.3.1 Drugs

Pharmaceuticals -> Antibiotics
S6 | ITNANTIBIOTIC | Antibiotic List from the ITN MSCA ANSWER | DOI:10.5281/zenodo.2621956

3.3.2 Lipids

Polyketides [PK] -> Cytochalasins [PK11]

5 Chemical Vendors

6 Drug and Medication Information

6.1 Therapeutic Uses

EXPTL USE: THE EFFECTS OF VINBLASTINE, COLCHICINE, LIDOCAINE, & CYTOCHALASIN B ON TUMOR CELL KILLING BY BCG-ACTIVATED MACROPHAGES WERE EXAMINED. CYTOCHALASIN B, WHICH DISRUPTS MICROFILAMENTS, ENHANCED TUMOR CELL LYSIS & STASIS DUE TO ACTIVATED MARCOPHAGES AT A CONCN OF 10-7 MOLES. WHERAS VINBLASTINE & LIDOCAINE SEEM TO ACT ON THE MACROPHAGE ITSELF, CYTOCHALASIN B EXERTS ITS EFFECT PREDOMINANTLY ON THE TUMOR CELL. MICROTUBULES & MICROFILAMENTS MAY PLAY A ROLE IN THE DESTRUCTION OF TUMOR CELLS BY ACTIVATED MARCOPHAGES.
MARTIN F ET AL; EFFECTS OF FOUR AGENTS THAT MODIFY MICROTUBULES AND MICROFILAMENTS (VINBLASTINE, COLCHICINE, LIDOCAINE, AND CYTOCHALASIN B) ON MACROPHAGE-MEDIATED CYTOTOXICITY TO TUMOR CELLS; CANCER IMMUNOL IMMUNOTHER 10(2-3) 113 (1981)
EXPTL USE: CYTOCHALASIN B & COLCHICINE DECREASED THE NUMBER OF MOTILE CELLS WHEN ADDED TO YOSHIDA SARCOMA CELLS AT 5 & 0.4 MUG/ML, RESPECTIVELY. CYTOCHALASIN B ALSO DECREASED THE MOTILITY OF THE CELLS & DOSE-DEPENDENTLY INHIBITED THEIR GROWTH.
HOSAKA S ET AL; EFFECTS OF CYTOCHALASIN B AND COLCHICINE ON THE MOTILITY AND GROWTH OF YOSHIDA SARCOMA CELLS IN VITRO; SCI REP RES INST TOHOKU UNIV SER C 27(1-4) 27 (1980)
EXPTL USE: IN CULTURED IRC 741 RAT LEUKEMIA CELLS, CYTOCHALASIN B (1.5-4 MUG/ML) CAUSED DOSE-DEPENDENT BINUCLEATION & INHIBITION OF THE NORMAL INCREASE IN CELL NUMBER. IN CELLS ENTERING DIVISION AFTER EXPOSURE TO CYTOCHALASIN B FOR UP TO 24 HR, FURROWING WAS COMPLETELY INHIBITED IN A DOSE-DEPENDENT PROPORTION OF CELLS.
LOW RS, AUERSPERG N; EFFECTS OF ACRONYCINE AND OF CYTOCHALASIN B ON THE DIVISION OF RAT LEUKEMIA CELLS; EXP CELL RES 131(1) 15 (1981)

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

...IN THE BIOSYNTHESES OF CYTOCHALASIN B (PHOMIN) BY PHOMA SPECIES & CYTOCHALASIN D BY ZYGOSPORIUM MASONII...A NUMBER OF (14)C & (3)H PRECURSORS WERE FED TO PHOMA SPECIES & PRECISE DEGRADATION REACTIONS WERE PERFORMED TO REVEAL THE FORMATION OF CYTOCHALASIN B FROM ONE UNIT OF PHENYLALANINE, NINE UNITS OF ACETATE-MALONATE, & TWO UNITS OF METHIONINE. THE LABELLING PATTERN WAS ALSO CONFIRMED IN THE CASE OF CYTOCHALASIN D.
Rodricks, J.V., C. W. Hesseltine, and M. A. Mehlman (eds.). Mycotoxins in Human and Animal Health, Proceedings of Conference....Univ. of MD. October 4-8, 1976. Park Forest South, Illinois: Pathotox Publishers, Inc. 1977., p. 570
THE FORMATION OF CYTOCHALASIN B (PHOMIN) BY AN ENZYMATIC BAYER-VILLIGER TYPE OXYGEN INSERTION WAS PROVED BY A DIRECT CONVERSION OF LABELLED DEOXAPHOMIN BY PHOMA SPECIES.
Rodricks, J.V., C. W. Hesseltine, and M. A. Mehlman (eds.). Mycotoxins in Human and Animal Health, Proceedings of Conference....Univ. of MD. October 4-8, 1976. Park Forest South, Illinois: Pathotox Publishers, Inc. 1977., p. 571

7.2 Mechanism of Action

MAJOR BIOLOGICAL EFFECTS ARE THE BLOCKAGE OF CYTOPLASMIC CLEAVAGE RESULTING IN MULTINUCLEATE CELL FORMATION, THE INHIBITION OF CELL MOVEMENT, & THE INDUCTION OF NUCLEAR EXTRUSION... OTHER REPORTED EFFECTS INCLUDE THE INHIBITION OF GLUCOSE TRANSPORT, OF THYROID SECRETION, OF GROWTH HORMONE RELEASE, OF PHAGOCYTOSIS, & OF PLATELET AGGREGATION & CLOT CONTRACTION. /CYTOCHALASINS/
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 365
THROUGH THE USE OF (3)H-LABELLED CYTOCHALASINS B & D THE PRECISE BINDING SITES & SUB-CELLULAR LOCALIZATION ARE NOW UNDER INVESTIGATION... EXPERIMENTAL RESULTS OBTAINED THUS FAR SUPPORT THE IDEA THAT THE PRIMARY EFFECT IS MEMBRANOTROPIC, PERHAPS INVOLVING THE ASSOCIATION OF MICROFILAMENTS WITH THE PLASMA MEMBRANE. IT SHOULD BE NOTED THAT THE EFFECT OF CYTOCHALASIN B ON NORMAL & TRANSFORMED CELLS DIFFERS; THE LATTER BECOME MORE HIGHLY MULTINUCLEATED THAN NORMAL CELLS.
Rodricks, J.V., C. W. Hesseltine, and M. A. Mehlman (eds.). Mycotoxins in Human and Animal Health, Proceedings of Conference....Univ. of MD. October 4-8, 1976. Park Forest South, Illinois: Pathotox Publishers, Inc. 1977., p. 576
THE INFLUENCE OF CYTOCHALASIN B & E ON INTESTINAL DIGESTION OF MALTOSE & SUCROSE, & THEIR DIGESTION PRODUCTS AS GLUCOSE & FRUCTOSE WAS INVESTIGATED IN THE MOUSE IN VITRO. NEITHER DIGESTION OF MALTOSE OR SUCROSE NOR ACTIVITIES OF MALTASE OR SUCRASE IN EVERTED SACS OF MOUSE JEJUNUM WAS AFFECTED BY CYTOCHALASIN B OR E AT 5.0 & 10.0 MUG/ML AFTER 60 MIN INCUBATION. HOWEVER, ABSORPTION OF GLUCOSE DERIVED FROM MALTOSE OR SUCROSE DIGESTION WAS INHIBITED BY 68.5 & 65.9% DUE TO CYTOCHALASIN E (5.0 MUG/ML) & BY 29.5 & 13.1% DUE TO CYTOCHALASIN B AT THE SAME CONCN. CYTOCHALASINS B & E SEEMED TO STIMULATE ABSORPTION OF FRUCTOSE DERIVED FROM SUCROSE DIGESTION IN MOUSE JEJUNUM.
GLINSUKON T ET AL; INFLUENCE OF CYTOCHALASINS B AND E ON INTESTINAL ABSORPTION OF MALTOSE AND SUCROSE-DIGESTION PRODUCTS IN THE MOUSE; NUTR REP INT 27(1) 137 (1983)
THE INHIBITORY EFFECT OF CYTOCHALASIN E ON GALACTOSE ABSORPTION IN EVERTED SACS OF MOUSE JEJUNUM WAS STUDIED. CYTOCHALASIN B HAD THE HIGHEST POTENCY ON THE INHIBITION OF GALACTOSE ABSORPTION WHEN IT WAS ADDED IN THE MUCOSAL SOLN FOLLOWED BY CYTOCHALASIN E, A, C, & D, RESPECTIVELY.
GLINSUKON T ET AL; INHIBITORY EFFECT OF CYTOCHALASIN E ON GALACTOSE ABSORPTION IN THE MOUSE IN VITRO; RES COMMUN CHEM PATHOL PHARMACOL 38(2) 247 (1982)
For more Mechanism of Action (Complete) data for CYTOCHALASIN B (14 total), please visit the HSDB record page.

8 Use and Manufacturing

8.1 Uses

Sources/Uses
Cytochalasins are a group of mold metabolites having various effects on animal cells; More than twenty cytochalasins have been isolated from different mold species; Used in cytological research and in studying the polymerization properties of actin; Most studied is cytochalasin B; [Merck Index]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.

8.2 Methods of Manufacturing

ISOLATION & STRUCTURE OF CYTOCHALASINS A, B, C, D: ALDRIDGE ET AL, J CHEM SOC (C) 1967, 1667; ALDRIDGE ET AL, CHEM COMMUN 1967, 26; OF E & F: ALDRIDGE ET AL, CHEM COMMUN 1972, 148. /CYTOCHALASINS/
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 365
CYTOCHALASIN B WAS RECENTLY ISOLATED FROM PHOMA EXIGUA...
Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 432

8.3 General Manufacturing Information

THE MOST IMPORTANT & BIOLOGICALLY STUDIED OF THE CYTOCHALASINS.
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 366
THE CYTOCHALASINS GENERALLY CAN BE DESCRIBED AS A PHENYLALANINE OR TRYPTOPHAN MOIETY LINKED TO PERHYDROISOINDOLE MOIETY WHICH IS IN TURN LINKED TO A C16-C18 POLYKETIDE RING SYSTEM CONTAINING A CARBOCYCLIC (CYTOCHALASIN C), A LACTONE (CYTOCHALASIN A), OR A CYCLIC CARBONATE (CYTOCHALASIN E) MOIETY. /CYTOCHALASINS/
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 264

9 Identification

9.1 Analytic Laboratory Methods

TLC DATA; DETECTION: A BLUE FLUORESCENT SPOT UNDER UV LIGHT AFTER SPRAYING WITH 50% ETHANOLIC H2SO4 & HEATING. WELLS JM ET AL; CAN J MICROBIOL 22: 1137 (1976).
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 281

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Health Hazard
Signal
Danger
GHS Hazard Statements

H300+H310+H330 (38.7%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal]

H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]

H361 (98.7%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Precautionary Statement Codes

P203, P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P320, P321, P330, P361+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 75 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 2 (100%)

Acute Tox. 1 (100%)

Acute Tox. 2 (100%)

Repr. 2 (98.7%)

10.1.3 Hazards Summary

Causes ataxia, cyanosis, and coma at lethal doses in rats; Intraperitoneal LD50 (rat) = 11 mg/kg; [RTECS] Cause inhibitory effects on cell processes; No reports of chronic effects or carcinogenicity in humans; [HSDB] Target organ is the liver; An irritant; May be fatal if inhaled or ingested; Teratogenic; [Aldrich MSDS]

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

11.1.2 Interactions

TREATMENT OF WILD TYPE S49 LYMPHOMA CELLS WITH THE MICROFILAMENT DISRUPTER CYTOCHALASIN B REVERSIBLY & IN A HIGHLY DOSE-DEPENDENT FASHION ENHANCES CELLULAR CYCLIC AMP ACCUMULATION IN RESPONSE TO SUBSEQUENT ADDITION OF THE BETA-ADRENERGIC AGONIST (-)-ISOPROTERENOL, PROSTAGLANDIN E1, OR CHOLERA TOXIN.
INSEL PA, KOACHMAN AM; CYTOCHALASIN B ENHANCES HORMONE AND CHOLERA TOXIN-STIMULATED CYCLIC AMP ACCUMULATION IN S49 LYMPHOMA CELLS; J BIO CHEM 257(16) 9717 (1982)
CYTOCHALASIN B WAS UNABLE TO TRANSFORM 3T3-LIKE TUMOR CELLS, BUT DID INCREASE 8-40 FOLD THE FREQUENCY OF CELL TRANSFORMATION BY POLYOMA VIRUS.
SEIF R; FACTORS WHICH DISORGANIZE MICROTUBULES OR MICROFILAMENTS INCREASE THE FREQUENCY OF CELL TRANSFORMATION BY POLYOMA VIRUS; J VIROL 36(2) 421 (1980)
THE PINOCYTOTIC ACTIVITY, INDUCED BY CONCANAVALIN A IN AMOEBA PROTEUS, IS GREATLY INTENSIFIED BY CYTOCHALASIN B.
PRUSCH RD; THE INFLUENCE OF CONCANAVALIN A AND CYTOCHALASIN B ON PINOCYTOTIC ACTIVITY IN AMOEBA PROTEUS; PROTOPLASMA 106(3-4) 223 (1981)
CYTOCHALASIN B INHIBITED THE ELONGATION OF WHEAT COLEOPTILE SEGMENTS IN INDOLE-3-ACETIC ACID & OF MAIZE ROOTS, WITH THE ONLY ULTRASTRUCTURAL CHANGES BEING THE ACCUMULATION OF SECRETORY VESICLES. CYTOCHALASIN B APPARENTLY BLOCKED ELONGATION GROWTH BY INHIBITING VESICLE TRANSPORT & SECRETION OF CELL WALL COMPONENTS.
POPE DG ET AL; THE EFFECT OF CYTOCHALASIN B ON THE RATE OF GROWTH AND ULTRASTRUCTURE OF WHEAT COLEOPTILES AND MAIZE ROOTS; PLANTA 144(4) 373 (1979)

11.1.3 Human Toxicity Excerpts

CYTOTOXICITY OF CYTOCHALASIN B ON HELA CELLS: SAMPLES WERE DISSOLVED IN DMSO AT 10 MG/ML & DILUTED IN THE MEDIUM. CELLS ON COVER-GLASSES WERE TREATED FOR 3-DAYS. DEGREE OF CYTOTOXICITY WAS ESTIMATED ON A SCALE RANGING '0' (LITTLE CELLULAR DAMAGE) THROUGH '4' (COMPLETE CYTOLYSIS) IN OBSERVING THE STAINED COVER-GLASSES. '2' DENOTES APPROXIMATE 50% GROWTH-INHIBITORY DOSE. SPECIFIC DOSAGE WITH RESPECTIVE CYTOTOXICITY RATING WAS NOTED: 32 UG/ML= 4 RATING; 10 UG/ML= 3.5 RATING; 3.2 UG/ML= 2.5 RATING; 1.0 UG/ML= 1 RATING; 0.32 UG/ML= 0 RATING. /FROM TABLE/
Rodricks, J.V., C. W. Hesseltine, and M. A. Mehlman (eds.). Mycotoxins in Human and Animal Health, Proceedings of Conference....Univ. of MD. October 4-8, 1976. Park Forest South, Illinois: Pathotox Publishers, Inc. 1977., p. 574
CYTOCHALASIN B CAUSED THE RAPID INHIBITION OF ORNITHINE DECARBOXYLASE & S-ADENOSYL METHIONINE DECARBOXYLASE ACTIVITIES FOLLOWED BY A GRADUAL BUT MARKED DECLINE IN INTRACELLULAR LEVELS OF PUTRESCINE & SPERMIDINE.
SUNKARA PS ET AL; CYTOCHALASIN B INHIBITS POLYAMINE BIOSYNTHESIS IN HELA CELLS; EUR J CELL BIOL 26(1) 154 (1981)
AN IN VITRO ASSAY SYSTEM WAS USED TO ASSESS THE INHIBITORY EFFECTS OF CYTOCHALASIN B ON HUMAN MONOCYTE FUNCTIONS. MICROMOLAR CONCN (1-2 MUMOL) OF CYTOCHALASIN B INHIBITED IGG-RBC ATTACHMENT & INGESTION BUT DID NOT HAVE MUCH EFFECT ON COMPLEMENT-MEDIATED RBC ADHERENCE OR LATEX PARTICLE INGESTION. HIGHER CONCN (10 & 20 MUMOL) SUPPRESSED ALL 3 MONOCYTE FUNCTIONS.
ZEIGLER Z, SCHUGAR S; THE EFFECT OF CYTOCHALASIN B AND ALKALOID COMPOUNDS ON HUMAN MONOCYTE FUNCTIONS; J RETICULOENDOTHEL SOC 25(3) 235 (1979)
IN PURIFIED HUMAN PERIPHERAL BLOOD LYMPHOCYTES, LOW (0.01-10 MUMOL) CONCN OF CYTOCHALASINS A, B, E, & D PRODUCED MARKED AUGMENTATION OF TRANSPORT & METABOLIC RESPONSES TO PHYTOHEMAGGLUTININ (PHA) & CONCANAVALIN A (CON A), INCLUDING EFFECTS ON DNA SYNTHESIS, CYCLIC AMP ACCUMULATION, PHOSPHATIDYLINOSITOL TURNOVER, & SODIUM-DEPENDENT AMINO ACID TRANSPORT.
GREENE WC ET AL; CYTOCHALASIN SENSITIVE STRUCTURES AND LYMPHOCYTE ACTIVATION; EXP CELL RES 103(1) 109 (1976)
For more Human Toxicity Excerpts (Complete) data for CYTOCHALASIN B (6 total), please visit the HSDB record page.

11.1.4 Non-Human Toxicity Excerpts

CYTOCHALASIN B INHIBITS CELLULAR MOTILITY OF MOVING L CELLS. CYTOPLASMIC CLEAVAGE IS INHIBITED WITHOUT INTERFERENCE WITH NUCLEAR DIVISION, RESULTING IN BINUCLEATE & MULTINUCLEATE CELLS. THE EFFECT IS REVERSIBLE.
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 281
MAMMALIAN CELLS CAN BE ENUCLEATED BY TREATMENT WITH CYTOCHALASIN B (10 UG/ML) FOLLOWED BY CENTRIFUGATION. CYTOCHALASIN B HAS BEEN REPORTED TO INHIBIT THE FOLLOWING CELLULAR FUNCTIONS: RELEASE OF GROWTH HORMONE; THYROID SECRETION; PHAGOCYTOSIS; PLATELET AGGREGATION & CLOT RETRACTION; & HEXOSE TRANSPORT.
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 281
EFFECTS OF CYTOCHALASINS ON MAMMALIAN CELLS: AMONG THE MORE PROMINENT EFFECTS ARE SEVERAL WHICH ARE CHARACTERIZED AS MORPHOLOGICAL IN NATURE, SUCH AS CYTOSKELETAL VARIATION, MULTINUCLEATION, DIFFUSE ORGANELLE ALTERATION, NUCLEAR EXTRUSION, & SURFACE PHENOMENA SUCH AS DIMINISHED MEMBRANE RUFFLING. OTHER EFFECTS ARE DESCRIBED AS FUNCTIONAL OR PHYSIOLOGICAL, & INCLUDE INHIBITION OF CELL MOTILITY, MITOTIC REPRODUCTION, & PHAGOCYTOSIS & PINOCYTOSIS; ALTERATION OF SURFACE ADHESION PROPERTIES & MICROFILAMENTS; DEPRESSION OF SYNTHESIS; & UPTAKE OF MEMBRANE COMPONENTS. THESE STUDIES WERE PERFORMED MAINLY WITH CYTOCHALASIN B & OCCASIONALLY WITH CYTOCHALASIN A, D (ZYGOSPORING A), & E.
Rodricks, J.V., C. W. Hesseltine, and M. A. Mehlman (eds.). Mycotoxins in Human and Animal Health, Proceedings of Conference....Univ. of MD. October 4-8, 1976. Park Forest South, Illinois: Pathotox Publishers, Inc. 1977., p. 574
...EXPOSED EXPLANTED PRE-SOMITE CHICK EMBRYOS TO 0.5 TO 1.0 MICROGRAMS...& OBSERVED A HIGH INCIDENCE OF NEURAL TUBE CLOSURE DEFECTS.
Shepard, T. H. Catalog of Teratogenic Agents. 3rd ed. Baltimore, MD.: Johns Hopkins University Press, 1980., p. 289
For more Non-Human Toxicity Excerpts (Complete) data for CYTOCHALASIN B (17 total), please visit the HSDB record page.

11.2 Ecological Information

11.2.1 Natural Pollution Sources

FUNGAL SOURCE: HELMINTHOSPORIUM DEMATIOIDEUM, HORMISCIUM SPECIES, & PHOMA SPECIES.
Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 281
A CLASS OF MOLD METABOLITES EXHIBITING INHIBITORY EFFECTS ON CELL PROCESSES. SIX CYTOCHALASINS HAVE BEEN ISOLATED: CYTOCHALASINS A, B & F FROM HELMINTHOSPORIUM DEMATIOIDEUM; C & D FROM METARRHIZIUM ANISOPLIAE; E FROM ROSELLINIA NECATRIX. /CYTOCHALASINS/
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 365

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Wiley References

13.4 Chemical Co-Occurrences in Literature

13.5 Chemical-Gene Co-Occurrences in Literature

13.6 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 Chemical Co-Occurrences in Patents

14.3 Chemical-Disease Co-Occurrences in Patents

14.4 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15.2 Chemical-Target Interactions

15.3 Pathways

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 LIPID MAPS Classification

18.4 KEGG: Lipid

18.5 KEGG: Natural Toxins

18.6 ChemIDplus

18.7 ChEMBL Target Tree

18.8 UN GHS Classification

18.9 NORMAN Suspect List Exchange Classification

18.10 EPA DSSTox Classification

18.11 LOTUS Tree

18.12 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione
    https://echa.europa.eu/substance-information/-/substanceinfo/100.035.440
    7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione (EC: 239-000-2)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/72302
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. ChEBI
  9. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  10. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  11. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  12. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  13. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  14. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  15. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  16. Natural Product Activity and Species Source (NPASS)
  17. Metabolomics Workbench
  18. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Cytochalasin B
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  19. Protein Data Bank in Europe (PDBe)
  20. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  21. Therapeutic Target Database (TTD)
  22. Wikidata
  23. Wikipedia
  24. Wiley
  25. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  26. PubChem
  27. GHS Classification (UNECE)
  28. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS