BLEBBISTATIN, (-)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H16N2O2
Molecular Weight	292.3318
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C2N=C3N(CC[C@@]3(O)C(=O)C2=C1)C4=CC=CC=C4

InChI

InChIKey=LZAXPYOBKSJSEX-GOSISDBHSA-N

InChI=1S/C18H16N2O2/c1-12-7-8-15-14(11-12)16(21)18(22)9-10-20(17(18)19-15)13-5-3-2-4-6-13/h2-8,11,22H,9-10H2,1H3/t18-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H16N2O2
Molecular Weight	292.3318
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18528569
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15750603 | https://www.ncbi.nlm.nih.gov/pubmed/16249490

(–)-Blebbistatin is the active enantiomer of (±)-Blebbistatin that accounts for the inhibitory activity towards ATPase and myosin II-dependent cellular processes. It is of great interest because it is specific for certain myosin isoforms: (–)-Blebbistatin potently inhibit the actomyosin ATPase activities of expressed nonmuscle myosin IIA, nonmuscle myosin IIB, rabbit skeletal muscle myosin II, and D. discoideum myosin II, but does not inhibit smooth muscle myosin II, nor myosins from classes I, V or X. Blebbistatin binds within the apex of the myosin cleft at the opposite end of the ‘phosphate tube’ from MgADP–vanadate.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Myosin-2 1 Target ID: Q9UKX2 Gene ID: 4620.0 Gene Symbol: MYH2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15750603	Binding Agent 1076		5.1 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
The small molecule tool (S)-(-)-blebbistatin: novel insights of relevance to myosin inhibitor design.	2008-06-21	18528569

Patents

Sample Use Guides

In Vivo Use Guide

The effects of a single IP injection of Blebbistatin (Both enantiomers) on tissue distribution and several measures of health in mice. Racemic Blebbistatin was used at 10 mg/kg, delivering 5 mg/kg of the active enantiomer ((–)-Blebbistatin).

Route of Administration: Intraperitoneal

In Vitro Use Guide

Porcine primary TM and CB cells were isolated from freshly obtained cadaveric eyes by collagenase IV digestion. Cells were then treated with blebbistatin (10–200 mkM) dissolved in dimethyl sulfoxide [DMSO]) for 2 hours. Changes in cell shape were recorded with a phase-contrast microscope

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:05:28 GMT 2025` Edited by `admin` on `Mon Mar 31 23:05:28 GMT 2025`
Record UNII	8WII7624I5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(-)-BLEBBISTATIN

Preferred Name

English

BLEBBISTATIN, (-)-

Common Name

English

BLEBBISTATIN (S)-FORM [MI]

Common Name

English

4H-PYRROLO(2,3-B)QUINOLIN-4-ONE, 1,2,3,3A-TETRAHYDRO-3A-HYDROXY-6-METHYL-1-PHENYL-, (3AS)-

Systematic Name

English

Code System Code Type Description

CAS

856925-71-8