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Identification
NameStaurosporine
Accession NumberDB02010  (EXPT02970, EXPT02972)
Typesmall molecule
Groupsexperimental
Description

An indolocarbazole that is a potent protein kinase C inhibitor which enhances cAMP-mediated responses in human neuroblastoma cells. (Biochem Biophys Res Commun 1995;214(3):1114-20)

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number62996-74-1
WeightAverage: 466.531
Monoisotopic: 466.200490718
Chemical FormulaC28H26N4O3
InChI KeyHKSZLNNOFSGOKW-UCBFMKAXSA-N
InChI
InChI=1S/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20+,26-,28-/m1/s1
IUPAC Name
(2R,3R,4R,6S)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^{2,6}.0^{7,28}.0^{8,13}.0^{15,19}.0^{20,27}.0^{21,26}]nonacosa-8,10,12,14(28),15(19),20(27),21,23,25-nonaen-16-one
SMILES
CN[C@@H]1C[C@@H]2O[C@](C)([C@@H]1OC)N1C3=C(C=CC=C3)C3=C1C1=C(C4=C(C=CC=C4)N21)C1=C3CNC1=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassIndoles and Derivatives
SubclassCarbazoles
Direct parentIndolocarbazoles
Alternative parentsPyrroloindoles; Isoindolones; Indoles; Benzene and Substituted Derivatives; Oxanes; Pyrroles; Secondary Carboxylic Acid Amides; Ethers; Polyamines; Dialkylamines; Carboxylic Acids; Isoindlines
Substituentspyrroloindole; isoindolone; isoindole or derivative; isoindoline; indole; oxane; benzene; pyrrole; carboxamide group; secondary carboxylic acid amide; carboxylic acid derivative; polyamine; carboxylic acid; secondary amine; ether; secondary aliphatic amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9737
Blood Brain Barrier - 0.5243
Caco-2 permeable - 0.5213
P-glycoprotein substrate Substrate 0.7192
P-glycoprotein inhibitor I Inhibitor 0.6683
P-glycoprotein inhibitor II Non-inhibitor 0.6315
Renal organic cation transporter Non-inhibitor 0.7748
CYP450 2C9 substrate Non-substrate 0.7682
CYP450 2D6 substrate Non-substrate 0.7667
CYP450 3A4 substrate Substrate 0.7987
CYP450 1A2 substrate Non-inhibitor 0.563
CYP450 2C9 substrate Non-inhibitor 0.6732
CYP450 2D6 substrate Non-inhibitor 0.8232
CYP450 2C19 substrate Non-inhibitor 0.6896
CYP450 3A4 substrate Non-inhibitor 0.5634
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5897
Ames test Non AMES toxic 0.6318
Carcinogenicity Non-carcinogens 0.8573
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.6695 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9986
hERG inhibition (predictor II) Inhibitor 0.5198
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility4.39e-02 g/lALOGPS
logP3.14ALOGPS
logP3.97ChemAxon
logS-4ALOGPS
pKa (strongest acidic)14.14ChemAxon
pKa (strongest basic)9.55ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area69.45ChemAxon
rotatable bond count2ChemAxon
refractivity132.37ChemAxon
polarizability51.38ChemAxon
number of rings8ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Chikara Murakata, Toshimitsu Takiguchi, Shigeo Katsumata, Akira Mihara, Keiichi Takahashi, Hiromitsu Saito, Shiro Akinaga, Masami Okabe, Yutaka Saito, “Process for producing staurosporine derivatives.” U.S. Patent US5344926, issued December, 1990.

US5344926
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC02079
PubChem Compound44120114
PubChem Substance46504923
ChemSpider5089
BindingDB2579
ChEBI15738
ChEMBL
Therapeutic Targets DatabaseDNC001380
PharmGKBPA165109623
HETSTO
WikipediaStaurosporine
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Tyrosine-protein kinase Lck

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tyrosine-protein kinase Lck P06239 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Serine/threonine-protein kinase pim-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serine/threonine-protein kinase pim-1 P11309 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

3. Tyrosine-protein kinase ITK/TSK

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tyrosine-protein kinase ITK/TSK Q08881 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

4. Tyrosine-protein kinase SYK

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tyrosine-protein kinase SYK P43405 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

5. MAP kinase-activated protein kinase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
MAP kinase-activated protein kinase 2 P49137 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

6. Glycogen synthase kinase-3 beta

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Glycogen synthase kinase-3 beta P49841 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

7. Tyrosine-protein kinase CSK

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tyrosine-protein kinase CSK P41240 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

8. Cyclin-dependent kinase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cyclin-dependent kinase 2 P24941 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

9. Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

10. 3-phosphoinositide-dependent protein kinase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
3-phosphoinositide-dependent protein kinase 1 O15530 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

11. Protein kinase C theta type

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Protein kinase C theta type Q04759 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

12. Tyrosine-protein kinase ZAP-70

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tyrosine-protein kinase ZAP-70 P43403 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Budworth J, Davies R, Malkhandi J, Gant TW, Ferry DR, Gescher A: Comparison of staurosporine and four analogues: their effects on growth, rhodamine 123 retention and binding to P-glycoprotein in multidrug-resistant MCF-7/Adr cells. Br J Cancer. 1996 May;73(9):1063-8. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17