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68475-42-3 molecular structure
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6,7-dichloro-1H,2H,3H,5H-imidazolidino[2,1-b]quinazolin-2-one hydrochloride

ChemBase ID: 146
Molecular Formular: C10H8Cl3N3O
Molecular Mass: 292.54902
Monoisotopic Mass: 290.97329493
SMILES and InChIs

SMILES:
N12C(=Nc3c(C1)c(c(cc3)Cl)Cl)NC(=O)C2.Cl
Canonical SMILES:
O=C1NC2=Nc3c(CN2C1)c(Cl)c(cc3)Cl.Cl
InChI:
InChI=1S/C10H7Cl2N3O.ClH/c11-6-1-2-7-5(9(6)12)3-15-4-8(16)14-10(15)13-7;/h1-2H,3-4H2,(H,13,14,16);1H
InChIKey:
TVWRQCIPWUCNMI-UHFFFAOYSA-N

Cite this record

CBID:146 http://www.chembase.cn/molecule-146.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
6,7-dichloro-1H,2H,3H,5H-imidazolidino[2,1-b]quinazolin-2-one hydrochloride
IUPAC Traditional name
agrylin hydrochloride
anagrelide hydrochloride
Brand Name
Agrylin
Xagrid
Synonyms
Anagrelide HCL
Anagrelide Hydrochloride
BL-4162A
Anagrelide
6,7-Dichloro-1,5-dihydroimidazo[2,1-b]quinazolin-2(3H)-one
BMY-26538-01
Agrylin
Tromboreductin
Xagrid
RL 603
Anagrelide Hydrochloride
CAS Number
68475-42-3
58579-51-4
PubChem SID
160963609
PubChem CID
42786

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
A637300 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.548792  H Acceptors
H Donor LogD (pH = 5.5) 1.9383392 
LogD (pH = 7.4) 1.9438572  Log P 1.9439309 
Molar Refractivity 63.2506 cm3 Polarizability 23.18002 Å3
Polar Surface Area 44.7 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Acetone expand Show data source
DMSO expand Show data source
Ethanol expand Show data source
Very slightly soluble expand Show data source
Apperance
Off-White to Pale Beige Solid expand Show data source
Melting Point
>280°C (dec.) expand Show data source
Hydrophobicity(logP)
2.4 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00261 external link
Item Information
Drug Groups approved
Description Anagrelide is a drug used for the treatment of essential thrombocytosis (ET; essential thrombocythemia). It also has been used in the treatment of chronic myeloid leukemia. [Wikipedia]
Indication For the treatment of patients with thrombocythemia, secondary to myeloproliferative disorders, to reduce the elevated platelet count and the risk of thrombosis and to ameliorate associated symptoms including thrombo-hemorrhagic events.
Pharmacology Anagrelide is a drug used for the treatment of essential thrombocytosis (ET; essential thrombocythemia). It works by inhibiting the maturation of megakaryocytes into platelets. The exact mechanism of action is unclear, although it is known to be a potent (IC50 = 36nM) inhibitor of phosphodiesterase-III.
Toxicity There are no reports of overdosage with anagrelide, however thrombocytopenia, which can potentially cause bleeding, is expected from overdosage. Single oral doses of anagrelide at 2,500, 1,500 and 200 mg/kg in mice, rats and monkeys, respectively, were not lethal. Symptoms of acute toxicity were: decreased motor activity in mice and rats and softened stools and decreased appetite in monkeys.
Affected Organisms
Humans and other mammals
Biotransformation Extensive, with < 1% recovered unchanged in the urine. Metabolized primarily in the liver by cytochrome P450 1A2 (CYP1A2). Recently, it was found that anagrelide is bio-transformed in humans into two major metabolites (6,7-dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one (BCH24426) and 2-amino-5,6-dichloro-3,4,-dihydroquinazoline (RL603). Whether these metabolites have biological activities that may underlie the mode of action of the parent drug is presently unclear.
Half Life At fasting and at a dose of 0.5 mg of anagrelide, the plasma half-life is 1.3 hours.
References
Voglova J, Maisnar V, Beranek M, Chrobak L: [Combination of imatinib and anagrelide in treatment of chronic myeloid leukemia in blastic phase] Vnitr Lek. 2006 Sep;52(9):819-22. [Pubmed]
Petrides PE: Anagrelide: what was new in 2004 and 2005? Semin Thromb Hemost. 2006 Jun;32(4 Pt 2):399-408. [Pubmed]
Harrison CN, Campbell PJ, Buck G, Wheatley K, East CL, Bareford D, Wilkins BS, van der Walt JD, Reilly JT, Grigg AP, Revell P, Woodcock BE, Green AR: Hydroxyurea compared with anagrelide in high-risk essential thrombocythemia. N Engl J Med. 2005 Jul 7;353(1):33-45. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - A637300 external link
A phosphodiesterase inhibitor with antiplatelet activity. Used as an antithrombocythemic.

REFERENCES

REFERENCES

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  • • Voglova J, Maisnar V, Beranek M, Chrobak L: [Combination of imatinib and anagrelide in treatment of chronic myeloid leukemia in blastic phase] Vnitr Lek. 2006 Sep;52(9):819-22. Pubmed
  • • Petrides PE: Anagrelide: what was new in 2004 and 2005? Semin Thromb Hemost. 2006 Jun;32(4 Pt 2):399-408. Pubmed
  • • Harrison CN, Campbell PJ, Buck G, Wheatley K, East CL, Bareford D, Wilkins BS, van der Walt JD, Reilly JT, Grigg AP, Revell P, Woodcock BE, Green AR: Hydroxyurea compared with anagrelide in high-risk essential thrombocythemia. N Engl J Med. 2005 Jul 7;353(1):33-45. Pubmed
  • • Fleming, J.S., et al.: Thromb. Res., 15, 373 (1979)
  • • Seiler, S., et al.: J. Pharmacol. Exp. Ther., 243, 767 (1979)
  • • Silverstein, M. N., et al.: N. Engl. J. Med., 318, 1292 (1979)
  • • Spencer, C.M., et al.: Drugs, 47, 809 (1979)
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PATENTS

PATENTS

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INTERNET

INTERNET

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