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Details

Stereochemistry ACHIRAL
Molecular Formula C10H7Cl2N3O
Molecular Weight 256.088
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANAGRELIDE

SMILES

ClC1=CC=C2NC3=NC(=O)CN3CC2=C1Cl

InChI

InChIKey=OTBXOEAOVRKTNQ-UHFFFAOYSA-N
InChI=1S/C10H7Cl2N3O/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)

HIDE SMILES / InChI

Description

Anagrelide is an orally active quinazinolone derivative that was originally developed as an antiplatelet drug. The drug inhibits cyclic nucleotide phosphodiesterase III (PDEIII) and phopholipase A2, which is thought to cause the side effects of vasodilation, positive inotropism, reduced platelet aggregation. However, significant inhibition of platelet aggregation is observed only at doses of anagrelide higher than those required to reduce platelet count. It is indicated for the treatment of patients with thrombocythemia, secondary to myeloproliferative disorders. Commonly reported side effects of anagrelide include: abdominal pain, dizziness, headache, nausea, and palpitations. Other side effects include: back pain, fever, tachycardia, vomiting, and anorexia. There is a single case report, which suggests that sucralfate may interfere with anagrelide absorption. Anagrelide is an inhibitor of cyclic AMP PDE III. The effects of medicinal products with similar properties such as inotropes milrinone, enoximone, amrinone, olprinone and cilostazol may be exacerbated by anagrelide.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AGRYLIN
PubMed

PubMed

TitleDatePubMed
New approaches to the treatment of thrombocytosis.
2003 Feb
Current treatment of myelofibrosis.
2005 Apr
Definition of subtypes of essential thrombocythaemia and relation to polycythaemia vera based on JAK2 V617F mutation status: a prospective study.
2005 Dec 3
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Essential thrombocythemia.
2005 Oct
Anagrelide: a review of its use in the management of essential thrombocythaemia.
2006
Bilateral adrenal hemorrhage associated with essential thrombocytosis.
2006 Feb
'Double hit' from streptococcal pneumonia and hypersensitivity pneumonitis associated with anagrelide.
2006 Feb
A preliminary investigation into the action of anagrelide: thrombopoietin-c-Mpl receptor interactions.
2006 Jan
Molecular basis of the diagnosis and treatment of polycythemia vera and essential thrombocythemia.
2006 Jun 1
Essential thrombocythemia: scientific advances and current practice.
2006 Mar
Patents

Sample Use Guides

In Vivo Use Guide
0.5 mg qid or 1 mg bid (2 capsules of 0.5 mg twice a day) for at least one week
Route of Administration: Oral
In Vitro Use Guide
Anagrelide was studied as an inhibitor of PDE fractions I, II and III separated from each other from rabbit heart supernatant. Anagrelide did not inhibit PDE I or II except at a concentration of 10(-4) M where inhibition of 33 and 39%, respectively, was noted. As expected, anagrelide inhibited PDE fraction III with a dose-response curve that was closely similar to that seen in the human platelet preparation. The IC50 for inhibition of the rabbit heart PDE fraction III was 7 x 10(-8) M.
Name Type Language
ANAGRELIDE
EMA EPAR   HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ANAGRELIDE [HSDB]
Common Name English
ANAGRELIDE [INN]
Common Name English
ANAGRELIDE [EMA EPAR]
Common Name English
6,7-DICHLORO-1,5-DIHYDROIMIDAZO(2,1-B)-QUINAZOLIN-2(3H)-ONE MONOHYDROCHLORIDE
Systematic Name English
ANAGRELIDE [VANDF]
Common Name English
ANAGRELIDE [WHO-DD]
Common Name English
IMIDAZO(2,1-B)QUINAZOLIN-2(3H)-ONE, 6,7-DICHLORO-1,5-DIHYDRO-, MONOHYDROCHLORIDE
Common Name English
ANAGRELIDE [MI]
Common Name English
Classification Tree Code System Code
LIVERTOX 54
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
NDF-RT N0000175972
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
WHO-VATC QL01XX35
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
NDF-RT N0000175638
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
WHO-ATC L01XX35
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
Code System Code Type Description
EPA CompTox
68475-42-3
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY
NCI_THESAURUS
C28825
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY
EVMPD
SUB05499MIG
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY
CAS
68475-42-3
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY
MERCK INDEX
M1886
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY Merck Index
IUPHAR
7114
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY
ChEMBL
CHEMBL760
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY
PUBCHEM
2182
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY
WIKIPEDIA
ANAGRELIDE
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY
RXCUI
596724
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY RxNorm
HSDB
68475-42-3
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY
DRUG BANK
DB00261
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY
INN
4672
Created by admin on Tue Mar 06 10:34:41 UTC 2018 , Edited by admin on Tue Mar 06 10:34:41 UTC 2018
PRIMARY