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Details

Stereochemistry ACHIRAL
Molecular Formula C22H44N2.2C4H4O4
Molecular Weight 568.7425
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of ATIPRIMOD DIMALEATE

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CCCC1(CCC)CCC2(CCN(CCCN(CC)CC)C2)CC1

InChI

InChIKey=WWCRKTZNNINNOT-SPIKMXEPSA-N
InChI=1S/C22H44N2.2C4H4O4/c1-5-10-21(11-6-2)12-14-22(15-13-21)16-19-24(20-22)18-9-17-23(7-3)8-4;2*5-3(6)1-2-4(7)8/h5-20H2,1-4H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C22H44N2
Molecular Weight 336.5982
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Atiprimod is an oral azaspirane which was initially developed by Smith Kline and French Laboratories for treating rheumatoid arthritis (discontinued in phase I). Due to its anti-inflammatory, antineoplastic, and antiangiogenic properties, the drug was tested in patients with Neuroendocrine Carcinoma and Multiple Myeloma and reached phase II (discontinued). In vitro studies revealed that atiprimod exerts its action by inhibiting the phosphorylation of signal transducer and activator of transcription 3 (STAT3), blocking the signalling pathways of interleukin-6 and vascular endothelial growth factor (VEGF) and downregulating the anti-apoptotic proteins Bcl-2, Bcl-XL, and Mcl-1, thereby inhibiting cell proliferation, inducing cell cycle arrest, and inducing apoptosis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Atiprimod is an inhibitor of cancer cell proliferation and angiogenesis.
2004 Dec
Atiprimod blocks STAT3 phosphorylation and induces apoptosis in multiple myeloma cells.
2005 Jul 11
Biological pathways and in vivo antitumor activity induced by Atiprimod in myeloma.
2007 Dec
Deactivation of Akt and STAT3 signaling promotes apoptosis, inhibits proliferation, and enhances the sensitivity of hepatocellular carcinoma cells to an anticancer agent, Atiprimod.
2007 Jan
Atiprimod: a multi-functional drug candidate for myeloid and other malignancies.
2007 Jan
Atiprimod blocks phosphorylation of JAK-STAT and inhibits proliferation of acute myeloid leukemia (AML) cells.
2007 Jan
Atiprimod inhibits the growth of mantle cell lymphoma in vitro and in vivo and induces apoptosis via activating the mitochondrial pathways.
2007 Jun 15
A severe combined immunodeficient-hu in vivo mouse model of human primary mantle cell lymphoma.
2008 Apr 1
New developments in the pathology of malignant lymphoma: a review of the literature published from May to July 2008.
2008 Sep
Advances in the treatment of gastroenteropancreatic neuroendocrine tumors.
2010

Sample Use Guides

In Vivo Use Guide
Neuroendocrine Carcinoma: Atiprimod is administered orally as a single daily dose of 120 mg/day for 14 days, followed by a 14-day treatment-free period. Multiple Myeloma: atiprimod was given at ten dose levels - 30, 60, 90, 120, 180, 240, 300, 360, 420, and 480 mg/day or 180, 240, 300, 360, 420, and 480 mg/day (in combination with ursodiol).
Route of Administration: Oral
In Vitro Use Guide
U266-B1 cells were incubated with 8 uM atiprimod to measure how the drug suppresses IL-6 production. Atiprimod attenuated IL6 supernatant levels to 23, 42, 53, and 130 pg/ml at 1, 6, 8, and 16 hours, respectively. NF-kB activity in the same cell line was blocked after 4 h of incubation with 50 uM atiprimod and after 24 h when using 8 uM of the drug. The percentage of cells undergoing apoptotic cell death also increased from 10.89 to 46.27% after exposure to 8 uM atiprimod.
Substance Class Chemical
Created
by admin
on Tue Oct 22 05:43:10 UTC 2019
Edited
by admin
on Tue Oct 22 05:43:10 UTC 2019
Record UNII
YNU265SSR3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ATIPRIMOD DIMALEATE
USAN  
USAN  
Official Name English
SK&F-106615-I2
Code English
2-(3-(DIETHYLAMINO)PROPYL)-8,8-DIPROPYL-2-AZASPIRO(4.5)DECANE MALEATE (1:2)
Systematic Name English
SK&F 106615-I2
Code English
2-AZASPIRO(4.5)DECANE-2-PROPANAMINE, N,N-DIETHYL,- 8,8-DIPROPYL-, (Z)-2-BUTENEDIOATE (1:2)
Common Name English
SKF-106615-I2
Code English
ATIPRIMOD DIMALEATE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1742
Created by admin on Tue Oct 22 05:43:10 UTC 2019 , Edited by admin on Tue Oct 22 05:43:10 UTC 2019
NCI_THESAURUS C308
Created by admin on Tue Oct 22 05:43:10 UTC 2019 , Edited by admin on Tue Oct 22 05:43:10 UTC 2019
FDA ORPHAN DRUG 227706
Created by admin on Tue Oct 22 05:43:10 UTC 2019 , Edited by admin on Tue Oct 22 05:43:10 UTC 2019
Code System Code Type Description
CAS
183063-72-1
Created by admin on Tue Oct 22 05:43:10 UTC 2019 , Edited by admin on Tue Oct 22 05:43:10 UTC 2019
PRIMARY
ChEMBL
CHEMBL103735
Created by admin on Tue Oct 22 05:43:10 UTC 2019 , Edited by admin on Tue Oct 22 05:43:10 UTC 2019
PRIMARY
PUBCHEM
9808089
Created by admin on Tue Oct 22 05:43:10 UTC 2019 , Edited by admin on Tue Oct 22 05:43:10 UTC 2019
PRIMARY
NCI_THESAURUS
C76970
Created by admin on Tue Oct 22 05:43:10 UTC 2019 , Edited by admin on Tue Oct 22 05:43:10 UTC 2019
PRIMARY
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