Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C22H44N2.2C4H4O4 |
| Molecular Weight | 568.7425 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
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-
| Molecular Formula | C22H44N2 |
| Molecular Weight | 336.5982 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C4H4O4 |
| Molecular Weight | 116.0722 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| A clinically relevant SCID-hu in vivo model of human multiple myeloma. | 2005 Jul 15 |
|
| Azaspirane (N-N-diethyl-8,8-dipropyl-2-azaspiro [4.5] decane-2-propanamine) inhibits human multiple myeloma cell growth in the bone marrow milieu in vitro and in vivo. | 2005 Jun 1 |
|
| 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
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
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
Edited
Fri Dec 15 15:59:24 UTC 2023
by
admin
on
Fri Dec 15 15:59:24 UTC 2023
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| Record UNII |
YNU265SSR3
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C1742
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NCI_THESAURUS |
C308
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FDA ORPHAN DRUG |
227706
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183063-72-1
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CHEMBL103735
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9808089
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YNU265SSR3
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C76970
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JJ-31
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