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Details

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

SHOW SMILES / InChI
Structure of ATIPRIMOD

SMILES

CCCC1(CCC)CCC2(CCN(CCCN(CC)CC)C2)CC1

InChI

InChIKey=SERHTTSLBVGRBY-UHFFFAOYSA-N
InChI=1S/C22H44N2/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/h5-20H2,1-4H3

HIDE SMILES / InChI

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

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
Target ID: map04630
Sources: www.ncbi.nlm.nih.gov/pubmed/20372971
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Atiprimod blocks phosphorylation of JAK-STAT and inhibits proliferation of acute myeloid leukemia (AML) cells.
2007 Jan

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 Fri Dec 15 16:15:30 UTC 2023
Edited
by admin
on Fri Dec 15 16:15:30 UTC 2023
Record UNII
MG7D3QD743
Record Status Validated (UNII)
Record Version
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Name Type Language
ATIPRIMOD
INN   MART.  
INN  
Official Name English
SKF-106615
Code English
ATIPRIMOD [MART.]
Common Name English
SK&F-106615
Code English
2-(3-(DIETHYLAMINO)PROPYL)-8,8-DIPROPYL-2-AZASPIRO(4.5)DECANE
Systematic Name English
2-AZASPIRO(4.5)DECANE-2-PROPANAMINE N,N-DIETHYL-8,8-DIPROPYL-
Common Name English
atiprimod [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C274
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
FDA ORPHAN DRUG 167103
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
NCI_THESAURUS C1742
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
Code System Code Type Description
PUBCHEM
129869
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
SMS_ID
100000086653
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
DRUG BANK
DB05513
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
WIKIPEDIA
ATIPRIMOD
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
EVMPD
SUB05595MIG
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
MESH
C099015
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
ChEMBL
CHEMBL103735
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
FDA UNII
MG7D3QD743
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
INN
7506
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
NCI_THESAURUS
C52184
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
EPA CompTox
DTXSID10153834
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
CAS
123018-47-3
Created by admin on Fri Dec 15 16:15:30 UTC 2023 , Edited by admin on Fri Dec 15 16:15:30 UTC 2023
PRIMARY
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