Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H28O2 |
Molecular Weight | 348.4779 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C\C(=C/C1=CC=C(C=C1)C(O)=O)C2=CC=C3C(=C2)C(C)(C)CCC3(C)C
InChI
InChIKey=FOIVPCKZDPCJJY-JQIJEIRASA-N
InChI=1S/C24H28O2/c1-16(14-17-6-8-18(9-7-17)22(25)26)19-10-11-20-21(15-19)24(4,5)13-12-23(20,2)3/h6-11,14-15H,12-13H2,1-5H3,(H,25,26)/b16-14+
Molecular Formula | C24H28O2 |
Molecular Weight | 348.4779 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Arotinoid acid (Ro 13-7410, TTNPB) is the third generation of synthetic retinoid, which was developed for the treatment of psoriasis and other hyperkeratotic skin disorders. The therapeutically active dose is less than 0.5 ug/kg body weight/day. Arotinoid Acid is an agonist of RAR with IC50 values of 3.8nM, 4nM and 4.5nM for RARα, RARβ and RARγ, respectively. Naturally occurring vitamin A-like compounds such as all-trans-retinoic acid (atRA) are responsible for regulating growth and differentiation in the cell, and many of them have shown promising anticancer effects. Bioassays in vivo and in culture showed that TTNPB is more potent than atRA, mainly because of its higher molecular stability. The effects of TTNPB, which include control of epidermal keratinocytes and murine teratocarcinoma cells and antiproliferative effects on Kaposi´s sarcoma, breast cancer, cervical carcinoma, and leukemia cells have been known for some time. Furthermore, TTNPB proved to be 100 times more effective than atRA in inhibiting the growth of breast cancer cells. However, TTNPB is more teratogenic than atRA, which limits its use as a chemotherapeutic agent in humans. Arotinoid acid (AGN193198) has being shown to be useful for the treatment of pancreatic cancer among other types of cancer.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2003 |
9.3 nM [IC50] | ||
Target ID: CHEMBL2055 |
5.1 nM [IC50] | ||
Target ID: CHEMBL1870 |
4.5 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Different agonist- and antagonist-induced conformational changes in retinoic acid receptors analyzed by protease mapping. | 1994 Jan |
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Upregulation of connexin 43 by retinoids but not by non-provitamin A carotenoids requires RARs. | 2005 |
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Mechanism of retinoid receptors in inhibiting proliferation and inducing apoptosis of human melanoma cell line A375. | 2005 Sep 5 |
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Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways. | 2006 Feb 1 |
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Retinoic acid regulates the expression of photoreceptor transcription factor NRL. | 2006 Sep 15 |
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Nuclear receptor agonists improve insulin responsiveness in cultured cardiomyocytes through enhanced signaling and preserved cytoskeletal architecture. | 2008 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2591420
Hamsters: arotinoid acid (TTNPB) was administered as a single oral bolus (100 ug/kg; 0.29 uM/kg; 35 uCi/animal) to pregnant hamsters (day 8). The maximum concentrations of circulating radioactive compound or metabolites after 100 ug/kg [3H]2-TTNPB occurred in liver greater than fetus greater than adrenal greater than lung approximately equal to kidney greater than plasma; after 1000 ug/kg, maternal liver accumulated the highest concentration followed by plasma greater than fetus = placenta = uterus.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10495774
Arotinoid acid (TTNPB) increases transcriptional activation of mouse RARs in JEG-3 cells after 72 h using conditioned media with EC50 of 2.0 nM, 1.1 nM and 0.8 nM for mRARα, β, and γ, respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:36:07 UTC 2023
by
admin
on
Fri Dec 15 18:36:07 UTC 2023
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Record UNII |
673M8C29UR
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Record Status |
Validated (UNII)
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Record Version |
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