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Details

Stereochemistry ACHIRAL
Molecular Formula C20H22O2
Molecular Weight 294.3882
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of UAB-30

SMILES

C/C(=C(\[H])/C(/[H])=C(\[H])/C(=C(\[H])/C(=O)O)/C)/C(/[H])=C/1\CCCc2ccccc21

InChI

InChIKey=PPGNMFUMZSAZCW-VOYUZAMQSA-N
InChI=1S/C20H22O2/c1-15(7-5-8-16(2)14-20(21)22)13-18-11-6-10-17-9-3-4-12-19(17)18/h3-5,7-9,12-14H,6,10-11H2,1-2H3,(H,21,22)/b8-5+,15-7-,16-14+,18-13+

HIDE SMILES / InChI

Molecular Formula C20H22O2
Molecular Weight 294.3882
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 4
Optical Activity NONE

9cUAB30 is a synthetic analog of 9-cis-RA with little or no RAR-binding activity relative to 9-cis-RA and other RA. 9cUAB30, is a selective rexinoid for the retinoid X nuclear receptors (RXR). Retinoid 9cUAB30 binds to and activates retinoid X receptor (RXR) homodimers and/or and retinoic acid receptor (RAR)/RXR heterodimers, which may result in the dissociation of corepressor protein and the recruitment of coactivator protein, followed by transcription of downstream target genes into mRNAs and protein translation. Gene transcription regulated by these transcription factors may result in inhibition of cell proliferation, induction of cell differentiation, and apoptosis of both normal cells and tumor cells. 9cUAB30 displays substantial chemopreventive capacity with little toxicity and is being translated to the clinic as a novel cancer prevention agent. 9cUAB30 has been assessed in vitro with human cell cultures. Human hepatocytes demonstrated no signs of cytotoxicity with treatment of 9cUAB30 up to 50 umol/L, although when human breast cancer cells were treated with 9cUAB30, they showed a significant inhibition of cell proliferation and apoptotic levels 2.5to 3.5 times the levels of untreated cells. 9cUAB30 inhibits telomerase and induces apoptosis in HL60 cells.

Approval Year

PubMed

PubMed

TitleDatePubMed
The Novel Retinoid, 9cUAB30, Inhibits Telomerase and Induces Apoptosis in HL60 Cells.
2008 Sep
A pilot, first-in-human, pharmacokinetic study of 9cUAB30 in healthy volunteers.
2010 Dec
Patents

Patents

Sample Use Guides

Pharmacokinetic study of 9cUAB30 enrolled 14 patients to receive a single dose of 5, 10, or 20 mg of 9cUAB30, given orally in the morning on an empty stomach.
Route of Administration: Oral
Human hepatocytes demonstrated no signs of cytotoxicity with treatment of 9cUAB30 up to 50 umol/L, although when human breast cancer cells were treated with 9cUAB30, they showed a significant inhibition of cell proliferation and apoptotic levels 2.5to 3.5 times the levels of untreated cells.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:38:12 UTC 2021
Edited
by admin
on Sat Jun 26 05:38:12 UTC 2021
Record UNII
PFP09575EX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UAB-30
Code English
2,4,6-OCTATRIENOIC ACID, 8-(3,4-DIHYDRO-1(2H)-NAPHTHALENYLIDENE)-3,7-DIMETHYL-, (2E,4E,6Z,8E)-
Common Name English
RETINOID 9CUAB30
Common Name English
UAB30
Common Name English
9CUAB30
Code English
9-CIS-UAB30
Code English
(9Z)-UAB-30
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C804
Created by admin on Sat Jun 26 05:38:12 UTC 2021 , Edited by admin on Sat Jun 26 05:38:12 UTC 2021
Code System Code Type Description
PUBCHEM
9904203
Created by admin on Sat Jun 26 05:38:12 UTC 2021 , Edited by admin on Sat Jun 26 05:38:12 UTC 2021
PRIMARY
CAS
205252-57-9
Created by admin on Sat Jun 26 05:38:12 UTC 2021 , Edited by admin on Sat Jun 26 05:38:12 UTC 2021
PRIMARY
FDA UNII
PFP09575EX
Created by admin on Sat Jun 26 05:38:12 UTC 2021 , Edited by admin on Sat Jun 26 05:38:12 UTC 2021
PRIMARY
DRUG BANK
DB12316
Created by admin on Sat Jun 26 05:38:12 UTC 2021 , Edited by admin on Sat Jun 26 05:38:12 UTC 2021
PRIMARY
NCI_THESAURUS
C80061
Created by admin on Sat Jun 26 05:38:12 UTC 2021 , Edited by admin on Sat Jun 26 05:38:12 UTC 2021
PRIMARY NCIT
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