Details
Stereochemistry | RACEMIC |
Molecular Formula | C12H10O4 |
Molecular Weight | 218.2054 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(OC(=CC1=O)C(O)=O)C2=CC=CC=C2
InChI
InChIKey=DFDGRKNOFOJBAJ-UHFFFAOYSA-N
InChI=1S/C12H10O4/c1-12(8-5-3-2-4-6-8)10(13)7-9(16-12)11(14)15/h2-7H,1H3,(H,14,15)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16389067 | https://www.ncbi.nlm.nih.gov/pubmed/21454438 | https://www.ncbi.nlm.nih.gov/pubmed/17358052 | http://adis.springer.com/drugs/800000311https://www.ncbi.nlm.nih.gov/pubmed/12522134Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16389067 | http://adisinsight.springer.com/drugs/800000311 | https://www.ncbi.nlm.nih.gov/pubmed/6818976 | https://www.ncbi.nlm.nih.gov/pubmed/3314798
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16389067 | https://www.ncbi.nlm.nih.gov/pubmed/21454438 | https://www.ncbi.nlm.nih.gov/pubmed/17358052 | http://adis.springer.com/drugs/800000311https://www.ncbi.nlm.nih.gov/pubmed/12522134
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16389067 | http://adisinsight.springer.com/drugs/800000311 | https://www.ncbi.nlm.nih.gov/pubmed/6818976 | https://www.ncbi.nlm.nih.gov/pubmed/3314798
Acifran (AY-25,712), an uncommercialized Ayerst compound exerting lipid-lowering activity in vivo, has been shown to also elicit similar effects as niacin in preliminary clinical testing and has been shown to bind to both high affinity (HM74A; GPR109A) and low affinity (HM74; GPR109B) niacin receptors. The EC50 values of the separated acifran enantiomers for the GPR109a and 109b receptors showed that, as with acifran itself, the (+)-enantiomers were essentially twice as active as the racemic mixtures, whereas the activity of the (-)-enantiomers was more variable and highly dependent on purity. S-enantiomer of acifran is the active principle. All of the activity of racemic acifran could be attributed to the (S)-enantiomer, and hence, from this precedent, (+)-enantiomers would be assigned to the S-configuration. However, the absolute configuration was not confirmed experimentally.
Originator
Sources: http://adis.springer.com/drugs/800000311 | https://www.ncbi.nlm.nih.gov/pubmed/17358052http://adisinsight.springer.com/drugs/800000311
Curator's Comment: # Ayerst (now Wyeth)
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3785 |
2.1 µM [EC50] | ||
Target ID: CHEMBL4421 |
20.0 µM [EC50] | ||
Target ID: CHEMBL3785 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17358052 |
0.52 µM [EC50] | ||
Target ID: CHEMBL4421 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17358052 |
3.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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5.22 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2295219 |
200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACIFRAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
4.26 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2295219 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACIFRAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2295219 |
200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACIFRAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
15.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2295219 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACIFRAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2295219 |
200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACIFRAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2295219 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACIFRAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2295219 |
200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ACIFRAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
300 mg 3 times / day multiple, oral Highest studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: Page: p.315 |
unhealthy, ADULT n = 13 Health Status: unhealthy Condition: hyperlipoproteinemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 13 Sources: Page: p.315 |
PubMed
Title | Date | PubMed |
---|---|---|
Molecular identification of high and low affinity receptors for nicotinic acid. | 2003 Mar 14 |
|
Triglyceride modulation by acifran analogs: activity towards the niacin high and low affinity G protein-coupled receptors HM74A and HM74. | 2006 Feb 10 |
|
Niacin induces PPARgamma expression and transcriptional activation in macrophages via HM74 and HM74a-mediated induction of prostaglandin synthesis pathways. | 2006 Feb 28 |
|
Analogues of acifran: agonists of the high and low affinity niacin receptors, GPR109a and GPR109b. | 2007 Apr 5 |
|
International Union of Basic and Clinical Pharmacology. LXXXII: Nomenclature and Classification of Hydroxy-carboxylic Acid Receptors (GPR81, GPR109A, and GPR109B). | 2011 Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16389067
neither 1 nor 10 mg/kg (R)-acifran ((-)-enantiomers would be assigned to the R-configuration) decrease serum triglycerides in fructose-fed rats
Route of Administration:
Oral
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C98151
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CHEMBL278488
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SUB05236MIG
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DTXSID9045685
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S-52
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Acifran
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C81534
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m999
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PRIMARY | Merck Index |
ACTIVE MOIETY