Details
| Stereochemistry | UNKNOWN |
| 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)
| Molecular Formula | C12H10O4 |
| Molecular Weight | 218.2054 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12522134https://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/800000311Curator'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/12522134https://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/800000311
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://adisinsight.springer.com/drugs/800000311http://adis.springer.com/drugs/800000311 | https://www.ncbi.nlm.nih.gov/pubmed/17358052
Curator's Comment: Racemic acifran (AY-25,712) was developed at Ayerst Laboratories (now Wyeth). (+)- and (-)-acifran were prepared at Arena Pharmaceuticals.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 2.1 µM [EC50] | |||
Target ID: CHEMBL4421 |
20.0 µM [EC50] | ||
Target ID: CHEMBL3785 |
0.52 µM [EC50] | ||
Target ID: CHEMBL4421 |
3.0 µM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| International Union of Basic and Clinical Pharmacology. LXXXII: Nomenclature and Classification of Hydroxy-carboxylic Acid Receptors (GPR81, GPR109A, and GPR109B). | 2011-06 |
|
| Analogues of acifran: agonists of the high and low affinity niacin receptors, GPR109a and GPR109b. | 2007-04-05 |
|
| Langerhans cells release prostaglandin D2 in response to nicotinic acid. | 2006-12 |
|
| Niacin induces PPARgamma expression and transcriptional activation in macrophages via HM74 and HM74a-mediated induction of prostaglandin synthesis pathways. | 2006-02-28 |
|
| Triglyceride modulation by acifran analogs: activity towards the niacin high and low affinity G protein-coupled receptors HM74A and HM74. | 2006-02-10 |
|
| (D)-beta-Hydroxybutyrate inhibits adipocyte lipolysis via the nicotinic acid receptor PUMA-G. | 2005-07-22 |
|
| Identification of a nicotinic acid receptor: is this the molecular target for the oldest lipid-lowering drug? | 2004-03 |
|
| Molecular identification of high and low affinity receptors for nicotinic acid. | 2003-03-14 |
Patents
Sample Use Guides
The antihyperlipoproteinemic agent acifran (AY-25,712) was administered double-blind to 14 Type IIa hyperlipoproteinemic patients for 12 weeks in dosages of 100 mg t.i.d. or 300 mg t.i.d.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
61IZ92GN57
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| Record Status |
Validated (UNII)
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| Record Version |
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61IZ92GN57
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| Related Record | Type | Details | ||
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ENANTIOMER -> ENANTIOMER |
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RACEMATE -> ENANTIOMER |
