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Compound Detail

CHEMBL573

NIACIN
💊 Approved Drug
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💊 Approved Drug
O=C(O)c1cccnc1

Basic Information

ChEMBL ID CHEMBL573
Name NIACIN
Phase Approved
Structure Type MOL
InChI Key PVNIIMVLHYAWGP-UHFFFAOYSA-N

Known Names

Acide nicotinique Acido nicotinico Acidum nicotinicum Niacin Niacin component of advicor Niacin component of simcor Niacin extended release Niacin td Niacor Niaspan Niaspan er Niaspan titration starter pack +7 more
10
Targets
79
Activities
4
Assay Types
15
PK Parameters
20
Publications
19
Known Names
20
Indications

Molecular Properties

123.1
MW (Da)
0.78
ALogP
2
HBA
1
HBD
50.2
PSA (Ų)
0.60
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula C6H5NO2
MW 123.11
Aromatic Rings 1
Heavy Atoms 9
NP-Likeness -0.71

Indications

Abdominal Pain Acne Vulgaris Anemia Anemia, Iron-Deficiency Atherosclerosis Cardiovascular Diseases Coronary Artery Disease Hypercholesterolemia Hyperlipidemias Kidney Failure, Chronic Myocardial Infarction Acute Coronary Syndrome Carotid Artery Diseases Carotid Artery Diseases Diabetes Mellitus, Type 2 Flushing Heart Diseases Hyperlipidemia, Familial Combined Hyperlipoproteinemia Type II Intermittent Claudication

ATC Classification

C04AC01
nicotinic acid
Level 1: CARDIOVASCULAR SYSTEM
Level 2: PERIPHERAL VASODILATORS
C10AD02
nicotinic acid
Level 1: CARDIOVASCULAR SYSTEM
Level 2: LIPID MODIFYING AGENTS
C10AD52
nicotinic acid, combinations
Level 1: CARDIOVASCULAR SYSTEM
Level 2: LIPID MODIFYING AGENTS

Activity Summary

EC50 45 meas. best 8.06
IC50 29 meas. best 7.22
Ki 4 meas. best 7.48
Kd 1 meas. best 5.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hydroxycarboxylic acid receptor 2
CHEMBL3785
EC50 8.06 6.6431 8.7 29
Unchecked
CHEMBL612545
EC50 7.58 7.295 26.0 4
Hydroxycarboxylic acid receptor 2
CHEMBL4420
EC50 7.54 7.2167 29.0 3
Hydroxycarboxylic acid receptor 2
CHEMBL4731
Ki 7.48 7.48 33.0 1
Hydroxycarboxylic acid receptor 2
CHEMBL4731
EC50 7.41 6.9967 39.0 3
Hydroxycarboxylic acid receptor 2
CHEMBL3785
Ki 7.3 7.1233 50.0 3
Molecular identity unknown
CHEMBL612546
IC50 7.22 7.22 60.0 1
Adipocyte
CHEMBL614658
IC50 7.16 7.13 70.0 2
Hydroxycarboxylic acid receptor 2
CHEMBL3785
IC50 6.89 6.6153 130.0 15
Hydroxycarboxylic acid receptor 2
CHEMBL4420
IC50 6.85 6.85 140.0 3
Unchecked
CHEMBL612545
IC50 6.85 6.425 140.0 2
Adipocyte
CHEMBL614658
EC50 6.05 6.05 900.0 1
Rattus norvegicus
CHEMBL376
EC50 6.02 5.8167 960.0 3
Unchecked
CHEMBL612545
Kd 5.85 5.85 1400.0 1
Canis familiaris
CHEMBL373
EC50 5.57 5.57 2700.0 1
Rattus norvegicus
CHEMBL376
IC50 5.3 5.3 5000.0 1
Amyloid-beta precursor protein
CHEMBL2487
IC50 4.88 4.62 13100.0 2
Hydroxycarboxylic acid receptor 3
CHEMBL4421
EC50 4.12 4.12 75857.8 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1.0 microM/hr/mg Mus musculus
AUC 6980.0 ng.hr.mL-1 Rattus norvegicus
AUC 466.0 ng.hr.mL-1 Rattus norvegicus
CL 167.0 mL.min-1.kg-1 Mus musculus
CL 145.0 mL.min-1.kg-1 Mus musculus
CL 145.0 mL.min-1.kg-1 Mus musculus
Cmax 71000.0 nM Mus musculus
Cmax 60653.07 nM Rattus norvegicus
Cmax 2997.32 nM Rattus norvegicus
F 100.0 % Mus musculus
F 100.0 % Mus musculus
F 100.0 % Mus musculus
T1/2 0.02 hr Mus musculus
T1/2 0.02 hr Mus musculus
T1/2 0.02 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hydroxycarboxylic acid receptor 2 EC50 = 8.71 nM 8.06 Agonist activity at human GPR109a expressed in human adipocytes assessed as decr... 17804224
Hydroxycarboxylic acid receptor 2 EC50 = 14.5 nM 7.84 Agonist activity at GPR109A (unknown origin) assessed as effect on beta-arrestin... 29939744
Hydroxycarboxylic acid receptor 2 EC50 = 17.6 nM 7.75 Agonist activity at GPR109A (unknown origin) assessed as inhibition of forskolin... 29939744
Hydroxycarboxylic acid receptor 2 EC50 = 20.75 nM 7.68 Agonist activity at human GPR109a expressed in HEK293 cells harboring glosensor-... 29709786
Hydroxycarboxylic acid receptor 2 EC50 = 20.7 nM 7.68 Agonist activity at human GPR109a expressed in HEK293 cells harboring glosensor-... 29709786
Unchecked EC50 = 26.0 nM 7.58 Agonist activity at cynomolgus monkey GPR109a 24900295
Hydroxycarboxylic acid receptor 2 EC50 = 26.92 nM 7.57 Agonist activity at GPR109a receptor transfected in CHOK1 cells assessed as inhi... 19524438
Hydroxycarboxylic acid receptor 2 EC50 = 27.0 nM 7.57 Agonist activity at GPR109a expressed in CHO cells assessed as inhibition of for... 20363624
Hydroxycarboxylic acid receptor 2 EC50 = 29.0 nM 7.54 Agonist activity at mouse GPR109a 24900295
Hydroxycarboxylic acid receptor 2 EC50 = 29.0 nM 7.54 Agonist activity at mouse GPR109a 24900372
Unchecked EC50 = 30.0 nM 7.52 Agonist activity at dog GPR109a 24900295
Unchecked EC50 = 31.0 nM 7.51 Agonist activity at dog GPR109a 24900372
Hydroxycarboxylic acid receptor 2 Ki = 33.0 nM 7.48 Inhibition of [3H]-nicotinic acid (20 nM) binding to nicotinic acid receptor in ... 12930155
Hydroxycarboxylic acid receptor 2 EC50 = 39.0 nM 7.41 Agonist activity at rat GPR109a 24900372
Hydroxycarboxylic acid receptor 2 EC50 = 39.0 nM 7.41 Agonist activity at rat GPR109a 24900295
Hydroxycarboxylic acid receptor 2 EC50 = 47.0 nM 7.33 Agonist activity at HCA2 receptor (unknown origin) expressed in CHOK1 cells asse... 25737085
Hydroxycarboxylic acid receptor 2 Ki = 50.0 nM 7.3 Displacement of [3H]nicotinic acid from human GPR109a receptor expressed in CHO ... 18665582
Hydroxycarboxylic acid receptor 2 EC50 = 51.0 nM 7.29 Agonist activity at human GPR109a expressed in CHO cells assessed as decrease in... 22435740
Molecular identity unknown IC50 = 60.0 nM 7.22 Antidyslipidemic activity in human adipocytes assessed as inhibition of isoprote... 20363624
Adipocyte IC50 = 70.0 nM 7.16 Inhibition of lipolysis in IBMX-stimulated human adipocytes assessed as glycerol... 19309152

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1390
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
- 10.1016/j.cropro.2007.02.012 Cenchrus americanus 21
28238612 10.1016/j.bmcl.2017.02.016 Unchecked 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
7143351 10.1021/jm00352a011 Rattus norvegicus 8
31204228 10.1016/j.bmc.2019.06.012 RAW264.7 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
32199732 10.1016/j.bmcl.2020.127105 Hydroxycarboxylic acid receptor 2 7
19307116 10.1016/j.bmcl.2009.03.014 Mus musculus 6
20615702 10.1016/j.bmcl.2010.06.041 Mus musculus 6
18477506 10.1016/j.bmcl.2008.04.071 Mus musculus 6
20014752 10.1021/tx900326k Hepatotoxicity 6
2299623 10.1021/jm00164a013 Rattus norvegicus 6
2909740 10.1021/jm00121a047 Rattus norvegicus 6
20184326 10.1021/jm100022r Canis familiaris 5
17994679 10.1021/jm700942d Hydroxycarboxylic acid receptor 2 5
19309152 10.1021/jm900151e Rattus norvegicus 5
24900295 10.1021/ml100251u Rattus norvegicus 5

Data from ChEMBL 36 via Core Engine