NIACINAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H6N2O
Molecular Weight	122.1246
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

NC(=O)C1=CN=CC=C1

InChI

InChIKey=DFPAKSUCGFBDDF-UHFFFAOYSA-N

InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)

HIDE SMILES / InChI

Description

Niacinamide, known as nicotinamide, is an important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. Pellagra is a nutritional disease that occurs due to insufficient dietary amounts of vitamin B3 or the chemical it is made from (tryptophan). Symptoms of pellagra include skin disease, diarrhea, dementia, and depression. In addition, was experiments, revealed, that niacinamide hydroiodide might have role in ophthalmology and parenteral use of niacinamide hydroiodide can treat arteriosclerotic syndromes.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
NAD-dependent deacetylase sirtuin 2 5	Inhibitor 8,297	11.0 µM [IC50]
NAD-dependent deacetylase sirtuin 1 16	Inhibitor 8,297	100.0 µM [IC50]
NAD-dependent deacetylase sirtuin 3 4	Inhibitor 8,297	14.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Ophthalmology 3	Primary	Not Provided 504	Unknown
Arteriosclerotic syndromes 3	Primary	Not Provided 504	Unknown
Pellagra 3	Preventing	Approved 8,429	Niacinamide

C_max

Value	Dose	Co-administered	Analyte	Population
213.2 ng/mL	500 mg single, oral	LOVASTATIN	NIACINAMIDE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
2669 ng × h/mL	500 mg single, oral	LOVASTATIN	NIACINAMIDE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
15.9 h	500 mg single, oral	LOVASTATIN	NIACINAMIDE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
6 g single, oral Highest studied dose	healthy, 27-45 n = 6	Other AEs: Vomiting...
80 mg/kg 1 times / day multiple, oral MTD	unhealthy, 41-82 n = 40	DLT: Nausea... Disc. AE: Nausea, Toxicity renal...
80 mg/kg 1 times / day multiple, oral MTD	unhealthy, 54-81 n = 7
100 mg/kg 1 times / day multiple, oral Highest studied dose	unhealthy, 75-82 n = 2	DLT: Hypotension, Oliguria... Disc. AE: Nausea, Vomiting...

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AEs

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AE	Significance	Dose	Population
Vomiting		6 g single, oral Highest studied dose	healthy, 27-45 n = 6
Toxicity renal	2.5% Disc. AE	80 mg/kg 1 times / day multiple, oral MTD	unhealthy, 41-82 n = 40
Nausea	20% Disc. AE	80 mg/kg 1 times / day multiple, oral MTD	unhealthy, 41-82 n = 40
Nausea	severe, 17.5% DLT	80 mg/kg 1 times / day multiple, oral MTD	unhealthy, 41-82 n = 40
Oliguria	50% DLT	100 mg/kg 1 times / day multiple, oral Highest studied dose	unhealthy, 75-82 n = 2

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2E1 882	CYP2E1 667 CYP2A6 543 CYP2B6 664	CYP1A2 701

Drug as perpetrator

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Target	Modality	Activity
CYP2E1 970	inhibitor 3,277	yes [Ki 13000 uM]
CYP3A4 1,925	inhibitor 3,277	yes [Ki 13000 uM]
CYP2D6 1,891	inhibitor 3,277	yes [Ki 3800 uM]
CYP1A2 1,692	inhibitor 3,277	yes [Ki 44000 uM]
CYP2C9 1,819	inhibitor 3,277	yes [Ki 51000 uM]

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Drug as victim

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Target	Modality	Activity
CYP2A6 543	substrate 3,367	no
CYP2B6 664	substrate 3,367	no
CYP2E1 667	substrate 3,367	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	DY583359	https://www.001chemical.com/chem/98-92-0
3B Scientific (Wuhan) Corp	3B1-00061	http://www.3bsc.com/index/pro_info.php?id=20273
3B Scientific (Wuhan) Corp	3B3-029729	http://www.3bsc.com/index/pro_info.php?id=50986
AA Blocks	AA00IJXK	http://www.aablocks.com/goods/Goods/detail?id=AA00IJXK
AHH Chemical co.,ltd	MT-19649	http://www.ahhchemical.com/product/MT-19649.html

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PubMed

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Title	Date	PubMed
Photodynamic therapy for malignant mesothelioma: preclinical studies for optimization of treatment protocols.	2001 Apr	11332037
Effect of high population density environment on skin barrier function in mice.	2001 Apr	11240266
Ca(2+)-calmodulin antagonist chlorpromazine and poly(ADP-ribose) polymerase modulators 4-aminobenzamide and nicotinamide influence hepatic expression of BCL-XL and P53 and protect against acetaminophen-induced programmed and unprogrammed cell death in mice.	2001 Aug 1	11461765
Cannabinoid receptors are absent in insects.	2001 Aug 6	11447587
Canine symmetrical lupoid onychodystrophy: a retrospective study with particular reference to management.	2001 Feb	11263704

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Patents

Sample Use Guides

In Vivo Use Guide

For mild vitamin B3 deficiency, niacin or niacinamide 50-100 mg per day is used. For pellagra in adults, niacin or niacinamide 300-500 mg daily is given in divided doses. For pellagra in children, niacin or niacinamide 100-300 mg daily is given in divided doses. For Hartnup disease, niacin or niacinamide 50-200 mg daily.

Route of Administration: Oral

In Vitro Use Guide

10 mM Niacinamide inhibited Resveratrol-mediated ROS suppression in B16F1 melanoma cells

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Name

Type

Language

NIACINAMIDE

Official Name

English

TPN COMPONENT NIACINAMIDE

Common Name