피리딘-3-카복스아미드

Nicotinamide

HCID 178903706CAS 1255150-40-3

기본 정보

표준 SMILES
NC(=O)c1cccnc1
InChIKey
DFPAKSUCGFBDDF-UHFFFAOYSA-N
분자식
C6H6N2O
평균 분자량
122.12 g/mol

개요

Nicotinamide is a white powder. (NTP, 1992)

이름 및 식별자

우선 이름
Nicotinamide
IUPAC
pyridine-3-carboxamide
현지명
피리딘-3-카복스아미드
영어명
pyridine-3-carboxamide
분자식
C6H6N2O
분자량
122.13

이름 및 동의어

nicotinamideniacinamide98-92-03-Pyridinecarboxamidepyridine-3-carboxamideNicotinic acid amideAminicotinAmixicotynBenicotDipegylNicofortPapulex
이름 더 보기
피리딘-3-카복스아미드
Nicotinic amideDelonin amidePelonin amideInovitan PPNicotilamideNicotylamideEndobionHansamid

데이터베이스 식별자

CAS
1255150-40-3
ChEMBL
CHEMBL1140
ChEBI
CHEBI:17154
UNII
25X51I8RD4
EC Number
202-713-4、234-265-0
Nikkaji
J3.988H

물성

구조 계산 물성

XLogP
-0.4
극성 표면적
56 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
1
무거운 원자 수
9

실험 및 물리화학적 성질

Chemical ClassesBiological Agents -> Vitamins and Derivatives
Drugs · 3건

Pharmaceuticals -> Metabolite of Nikethamide

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

Cosmetics · 3건

Cosmetic ingredients (Niacinamide) -> CIR (Cosmetic Ingredient Review)

Personal care product -> emollient -> amide

Smoothing

pH10% "wt in vol" solution in water is neutral to litmus
SpringerMaterials PropertiesSchoenflies notation
LogP · 4건

log Kow = -0.37

-0.37

-0.38

-0.34

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 0.3% (3 of 1154) of reports.

Warning

H315 (28.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1154 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

유해성 정보

Regulatory Information · 4건

Chemical: 3-Pyridinecarboxamide

3-Pyridinecarboxamide is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 3-Pyridinecarboxamide are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 25-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14571

Nicotinamide: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
Fire PotentialThis chemical is a noncombustible solid.
Hazards SummarySee Nicotinic acid.
FDA Requirements · 4건

Nicotinamide-ascorbic acid complex may be safely used in accordance with the following prescribed conditions: (a) The additive is the product of the controlled reaction between ascorbic acid and nicotinamide, melting in the range 141 °C to 145 °C. (b) It is used as a source of ascorbic acid and nicotinamide in multivitamin preparations. /Nicotinamide-Ascorbic Acid Complex/

Substance added directly to human food affirmed as generally recognized as safe (GRAS).

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses ... . However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: niacinamide is included in orally administered menstrual drug products and weight control drug products.

Niacinamide used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

안전 및 보호

Fire FightingUse water spray, foam, powder, carbon dioxide.
First Aid Measures · 4건

Fresh air, rest.

Rinse skin with plenty of water or shower.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Give one or two glasses of water to drink.

First Aid · 1건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from oxidants.
Fire Fighting Procedures · 3건

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

... Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers. ... If material of contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increase in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156. The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

독성 정보

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Interactions · 5건

Addition of 0.5 mg of nicotinamide reduced the action of dicrotophos on cultured chick embryo tibiae.

Nicotinamide will prevent depletion of NAD coenzymes by alkylating agents.

Renal oncogenic activity of Streptozotocin in male rats was significantly decreased by nicotinamide.

Oral or iv administered nicotinamide prevented Streptozotocin-induced diabetes in Rhesus monkeys and dogs.

For more Interactions (Complete) data for Nicotinamide (25 total), please visit the HSDB record page.

Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Ecotoxicity Values · 4건

LC50; Species: Poecilia reticulata (Guppy) age 1.5-2.5 weeks; Conditions: freshwater, static, 22-23 °C, pH 7.8-8.2, dissolved oxygen >5 mg/L; Concentration: >1000 mg/L for 96 hr />99% purity/

EC50; Species: Daphnia magna (Water flea) age <24 hr; Conditions: freshwater, static, 18.5-20 °C, pH 8.1-8.2; Concentration: >1000 mg/L for 24 hr; Effect: immobilization />99% purity/

EC50; Species: Scenedesmus subspicatus (algae) strain CCAP 276/20; Conditions: freshwater, static, 21.5-25.5 °C, pH 8.1-9.9; Concentration: >1000 mg/L for 72 hr; Effect: growth inhibition />99% purity/

EC50; Species: Xenopus laevis (African clawed frog) embryos; Conditions: freshwater, renewal, 23 °C; Concentration: 340 ug/L for 96 hr (95% confidence interval: 310-360 ug/L); Effect: abnormal growth

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8(SRC), determined from a structure estimation method(2), indicates that nicotinamide is expected to have very high /mobility in soil(SRC). Volatilization of nicotinamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Nicotinamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.2X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Nicotinamide was determined to be readily biodegradable in an aerobic screening test(3) suggesting that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8(SRC), determined from a structure estimation method(2), indicates that nicotinamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.9X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of -0.37(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Nicotinamide was determined to be readily biodegradable in an aerobic screening test(6) suggesting that biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nicotinamide, which has an estimated vapor pressure of 4.2X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase nicotinamide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 6 days(SRC), calculated from its rate constant of 2.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase nicotinamide may be removed from the air by wet and dry deposition(SRC). Nicotinamide absorbs UV light at wavelengths >300 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 3건

Nicotinamide is prevalent in many common foodstuffs and is especially concentrated in brewer's yeast, wheat germ and liver(1).

Nicotinic Acid and Nicotinamide (Vitamin B3) Foodstuff Content(1).

Nicotinic Acid and Nicotinamide (Vitamin B3) in Coffee(1).

규제 정보

FDA Requirements · 4건

Nicotinamide-ascorbic acid complex may be safely used in accordance with the following prescribed conditions: (a) The additive is the product of the controlled reaction between ascorbic acid and nicotinamide, melting in the range 141 °C to 145 °C. (b) It is used as a source of ascorbic acid and nicotinamide in multivitamin preparations. /Nicotinamide-Ascorbic Acid Complex/

Substance added directly to human food affirmed as generally recognized as safe (GRAS).

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses ... . However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: niacinamide is included in orally administered menstrual drug products and weight control drug products.

Niacinamide used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

FIFRA Requirements · 1건

Residues of nicotinamide are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: Synergist. Limit: Maximum of 0.5% of formulation.

화학 및 산업

약리 정보

ATC Code · 4건

A11HA01

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

A11HA01

Bionecessity · 3건

At high doses (up to 3.5 g/day), nicotinamide is protective against cell death and inhibits the production of inflammatory mediators in animal and in in vitro models of oxidant-induced cell injury.

Nicotinamide, via its major metabolite NAD+ (nicotinamide adenine dinucleotide), is involved in a wide range of biological processes, including the product of energy, the synthesis of fatty acids, cholesterol and steroids, signal transduction and the maintenance of the integrity of the genome.

In humans, niacinamide is required for lipid metabolism, tissue respiration, and glycogenolysis. In vivo, niacinamide is formed from conversion of niacin. In addition, some dietary tryptophan is oxidized to niacin and then to niacinamide in vivo. Niacinamide is incorporated into 2 coenzymes: nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP). NAD and NADP act as hydrogen-carrier molecules in glycogenolysis, tissue respiration, and lipid metabolism.

Biological Half-LifeThe mean half life values were 2.7 hr, 5.9 hr, and 8.1 hr after taking 1, 3, or 6 g of Niacinamide, respectively.
Metabolism/Metabolites · 6건

In amounts needed for physiologic function as a coenzyme (12-18 mg daily), niacin is converted to niacinamide; larger doses of niacin are converted to niacinamide to only a minor degree. Niacinamide is metabolized in the liver to N-methylniacinamide, other N-methylated derivatives, and nicotinuric acid (the glycine conjugate of niacin). These metabolites are excreted in urine. Following administration of physiologic doses of niacin or niacinamide, only a small amount of niacinamide is excreted unchanged in urine; however, following administration of larger doses, a greater proportion of niacin and niacinamide is excreted unchanged.

N1-Methyl-4-pyridone-3-carboxamide was detected on chromatograms of plasma extracts after oral administration of niacinamide to two human subjects.

6-Hydroxynicotinamide and 6-hydroxynicotinic acid /were detected/ as urinary metabolites by comparison of ultraviolet, infrared, and mass spectra following intraperitoneal injections of 14(C)Niacin or 14(C)Niacinamide into rats.

N1-methyl-4- pyridone-3-carboxamide is a major metabolite of niacin and niacinamide which has been found to be synthesized from N1- methylnicotinamide.

For more Metabolism/Metabolites (Complete) data for Nicotinamide (7 total), please visit the HSDB record page.

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

MeSH Pharmacological ClassificationA group of water-soluble vitamins, some of which are COENZYMES.
Absorption, Distribution and Excretion · 5건

14(C)Niacinamide was incorporated into an oil-in-water (o/w) skin cream and into a 30% (w/w) soap base and applied to the skin of female Colworth Wistar rats. The final concentration of niacinamide in the soap solution was approximately 0.3% (w/v) and was 1% (w/w) in the skin cream. Application of the skin cream and soap paste was made to rat skin at approximately 20 mg/sq cm. The cream was carefully massaged over 10 sq cm of skin for up to 5 min before covering with polythene-lined occlusive protective patches. The rats were placed in metabolism cages for 48 hr during which time all excreta was collected. At 48 hr, the animals were killed and the patch, carcass, and treated area of skin were assayed for 14(C). Up to 32% 14(C) was recovered in excreta and in the carcasses from rats treated with skin cream containing 14(C)Niacinamide and up to 30% from those treated with soap paste.

Nicotinamide is efficiently absorbed from the gastrointestinal tract. At low doses, absorption is mediated via sodium-dependent facilitated diffusion. Passive diffusion is the principal mechanism of absorption at higher doses. Doses of up to three to four grams of nicotinamide are almost completely absorbed. Nicotinamide is transported via the portal circulation to the liver and via the systemic circulation to the various tissues of the body. Nicotinamide enters most cells by passive diffusion and enters erythrocytes by facilitated transport.

Niacinamide is widely distributed /throughout/ body tissues.

Niacin and niacinamide are readily absorbed from the GI tract following oral administration, and niacinamide (no longer commercially available in the US) is readily absorbed from subcutaneous and IM injection sites.

For more Absorption, Distribution and Excretion (Complete) data for Nicotinamide (16 total), please visit the HSDB record page.

용도 및 제조

Uses · 6건

CIR ingredient: Niacinamide

Nicotinamide is usually used to treat deficiency, because nicotinamide, unlike nicotinic acid (the most common form of niacin), does not cause flushing, itching, burning, or tingling sensations. [Merck Manual, p. 41]

Vitamin B Complex

Nicotinamide is ... used in cosmetics as hair and skin conditioning agent.

.../Has/ been used in the enrichment of bread, flour, and other grain-derived products. Animal feed is routinely supplemented with ... nicotinamide. Nicotinamide is also used in multivitamin preparations.

MEDICATION

U.S. Imports · 3건

(1972) 1.45X10+9 GRAMS

(1975) 7.5X10+7 GRAMS (NICOTINAMIDE ONLY)

In 1980, 297.1 tons of nicotinamide were imported.

U.S. Production · 4건

2023: 1,000,000 - <8,500,000 lb

(1972) 2.49X10+9 GRAMS (NIACIN & NICOTINAMIDE)

(1975) 2.5X10+9 GRAMS (NIACIN & NICOTINAMIDE)

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Nicotinamide:

Consumption PatternsAPPROX 80% BY ITSELF AS AN ESSENTIAL B VITAMIN; APPROX 20% AS AN ESSENTIAL B VITAMIN IN OTHER APPLICATIONS SUCH AS FLOUR, BAKED GOODS & CEREAL PRODUCTS, & PHARMACEUTICALS (1973)
Consumer UsesFlavoring and nutrient
Industry UsesBrightener

공급사2 곳

上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
宝鸡缔都医药化工有限公司029-029-81148929 17792602132 · [email protected]

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