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FAD

Names

[ CAS No. ]:
146-14-5

[ Name ]:
FAD

[Synonym ]:
Adenosine 5'-(Trihydrogen Diphosphate) 5'®5'-Ester With Riboflavine
Riboflavine 5'-(Trihydrogen Diphosphate) 5'®5'-Ester with Adenosine
Riboflavine 5'-Adenosine Diphosphate
Flavin adenin dinucleotide
FLAVIN ADENINE DINUCLEOTIDE
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]methyl (2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-2,3,4-trihydroxypentyl dihydrogen diphosphate (non-preferred name)
Flavine Adenine
1H-Purin-6-amine Flavin Dinucleotide
EINECS 282-733-8
Riboflavine 5'-Ester with Adenosine 5'-Diphosphate
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-2,3,4-trihydroxypentyl dihydrogen diphosphate (non-preferred name)
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]methyl (2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-2,3,4-trihydroxypentyl dihydrogen diphosphate

Biological Activity

[Description]:

Flavin Adenin Dinucleotide is a redox cofactor, more specifically a prosthetic group of a protein, involved in several important enzymatic reactions in metabolism.

[Related Catalog]:

Research Areas >> Cardiovascular Disease
Natural Products >> Others

[Target]

Human Endogenous Metabolite


[In Vitro]

Poly(Flavin Adenin Dinucleotide, FAD) characterized by an additional polymer-type redox reaction is a highly effective electrocatalyst for NADH oxidation: operating at the lowest potentials reported for NADH transducers (0.00 V, pH 7.4), poly(FAD) is characterized by the electrochemical rate constant of 1.8 ± 0.6×10-3 cm/s, which is at the level of the NADH mass-transfer constant. Poly(FAD)-modified electrodes are characterized by the dramatically improved stability and, is the most advantageous NADH transducers for analytical chemistry[2].

[In Vivo]

Flavin Adenin Dinucleotide (2 mg/kg, i.v.) significantly cancels chlorpromazine (CPZ)-induced decrease in ventricular fibrillation threshold (VFT). Flavin Adenin Dinucleotide cancels the effect of CPZ on canine heart mitochondria. After injection of Flavin Adenin Dinucleotide, the dogs show a transient hypotension within 10 min, then their blood pressures recover to the initial level. Flavin Adenin Dinucleotide also prevents mitochondrial dysfunction induced by chlorpromazine[1].

[Animal admin]

Dogs[1] The dogs are divided into 3 groups and they are received the following treatments. Each group consists of 6 dogs. Dogs in group I as control, are given 2 mL/kg of physiological saline by intravenous injection. Ten min after the start of the first injection, another dose of saline, 1 mL/kg, is injected intravenously. Dogs in group II are given i.v. 2 mL saline/kg. Ten min afterwards, 1 mg chlorpromazine(CPZ)/kg is injected. Dogs in group III are given i.v. Flavin Adenin Dinucleotide, 2 mg/kg. Ten min later, they are given CPZ, 1 mg/kg. All solutions is administrated in 1 min or 2. Blood samples are taken before and 10, 20, 30, and 40 min after the intravenous injection of saline (groups I and II) or Flavin Adenin Dinucleotide (group III). Serum K+ and blood pH are also measured. Heart rate, blood pressure and ventricular fibrillation threshold (VFT) of each dog are recorded at the same intervals[1].

[References]

[1]. Sugiyama S, et al. Protection of chlorpromazine-induced arrhythmia by flavin-adenine-dinucleotide in canine heart. Jpn Heart J. 1979 Sep;20(5):657-65.

[2]. Karyakin AA, et al. Electropolymerized flavin adenine dinucleotide as an advanced NADH transducer. Anal Chem. 2004 Apr 1;76(7):2004-9.


[Related Small Molecules]

3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Retinoic acid | Melatonine | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | Dehydroepiandrosterone | Corticosterone | Progesterone | Docosahexaenoic Acid | NAD+

Chemical & Physical Properties

[ Density]:
2.1±0.1 g/cm3

[ Molecular Formula ]:
C27H33N9O15P2

[ Molecular Weight ]:
785.550

[ Exact Mass ]:
785.157104

[ PSA ]:
382.55000

[ LogP ]:
-2.93

[ Index of Refraction ]:
1.850

[ Storage condition ]:
−20°C

[ Stability ]:
Stable. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AU7470000
CHEMICAL NAME :
Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavine
CAS REGISTRY NUMBER :
146-14-5
BEILSTEIN REFERENCE NO. :
0078150
LAST UPDATED :
199806
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C27-H33-N9-O15-P2
MOLECULAR WEIGHT :
785.63
WISWESSER LINE NOTATION :
DT56 BN DN FN HNJ IZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>7 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1124,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
589 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1124,1995 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3863 No. of Facilities: 3 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 29 (estimated) No. of Female Employees: 22 (estimated)

Safety Information

[ Safety Phrases ]:
24/25

[ WGK Germany ]:
3

[ RTECS ]:
AU7470000

[ HS Code ]:
29349990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds