メチルコバラミン
WordNet
- the 2nd letter of the Roman alphabet (同)b
- the blood group whose red cells carry the B antigen (同)type_B, group B
- the univalent radical CH3- derived from methane (同)methyl_group, methyl radical
PrepTutorEJDIC
- black(鉛筆の軟度を示す;硬度は『H』(=hard)で表す) / boronの化学記号
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/02/01 17:33:52」(JST)
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Methylcobalamin
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Systematic (IUPAC) name |
carbanide; cobalt(3+); |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Pregnancy cat. |
? |
Legal status |
? |
Routes |
oral,sublingual,injection. |
Identifiers |
CAS number |
13422-55-4 Y |
ATC code |
B03BA05 |
PubChem |
CID 6436232 |
UNII |
BR1SN1JS2W N |
ChEMBL |
CHEMBL1697757 N |
Chemical data |
Formula |
C63H91CoN13O14P |
Mol. mass |
1344.40 g/mol |
N (what is this?) (verify)
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Methylcobalamin (mecobalamin, MeCbl, or MeB12) is a cobalamin used in the treatment of peripheral neuropathy, diabetic neuropathy, and as a preliminary treatment for amyotrophic lateral sclerosis. It is a form of vitamin B12 and differs from cyanocobalamin in that the cyanide is replaced by a methyl group.[1] Methylcobalamin features an octahedral cobalt(III) centre. Methylcobalamin can be obtained as bright red crystals.[2]
From the perspective of coordination chemistry, methylcobalamin is notable as a rare example of an enzyme that contains metal-alkyl bonds. Nickel-methyl intermediates have been proposed for the final step of methanogenesis.
Contents
- 1 Production
- 2 Functions
- 3 See also
- 4 References
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Production
Methylcobalamin physically resembles the other forms of vitamin B
12, occuring as dark red crystals that freely form cherry-colored transparent solutions in water.
Methylcobalamin can be produced in the laboratory by reducing cyanocobalamin with sodium borohydride in alkaline solution, followed by the addition of methyl iodide.[2]
Functions
This vitamer is one of two active coenzymes used by vitamin B12-dependent enzymes and is the specific vitamin B12 form used by 5-methyltetrahydrofolate-homocysteine methyltransferase (MTR), also known as methionine synthase. In physiological terms, it is equivalent to vitamin B12, e.g. for addressing pathologies arising from a lack of vitamin B12, such as pernicious anemia.
Methylcobalamin participates in the Wood-Ljungdahl pathway, which is a pathway by which some organisms utilize carbon dioxide as their source of organic compounds. In this pathway, methylcobalamin provides the methyl group that couples to carbon monoxide (derived from CO2) to afford acetyl-CoA. Acetyl-CoA is a derivative of acetic acid that is converted to more complex molecules as required by the organism.[3]
Methylcobalamin is produced by some bacteria. It plays an important role in the environment. In the environment, it is responsible for the biomethylation of certain heavy metals. For example, the highly toxic methylmercury is produced by the action of methylcobalamin.[4] In this role, methylcobalamin serves as a source "CH3+".
See also
- Cobamamide
- Cyanocobalamin
- Hydroxocobalamin
- Vitamin B12
References
- ^ L. R. McDowell, Vitamins in animal and human nutrition, http://books.google.co.uk/books?id=dXOPBMYIPcQC&pg=PA526
- ^ a b David Dophin. Preparation of the Reduced Forms of Vitamin B12 and of Some Analogs of the Vitamin B12 Coenzyme Containing a Cobalt-Carbon Bond. D.B. McCormick and L.D. Wright, Eds. 1971;Vol. XVIII:34-54.
- ^ 1. J. C. Fontecilla-Camps, P. Amara, C. Cavazza, Y. Nicolet and A. Volbeda, "Structure-function relationships of anaerobic gas-processing metalloenzymes", Nature 2009, volume 460, p. 814-822.doi:10.1038/nature08299
- ^ Zenon Schneider, Andrzej Stroiński, Comprehensive B12: Chemistry, Biochemistry, Nutrition, Ecology, Medicine, http://books.google.co.uk/books?id=OBlxCKbYCx8C&pg=PA32
Vitamins (A11)
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Fat soluble |
A
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α-Carotene · β-Carotene · Retinol# · Tretinoin
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D
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D2 (Ergosterol, Ergocalciferol#) · D3 (7-Dehydrocholesterol, Previtamin D3, Cholecalciferol, 25-hydroxycholecalciferol, Calcitriol (1,25-dihydroxycholecalciferol), Calcitroic acid) · D4 (Dihydroergocalciferol) · D5 · D analogues (Alfacalcidol, Dihydrotachysterol, Calcipotriol, Tacalcitol, Paricalcitol)
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E
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Tocopherol (Alpha, Beta, Gamma, Delta) · Tocotrienol (Alpha, Beta, Gamma, Delta) · Tocofersolan
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K
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Naphthoquinone · Phylloquinone (K1) · Menaquinones (K2) · Menadione (K3) · Menadiol (K4)
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Water soluble |
B
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B1 (Thiamine#) · B2 (Riboflavin#) · B3 (Niacin, Nicotinamide#) · B5 (Pantothenic acid, Dexpanthenol, Pantethine) · B6 (Pyridoxine#, Pyridoxal phosphate, Pyridoxamine) · B7 (Biotin) · B9 (Folic acid, Dihydrofolic acid, Folinic acid, L-methylfolate) · B12 (Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide) · Choline
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C
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Ascorbic acid# · Dehydroascorbic acid
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Combinations |
Multivitamins
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco, nuvi, sysi/epon, met
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Enzyme cofactors
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Active forms |
vitamins |
- TPP / ThDP (B1)
- FMN, FAD (B2)
- NAD+, NADH, NADP+, NADPH (B3)
- Coenzyme A (B5)
- PLP / P5P (B6)
- Biotin (B7)
- THFA / H4FA, DHFA / H2FA, MTHF (B9)
- AdoCbl, MeCbl (B12)
- Ascorbic Acid (C)
- Phylloquinone (K1), Menaquinone (K2)
- Coenzyme F420
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non-vitamins |
- ATP
- CTP
- SAMe
- PAPS
- GSH
- Coenzyme B
- Cofactor F430
- Coenzyme M
- Coenzyme Q
- Heme / Haem (A, B, C, O)
- Lipoic Acid
- Methanofuran
- Molybdopterin/Molybdenum cofactor
- PQQ
- THB / BH4
- THMPT / H4MPT
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minerals |
- Ca2+
- Cu2+
- Fe2+, Fe3+
- Mg2+
- Mn2+
- Mo
- Ni2+
- Se
- Zn2+
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Base forms |
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noco, nuvi, sysi/epon, met
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UpToDate Contents
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English Journal
- Pilot study of the effect of methyl B12 treatment on behavioral and biomarker measures in children with autism.
- Bertoglio K, Jill James S, Deprey L, Brule N, Hendren RL.SourceDepartment of Psychiatry and Behavioral Sciences, University of California, Davis Medical Center, Sacramento, CA, USA.
- Journal of alternative and complementary medicine (New York, N.Y.).J Altern Complement Med.2010 May;16(5):555-60.
- OBJECTIVES: The study objectives were to determine whether methyl B12 treatment improves behavioral measures in children with autism and whether improvement is associated with increased plasma concentrations of glutathione (GSH) and an increased redox ratio of reduced glutathione to oxidized glutath
- PMID 20804367
Japanese Journal
- 絞扼性神経障害に対するmethyl B_<12> one shot静注の短期的効果
- 佐々木 正造,原 弘明,倉橋 豊,堀内 静夫,山口 智
- 日本手の外科学会雑誌 = The Journal of Japanese Society for Surgery of the Hand 12(3), 399-403, 1995-11-30
- NAID 10008578017
Related Links
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- Active B12 Lozenge With L-5-MTHF | Sublingal Active B12 | 1000 mcg of Pure Non-racemc L-methylfolate | 800 mcg of Methylcobalamin and Adenosylcobalamin Vitamin B12 | 60 Sublingual Tablets | Physician Formulated | Seeking ...
Related Pictures
★リンクテーブル★
[★]
- 英
- methylcobalamin MeCbl
- 同
- メチルB12 methyl-B12 MeB12
- 関
- ビタミンB12
[★]
- Mg2+存在下でC3, B, Dが反応してC3bBbとなり、これがC3転換酵素(C3bBb)あるいはC5転換酵素(C3bBb3b)を形成する。これらはP(properdin)と結合して活性化し、それぞれC3、C5を活性化する