Methylcobalamin/ja: Difference between revisions

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Created page with "{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 416418921 | IUPAC_name = carbanide; cobalt(3+); | image = Methylcobalamin.png | image2 = Mecobalamin 3D sticks.png"
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Created page with "<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 13422-55-4 | ATC_prefix = B03 | ATC_suffix = BA05 | PubChem = 6436232 | ChemSpiderID = 29368587 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | UNII_Ref = {{fdacite|changed|FDA}} | UNII = BR1SN1JS2W | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1697757 | StdInChI=1S/C62H90N13O14P.CH3.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26..."
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'''Methylcobalamin''' (mecobalamin, MeCbl, or MeB{{sub|12}}) is a [[cobalamin]], a form of [[vitamin B12|vitamin B{{sub|12}}]]. It differs from [[cyanocobalamin]] in that the [[cyanide|cyano group]] at the cobalt is replaced with a [[methyl group]]. Methylcobalamin features an octahedral cobalt(III) centre and can be obtained as bright red crystals.  From the perspective of [[coordination chemistry]], methylcobalamin is notable as a rare example of a compound that contains metal–alkyl bonds. [[Nickel]]–methyl intermediates have been proposed for the final step of [[methanogenesis]].
'''メチルコバラミン'''（'''Methylcobalamin''', メコバラミン、MeCbl、MeB{{sub|12}}）は、[[Vitamin B12|ビタミンB{{sub|12}}]の一種である[[cobalamin/ja|コバラミン]]である。］ コバルトの[[cyanide/ja|シアノ基]]が[[methyl group/ja|メチル基]]に置換されている点で[[cyanocobalamin/ja|シアノコバラミン]]とは異なる。メチルコバラミンは八面体のコバルト(III)中心を持ち、明るい赤色の結晶として得られる。 [[coordination chemistry/ja|配位化学]]の観点からは、メチルコバラミンが金属-アルキル結合を含む化合物の珍しい例として注目される。[[Nickel/ja|ニッケル]]-メチル中間体は、[[methanogenesis/ja|メタン生成]]の最終段階として提案されている。
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Revision as of 14:00, 7 April 2024

Other languages:
Methylcobalamin/ja
Clinical data
Trade namesCobolmin
AHFS/Drugs.comInternational Drug Names
Routes of
administration		口から, 舌下, 注射
ATC code
Legal status
Legal status
Pharmacokinetic data
Excretion
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC63H91CoN13O14P
Molar mass1344.405 g·mol−1
3D model (JSmol)
 ☒NcheckY (what is this?)  (verify)

メチルコバラミン（Methylcobalamin, メコバラミン、MeCbl、MeB12）は、[[Vitamin B12|ビタミンB12]の一種であるコバラミンである。］ コバルトのシアノ基がメチル基に置換されている点でシアノコバラミンとは異なる。メチルコバラミンは八面体のコバルト(III)中心を持ち、明るい赤色の結晶として得られる。 配位化学の観点からは、メチルコバラミンが金属-アルキル結合を含む化合物の珍しい例として注目される。ニッケル-メチル中間体は、メタン生成の最終段階として提案されている。

Methylcobalamin is equivalent physiologically to vitamin B12, and can be used to prevent or treat pathology arising from a lack of vitamin B12 intake (vitamin B12 deficiency).

Methylcobalamin is also used in the treatment of peripheral neuropathy, diabetic neuropathy, and as a preliminary treatment for amyotrophic lateral sclerosis.

Methylcobalamin that is ingested is not used directly as a cofactor, but is first converted by MMACHC into cob(II)alamin. Cob(II)alamin is then later converted into the other two forms, adenosylcobalamin and methylcobalamin for use as cofactors. That is, methylcobalamin is first dealkylated and then regenerated.

According to one author, it is important to treat vitamin B12 deficiency with hydroxocobalamin or cyanocobalamin or a combination of adenosylcobalamin and methylcobalamin, and not methylcobalamin alone.

Production

Methylcobalamin physically resembles the other forms of vitamin B12, occurring 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.

Functions

This vitamer, along with adenosylcobalamin, 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.

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.

Methylcobalamin is produced by some bacteria. It plays an important role in the environment, where it is responsible for the biomethylation of certain heavy metals. For example, the highly toxic methylmercury is produced by the action of methylcobalamin. In this role, methylcobalamin serves as a source of "CH3+".

A lack of cobalamin can lead to megaloblastic anemia and subacute combined degeneration of the spinal cord.

See also

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