Metilkobalamin

Nama sistematis (IUPAC)
	karbanid; kobalt(3+);
Data klinis
Nama dagang	Cobolmin
AHFS/Drugs.com	International Drug Names
Kat. kehamilan	?
Status hukum	OTC (US)
Rute	Oral, sublingual, injeksi.
Pengenal
Nomor CAS	13422-55-4
Kode ATC	B03BA05
PubChem	CID 6436232
ChemSpider	29368587
UNII	BR1SN1JS2W
ChEMBL	CHEMBL1697757
Data kimia
Rumus	C63H91CoN13O14P
	InChI InChI=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)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);1H3;/q;-1;+3/p-2; Key:ZFLASALABLFSNM-UHFFFAOYSA-L;

Metilkobalamin (mekobalamin, MeCbl, atau MeB12) adalah sebuah kobalamin, yakni suatu bentuk vitamin B12. Metilkobalamin berbeda dari sianokobalamin karena gugus siano pada kobalt diganti dengan gugus metil.^[1] Metilkobalamin memiliki pusat kobalt(III) oktahedral dan dapat diperoleh sebagai kristal merah terang.^[2] Dari perspektif kimia koordinasi, metilkobalamin terkenal sebagai contoh langka senyawa yang mengandung ikatan logam-alkil. Zat antara nikel-metil telah diusulkan untuk langkah terakhir metanogenesis.

Metilkobalamin secara fisiologis setara dengan vitamin B12,^[3] dan dapat digunakan untuk mencegah atau mengobati patologi yang timbul akibat kekurangan asupan vitamin B12 (defisiensi vitamin B12).

Metilkobalamin juga digunakan dalam pengobatan neuropati perifer, neuropati diabetik, dan sebagai pengobatan awal untuk sklerosis lateral amiotrofik.^[4]

Metilkobalamin yang tertelan tidak digunakan secara langsung sebagai kofaktor, namun diubah terlebih dahulu oleh MMACHC menjadi kob(II)alamin. Kob(II)alamin kemudian diubah menjadi dua bentuk lainnya, adenosilkobalamin dan metilkobalamin untuk digunakan sebagai kofaktor. Artinya, metilkobalamin mula-mula didealkilasi dan kemudian diregenerasi.^[5]^[6]^[7]

Menurut salah satu penulis, metilkobalamin penting untuk mengobati kekurangan vitamin B12 dengan hidroksokobalamin atau sianokobalamin atau kombinasi adenosilkobalamin dan metilkobalamin, dan bukan hanya metilkobalamin saja.^[8]

Pembuatan

Metilkobalamin dapat dibuat di laboratorium dengan mereduksi sianokobalamin dengan natrium borohidrida dalam larutan basa, diikuti dengan penambahan iodometana.^[2]

Kegunaan

Referensi

^ McDowell LR (2000). Vitamins in animal and human nutrition. Wiley. ISBN 978-0813826301. Diakses tanggal 28 January 2018 – via Booksgoogle.com.
^ ^a ^b David D (January 1971). "Preparation of the Reduced Forms of Vitamin B₁₂ and of Some Analogs of the Vitamin B₁₂ Coenzyme Containing a Cobalt-Carbon Bond". Dalam McCormick DB, Wright LD. Vitamins and Coenzymes. Methods in Enzymology. 18. Academic Press. hlm. 34–54. doi:10.1016/S0076-6879(71)18006-8. ISBN 9780121818821.
^ Sil A, Kumar H, Mondal RD, Anand SS, Ghosal A, Datta A, Sawant SV, Kapatkar V, Kadhe G, Rao S (July 2018). "A randomized, open labeled study comparing the serum levels of cobalamin after three doses of 500 mcg vs. a single dose methylcobalamin of 1500 mcg in patients with peripheral neuropathy". The Korean Journal of Pain. 31 (3): 183–190. doi:10.3344/kjp.2018.31.3.183. PMC 6037815 . PMID 30013732.
^ "Eisai Submits New Drug Application for Mecobalamin Ultra-High Dose Preparation as Treatment for Amyotrophic Lateral Sclerosis in Japan" (PDF). Eisai.com. Diakses tanggal 28 January 2018.
^ Kim J, Hannibal L, Gherasim C, Jacobsen DW, Banerjee R (November 2009). "A human vitamin B12 trafficking protein uses glutathione transferase activity for processing alkylcobalamins". The Journal of Biological Chemistry. 284 (48): 33418–33424. doi:10.1074/jbc.M109.057877 . PMC 2785186 . PMID 19801555.
^ Hannibal L, Kim J, Brasch NE, Wang S, Rosenblatt DS, Banerjee R, Jacobsen DW (August 2009). "Processing of alkylcobalamins in mammalian cells: A role for the MMACHC (cblC) gene product". Molecular Genetics and Metabolism. 97 (4): 260–266. doi:10.1016/j.ymgme.2009.04.005. PMC 2709701 . PMID 19447654.
^ Froese DS, Gravel RA (November 2010). "Genetic disorders of vitamin B₁₂ metabolism: eight complementation groups–eight genes". Expert Reviews in Molecular Medicine. 12: e37. doi:10.1017/S1462399410001651. PMC 2995210 . PMID 21114891.
^ Thakkar K, Billa G (January 2015). "Treatment of vitamin B12 deficiency – Methylcobalamine? Cyancobalamine? Hydroxocobalamin? – clearing the confusion". European Journal of Clinical Nutrition. 69 (1): 1–2. doi:10.1038/ejcn.2014.165 . PMID 25117994.

[1] McDowell LR (2000). Vitamins in animal and human nutrition. Wiley. ISBN 978-0813826301. Diakses tanggal 28 January 2018 – via Booksgoogle.com.

[MechB12-2] David D (January 1971). "Preparation of the Reduced Forms of Vitamin B₁₂ and of Some Analogs of the Vitamin B₁₂ Coenzyme Containing a Cobalt-Carbon Bond". Dalam McCormick DB, Wright LD. Vitamins and Coenzymes. Methods in Enzymology. 18. Academic Press. hlm. 34–54. doi:10.1016/S0076-6879(71)18006-8. ISBN 9780121818821.

[3] Sil A, Kumar H, Mondal RD, Anand SS, Ghosal A, Datta A, Sawant SV, Kapatkar V, Kadhe G, Rao S (July 2018). "A randomized, open labeled study comparing the serum levels of cobalamin after three doses of 500 mcg vs. a single dose methylcobalamin of 1500 mcg in patients with peripheral neuropathy". The Korean Journal of Pain. 31 (3): 183–190. doi:10.3344/kjp.2018.31.3.183. PMC 6037815 . PMID 30013732.

[4] "Eisai Submits New Drug Application for Mecobalamin Ultra-High Dose Preparation as Treatment for Amyotrophic Lateral Sclerosis in Japan" (PDF). Eisai.com. Diakses tanggal 28 January 2018.

[5] Kim J, Hannibal L, Gherasim C, Jacobsen DW, Banerjee R (November 2009). "A human vitamin B12 trafficking protein uses glutathione transferase activity for processing alkylcobalamins". The Journal of Biological Chemistry. 284 (48): 33418–33424. doi:10.1074/jbc.M109.057877 . PMC 2785186 . PMID 19801555.

[6] Hannibal L, Kim J, Brasch NE, Wang S, Rosenblatt DS, Banerjee R, Jacobsen DW (August 2009). "Processing of alkylcobalamins in mammalian cells: A role for the MMACHC (cblC) gene product". Molecular Genetics and Metabolism. 97 (4): 260–266. doi:10.1016/j.ymgme.2009.04.005. PMC 2709701 . PMID 19447654.

[7] Froese DS, Gravel RA (November 2010). "Genetic disorders of vitamin B₁₂ metabolism: eight complementation groups–eight genes". Expert Reviews in Molecular Medicine. 12: e37. doi:10.1017/S1462399410001651. PMC 2995210 . PMID 21114891.

[:0-8] Thakkar K, Billa G (January 2015). "Treatment of vitamin B12 deficiency – Methylcobalamine? Cyancobalamine? Hydroxocobalamin? – clearing the confusion". European Journal of Clinical Nutrition. 69 (1): 1–2. doi:10.1038/ejcn.2014.165 . PMID 25117994.

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