Cobamamide

Cobamamide
Systematic (IUPAC) name


Coα-[α-(5,6-dimethylbenzimidazolyl)]-Coβ- (5'-deoxy-5'-adenosyl)cobamide
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
Legal status
Legal status	US: OTC
Identifiers
CAS Number	13870-90-1^Y
ATC code	B03BA04 (WHO)
PubChem	CID 5459907
ChemSpider	16736117^Y
KEGG	D00042^Y
ChEBI	CHEBI:18408^N
Chemical data
Formula	C₇₂H₁₀₀CoN₁₈O₁₇P
Molar mass	1579.58 g/mol
InChI InChI=1S/C62H90N13O14P.C10H12N5O3.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;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/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);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-2/t31?,34?,35?,36?,37?,41-,52-,53-,56?,57+,59?,60?,61?,62?;4-,6-,7-,10-;/m11./s1^Y Key:ZIHHMGTYZOSFRC-CXGXMSGESA-L^Y
^NY (what is this?) (verify)

Cobamamide (AdoCbl), which is also known as adenosylcobalamin and dibencozide, is, along with methylcobalamin (MeCbl), one of the active forms of vitamin B₁₂. As a nutritional supplement, it is available in tabletted form, but unlike cyanocobalamin, methylcobalamin, and hydroxocobalamin, it is not available in injectable form.

An enzyme that uses adenosylcobalamin as a cofactor is methylmalonyl-CoA mutase (MCM).

External links

B03BA04 (WHO)

Enzyme cofactors

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

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

minerals	Ca²⁺ Cu²⁺ Fe²⁺, Fe³⁺ Mg²⁺ Mn²⁺ Mo Ni²⁺ Zn²⁺

Base forms

vitamins: see vitamins

Vitamins (A11)

Fat soluble

A	α-Carotene β-Carotene Retinol^# Tretinoin

D	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

E	Tocopherol Alpha Beta Gamma Delta Tocotrienol Alpha Beta Gamma Delta Tocofersolan

K	Naphthoquinone Phylloquinone (K₁) Menaquinones (K₂) Menadione (K₃)‡ Menadiol (K₄)

Water soluble

B	B₁ Thiamine^# B₁ analogues Acefurtiamine Allithiamine Benfotiamine Fursultiamine Octotiamine Prosultiamine Sulbutiamine B₂ Riboflavin^# B₃ Niacin Nicotinamide^# B₅ Pantothenic acid Dexpanthenol Pantethine B₆ Pyridoxine^#, Pyridoxal phosphate Pyridoxamine Pyritinol B₇ Biotin B₉ Folic acid Dihydrofolic acid Folinic acid Levomefolic acid B₁₂ Cyanocobalamin Hydroxocobalamin Methylcobalamin Cobamamide Choline

C	Ascorbic acid^# Dehydroascorbic acid

Combinations

Multivitamins

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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