Identification

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Name
Cyanocobalamin
Commonly known or available as Vitamin B12
Accession Number
DB00115  (NUTR00004, APRD00326, EXPT00965)
Type
Small Molecule
Groups
Approved, Nutraceutical
Description

Cyanocobalamin (commonly known as Vitamin B12) is a highly complex, essential vitamin, owing its name to the fact that it contains the mineral, cobalt. This vitamin is produced naturally by bacteria 16, and is necessary for DNA synthesis and cellular energy production. Vitamin B12 has many forms, including the cyano-, methyl-, deoxyadenosyl- and hydroxy-cobalamin forms. The cyano form, is the most widely used form in supplements and prescription drugs 10, Label. Several pharmaceutical forms of cyanocobalamin have been developed, including the tablet, injection, and nasal spray forms Label, 19, 20. This drug was initially approved by the FDA in 1942 Label.

Structure
Thumb
Synonyms
  • Cianocobalamina
  • Cyanocob(III)alamin
  • Cyanocobalamin
  • Vitamin B12
  • Vitamin B12 complex
  • Vitamin B12 NOS
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
B-12 1000 Inj 1000mcg/mlSolutionIntramuscular; SubcutaneousOmega Laboratories Ltd1985-12-31Not applicableCanada
Bedoz 1000injLiquidIntramuscularLab Nadeau LtÉe, Division Of Technilab Inc.1951-12-312005-08-05Canada
CaloMistSpray, metered25 ug/0.1mLNasalFleming & Company, Pharmaceuticals2007-10-012010-01-26Us
Cobex Inj 1000mcg/mlSolutionIntramuscular; SubcutaneousKripps Pharmacy Ltd.1979-12-31Not applicableCanada
Crystalline Vitamin B12-liq Im Sc 1000mcg/mlLiquidIntramuscular; SubcutaneousGermiphene Corporation1996-12-311999-06-28Canada
Cyanocobalamin Injection USPLiquidIntramuscular; SubcutaneousTeligent Ou2018-01-16Not applicableCanada
Cyanocobalamin Injection USPSolutionIntramuscular; SubcutaneousSterimax Inc1992-12-31Not applicableCanada
Cyanocobalamin Injection USPSolutionIntramuscular; SubcutaneousTeligent OuNot applicableNot applicableCanada
Cyanocobalamin Injection USP 1000mcg/mlLiquidIntramuscular; SubcutaneousTaro Pharmaceuticals, Inc.1987-12-31Not applicableCanada
Cyanocobalamin Injection, USPSolutionIntramuscular; SubcutaneousMylan Pharmaceuticals2014-07-25Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aj-cyanocobalaminSolutionIntramuscular; SubcutaneousAgila Jamp Canada IncNot applicableNot applicableCanada
B12 Inject KitKit1000 ug/1mLIntramuscularOaklock, Llc2015-07-08Not applicableUs
B12 Inject KitKit1000 ug/1mLIntramuscular; SubcutaneousOaklock, Llc2015-06-19Not applicableUs
CyanocobalaminInjection1000 ug/1mLIntramuscular; SubcutaneousA-S Medication Solutions1971-10-20Not applicableUs
CyanocobalaminInjection, solution1000 ug/1mLIntramuscularCardinal Health2003-05-292016-03-31Us
CyanocobalaminInjection1000 ug/1mLIntramuscular; SubcutaneousWest-Ward Pharmaceuticals Corp1971-10-20Not applicableUs
CyanocobalaminInjection, solution1000 ug/1mLIntramuscularUbi Pharma Inc.2019-01-02Not applicableUs
CyanocobalaminInjection1000 ug/1mLIntramuscular; SubcutaneousGeneral Injectables and Vaccines, Inc.2018-07-20Not applicableUs
CyanocobalaminInjection, solution1000 ug/1mLIntramuscular; SubcutaneousFresenius Kabi USA, LLC2000-10-18Not applicableUs
CyanocobalaminInjection, solution1000 ug/1mLIntramuscularCardinal Health1990-09-302017-01-31Us
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
B-12 1000mcg Continuous Released TabTablet, extended releaseOralGahler Enterprises Ltd.1981-12-312000-10-03Canada
B-plexTabletOralBeverly International Nutrition1986-12-311998-08-01Canada
B12 1000mcgTabletOralNatural Factors Nutritional Products Ltd.2000-09-012007-08-07Canada
B12 250mcg CyanocobalaminTabletOralWn Pharmaceuticals Ltd.2001-10-012009-09-28Canada
Forphyll 3mcgTabletOralTherapeutic Foods Co.1989-12-152004-07-22Canada
Gsf Tab 24mcgTabletOralNutri Dyn Products Ltd.1980-12-311996-09-09Canada
Puro Sang Tab 1mcgTabletOralPharmetics (2011) Inc.1966-12-312001-07-26Canada
Vit B12 Ctr Srt 1200mcgTablet, extended releaseOralBioenergy Inc.1979-12-311998-06-03Canada
Vit B12 Tab 500mcgTabletOralPure Life International Prods Inc.1992-12-312001-08-07Canada
Vitamin B 12 Tab 25mcgTabletOralSwiss Herbal Remedies Ltd.1971-12-312003-09-10Canada
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
24 Multivitamins + MineralsCyanocobalamin (25 mcg) + Ascorbic acid (150 mg) + Beta carotene (10000 unit) + Biotin (25 mcg) + Calcium (130 mg) + Cholecalciferol (400 unit) + Choline bitartrate (25 mg) + Chromium (20 mcg) + Copper (1 mg) + Ferrous fumarate (15 mg) + Folic acid (.8 mg) + Inositol (25 mg) + Magnesium (65 mg) + Manganese (2 mg) + Molybdenum (20 mcg) + Niacin (25 mg) + Calcium pantothenate (25 mg) + Potassium (15 mg) + Potassium Iodide (.1 mg) + Pyridoxine hydrochloride (25 mg) + Racemethionine (25 mg) + Riboflavin (25 mg) + Selenium (20 mcg) + Thiamine hydrochloride (25 mg) + Vanadium (20 mcg) + Vitamin A palmitate (5000 unit) + Vitamin E (50 unit) + Zinc (10 mg)TabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1997-04-302002-07-31Canada
50 PlusCyanocobalamin (20 mcg) + Ascorbic acid (200 mg) + Biotin (20 mcg) + Choline bitartrate (20 mg) + Folic acid (.2 mg) + Inositol (20 mg) + Niacin (20 mg) + Calcium pantothenate (20 mg) + Pyridoxine hydrochloride (20 mg) + Racemethionine (20 mg) + Riboflavin (20 mg) + Thiamine hydrochloride (20 mg) + Vitamin A palmitate (10000 unit) + Vitamin D (400 unit) + Vitamin E (20 unit)TabletOralQuest Vitamins A Div Of Purity Life Health Products1998-08-042001-07-06Canada
50 Plus Multiple Vitamins & MineralsCyanocobalamin (25 mcg) + Ascorbic acid (90 mg) + Biotin (45 mcg) + Calcium (200 mg) + Cholecalciferol (400 unit) + Chromium (10 mcg) + Copper (2 mg) + Folic acid (0.4 mg) + Magnesium (100 mg) + Manganese (5 mg) + Molybdenum (25 mcg) + Nicotinamide (40 mg) + Pantothenic acid (10 mg) + Potassium Iodide (0.15 mg) + Pyridoxine hydrochloride (3 mg) + Riboflavin (3.2 mg) + Selenium (25 mcg) + Thiamine mononitrate (2.25 mg) + Vanadium (10 mcg) + Vitamin A palmitate (6000 unit) + Zinc (15 mg)TabletOralGfr Pharma Ltd.2002-10-202004-06-15Canada
Adult Formula 50+Cyanocobalamin (25 mcg) + Ascorbic acid (120 mg) + Beta carotene (3000 unit) + Biotin (30 mcg) + Calcium (220 mg) + Cholecalciferol (400 unit) + Chromium (10 mcg) + Copper (2 mg) + Folic acid (0.4 mg) + Iodine (0.15 mg) + Magnesium (100 mg) + Manganese (2.5 mg) + Molybdenum (10 mcg) + Nicotinamide (20 mg) + Calcium pantothenate (20 mg) + Potassium (37.5 mg) + Pyridoxine hydrochloride (6 mg) + Riboflavin (3.4 mg) + Selenium (10 mcg) + Thiamine hydrochloride (4.5 mg) + Vitamin A palmitate (3000 unit) + Zinc (15 mg) + alpha-Tocopherol acetate (60 unit)TabletOralWn Pharmaceuticals Ltd.2002-04-252009-09-28Canada
Adult Infuvite Multiple VitaminsCyanocobalamin (5 ug/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Dexpanthenol (15 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Folic acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz Inc2005-05-18Not applicableUs
Adult Infuvite Multiple VitaminsCyanocobalamin (5 ug/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Dexpanthenol (15 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Folic acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz Inc2003-06-16Not applicableUs
Adult Infuvite Multiple VitaminsCyanocobalamin (5 ug/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Dexpanthenol (15 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Folic acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz Inc2003-06-16Not applicableUs
Adult Infuvite Multiple VitaminsCyanocobalamin (5 ug/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Dexpanthenol (15 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Folic acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz Inc2005-05-18Not applicableUs
Advanced B & T FormulaCyanocobalamin (6.67 mcg) + Ascorbic acid (33.3 mg) + Calcium (200 mg) + Chromium (33.33 mcg) + Copper (0.5 mg) + Folic acid (0.133 mg) + Iron (1.67 mg) + Magnesium (83.3 mg) + Manganese (3.33 mg) + Nicotinamide (6.67 mg) + Calcium pantothenate (5 mg) + Phosphorus (100 mg) + Potassium (16.67 mg) + Pyridoxine hydrochloride (6.67 mg) + Riboflavin (2.67 mg) + Selenium (33.33 mcg) + Silicon (0.333 mg) + Sodium molybdate (16.67 mcg) + Thiamine (2.67 mg) + Vanadium (8.33 mg) + Vitamin D (66.67 unit) + Zinc (5 mg)CapsuleOralNutraceutical CorporationNot applicableNot applicableCanada
Alkadrenergy TabletsCyanocobalamin (45 mcg) + Ascorbic acid (60 mg) + Beta carotene (2500 unit) + Biotin (150 mcg) + Calcium (50 mg) + Choline (100 mg) + Chromic chloride (5 mcg) + Folic acid (0.2 mg) + Inositol (25 mg) + Iodine (0.1 mg) + Magnesium (50 mg) + Manganese (0.5 mg) + Molybdenum (3 mcg) + Nicotinamide (40 mg) + Pantothenic acid (15 mg) + Pyridoxine hydrochloride (6.25 mg) + Riboflavin (6.25 mg) + Sodium selenite (37.5 mcg) + Thiamine (6.25 mg) + Zinc (9 mg) + alpha-Tocopherol acetate (15 unit)TabletOralMorter HealthsystemNot applicableNot applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Active FECyanocobalamin (30 ug/1) + Ascorbic acid (160 mg/1) + Beta carotene (2100 [iU]/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (1 mg/1) + DL-alpha tocopheryl acetate (40 [iU]/1) + Folic acid (1250 ug/1) + Iron (75 mg/1) + Magnesium oxide (30 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (4 mg/1) + Thiamine hydrochloride (4 mg/1) + Zinc oxide (20 mg/1)TabletOralGm Pharmaceuticals2013-11-11Not applicableUs
Active OBCyanocobalamin (30 ug/1) + Ascorbic acid (100 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric sulfate pentahydrate (2 mg/1) + D-alpha-Tocopherol acetate (30 [iU]/1) + Doconexent (320 mg/1) + Folic acid (1 mg/1) + Iron (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (2 mg/1) + Zinc oxide (30 mg/1)Capsule, liquid filledOralGm Pharmaceuticals2013-10-282017-03-31Us
Animi-3Cyanocobalamin (500 ug/1) + Cholecalciferol (1000 [iU]/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1)CapsuleOralPbm Pharmaceuticals Inc.2011-06-01Not applicableUs
Animi-3 with Vitamin DCyanocobalamin (500 ug/1) + Cholecalciferol (1000 [iU]/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1)CapsuleOralPbm Pharmaceuticals Inc.2011-06-01Not applicableUs
Av-VITE FBCyanocobalamin (1 mg/1) + Folic acid (2.5 mg/1) + Pyridoxine hydrochloride (25 mg/1)TabletOralAv Kare, Inc.2015-11-052016-01-13Us
BacminCyanocobalamin (50 ug/1) + Ascorbic acid (500 mg/1) + Biotin (150 ug/1) + Chromium Cr-51 chloride (0.1 mg/1) + Cupric oxide (3 mg/1) + Ferrous fumarate (27 mg/1) + Flavone (50 mg/1) + Folic acid (1 mg/1) + Magnesium oxide (50 mg/1) + Manganese gluconate (5 mg/1) + Nicotinamide (100 mg/1) + Calcium pantothenate (25 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (20 mg/1) + Selenomethionine (50 ug/1) + Thiamine mononitrate (20 mg/1) + Vitamin A acetate (2000 [iU]/1) + Zinc oxide (22.5 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)Tablet, coatedOralMarnel Pharmaceuticals, Llc2000-04-01Not applicableUs
Bal-Care DHACyanocobalamin (.012 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (2850 [iU]/1) + Calcium carbonate (219 mg/1) + Cholecalciferol (840 [iU]/1) + Cupric oxide (2 mg/1) + DL-alpha tocopheryl acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (.223 mg/1) + Iron sucrose (1.35 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Omega-3 fatty acids (430 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (4 mg/1) + Sodium feredetate (25.65 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1)KitOralPru Gen Pharmaceuticals2012-05-01Not applicableUs
Bal-Care DHA EssentialCyanocobalamin (.012 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (2850 [iU]/1) + Calcium carbonate (219 mg/1) + Cholecalciferol (840 [iU]/1) + Cupric oxide (2 mg/1) + DL-alpha tocopheryl acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (.223 mg/1) + Iron sucrose (1.35 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Omega-3 fatty acids (374 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (4 mg/1) + Sodium feredetate (25.65 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1)KitOralPru Gen Pharmaceuticals2012-05-01Not applicableUs
BiferaRxCyanocobalamin (25 ug/1) + Folic acid (1 mg/1) + Heme iron polypeptide (6 mg/1) + Iron Dextran (22 mg/1)TabletOralAlaven Pharmaceutical2010-05-01Not applicableUs68220 0085 90 nlmimage10 2d1316d8
BiferaRxCyanocobalamin (25 ug/1) + Folic acid (1 mg/1) + Heme iron polypeptide (6 mg/1) + Iron Dextran (22 mg/1)TabletOralMEDA Pharmaceuticals2012-10-312018-09-30Us
International/Other Brands
Bedodeka (Teva) / Bedoz / Berubigen (Upjohn) / Betalin (Lilly) / Cobione (MSD) / Cobolin-M / Crystamine / Cyanoject / Cyomin / Cytakon (GlaxoSmithKline) / Cytamen (GlaxoSmithKline) / Dicopac / Neuroforte-R / Primabalt / Vitabee 12
Categories
UNII
P6YC3EG204
CAS number
68-19-9
Weight
Average: 1355.3652
Monoisotopic: 1354.5674053
Chemical Formula
C63H88CoN14O14P
InChI Key
RMRCNWBMXRMIRW-WZHZPDAFSA-L
InChI
InChI=1S/C62H90N13O14P.CN.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;1-2;/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);;/q;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1
IUPAC Name
(10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-1-cyano-46-hydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2λ⁵,9,19,26,43λ⁵,44λ⁵,45λ⁵-heptaaza-15λ⁵-phospha-1-cobaltadodecacyclo[27.14.1.1¹,³⁴.1²,⁹.1¹⁰,¹³.0¹,²⁶.0³,⁸.0²³,²⁷.0²⁵,⁴².0³²,⁴⁴.0³⁹,⁴³.0³⁷,⁴⁵]heptatetraconta-2(47),3,5,7,27,29(44),32,34(45),37,39(43)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1-triuid-15-olate
SMILES
[C@H]1([C@@H]2[C@H]([C@@H](N3C4=CC(=C(C)C=C4[N+]([Co-3]456(N7C8=C(C9=[N+]4C(C([C@@H]9CCC(N)=O)(C)C)=CC4=[N+]5C(=C(C5=[N+]6[C@@]([C@]7([C@@H]([C@@]8(C)CCC(=O)NC[C@@]([H])(C)OP([O-])(=O)O2)CC(N)=O)[H])([C@@]([C@@H]5CCC(N)=O)(C)CC(N)=O)C)C)[C@@]([C@@H]4CCC(N)=O)(C)CC(N)=O)C)C#N)=C3)C)O1)O)CO

Pharmacology

Indication

Nasal spray

The cyanocobalamin nasal spray is indicated for the maintenance of vitamin B12 concentrations after normalization with intramuscular vitamin B12 therapy in patients with deficiency of this vitamin who have no nervous system involvement Label.

Note: CaloMist Label, the nasal spray form, has not been evaluated for the treatment of newly diagnosed vitamin B12 deficiency.

Injection forms (subcutaneous, intramuscular)

These forms are indicated for vitamin B12 deficiencies due to various causes, with or without neurologic manifestations 26. Vitamin B12 deficiency is frequently caused by malabsorption, which is often associated with the following conditions 20:

Addisonian (pernicious) anemia

Gastrointestinal pathology, dysfunction, or surgery, including gluten enteropathy or sprue, small bowel bacterial overgrowth, total or partial gastrectomy

Fish tapeworm infestation

Malignancy of the pancreas or bowel

Folic acid deficiency

Oral forms

Vitamin B12 supplements are widely available and indicated in patients who require supplementation for various reasons. Dose requirements for vitamin B12 which are higher than normal (caused by pregnancy, thyrotoxicosis, hemolytic anemia, hemorrhage, malignancy, hepatic and renal disease) can usually be achieved with oral supplementation 20. Oral products of vitamin B12 are not recommended in patients with malabsorption, as these forms are primarily absorbed in the gastrointestinal tract 27.

Associated Conditions
Pharmacodynamics

General effects

Cyanocobalamin corrects vitamin B12 deficiency and improves the symptoms and laboratory abnormalities associated with pernicious anemia (megaloblastic indices, gastrointestinal lesions, and neurologic damage). This drug aids in growth, cell reproduction, hematopoiesis, nucleoprotein, and myelin synthesis. It also plays an important role in fat metabolism, carbohydrate metabolism, as well as protein synthesis. Cells that undergo rapid division (for example, epithelial cells, bone marrow, and myeloid cells) have a high demand for vitamin B12 10.

Parenteral cyanocobalamin effects

The parenteral administration of vitamin B12 rapidly and completely reverses the megaloblastic anemia and gastrointestinal symptoms of vitamin B12 deficiency. Rapid parenteral administration of vitamin B12 in deficiency related neurological damage prevents the progression of this condition 20.

Nasal spray effects

In 24 vitamin B12 deficient patients who were already stabilized on intramuscular (IM) vitamin B12 therapy, single daily doses of intranasal cyanocobalamin for 8 weeks lead to serum vitamin B12 concentrations that were within the target therapeutic range (>200 ng/L) Label.

Mechanism of action

Vitamin B12 serves as a cofactor for methionine synthase and L-methylmalonyl-CoA mutase enzymes. Methionine synthase is essential for the synthesis of purines and pyrimidines that form DNA. L-methylmalonyl-CoA mutase converts L-methylmalonyl-CoA to succinyl-CoA in the degradation of propionate 24, an important reaction required for both fat and protein metabolism. It is a lack of vitamin B12 cofactor in the above reaction and the resulting accumulation of methylmalonyl CoA that is believed to be responsible for the neurological manifestations of B12 deficiency 10. Succinyl-CoA is also necessary for the synthesis of hemoglobin 24.

In tissues, vitamin B12 is required for the synthesis of methionine from homocysteine. Methionine is required for the formation of S-adenosylmethionine, a methyl donor for nearly 100 substrates, comprised of DNA, RNA, hormones, proteins, as well as lipids 24. Without vitamin B12, tetrahydrofolate cannot be regenerated from 5-methyltetrahydrofolate, and this can lead to functional folate deficiency 22, Label. This reaction is dependent on methylcobalamin (vitamin B12) as a co-factor and is also dependent on folate, in which the methyl group of methyltetrahydrofolate is transferred to homocysteine to form methionine and tetrahydrofolate. Vitamin B12 incorporates into circulating folic acid into growing red blood cells; retaining the folate in these cells 23. A deficiency of vitamin B12 and the interruption of this reaction leads to the development of megaloblastic anemia.

TargetActionsOrganism
AMethionine synthase
cofactor
Humans
AMethylmalonyl-CoA mutase, mitochondrial
cofactor
Humans
UMethionine synthase reductase
cofactor
Humans
UMethylmalonic aciduria type A protein, mitochondrial
binder
Humans
UMethylmalonic aciduria and homocystinuria type C protein
cofactor
Humans
UMethylenetetrahydrofolate reductase
cofactor
Humans
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Absorption

Vitamin B12 is quickly absorbed from intramuscular (IM) and subcutaneous (SC) sites of injection; with peak plasma concentrations achieved about 1 hour after IM injection 26.

Orally administered vitamin B12 binds to intrinsic factor (IF) during its transport through the stomach. The separation of Vitamin B12 and IF occurs in the terminal ileum when calcium is present, and vitamin B12 is then absorbed into the gastrointestinal mucosal cells. It is then transported by transcobalamin binding proteins 20. Passive diffusion through the intestinal wall can occur, however, high doses of vitamin B12 are required in this case (i.e. >1 mg). After the administration of oral doses less than 3 mcg, peak plasma concentrations are not reached for 8 to 12 hours, because the vitamin is temporarily retained in the wall of the lower ileum 26.

Volume of distribution

Cobalamin is distributed to tissues and stored mainly in the liver and bone marrow Label.

Protein binding

Very high (to specific plasma proteins called transcobalamins); binding of hydroxocobalamin is slightly higher than cyanocobalamin [FDA label.

Metabolism

Vitamin B12 or cyanocobalamin obtained from food is initially bound by haptocorrin, a protein found in the saliva with high affinity for B12. This forms a haptocorrin-B12 complex. Cyanocobalamin passes through the stomach and is protected from acid degradation due to its binding to haptocorrin. In the duodenum, pancreatic proteases release cobalamin from the haptocorrin-B12 complex and from other proteins containing protein-bound B12 that have been ingested. Following this, the binding of cobalamin to a second glycoprotein, intrinsic factor, promotes its uptake by terminal ileum mucosal cells by a process called cubilin/AMN receptor-mediated endocytosis. After absorption into enterocytes, intrinsic factor is broken down in the lysosome, and cobalamin is then released into the bloodstream. The transporter ABCC1, found in the basolateral membrane of intestinal epithelial and other cells, exports cobalamin bound to transcobalamin out of the cell 15. Cyanocobalamin then passes through the portal vein in the liver, and then reaches the systemic circulation. The active forms of cyanocobalamin are methylcobalamin and adenosylcobalamin 15, 24.

Route of elimination

This drug is partially excreted in the urine 27. According to a clinical study, approximately 3-8 mcg of vitamin B12 is secreted into the gastrointestinal tract daily via the bile. In patients with adequate levels of intrinsic factor, all except approximately 1 mcg is reabsorbed. When vitamin B12 is administered in higher doses that saturate the binding capacity of plasma proteins and the liver, the unbound vitamin B12 is eliminated rapidly in the urine. The body storage of vitamin B12 is dose-dependent Label.

Half life

Approximately 6 days (400 days in the liver) 27.

Clearance

During vitamin loading, the kidney accumulates large amounts of unbound vitamin B12. This drug is cleared partially by the kidney, however, multiligand receptor megalin promotes the reuptake and reabsorption of vitamin B12 into the body 13, 14.

Toxicity

LD50 Oral (mouse): > 5,000 mg/kg 25.

General toxicity

Vitamin B12 is generally non-toxic, even at higher doses. Mild, transient diarrhea, polycythemia vera, peripheral vascular thrombosis, itching, transitory exanthema, a feeling of swelling of entire body, pulmonary edema and congestive heart failure in early treatment stages, anaphylactic shock and death have been observed after vitamin B12 administration 26.

Carcinogenesis and mutagenesis

Long term studies in animals examining the carcinogenic potential of any of the vitamin B12 formulations have not completed to date. There is no evidence from long-term use in patients with pernicious anemia that vitamin B12 has carcinogenic potential. Pernicious anemia is known to be associated with an increased incidence of stomach carcinoma, however, this malignancy has been attributed to the underlying cause of pernicious anemia and has not been found to be related to treatment with vitamin B12 Label.

Use in pregnancy

No adverse effects have been reported with ingestion of normal daily requirements during pregnancy 26.

A note on the use of the nasal spray in pregnancy

Although vitamin B12 is an essential vitamin and requirements are increased during pregnancy, it is currently unknown whether the nasal spray form can cause fetal harm when administered to a pregnant woman or can affect reproduction capacity. The nasal spray form should be given to a pregnant woman only if clearly needed, as it is considered a pregnancy category C drug in this form. Sufficient well-controlled studies have not been done to this date in pregnant women Label.

Use in lactation

Vitamin B12 has been found distributed into the milk of nursing women in concentrations similar to the maternal blood vitamin B12 concentrations. No adverse effects have been reported to date with intake of normal required doses during lactation 26.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirCyanocobalamin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseCyanocobalamin may decrease the excretion rate of Acarbose which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Cyanocobalamin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Cyanocobalamin which could result in a higher serum level.
AcetaminophenCyanocobalamin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Cyanocobalamin which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Cyanocobalamin which could result in a higher serum level.
AclidiniumCyanocobalamin may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineCyanocobalamin may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Cyanocobalamin which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

Synthesis Reference

Robert H. Allen, "Preparation of samples for vitamin B12 and/or folate assay and assay." U.S. Patent US4451571, issued October, 1982.

US4451571
General References
  1. Wickramasinghe SN: Morphology, biology and biochemistry of cobalamin- and folate-deficient bone marrow cells. Baillieres Clin Haematol. 1995 Sep;8(3):441-59. [PubMed:8534956]
  2. Sharabi A, Cohen E, Sulkes J, Garty M: Replacement therapy for vitamin B12 deficiency: comparison between the sublingual and oral route. Br J Clin Pharmacol. 2003 Dec;56(6):635-8. [PubMed:14616423]
  3. Hall AH, Rumack BH: Hydroxycobalamin/sodium thiosulfate as a cyanide antidote. J Emerg Med. 1987;5(2):115-21. [PubMed:3295013]
  4. Andres E, Noel E, Goichot B: Metformin-associated vitamin B12 deficiency. Arch Intern Med. 2002 Oct 28;162(19):2251-2. [PubMed:12390080]
  5. Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. [PubMed:11863489]
  6. Bonaa KH, Njolstad I, Ueland PM, Schirmer H, Tverdal A, Steigen T, Wang H, Nordrehaug JE, Arnesen E, Rasmussen K: Homocysteine lowering and cardiovascular events after acute myocardial infarction. N Engl J Med. 2006 Apr 13;354(15):1578-88. doi: 10.1056/NEJMoa055227. Epub 2006 Mar 12. [PubMed:16531614]
  7. Lonn E, Yusuf S, Arnold MJ, Sheridan P, Pogue J, Micks M, McQueen MJ, Probstfield J, Fodor G, Held C, Genest J Jr: Homocysteine lowering with folic acid and B vitamins in vascular disease. N Engl J Med. 2006 Apr 13;354(15):1567-77. doi: 10.1056/NEJMoa060900. Epub 2006 Mar 12. [PubMed:16531613]
  8. Russell-Jones GJ, Alpers DH: Vitamin B12 transporters. Pharm Biotechnol. 1999;12:493-520. [PubMed:10742986]
  9. Seetharam B: Receptor-mediated endocytosis of cobalamin (vitamin B12). Annu Rev Nutr. 1999;19:173-95. doi: 10.1146/annurev.nutr.19.1.173. [PubMed:10448521]
  10. O'Leary F, Samman S: Vitamin B12 in health and disease. Nutrients. 2010 Mar;2(3):299-316. doi: 10.3390/nu2030299. Epub 2010 Mar 5. [PubMed:22254022]
  11. Scott JM: Folate and vitamin B12. Proc Nutr Soc. 1999 May;58(2):441-8. [PubMed:10466189]
  12. Zhang M, Han W, Hu S, Xu H: Methylcobalamin: a potential vitamin of pain killer. Neural Plast. 2013;2013:424651. doi: 10.1155/2013/424651. Epub 2013 Dec 26. [PubMed:24455309]
  13. Birn H: The kidney in vitamin B12 and folate homeostasis: characterization of receptors for tubular uptake of vitamins and carrier proteins. Am J Physiol Renal Physiol. 2006 Jul;291(1):F22-36. doi: 10.1152/ajprenal.00385.2005. [PubMed:16760376]
  14. Moestrup SK, Birn H, Fischer PB, Petersen CM, Verroust PJ, Sim RB, Christensen EI, Nexo E: Megalin-mediated endocytosis of transcobalamin-vitamin-B12 complexes suggests a role of the receptor in vitamin-B12 homeostasis. Proc Natl Acad Sci U S A. 1996 Aug 6;93(16):8612-7. [PubMed:8710919]
  15. Gherasim C, Lofgren M, Banerjee R: Navigating the B(12) road: assimilation, delivery, and disorders of cobalamin. J Biol Chem. 2013 May 10;288(19):13186-93. doi: 10.1074/jbc.R113.458810. Epub 2013 Mar 28. [PubMed:23539619]
  16. Fang H, Kang J, Zhang D: Microbial production of vitamin B12: a review and future perspectives. Microb Cell Fact. 2017 Jan 30;16(1):15. doi: 10.1186/s12934-017-0631-y. [PubMed:28137297]
  17. Amidon, Gordon L., Sadée, Wolfgang (2002). Vitamin B12 Transporters (12th ed.). Springer, Boston MA.
  18. Methylcobalamin vs cyanocobalamin [Link]
  19. B12, cyanocobalamin tablets, DailyMed [Link]
  20. Cyanocobalamin injection, DailyMed [Link]
  21. Vitamin B12 [Link]
  22. The metabolic processes of folic acid and Vitamin B12 deficiency [Link]
  23. University of Virginia: Megaloblastic anemia [Link]
  24. Vitamin B 12 Health Professional Fact Sheet [Link]
  25. Cyanocobalamin VitB12, MSDS [File]
  26. Cyanocobalamin injection, monograph [File]
  27. Cyanocobalamin label [File]
External Links
KEGG Drug
D00166
KEGG Compound
C02823
PubChem Compound
70678590
PubChem Substance
46509031
ChemSpider
21864832
ChEBI
17439
ChEMBL
CHEMBL2110563
PharmGKB
PA451892
HET
CNC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Cyanocobalamin
ATC Codes
B03BA01 — CyanocobalaminB03AE01 — Iron, vitamin b12 and folic acidB03BA51 — Cyanocobalamin, combinations
AHFS Codes
  • 88:08.00 — Vitamin B Complex
FDA label
Download (208 KB)
MSDS
Download (37.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentBMI >30 kg/m2 / High Blood Pressure (Hypertension)1
0CompletedTreatmentVitamin B 12 Deficiency1
1CompletedOtherHeart Rate / Heart Rate Variability / Inflammatory Reaction1
1CompletedTreatmentFocus: Bioavailability1
1CompletedTreatmentLeptomeningeal Metastases1
1CompletedTreatmentMalignancies / Metastases1
1, 2CompletedPreventionDeficiency, Vitamin D / Prophylaxis of preeclampsia1
1, 2CompletedTreatmentCancer of the Ovary / Fallopian Tube Cancer / Malignant Peritoneal Neoplasm1
1, 2CompletedTreatmentRetinal Vein Occlusions(RVO)1
1, 2Not Yet RecruitingTreatmentMutation Ala393Thr of the MARS Gene / MutationSer567Leu of the MARS Gene / Pulmonary Alveolar Proteinosis (PAP)1
1, 2RecruitingTreatmentPostpartum Anemia1
1, 2TerminatedTreatmentPsoriasis1
2Active Not RecruitingTreatmentLung Cancers / Neoplasms Metastasis1
2CompletedPreventionCardiovascular Disease (CVD) / Coronary Arteriosclerosis / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Infarction / Myocardial Ischemia1
2CompletedPreventionDepression / Depressive Disorders1
2CompletedPreventionRefractory Peripheral T-cell Lymphoma Unspecified / Relapsed Peripheral T-Cell Lymphoma1
2CompletedTreatmentCardiovascular Disease (CVD) / Endothelial Dysfunction1
2CompletedTreatmentEfficacy / Lung Cancer Non-Small Cell Cancer (NSCLC)1
2CompletedTreatmentHead and Neck Carcinoma1
2CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2Not Yet RecruitingTreatmentNasopharyngeal Neoplasms / Vesicular Stomatitis1
2Not Yet RecruitingTreatmentVesicular Stomatitis1
2RecruitingPreventionVincristine Induced Peripheral Neuropathy (VIPN)1
2RecruitingSupportive CareAcute Lymphoblastic Leukaemias (ALL) / Hyperbilirubinemia1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
2Unknown StatusTreatmentAnemias1
2Unknown StatusTreatmentMalignant Neoplasm of Nasopharynx1
2, 3CompletedTreatmentAtherosclerosis1
2, 3CompletedTreatmentAutistic Disorder1
2, 3CompletedTreatmentFirst Episode Psychosis1
2, 3RecruitingPreventionAcute Lymphoblastic Leukaemias (ALL) / Vincristine Induced Neurotoxicity1
3CompletedPreventionCerebral Infarctions / Myocardial Infarction / Strokes1
3CompletedPreventionCerebrovascular Stroke / Coronary Artery Disease / Myocardial Infarction1
3CompletedTreatmentAlzheimer's Disease (AD)1
3CompletedTreatmentAnemia in End-Stage Renal Disease1
3CompletedTreatmentChronic Plaque Psoriasis1
3CompletedTreatmentPremature Ejaculation1
3RecruitingTreatmentBladder Cancers / Transitional Cell Carcinoma / Ureteral Cancer1
4CompletedPreventionDyslipidemias / Homocystinaemia / Menopause1
4CompletedTreatmentAnemias / Iron Deficiency1
4CompletedTreatmentDiabetic Macular Edema (DME)1
4CompletedTreatmentDiabetic Peripheral Neuropathic Pain (DPN)1
4CompletedTreatmentHyperemesis Gravidarum / Morning Sickness / Nausea / Pregnancy / Vomiting1
4CompletedTreatmentPregnancy1
4CompletedTreatmentVitamin B 12 Deficiency1
4RecruitingTreatmentAntioxidants / Male Infertility / Semen Quality1
4RecruitingTreatmentHyperuricemia1
4RecruitingTreatmentVitamin B12 Deficiency1
4TerminatedTreatmentAnemias1
4Unknown StatusDiagnosticVitamin B12 Deficiency1
4Unknown StatusPreventionHepatitis C Viral Infection1
Not AvailableCompletedNot AvailableVitamin B12 Deficiency1
Not AvailableCompletedBasic ScienceVitamin B 12 Deficiency1
Not AvailableCompletedDiagnosticCoronary Artery Disease / Major Surgery1
Not AvailableCompletedDiagnosticVitamin B12 Absorption1
Not AvailableCompletedPreventionDeep Vein Thrombosis (DVT) / Pulmonary Embolism (PE)1
Not AvailableCompletedPreventionVitamin B12 Deficiency1
Not AvailableCompletedScreeningOther Diseases or Conditions1
Not AvailableCompletedSupportive CareNon-thyroidal Illness Syndrome1
Not AvailableCompletedTreatmentAcute Myocardial Infarction (AMI)1
Not AvailableCompletedTreatmentAngelman's syndrome / Nervous System Diseases1
Not AvailableCompletedTreatmentAutistic Disorder1
Not AvailableCompletedTreatmentEnd Stage Renal Disease (ESRD) / Hyperhomocysteinaemia1
Not AvailableCompletedTreatmentHealthy Volunteers1
Not AvailableCompletedTreatmentMale Pattern of Hair Loss, Androgenic Alopecia1
Not AvailableCompletedTreatmentSleep Disorders, Circadian Rhythm1
Not AvailableCompletedTreatmentVitamin B 12 Deficiency1
Not AvailableRecruitingPreventionPost Operative Cognitive Dysfunction1
Not AvailableRecruitingTreatmentCarpal Tunnel Syndrome (CTS)1
Not AvailableTerminatedTreatmentRecurrent Aphthous Stomatitis1
Not AvailableWithdrawnPreventionStrokes / Transient Ischaemic Attack (TIA)1

Pharmacoeconomics

Manufacturers
  • Par pharmaceutical inc
  • Pharmacia and upjohn co
  • Eli lilly and co
  • Watson laboratories inc
  • Abraxis pharmaceutical products
  • Akorn inc
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia and critical care
  • Bioniche pharma usa llc
  • Dell laboratories inc
  • Luitpold pharmaceuticals inc
  • Sanofi aventis us llc
  • Solopak medical products inc
  • Warner chilcott inc
  • Wyeth ayerst laboratories
  • Merck and co inc
  • Bel mar laboratories inc
  • Bristol myers squibb co
  • Savage laboratories inc div altana inc
  • Bayer healthcare pharmaceuticals inc
  • West ward pharmaceutical corp
  • Bracco diagnostics inc
Packagers
  • American Regent
  • APP Pharmaceuticals
  • Baxter International Inc.
  • Bayer Healthcare
  • C.O. Truxton Inc.
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Central Pharmaceuticals
  • Chain Drug
  • Choice Rx Ltd.
  • Clint Pharmaceutical Inc.
  • CVS Pharmacy
  • Darby Dental Supply Co. Inc.
  • General Injectables and Vaccines Inc.
  • Gonberetica
  • Gyn Nutriment Pharmacology
  • H and H Laboratories
  • International Ethical Labs Inc.
  • Ivax Pharmaceuticals
  • Keene Pharmaceuticals Inc.
  • Luitpold Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Martica Enterprises Inc.
  • Martin Surgical Supply
  • Mason Distributors
  • Mckesson Corp.
  • MDRNA Inc.
  • Merck & Co.
  • Merit Pharmaceuticals
  • National Pharmaceuticals
  • National Vitamin Company
  • Neuman Distributors Inc.
  • Par Pharmaceuticals
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Primedics Laboratories
  • Rite Aid Corp.
  • Rugby Laboratories
  • Spectrum Pharmaceuticals
  • Sunmark
  • Torrance Co.
  • Vitaline Corp.
  • Walgreen Co.
Dosage forms
FormRouteStrength
Capsule; liquidOral
TabletOral1000 ug/1
KitTopical
PatchTransdermal
KitIntramuscular1000 ug/1mL
KitIntramuscular; Subcutaneous1000 ug/1mL
LiquidIntramuscular
ElixirOral
PowderOral
Spray, meteredNasal25 ug/0.1mL
SolutionIntramuscular; Subcutaneous
Capsule, liquid filledOral
InjectionIntramuscular1 mg/1mL
InjectionIntramuscular; Subcutaneous1000 ug/1mL
Injection, solutionIntramuscular; Subcutaneous1000 ug/1mL
CapsuleOral
Tablet, effervescentOral
LiquidOral
LozengeOral
LiquidIntramuscular; Intravenous
Tablet, delayed releaseOral
Tablet, coatedOral
Injection, powder, lyophilized, for solutionIntravenous
SolutionIntravenous
SolutionOral
Tablet, chewableOral
TabletOral
LiquidIntravenous
SprayNasal500 ug/1
Tablet, orally disintegratingOral
SyrupOral
KitIntravenous
Injection, solutionIntravenous
Solution / dropsOral
Tablet, film coatedOral
Capsule, gelatin coatedOral
WaferOral
LiquidIntramuscular; Intravenous; Subcutaneous
Injection, solutionIntramuscular1000 ug/1mL
Liquid; tabletOral
Capsule, extended releaseOral
Tablet, extended releaseOral
Capsule, coatedOral
StripOral
TabletOral
CapsuleOral
LiquidIntramuscular; Subcutaneous
Tablet, extended releaseOral
KitOral
Prices
Unit descriptionCostUnit
Nascobal 500 mcg/0.1ml Solution 2.3ml Bottle277.97USD bottle
Cyanocobalamin crystals161.18USD g
Infuvite pediatric vial2.58USD ml
Cyanocobalamin 1000 mcg/ml vial1.44USD vial
Cyanocobalamin 1000 mcg/ml1.2USD ml
Cyanocobalamin 1000 mcg/ml Solution1.03USD ml
Rubesol-1000 mcg/ml vial0.48USD ml
Vitamin B-12 1000 mcg/ml0.47USD ml
Vitamin b-12 2.5 mg tablet sl0.17USD tablet
Cyanocobalamin 1000 mcg tablet0.16USD tablet
Cyanocobalamin 100 mcg tablet0.14USD tablet
Vitamin b-12 1000 mcg tablet sl0.08USD tablet
B12 2500 mcg tablet sl0.07USD tablet
Sm vitamin b-12 500 mcg tablet0.06USD tablet
Vitamin b-12 1000 mcg tablet0.06USD tablet
Vitabee with vit c caplet0.05USD caplet
Vitamin b-12 500 mcg tablet0.05USD tablet
CVS Pharmacy vitamin b-12 1000 mcg tablet0.04USD tablet
CVS Pharmacy vitamin b-12 500 mcg tablet0.04USD tablet
Vitamin b-12 50 mcg tablet0.04USD tablet
CVS Pharmacy vitamin b12 100 mcg tablet0.03USD tablet
Pv vit b-12 1000 mcg tablet sl0.03USD tablet
Ra vitamin b-12 50 mcg tablet0.03USD tablet
Vitamin b-12 250 mcg tablet0.03USD tablet
Pv b-12 250 mcg tablet0.02USD tablet
Vitamin b-12 100 mcg tablet0.02USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7229636No2007-06-122024-08-01Us
US7879349No2011-02-012024-08-01Us
US8003353No2011-08-232024-08-01Us
US8940714No2015-01-272024-02-26Us
US7404489No2008-07-292024-03-12Us
US9415007No2016-08-162024-07-28Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)> 300 https://www.lookchem.com/Cyanocobalamin/
boiling point (°C)> 300http://dept.harpercollege.edu/chemistry/msds/Cyanocobalamin%20Vit%20B12.pdf
water solubility12.5 mg/mLhttp://www.hmdb.ca/metabolites/HMDB00607
logP1.897http://www.hmdb.ca/metabolites/HMDB00607
logS-4.5http://www.hmdb.ca/metabolites/HMDB00607
pKa1.84, 8.77http://foodb.ca/compounds/FDB013264
Predicted Properties
PropertyValueSource
logP-14ChemAxon
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)-0.55ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area440.79 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity344.12 m3·mol-1ChemAxon
Polarizability134.61 Å3ChemAxon
Number of Rings12ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9574
Blood Brain Barrier-0.7447
Caco-2 permeable-0.6455
P-glycoprotein substrateSubstrate0.8341
P-glycoprotein inhibitor INon-inhibitor0.5082
P-glycoprotein inhibitor IIInhibitor0.6369
Renal organic cation transporterNon-inhibitor0.898
CYP450 2C9 substrateNon-substrate0.8104
CYP450 2D6 substrateNon-substrate0.8085
CYP450 3A4 substrateSubstrate0.65
CYP450 1A2 substrateNon-inhibitor0.8775
CYP450 2C9 inhibitorNon-inhibitor0.8775
CYP450 2D6 inhibitorNon-inhibitor0.8737
CYP450 2C19 inhibitorNon-inhibitor0.7076
CYP450 3A4 inhibitorInhibitor0.7118
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8125
Ames testNon AMES toxic0.5707
CarcinogenicityNon-carcinogens0.7782
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity2.6731 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8988
hERG inhibition (predictor II)Non-inhibitor0.682
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as cobalamin derivatives. These are organic compounds containing a corrin ring, a cobalt atom, an a nucleotide moiety. Cobalamin Derivatives are actually derived from vitamin B12.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Tetrapyrroles and derivatives
Sub Class
Corrinoids
Direct Parent
Cobalamin derivatives
Alternative Parents
Metallotetrapyrroles / Benzimidazole ribonucleosides and ribonucleotides / Pentose phosphates / Glycosylamines / Monosaccharide phosphates / Benzimidazoles / Phosphoethanolamines / Dialkyl phosphates / Benzenoids / Fatty amides
show 21 more
Substituents
Cobalamin / Metallotetrapyrrole skeleton / 1-ribofuranosylbenzimidazole / Pentose phosphate / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Monosaccharide phosphate / Benzimidazole / Phosphoethanolamine
show 45 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cob(III)alamins (CHEBI:17439)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Cofactor
General Function
Zinc ion binding
Specific Function
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofola...
Gene Name
MTR
Uniprot ID
Q99707
Uniprot Name
Methionine synthase
Molecular Weight
140525.91 Da
References
  1. Stover PJ: Vitamin B12 and older adults. Curr Opin Clin Nutr Metab Care. 2010 Jan;13(1):24-7. doi: 10.1097/MCO.0b013e328333d157. [PubMed:19904199]
  2. Allen LH: Causes of vitamin B12 and folate deficiency. Food Nutr Bull. 2008 Jun;29(2 Suppl):S20-34; discussion S35-7. [PubMed:18709879]
  3. O'Leary F, Samman S: Vitamin B12 in health and disease. Nutrients. 2010 Mar;2(3):299-316. doi: 10.3390/nu2030299. Epub 2010 Mar 5. [PubMed:22254022]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Cofactor
General Function
Modified amino acid binding
Specific Function
Involved in the degradation of several amino acids, odd-chain fatty acids and cholesterol via propionyl-CoA to the tricarboxylic acid cycle. MCM has different functions in other species.
Gene Name
MUT
Uniprot ID
P22033
Uniprot Name
Methylmalonyl-CoA mutase, mitochondrial
Molecular Weight
83133.755 Da
References
  1. Worgan LC, Niles K, Tirone JC, Hofmann A, Verner A, Sammak A, Kucic T, Lepage P, Rosenblatt DS: Spectrum of mutations in mut methylmalonic acidemia and identification of a common Hispanic mutation and haplotype. Hum Mutat. 2006 Jan;27(1):31-43. [PubMed:16281286]
  2. Brooks AJ, Vlasie M, Banerjee R, Brunold TC: Co-C bond activation in methylmalonyl-CoA mutase by stabilization of the post-homolysis product Co2+ cobalamin. J Am Chem Soc. 2005 Nov 30;127(47):16522-8. [PubMed:16305240]
  3. Kozlowski PM, Andruniow T, Jarzecki AA, Zgierski MZ, Spiro TG: DFT analysis of co-alkyl and co-adenosyl vibrational modes in B12-cofactors. Inorg Chem. 2006 Jul 10;45(14):5585-90. [PubMed:16813422]
  4. Moras E, Hosack A, Watkins D, Rosenblatt DS: Mitochondrial vitamin B12-binding proteins in patients with inborn errors of cobalamin metabolism. Mol Genet Metab. 2007 Feb;90(2):140-7. Epub 2006 Sep 29. [PubMed:17011224]
  5. Stover PJ: Vitamin B12 and older adults. Curr Opin Clin Nutr Metab Care. 2010 Jan;13(1):24-7. doi: 10.1097/MCO.0b013e328333d157. [PubMed:19904199]
  6. O'Leary F, Samman S: Vitamin B12 in health and disease. Nutrients. 2010 Mar;2(3):299-316. doi: 10.3390/nu2030299. Epub 2010 Mar 5. [PubMed:22254022]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Oxidoreductase activity, oxidizing metal ions, nad or nadp as acceptor
Specific Function
Involved in the reductive regeneration of cob(I)alamin (vitamin B12) cofactor required for the maintenance of methionine synthase in a functional state. Necessary for utilization of methylgroups fr...
Gene Name
MTRR
Uniprot ID
Q9UBK8
Uniprot Name
Methionine synthase reductase
Molecular Weight
80409.22 Da
References
  1. O'Leary VB, Mills JL, Pangilinan F, Kirke PN, Cox C, Conley M, Weiler A, Peng K, Shane B, Scott JM, Parle-McDermott A, Molloy AM, Brody LC: Analysis of methionine synthase reductase polymorphisms for neural tube defects risk association. Mol Genet Metab. 2005 Jul;85(3):220-7. Epub 2005 Mar 17. [PubMed:15979034]
  2. Miriuka SG, Langman LJ, Evrovski J, Miner SE, D'Mello N, Delgado DH, Wong BY, Ross HJ, Cole DE: Genetic polymorphisms predisposing to hyperhomocysteinemia in cardiac transplant patients. Transpl Int. 2005 Jan;18(1):29-35. [PubMed:15612980]
  3. Berkun Y, Abou Atta I, Rubinow A, Orbach H, Levartovsky D, Aamar S, Arbel O, Dresner-Pollak R, Friedman G, Ben-Yehuda A: 2756GG genotype of methionine synthase reductase gene is more prevalent in rheumatoid arthritis patients treated with methotrexate and is associated with methotrexate-induced nodulosis. J Rheumatol. 2007 Aug;34(8):1664-9. Epub 2007 Jul 1. [PubMed:17611986]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Hydrolase activity
Specific Function
Probable GTPase. May function as chaperone. May be involved in the transport of cobalamin (Cbl) into mitochondria for the final steps of adenosylcobalamin (AdoCbl) synthesis.
Gene Name
MMAA
Uniprot ID
Q8IVH4
Uniprot Name
Methylmalonic aciduria type A protein, mitochondrial
Molecular Weight
46537.865 Da
References
  1. Lerner-Ellis JP, Dobson CM, Wai T, Watkins D, Tirone JC, Leclerc D, Dore C, Lepage P, Gravel RA, Rosenblatt DS: Mutations in the MMAA gene in patients with the cblA disorder of vitamin B12 metabolism. Hum Mutat. 2004 Dec;24(6):509-16. [PubMed:15523652]
  2. Dobson CM, Gradinger A, Longo N, Wu X, Leclerc D, Lerner-Ellis J, Lemieux M, Belair C, Watkins D, Rosenblatt DS, Gravel RA: Homozygous nonsense mutation in the MCEE gene and siRNA suppression of methylmalonyl-CoA epimerase expression: a novel cause of mild methylmalonic aciduria. Mol Genet Metab. 2006 Aug;88(4):327-33. Epub 2006 May 11. [PubMed:16697227]
  3. Zhou X, Cui Y, Han J: Methylmalonic acidemia: Current status and research priorities. Intractable Rare Dis Res. 2018 May;7(2):73-78. doi: 10.5582/irdr.2018.01026. [PubMed:29862147]
  4. Froese DS, Zhang J, Healy S, Gravel RA: Mechanism of vitamin B12-responsiveness in cblC methylmalonic aciduria with homocystinuria. Mol Genet Metab. 2009 Dec;98(4):338-43. doi: 10.1016/j.ymgme.2009.07.014. Epub 2009 Aug 3. [PubMed:19700356]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Cobalamin binding
Specific Function
May be involved in the binding and intracellular trafficking of cobalamin (vitamin B12).
Gene Name
MMACHC
Uniprot ID
Q9Y4U1
Uniprot Name
Methylmalonic aciduria and homocystinuria type C protein
Molecular Weight
31728.095 Da
References
  1. Chandler RJ, Aswani V, Tsai MS, Falk M, Wehrli N, Stabler S, Allen R, Sedensky M, Kazazian HH, Venditti CP: Propionyl-CoA and adenosylcobalamin metabolism in Caenorhabditis elegans: evidence for a role of methylmalonyl-CoA epimerase in intermediary metabolism. Mol Genet Metab. 2006 Sep-Oct;89(1-2):64-73. Epub 2006 Jul 14. [PubMed:16843692]
  2. Ben-Omran TI, Wong H, Blaser S, Feigenbaum A: Late-onset cobalamin-C disorder: a challenging diagnosis. Am J Med Genet A. 2007 May 1;143A(9):979-84. [PubMed:17431913]
  3. Morel CF, Lerner-Ellis JP, Rosenblatt DS: Combined methylmalonic aciduria and homocystinuria (cblC): phenotype-genotype correlations and ethnic-specific observations. Mol Genet Metab. 2006 Aug;88(4):315-21. Epub 2006 May 22. [PubMed:16714133]
  4. Lerner-Ellis JP, Tirone JC, Pawelek PD, Dore C, Atkinson JL, Watkins D, Morel CF, Fujiwara TM, Moras E, Hosack AR, Dunbar GV, Antonicka H, Forgetta V, Dobson CM, Leclerc D, Gravel RA, Shoubridge EA, Coulton JW, Lepage P, Rommens JM, Morgan K, Rosenblatt DS: Identification of the gene responsible for methylmalonic aciduria and homocystinuria, cblC type. Nat Genet. 2006 Jan;38(1):93-100. Epub 2005 Nov 27. [PubMed:16311595]
  5. Obeid R, Fedosov SN, Nexo E: Cobalamin coenzyme forms are not likely to be superior to cyano- and hydroxyl-cobalamin in prevention or treatment of cobalamin deficiency. Mol Nutr Food Res. 2015 Jul;59(7):1364-72. doi: 10.1002/mnfr.201500019. Epub 2015 May 12. [PubMed:25820384]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Protein complex binding
Specific Function
Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
Gene Name
MTHFR
Uniprot ID
P42898
Uniprot Name
Methylenetetrahydrofolate reductase
Molecular Weight
74595.895 Da
References
  1. Nakamura T, Saionji K, Hiejima Y, Hirayama H, Tago K, Takano H, Tajiri M, Hayashi K, Kawabata M, Funamizu M, Makita Y, Hata A: Methylenetetrahydrofolate reductase genotype, vitamin B12, and folate influence plasma homocysteine in hemodialysis patients. Am J Kidney Dis. 2002 May;39(5):1032-9. [PubMed:11979347]
  2. Erdogan MO, Yildiz SH, Solak M, Eser O, Cosar E, Eser B, Koken R, Buyukbas S: C677T polymorphism of the methylenetetrahydrofolate reductase gene does not affect folic acid, vitamin B12, and homocysteine serum levels in Turkish children with neural tube defects. Genet Mol Res. 2010 Jun 22;9(2):1197-203. doi: 10.4238/vol9-2gmr816. [PubMed:20589617]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Cob(i)yrinic acid a,c-diamide adenosyltransferase activity
Specific Function
Not Available
Gene Name
MMAB
Uniprot ID
Q96EY8
Uniprot Name
Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrial
Molecular Weight
27387.975 Da
References
  1. Zhang J, Dobson CM, Wu X, Lerner-Ellis J, Rosenblatt DS, Gravel RA: Impact of cblB mutations on the function of ATP:cob(I)alamin adenosyltransferase in disorders of vitamin B12 metabolism. Mol Genet Metab. 2006 Apr;87(4):315-22. Epub 2006 Jan 24. [PubMed:16439175]
  2. Lerner-Ellis JP, Gradinger AB, Watkins D, Tirone JC, Villeneuve A, Dobson CM, Montpetit A, Lepage P, Gravel RA, Rosenblatt DS: Mutation and biochemical analysis of patients belonging to the cblB complementation class of vitamin B12-dependent methylmalonic aciduria. Mol Genet Metab. 2006 Mar;87(3):219-25. Epub 2006 Jan 10. [PubMed:16410054]
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
Actions
Product of
General Function
Gtp binding
Specific Function
Catalyzes ATP-dependent phosphorylation of adenosylcobinamide and addition of GMP to adenosylcobinamide phosphate.
Gene Name
cobU
Uniprot ID
Q05599
Uniprot Name
Bifunctional adenosylcobalamin biosynthesis protein CobU
Molecular Weight
19901.7 Da
References
  1. Fang H, Li D, Kang J, Jiang P, Sun J, Zhang D: Metabolic engineering of Escherichia coli for de novo biosynthesis of vitamin B12. Nat Commun. 2018 Nov 21;9(1):4917. doi: 10.1038/s41467-018-07412-6. [PubMed:30464241]
  2. Warren MJ, Raux E, Schubert HL, Escalante-Semerena JC: The biosynthesis of adenosylcobalamin (vitamin B12). Nat Prod Rep. 2002 Aug;19(4):390-412. [PubMed:12195810]
3. Pancreatic proteases
Kind
Group
Organism
Not Available
Pharmacological action
Unknown
Actions
Substrate
This group is comprised of proteases secreted from the pancreas.
References
  1. Gherasim C, Lofgren M, Banerjee R: Navigating the B(12) road: assimilation, delivery, and disorders of cobalamin. J Biol Chem. 2013 May 10;288(19):13186-93. doi: 10.1074/jbc.R113.458810. Epub 2013 Mar 28. [PubMed:23539619]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Receptor binding
Specific Function
Necessary for efficient absorption of vitamin B12. May direct the production of trunk mesoderm during development by modulating a bone morphogenetic protein (BMP) signaling pathway in the underlyin...
Gene Name
AMN
Uniprot ID
Q9BXJ7
Uniprot Name
Protein amnionless
Molecular Weight
47753.91 Da
References
  1. Al-Alami JR, Tanner SM, Tayeh MK, de la Chapelle A, El-Shanti H: Homozygous AMN mutation in hereditary selective intestinal malabsorption of vitamin B12 in Jordan. Saudi Med J. 2005 Jul;26(7):1061-4. [PubMed:16047053]
  2. Alpers DH: Absorption and blood/cellular transport of folate and cobalamin: Pharmacokinetic and physiological considerations. Biochimie. 2016 Jul;126:52-6. doi: 10.1016/j.biochi.2015.11.006. Epub 2015 Nov 14. [PubMed:26586110]
  3. O'Leary F, Samman S: Vitamin B12 in health and disease. Nutrients. 2010 Mar;2(3):299-316. doi: 10.3390/nu2030299. Epub 2010 Mar 5. [PubMed:22254022]
  4. He Q, Madsen M, Kilkenney A, Gregory B, Christensen EI, Vorum H, Hojrup P, Schaffer AA, Kirkness EF, Tanner SM, de la Chapelle A, Giger U, Moestrup SK, Fyfe JC: Amnionless function is required for cubilin brush-border expression and intrinsic factor-cobalamin (vitamin B12) absorption in vivo. Blood. 2005 Aug 15;106(4):1447-53. Epub 2005 Apr 21. [PubMed:15845892]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Cobalamin binding
Specific Function
Binds vitamin B12 with femtomolar affinity and protects it from the acidic environment of the stomach.
Gene Name
TCN1
Uniprot ID
P20061
Uniprot Name
Transcobalamin-1
Molecular Weight
48206.32 Da
References
  1. Carmel R: Haptocorrin (transcobalamin I) and cobalamin deficiencies. Clin Chem. 2007 Feb;53(2):367-8; author reply 368-9. [PubMed:17259255]
  2. Al-Alami JR, Tanner SM, Tayeh MK, de la Chapelle A, El-Shanti H: Homozygous AMN mutation in hereditary selective intestinal malabsorption of vitamin B12 in Jordan. Saudi Med J. 2005 Jul;26(7):1061-4. [PubMed:16047053]
  3. Russell-Jones GJ, Alpers DH: Vitamin B12 transporters. Pharm Biotechnol. 1999;12:493-520. [PubMed:10742986]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Metal ion binding
Specific Function
Primary vitamin B12-binding and transport protein. Delivers cobalamin to cells.
Gene Name
TCN2
Uniprot ID
P20062
Uniprot Name
Transcobalamin-2
Molecular Weight
47534.54 Da
References
  1. Chen X, Remacha AF, Sarda MP, Carmel R: Influence of cobalamin deficiency compared with that of cobalamin absorption on serum holo-transcobalamin II. Am J Clin Nutr. 2005 Jan;81(1):110-4. [PubMed:15640468]
  2. Alessio AC, Hoehr NF, Siqueira LH, Bydlowski SP, Annichino-Bizzacchi JM: Polymorphism C776G in the transcobalamin II gene and homocysteine, folate and vitamin B12 concentrations. Association with MTHFR C677T and A1298C and MTRR A66G polymorphisms in healthy children. Thromb Res. 2007;119(5):571-7. Epub 2006 Jul 3. [PubMed:16820193]
  3. Bowen RA, Drake SK, Vanjani R, Huey ED, Grafman J, Horne MK 3rd: Markedly increased vitamin B12 concentrations attributable to IgG-IgM-vitamin B12 immune complexes. Clin Chem. 2006 Nov;52(11):2107-14. [PubMed:17068171]
  4. Bosco P, Gueant-Rodriguez RM, Anello G, Spada R, Romano A, Fajardo A, Caraci F, Ferri R, Gueant JL: Association of homocysteine (but not of MTHFR 677 C>T, MTR 2756 A>G, MTRR 66 A>G and TCN2 776 C>G) with ischaemic cerebrovascular disease in Sicily. Thromb Haemost. 2006 Aug;96(2):154-9. [PubMed:16894458]
  5. Al-Alami JR, Tanner SM, Tayeh MK, de la Chapelle A, El-Shanti H: Homozygous AMN mutation in hereditary selective intestinal malabsorption of vitamin B12 in Jordan. Saudi Med J. 2005 Jul;26(7):1061-4. [PubMed:16047053]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Cobalamin binding
Specific Function
Promotes absorption of the essential vitamin cobalamin (Cbl) in the ileum. After interaction with CUBN, the GIF-cobalamin complex is internalized via receptor-mediated endocytosis.
Gene Name
GIF
Uniprot ID
P27352
Uniprot Name
Gastric intrinsic factor
Molecular Weight
45415.67 Da
References
  1. Fedosov SN, Fedosova NU, Berglund L, Moestrup SK, Nexo E, Petersen TE: Composite organization of the cobalamin binding and cubilin recognition sites of intrinsic factor. Biochemistry. 2005 Mar 8;44(9):3604-14. [PubMed:15736970]
  2. He Q, Madsen M, Kilkenney A, Gregory B, Christensen EI, Vorum H, Hojrup P, Schaffer AA, Kirkness EF, Tanner SM, de la Chapelle A, Giger U, Moestrup SK, Fyfe JC: Amnionless function is required for cubilin brush-border expression and intrinsic factor-cobalamin (vitamin B12) absorption in vivo. Blood. 2005 Aug 15;106(4):1447-53. Epub 2005 Apr 21. [PubMed:15845892]
  3. Moestrup SK: New insights into carrier binding and epithelial uptake of the erythropoietic nutrients cobalamin and folate. Curr Opin Hematol. 2006 May;13(3):119-23. [PubMed:16567952]
  4. Seetharam B: Receptor-mediated endocytosis of cobalamin (vitamin B12). Annu Rev Nutr. 1999;19:173-95. doi: 10.1146/annurev.nutr.19.1.173. [PubMed:10448521]
  5. O'Leary F, Samman S: Vitamin B12 in health and disease. Nutrients. 2010 Mar;2(3):299-316. doi: 10.3390/nu2030299. Epub 2010 Mar 5. [PubMed:22254022]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Cotransporter which plays a role in lipoprotein, vitamin and iron metabolism, by facilitating their uptake. Binds to ALB, MB, Kappa and lambda-light chains, TF, hemoglobin, GC, SCGB1A1, APOA1, high...
Gene Name
CUBN
Uniprot ID
O60494
Uniprot Name
Cubilin
Molecular Weight
398732.93 Da
References
  1. Fedosov SN, Fedosova NU, Berglund L, Moestrup SK, Nexo E, Petersen TE: Composite organization of the cobalamin binding and cubilin recognition sites of intrinsic factor. Biochemistry. 2005 Mar 8;44(9):3604-14. [PubMed:15736970]
  2. He Q, Madsen M, Kilkenney A, Gregory B, Christensen EI, Vorum H, Hojrup P, Schaffer AA, Kirkness EF, Tanner SM, de la Chapelle A, Giger U, Moestrup SK, Fyfe JC: Amnionless function is required for cubilin brush-border expression and intrinsic factor-cobalamin (vitamin B12) absorption in vivo. Blood. 2005 Aug 15;106(4):1447-53. Epub 2005 Apr 21. [PubMed:15845892]
  3. Gherasim C, Lofgren M, Banerjee R: Navigating the B(12) road: assimilation, delivery, and disorders of cobalamin. J Biol Chem. 2013 May 10;288(19):13186-93. doi: 10.1074/jbc.R113.458810. Epub 2013 Mar 28. [PubMed:23539619]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Calcium ion binding
Specific Function
Acts together with cubilin to mediate HDL endocytosis (By similarity). May participate in regulation of parathyroid-hormone and para-thyroid-hormone-related protein release.
Gene Name
LRP2
Uniprot ID
P98164
Uniprot Name
Low-density lipoprotein receptor-related protein 2
Molecular Weight
521952.77 Da
References
  1. Moestrup SK, Birn H, Fischer PB, Petersen CM, Verroust PJ, Sim RB, Christensen EI, Nexo E: Megalin-mediated endocytosis of transcobalamin-vitamin-B12 complexes suggests a role of the receptor in vitamin-B12 homeostasis. Proc Natl Acad Sci U S A. 1996 Aug 6;93(16):8612-7. [PubMed:8710919]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Gherasim C, Lofgren M, Banerjee R: Navigating the B(12) road: assimilation, delivery, and disorders of cobalamin. J Biol Chem. 2013 May 10;288(19):13186-93. doi: 10.1074/jbc.R113.458810. Epub 2013 Mar 28. [PubMed:23539619]
  2. Quadros EV, Sequeira JM: Cellular uptake of cobalamin: transcobalamin and the TCblR/CD320 receptor. Biochimie. 2013 May;95(5):1008-18. doi: 10.1016/j.biochi.2013.02.004. Epub 2013 Feb 14. [PubMed:23415653]

Drug created on June 13, 2005 07:24 / Updated on September 17, 2019 03:30