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Vitamin B12 information


Vitamin B12
General skeletal formula of cobalamins
Stick model of cyanocobalamin (R = CN) based on the crystal structure[1]
Clinical data
Other namesVitamin B12, vitamin B-12, cobalamin
AHFS/Drugs.comMonograph
MedlinePlusa605007
License data
  • US DailyMed: Vitamin_b12
Routes of
administration
By mouth, sublingual, intravenous (IV), intramuscular (IM), intranasal
ATC code
  • B03BA01 (WHO)
Legal status
Legal status
  • UK: OTC
  • US: OTC
Pharmacokinetic data
BioavailabilityReadily absorbed in distal half of the ileum.
Protein bindingVery high to specific transcobalamins plasma proteins.
Binding of hydroxocobalamin is slightly higher than cyanocobalamin.
MetabolismLiver
Elimination half-lifeApproximately 6 days
(400 days in the liver).
ExcretionKidney
Identifiers
IUPAC name
  • α-(5,6-Dimethylbenzimidazolyl)cobamidcyanide
CAS Number
  • 68-19-9
PubChem CID
  • 184933
DrugBank
  • DB00115
ChemSpider
  • 10469504
UNII
  • P6YC3EG204
KEGG
  • D00166
ChEMBL
  • ChEMBL2110563
Chemical and physical data
FormulaC63H88CoN14O14P
Molar mass1355.388 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • NC(=O)C[C@@]8(C)[C@H](CCC(N)=O)C=2/N=C8/C(/C)=C1/[C@@H](CCC(N)=O)[C@](C)(CC(N)=O)[C@@](C)(N1[Co+]C#N)[C@@H]7/N=C(C(\C)=C3/N=C(/C=2)C(C)(C)[C@@H]3CCC(N)=O)[C@](C)(CCC(=O)NCC(C)OP([O-])(=O)O[C@@H]6[C@@H](CO)O[C@H](n5cnc4cc(C)c(C)cc45)[C@@H]6O)[C@H]7CC(N)=O
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 checkY
  • Key:RMRCNWBMXRMIRW-WYVZQNDMSA-L checkY

Vitamin B12, also known as cobalamin, is a water-soluble vitamin involved in metabolism.[2] It is one of eight B vitamins. It is required by animals, which use it as a cofactor in DNA synthesis, and in both fatty acid and amino acid metabolism.[3] It is important in the normal functioning of the nervous system via its role in the synthesis of myelin, and in the circulatory system in the maturation of red blood cells in the bone marrow.[2][4] Plants do not need cobalamin and carry out the reactions with enzymes that are not dependent on it.[5]

Vitamin B12 is the most chemically complex of all vitamins,[6] and for humans the only vitamin that must be sourced from animal-derived foods or supplements.[2][7] Only some archaea and bacteria can synthesize vitamin B12.[8] Vitamin B12 deficiency is a widespread condition that is particularly prevalent in populations with low consumption of animal foods. This can be due to a variety of reasons, such as low socioeconomic status, ethical considerations, or lifestyle choices such as veganism.[9]

Foods containing vitamin B12 include meat, shellfish, liver, fish, poultry, eggs, and dairy products.[2] Many breakfast cereals are fortified with the vitamin.[2] Supplements and medications are available to treat and prevent vitamin B12 deficiency.[2] They are usually taken by mouth, but for the treatment of deficiency may also be given as an intramuscular injection.[2][6]

Vitamin B12 deficiencies have a greater effect on the pregnant, young children, and elderly people, and are more common in middle and lower developed countries due to malnutrition.[10] The most common cause of vitamin B12 deficiency in developed countries is impaired absorption due to a loss of gastric intrinsic factor (IF) which must be bound to a food-source of B12 in order for absorption to occur.[11] A second major cause is an age-related decline in stomach acid production (achlorhydria), because acid exposure frees protein-bound vitamin.[12] For the same reason, people on long-term antacid therapy, using proton-pump inhibitors, H2 blockers or other antacids are at increased risk.[13]

The diets of vegetarians and vegans may not provide sufficient B12 unless a dietary supplement is taken.[2] A deficiency may be characterized by limb neuropathy or a blood disorder called pernicious anemia, a type of anemia in which red blood cells become abnormally large.[2] This can result in fatigue, decreased ability to think, lightheadedness, shortness of breath, frequent infections, poor appetite, numbness in the hands and feet, depression, memory loss, confusion, difficulty walking, blurred vision, irreversible nerve damage, and many others.[14] If left untreated in infants, deficiency may lead to neurological damage and anemia.[2] Folate levels in the individual may affect the course of pathological changes and symptomatology of vitamin B12 deficiency. Vitamin B12 deficiency in pregnant women is strongly associated with an increased risk of spontaneous abortion, congenital malformations such as neural tube defects, problems with brain development growth in the unborn child.[10]

Vitamin B12 was discovered as a result of pernicious anemia, an autoimmune disorder in which the blood has a lower than normal number of red blood cells, due to a deficiency of vitamin B12.[5][15] The ability to absorb the vitamin declines with age, especially in people over 60.[16]

  1. ^ Prieto T, Neuburger M, Spingler B, Zelder F (2016). "Inorganic Cyanide as Protecting Group in the Stereospecific Reconstitution of Vitamin B12 from an Artificial Green Secocorrinoid" (PDF). Org. Lett. 18 (20): 5292–5295. doi:10.1021/acs.orglett.6b02611. PMID 27726382.
  2. ^ a b c d e f g h i j Office of Dietary Supplements (6 April 2021). "Vitamin B12: Fact Sheet for Health Professionals". Bethesda, Maryland: US National Institutes of Health. Archived from the original on 2021-10-08. Retrieved 24 December 2021.
  3. ^ Yamada K (2013). "Cobalt: Its Role in Health and Disease". In Sigel A, Sigel H, Sigel RK (eds.). Interrelations between Essential Metal Ions and Human Diseases. Metal Ions in Life Sciences. Vol. 13. Springer. pp. 295–320. doi:10.1007/978-94-007-7500-8_9. ISBN 978-94-007-7499-5. PMID 24470095.
  4. ^ Cite error: The named reference Calderon2020 was invoked but never defined (see the help page).
  5. ^ a b Cite error: The named reference Smith2019 was invoked but never defined (see the help page).
  6. ^ a b "Vitamin B12". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, OR. 4 June 2015. Archived from the original on 29 October 2019. Retrieved 5 April 2019.
  7. ^ Vincenti A, Bertuzzo L, Limitone A, D'Antona G, Cena H (June 2021). "Perspective: Practical Approach to Preventing Subclinical B12 Deficiency in Elderly Population". Nutrients. 13 (6): 1913. doi:10.3390/nu13061913. PMC 8226782. PMID 34199569.
  8. ^ Watanabe F, Bito T (January 2018). "Vitamin B12 sources and microbial interaction". Exp Biol Med (Maywood). 243 (2): 148–158. doi:10.1177/1535370217746612. PMC 5788147. PMID 29216732.
  9. ^ Obeid R, Heil SG, Verhoeven MM, van den Heuvel EG, de Groot LC, Eussen SJ (2019). "Vitamin B12 Intake From Animal Foods, Biomarkers, and Health Aspects". Front Nutr. 6: 93. doi:10.3389/fnut.2019.00093. PMC 6611390. PMID 31316992.
  10. ^ a b Cite error: The named reference :0 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference PKIN2020VitB12 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference DRItext was invoked but never defined (see the help page).
  13. ^ "Acid-Reflux Drugs Tied to Lower Levels of Vitamin B-12". WebMD. Archived from the original on 2018-07-23. Retrieved 2018-07-23.
  14. ^ "Vitamin B12 Deficiency Anemia". www.hopkinsmedicine.org. 8 August 2021. Retrieved 2022-02-16.
  15. ^ "Pernicious anemia: MedlinePlus Medical Encyclopedia". medlineplus.gov. Retrieved 2022-01-06.
  16. ^ Baik HW, Russell RM (2021-11-18). "Vitamin B12 deficiency in the elderly". Annual Review of Nutrition. 19: 357–377. doi:10.1146/annurev.nutr.19.1.357. PMID 10448529.

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Vitamin B12

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Vitamin B12, also known as cobalamin, is a water-soluble vitamin involved in metabolism. It is one of eight B vitamins. It is required by animals, which...

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Vitamin B12 deficiency

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Vitamin B12 deficiency, also known as cobalamin deficiency, is the medical condition in which the blood and tissue have a lower than normal level of vitamin...

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Pernicious anemia

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where not enough red blood cells are produced due to a deficiency of vitamin B12. Those affected often have a gradual onset. The most common initial symptoms...

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B vitamins

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contain sulfur and B12 contains cobalt. Dietary supplements containing all eight are referred to as a vitamin B complex. Individual B vitamins are referred...

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Vitamin

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folates) Vitamin B12 (cobalamins) Vitamin C (ascorbic acid and ascorbates) Vitamin D (calciferols) Vitamin E (tocopherols and tocotrienols) Vitamin K (phylloquinones...

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Vitamin B12 total synthesis

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The total synthesis of the complex biomolecule vitamin B12 was accomplished in two different approaches by the collaborating research groups of Robert...

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Vitamin deficiency

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Vitamin fortification programs exist in one or more countries for folate, niacin, riboflavin, thiamin, vitamin A, vitamin B6, vitamin B12, vitamin D...

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Methylcobalamin

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Methylcobalamin (mecobalamin, MeCbl, or MeB12) is a cobalamin, a form of vitamin B12. It differs from cyanocobalamin in that the cyano group at the cobalt...

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Vegan nutrition

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acids, vitamin D, calcium, zinc, and vitamin B12. Researchers agree that those on a vegan diet should take a vitamin B12 dietary supplement. The American...

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Methylmalonic acid

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do not have vitamin B12 deficiency may have elevated levels of methylmalonic acid detected). MMA is elevated in 90–98% of patients with B12 deficiency...

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Schilling test

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for patients with vitamin B12 (cobalamin) deficiency. The purpose of the test was to determine how well a patient is able to absorb B12 from their intestinal...

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Nitrous oxide

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vitamin B12 deficiency. Symptoms are treated with high doses of vitamin B12, but recovery can be slow and incomplete. People with normal vitamin B12 levels...

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Folate

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are concerns that large amounts of supplemental folic acid can hide vitamin B12 deficiency. Not consuming enough folate can lead to folate deficiency...

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Hydroxocobalamin

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as vitamin B12a and hydroxycobalamin, is a vitamin found in food and used as a dietary supplement. As a supplement it is used to treat vitamin B12 deficiency...

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Porphyra

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coast. Porphyra contains vitamin B12 and one study suggests that it is the most suitable non-meat source of this essential vitamin. In the view of the Academy...

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Intrinsic factor

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cells (in rodents) of the stomach. It is necessary for the absorption of vitamin B12 later on in the distal ileum of the small intestine. In humans, the gastric...

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Cyanocobalamin

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1971). "[205] Preparation of the reduced forms of vitamin B12 and of some analogs of the vitamin B12 coenzyme containing a cobalt-carbon bond". In McCormick...

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Fruitarianism

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increase the risk of nutritional deficiencies, such as reduced intake of vitamin B12, calcium, iron, zinc, omega-3 or protein. Some fruitarians will eat only...

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Nutrition and cognition

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(B12), and biotin. B vitamins are not synthesized in the body, and thus need to be obtained from food. B-complex vitamins are water-soluble vitamins,...

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Anemia

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of decreased production include iron deficiency, folate deficiency, vitamin B12 deficiency, thalassemia and a number of bone marrow tumors. Causes of...

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Nutritional yeast

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B-complex vitamins and contains trace amounts of several other vitamins and minerals. Sometimes nutritional yeast is fortified with vitamin B12, another...

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Methylmalonic acidemias

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methylmalonic acidemias. Methylmalonyl-CoA requires vitamin B12 to form succinyl-CoA. When the amount of B12 is insufficient for the conversion of cofactor...

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Vitamin B6

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Zhang D (April 2021). "Associations of dietary vitamin B1, vitamin B2, vitamin B6, and vitamin B12 with the risk of depression: a systematic review...

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Vegetarian nutrition

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childhood, and adolescence. However, vegetarian diets deficient in vitamin B12 or calories may compromise children's health and development. The UK...

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Marmite

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British company Unilever. Marmite is a vegan source of B vitamins, including supplemental vitamin B12. A traditional method of use is to spread it very thinly...

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Nutritional neuroscience

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deficiency very rare. Copper deficiency can manifest in parallel with vitamin B12 and other nutritional deficiencies. The most common cause of copper deficiency...

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Serum vitamin B12

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Serum vitamin B12 is a medical laboratory test that measure vitamin B12 only in the blood binding to both transcobalamins. Most of the time, 80–94% of...

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Megaloblastic anemia

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cell DNA synthesis is most often due to hypovitaminosis, specifically vitamin B12 deficiency or folate deficiency. Loss of micronutrients may also be a...

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Vegetarianism

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some difficulties. For vitamin B12, depending on the presence or absence of eggs and dairy products in the diet or other reliable B12 sources, vegetarians...

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