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Identification
Name Cyanocobalamin
Accession Number DB00115 (APRD00326, EXPT00965, NUTR00004)
Type small molecule
Groups approved, nutraceutical
Description

Cyanocobalamin (commonly known as Vitamin B12) is the most chemically complex of all the vitamins. Cyanocobalamin’s structure is based on a corrin ring, which, although similar to the porphyrin ring found in heme, chlorophyll, and cytochrome, has two of the pyrrole rings directly bonded. The central metal ion is Co (cobalt). Cyanocobalamin cannot be made by plants or by animals, as the only type of organisms that have the enzymes required for the synthesis of cyanocobalamin are bacteria and archaea. Higher plants do not concentrate cyanocobalamin from the soil and so are a poor source of the substance as compared with animal tissues. Cyanocobalamin is naturally found in foods including meat (especially liver and shellfish), eggs, and milk products. [HMDB]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Cyanocob(III)alamin
Vitamin B12
Vitamin B12 complex
Salts Not Available
Brand names
Name Company
Bedoz
Berocca PN
Berubigen
Cobex
Cobolin-M
Crystamine
Cyanoject
Cyomin
Depinar
Neuroforte-R
Primabalt
Rubivite
Rubramin PC
Ruvite
Shovite
Vibal
Vitabee 12
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Brand mixtures
Brand Name Ingredients
Infuvite Pediatric
Liver-Stomach Concentrate with Intrinsic Factor Special Liver-Stomach Concentrate + Vitamin B 12 + Iron + Ascorbic Acid + Folic Acid
Categories
  • Antianemic Agents
  • Essential Vitamin
  • Vitamins (Vitamin B Complex)
CAS number 68-19-9
Weight Average: 1356.3731
Monoisotopic: 1355.575230332
Chemical Formula C63H89CoN14O14P
InChI Key InChIKey=SEKGMJVHSBBHRD-WZHZPDAFSA-M
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;;+1/p-1/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1
Plain Text
IUPAC Name
SMILES
OC[C@H]1O[C@@H]([C@H](O)[C@@H]1OP(O)(=O)O[C@]([H])(C)CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co]C#N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]3CCC(=O)N)/C(C)(C)[C@@H]1CCC(=O)N)N1C=NC2=CC(C)=C(C)C=C12
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Cobalamin Derivatives
Substructures
  • Cobalamin Derivatives
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Anions
  • Phosphonic Acids and Derivatives
  • Benzimidazoles
  • Amino Ketones
  • Organophosphate Esters
  • Nitriles and Derivatives
  • Pyrrolidines
  • Ethers
  • Benzene and Derivatives
  • Carboxylic Acids and Derivatives
  • Carbamates and Derivatives
  • Enamines
  • Alcohols and Polyols
  • Cyanides
  • Imidazoles
  • Corrinoids
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Phosphinic Acids and Derivatives
  • Furans
  • Imines
  • Cyanamides
  • Carbohydrates
  • Pyrrolines
  • Cations
Pharmacology
Indication For treatment of pernicious anemia (due to lack of or inhibition of intrinsic factor) and for prevention and treatment of vitamin B 12 deficiency.
Pharmacodynamics Cyanocobalamin (Vitamin B12) is a water-soluble organometallic compound with a trivalent cobalt ion bound inside a corrin ring. It is needed for nerve cells and red blood cells, and to make DNA. Vitamin B12 deficiency is the cause of several forms of anemia.
Mechanism of action Vitamin B12 is used in the body in two forms: Methylcobalamin and 5-deoxyadenosyl cobalamin. The enzyme methionine synthase needs methylcobalamin as a cofactor. This enzyme is involved in the conversion of the amino acid homocysteine into methionine. Methionine in turn is required for DNA methylation. 5-Deoxyadenosyl cobalamin is a cofactor needed by the enzyme that converts L-methylmalonyl-CoA to succinyl-CoA. This conversion is an important step in the extraction of energy from proteins and fats. Furthermore, succinyl CoA is necessary for the production of hemoglobin, the substances that carries oxygen in red blood cells.
Absorption Readily absorbed in the lower half of the ileum.
Volume of distribution Not Available
Protein binding Very high (to specific plasma proteins called transcobalamins); binding of hydroxocobalamin is slightly higher than cyanocobalamin.
Metabolism Hepatic
Route of elimination Not Available
Half life Approximately 6 days (400 days in the liver).
Clearance Not Available
Toxicity Anaphylactic reaction (skin rash, itching, wheezing)-after parenteral administration. ORL-MUS LD50 > 8000 mg/kg
Affected organisms
  • Humans and other mammals
Pathways Not Available
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
Dosage forms
Form Route Strength
Capsule Oral
Liquid Intramuscular
Liquid Oral
Powder Oral
Solution Intramuscular
Tablet Oral
Tablet, extended release Oral
Prices
Unit description Cost Unit
Nascobal 500 mcg/0.1ml Solution 2.3ml Bottle 277.97 USD bottle
Cyanocobalamin crystals 161.18 USD g
Infuvite pediatric vial 2.58 USD ml
Cyanocobalamin 1000 mcg/ml vial 1.44 USD vial
Cyanocobalamin 1000 mcg/ml 1.2 USD ml
Cyanocobalamin 1000 mcg/ml Solution 1.03 USD ml
Rubesol-1000 mcg/ml vial 0.48 USD ml
Vitamin B-12 1000 mcg/ml 0.47 USD ml
Vitamin b-12 2.5 mg tablet sl 0.17 USD tablet
Cyanocobalamin 1000 mcg tablet 0.16 USD tablet
Cyanocobalamin 100 mcg tablet 0.14 USD tablet
Vitamin b-12 1000 mcg tablet sl 0.08 USD tablet
B12 2500 mcg tablet sl 0.07 USD tablet
Sm vitamin b-12 500 mcg tablet 0.06 USD tablet
Vitamin b-12 1000 mcg tablet 0.06 USD tablet
Vitabee with vit c caplet 0.05 USD caplet
Vitamin b-12 500 mcg tablet 0.05 USD tablet
CVS Pharmacy vitamin b-12 1000 mcg tablet 0.04 USD tablet
CVS Pharmacy vitamin b-12 500 mcg tablet 0.04 USD tablet
Vitamin b-12 50 mcg tablet 0.04 USD tablet
CVS Pharmacy vitamin b12 100 mcg tablet 0.03 USD tablet
Pv vit b-12 1000 mcg tablet sl 0.03 USD tablet
Ra vitamin b-12 50 mcg tablet 0.03 USD tablet
Vitamin b-12 250 mcg tablet 0.03 USD tablet
Pv b-12 250 mcg tablet 0.02 USD tablet
Vitamin b-12 100 mcg tablet 0.02 USD tablet
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States 7229636 2004-06-11 2024-06-11
United States 7404489 2004-03-12 2024-03-12
Properties
State solid
Experimental Properties
Property Value Source
melting point > 300 °C PhysProp
water solubility 1.25E+004 mg/L MERCK INDEX (1996)
Predicted Properties
Property Value Source
water solubility 3.84e-02 g/l ALOGPS
logP 1.87 ALOGPS
logS -4.5 ALOGPS
pKa (strongest acidic) 1.84 ChemAxon
pKa (strongest basic) 8.77 ChemAxon
physiological charge 2 ChemAxon
References
Synthesis Reference Not Available
General Reference
  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
  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
  3. Hall AH, Rumack BH: Hydroxycobalamin/sodium thiosulfate as a cyanide antidote. J Emerg Med. 1987;5(2):115-21. Pubmed
  4. Andres E, Noel E, Goichot B: Metformin-associated vitamin B12 deficiency. Arch Intern Med. 2002 Oct 28;162(19):2251-2. Pubmed
  5. Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. Pubmed
External Links
Resource Link
KEGG Drug D00166 Link_out
KEGG Compound C02823 Link_out
PubChem Compound 44176380 Link_out
PubChem Substance 46509031 Link_out
ChemSpider 4575342 Link_out
ChEBI 17439 Link_out
ChEMBL 17439 Link_out
PharmGKB PA451892 Link_out
HET CNC Link_out
Drug Product Database 274186 Link_out
RxList http://www.rxlist.com/cgi/generic/b12inj.htm Link_out
Drugs.com http://www.drugs.com/cdi/cyanocobalamin-b12.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/vit_0262.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Cyanocobalamin Link_out
ATC Codes
  • B03BB01
  • B03BA01
AHFS Codes
  • 88:08.00
PDB Entries Not Available
FDA label show (202 KB)
MSDS show (37.1 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Methionine synthase

Pharmacological action: yes
Actions: cofactor
Organism class: human
UniProt ID: Q99707 Link_out
Gene: MTR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Stover PJ: Vitamin B12 and older adults. Curr Opin Clin Nutr Metab Care. 2010 Jan;13(1):24-7. Pubmed
  2. Allen LH: Causes of vitamin B12 and folate deficiency. Food Nutr Bull. 2008 Jun;29(2 Suppl):S20-34; discussion S35-7. Pubmed

2. Methylmalonyl-CoA mutase, mitochondrial

Pharmacological action: yes
Actions: cofactor

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

Organism class: human
UniProt ID: P22033 Link_out
Gene: MUT Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  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
  5. Stover PJ: Vitamin B12 and older adults. Curr Opin Clin Nutr Metab Care. 2010 Jan;13(1):24-7. Pubmed

3. Methionine synthase reductase, mitochondrial

Pharmacological action: unknown
Actions: cofactor

Involved in the reductive regeneration of cob(I)alamin cofactor required for the maintenance of methionine synthase in a functional state

Organism class: human
UniProt ID: Q9UBK8 Link_out
Gene: MTRR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  2. Gueant-Rodriguez RM, Juilliere Y, Candito M, Adjalla CE, Gibelin P, Herbeth B, Van Obberghen E, Gueant JL: Association of MTRRA66G polymorphism (but not of MTHFR C677T and A1298C, MTRA2756G, TCN C776G) with homocysteine and coronary artery disease in the French population. Thromb Haemost. 2005 Sep;94(3):510-5. Pubmed
  3. 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
  4. 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
  5. van der Linden IJ, den Heijer M, Afman LA, Gellekink H, Vermeulen SH, Kluijtmans LA, Blom HJ: The methionine synthase reductase 66A>G polymorphism is a maternal risk factor for spina bifida. J Mol Med. 2006 Dec;84(12):1047-54. Epub 2006 Oct 6. Pubmed

4. Methylmalonic aciduria type A protein, mitochondrial

Pharmacological action: unknown
Actions: cofactor

May be involved in the transport of cobalamin (Cbl) into mitochondria for the final steps of adenosylcobalamin (AdoCbl) synthesis

Organism class: human
UniProt ID: Q8IVH4 Link_out
Gene: MMAA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. 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
  4. 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

5. Methylmalonic aciduria and homocystinuria type C protein

Pharmacological action: unknown
Actions: cofactor

May be involved in the binding and intracellular trafficking of cobalamin (vitamin B12)

Organism class: human
UniProt ID: Q9Y4U1 Link_out
Gene: MMACHC Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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;143(9):979-84. Pubmed
  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
  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

6. Methylenetetrahydrofolate reductase

Pharmacological action: unknown
Actions: cofactor

Catalyzes the conversion of 5,10- methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co- substrate for homocysteine remethylation to methionine

Organism class: human
UniProt ID: P42898 Link_out
Gene: MTHFR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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. Pubmed
Enzymes

1. Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrial

Actions: substrate
UniProt ID: Q96EY8 Link_out
Gene: MMAB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
Transporters

1. Amnionless protein

Actions: substrate

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 underlying visceral endoderm

UniProt ID: Q9BXJ7 Link_out
Gene: AMN Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

2. Transcobalamin-1

Actions: substrate

Vitamin B12-binding protein. Transports cobalamin into cells

UniProt ID: P20061 Link_out
Gene: TCN1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Carmel R: Haptocorrin (transcobalamin I) and cobalamin deficiencies. Clin Chem. 2007 Feb;53(2):367-8; author reply 368-9. Pubmed
  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

3. Transcobalamin-2

Actions: substrate

Primary vitamin B12-binding and transport protein. Delivers cobalamin to cells

UniProt ID: P20062 Link_out
Gene: TCN2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  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
  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

4. Gastric intrinsic factor

Actions: substrate
UniProt ID: P27352 Link_out

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
  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
  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

5. Cubilin

Actions: substrate

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 density lipoprotein, and the GIF-cobalamin complex. The binding of all ligands required calcium. Serves as important transporter in several absorptive epithelia, including intestine, renal proximal tubules and embryonic yolk sac. Interaction with LRP2 mediates its trafficking throughout vesicles and facilitates the uptake of specific ligands like GC, hemoglobin, ALB, TF and SCGB1A1. Interaction with AMN controls its trafficking to the plasma membrane and facilitates endocytosis of ligands. May play an important role in the development of the peri-implantation embryo through internalization of APOA1 and cholesterol. Binds to LGALS3 at the maternal-fetal interface

UniProt ID: O60494 Link_out
Gene: CUBN Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19