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Identification
NameCyanocobalamin
Accession NumberDB00115  (APRD00326, EXPT00965, NUTR00004)
TypeSmall Molecule
GroupsApproved, 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
Synonyms
SynonymLanguageCode
Cyanocob(III)alaminNot AvailableNot Available
Vitamin B12Not AvailableNot Available
Vitamin B12 complexNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nascobalspray500 ugnasalPar Pharmaceutical , Inc2009-08-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nascobalspray500 ugnasalPar Pharmaceutical , Inc2009-08-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cyanocobalamininjection, solution1000 ug/mLintramuscularAmerican Regent, Inc.1990-09-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cyanocobalamininjection, solution1000 ug/mLintramuscularAmerican Regent, Inc.1996-11-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cyanocobalamininjection, solution1000 ug/mLintramuscularAmerican Regent, Inc.2003-05-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cyanocobalamininjection, solution1000 ug/mLintramuscular; subcutaneousGeneral Injectables & Vaccines, Inc2010-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cyanocobalamininjection, solution1000 ug/mLintramuscular; subcutaneousGeneral Injectables & Vaccines, Inc2010-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cyanocobalamininjection, solution1000 ug/mLintramuscular; subcutaneousPhysicians Total Care, Inc.2003-09-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cyanocobalamininjection, solution1000 ug/mLintramuscularCardinal Health2003-05-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cyanocobalamininjection, solution1000 ug/mLintramuscularCardinal Health1990-09-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cyanocobalamininjection, solution1000 ug/mLintramuscular; subcutaneousAPP Pharmaceuticals, LLC2000-10-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
BedodekaTeva
BedozNot Available
BerubigenUpjohn
BetalinLilly
CobioneMSD
Cobolin-MNot Available
CrystamineNot Available
CyanojectNot Available
CyominNot Available
CytakonGlaxoSmithKline
CytamenGlaxoSmithKline
DicopacNot Available
Neuroforte-RNot Available
PrimabaltNot Available
Rubramin PCNot Available
Vitabee 12Not Available
Brand mixtures
Brand NameIngredients
Infuvite Pediatric
Liver-Stomach Concentrate with Intrinsic FactorSpecial Liver-Stomach Concentrate + Vitamin B 12 + Iron + Ascorbic Acid + Folic Acid
SaltsNot Available
Categories
CAS number68-19-9
WeightAverage: 1356.3731
Monoisotopic: 1355.575230332
Chemical FormulaC63H89CoN14O14P
InChI KeySEKGMJVHSBBHRD-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
IUPAC Name
[(1R,2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-2-[({[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]propyl]carbamoyl}ethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltcarbonitrile
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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassCorrinoids
Direct ParentCobalamin derivatives
Alternative Parents
Substituents
  • Cobalamin
  • Metallotetrapyrrole skeleton
  • 1-ribofuranosylbenzimidazole
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Benzimidazole
  • Phosphoethanolamine
  • Dialkyl phosphate
  • Fatty acyl
  • Benzenoid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Fatty amide
  • Heteroaromatic compound
  • Pyrroline
  • Pyrrolidine
  • Oxolane
  • Imidazole
  • Azole
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Ketimine
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Transition metal cyanide salt
  • Organic metal salt
  • Organic cyanide salt
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organic transition metal salt
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organometallic compound
  • Organic transition metal moeity
  • Imine
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor treatment of pernicious anemia (due to lack of or inhibition of intrinsic factor) and for prevention and treatment of vitamin B 12 deficiency.
PharmacodynamicsCyanocobalamin (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 actionVitamin 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.
AbsorptionReadily absorbed in the lower half of the ileum.
Volume of distributionNot Available
Protein bindingVery high (to specific plasma proteins called transcobalamins); binding of hydroxocobalamin is slightly higher than cyanocobalamin.
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeApproximately 6 days (400 days in the liver).
ClearanceNot Available
ToxicityAnaphylactic reaction (skin rash, itching, wheezing)-after parenteral administration. ORL-MUS LD50 > 8000 mg/kg
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.8775
CYP450 2D6 substrateNon-inhibitor0.8737
CYP450 2C19 substrateNon-inhibitor0.7076
CYP450 3A4 substrateInhibitor0.7118
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
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
FormRouteStrength
Injection, solutionintramuscular1000 ug/mL
Injection, solutionintramuscular; subcutaneous1000 ug/mL
Spraynasal500 ug
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
CountryPatent NumberApprovedExpires (estimated)
United States72296362004-06-112024-06-11
United States74044892004-03-122024-03-12
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point> 300 °CPhysProp
water solubility1.25E+004 mg/LMERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.0384 mg/mLALOGPS
logP1.87ALOGPS
logS-4.5ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge2ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 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
ATC CodesB03BA01
AHFS Codes
  • 88:08.00
PDB EntriesNot Available
FDA labelDownload (202 KB)
MSDSDownload (37.1 KB)
Interactions
Drug Interactions
Drug
ChloramphenicolMay diminish the therapeutic effect of Vitamin B12.
ColchicineMay decrease the serum concentration of Cyanocobalamin.
Food InteractionsNot Available

Targets

1. Methionine synthase

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: cofactor

Components

Name UniProt ID Details
Methionine synthase Q99707 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: cofactor

Components

Name UniProt ID Details
Methylmalonyl-CoA mutase, mitochondrial P22033 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: cofactor

Components

Name UniProt ID Details
Methionine synthase reductase Q9UBK8 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: cofactor

Components

Name UniProt ID Details
Methylmalonic aciduria type A protein, mitochondrial Q8IVH4 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: cofactor

Components

Name UniProt ID Details
Methylmalonic aciduria and homocystinuria type C protein Q9Y4U1 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: cofactor

Components

Name UniProt ID Details
Methylenetetrahydrofolate reductase P42898 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrial Q96EY8 Details

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. Protein amnionless

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Protein amnionless Q9BXJ7 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Transcobalamin-1 P20061 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Transcobalamin-2 P20062 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Gastric intrinsic factor P27352 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cubilin O60494 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08