Back هيدروكسوكوبالامين Arabic Hidroksokobalamin BS Hydrocsocobalamin Welsh Hydroxycobalamin German Hidroxocobalamina Spanish Hidroxokobalamina Basque هیدروکسوکبالامین Persian Hydroksikobalamiini Finnish Hydroxocobalamine French Hidroxocobalamina Galician

Hydroxocobalamin

Hydroxocobalamin
Clinical data
Other namesvitamin B12, vitamin B12a, hydroxycobalamin
AHFS/Drugs.comMonograph
MedlinePlusa605007
Routes of
administration		Oral, Intramuscular, intravenous
ATC code
Legal status
Legal status
  • NZ: Prescription only (IM ampule)
  • US: OTC (by prescription when injectable), not DEA-controlled
Pharmacokinetic data
Protein bindingVery high (90%)
MetabolismPrimarily liver, cobalamins are absorbed in the ileum and stored in the liver.
Elimination half-life~6 days
Identifiers
  • Coα-[α-(5,6-dimethylbenzimidazolyl)]-
    Coβ-hydroxocobamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.033.198 Edit this at Wikidata
Chemical and physical data
FormulaC62H89CoN13O15P
Molar mass1346.377 g·mol−1
3D model (JSmol)
  • Cc1cc2ncn(c2cc1C)C9OC(CO)C(OP3(=O)OC(C)CNC(=O)CCC5C4=C(C)C8=NC(=CC7=NC(=C(C)C6=NC(C)(C(N4[Co](O)O3)C5(C)CC(N)=O)C(C)(CC(N)=O)C6CCC(N)=O)C(C)(CC(N)=O)C7CCC(N)=O)C(CCC(N)=O)C8(C)C)C9O
  • InChI=1S/C62H90N13O14P.Co.H2O/c1-29-20-40-41(21-30(29)2)75(28-70-40)56-52(84)53(42(27-76)87-56)89-90(85,86)88-31(3)26-69-49(83)19-15-36-50-32(4)54-58(6,7)34(12-16-43(63)77)38(71-54)22-39-35(13-17-44(64)78)59(8,23-46(66)80)55(72-39)33(5)51-37(14-18-45(65)79)61(10,25-48(68)82)62(11,74-51)57(73-50)60(36,9)24-47(67)81;;/h20-22,28,31,34-37,42,52-53,56-57,76,84H,12-19,23-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;1H2/q;+3;/p-3 checkY
  • Key:GTSMWDDKWYUXGH-UHFFFAOYSA-K checkY
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Hydroxocobalamin, also known as vitamin B12a and hydroxycobalamin, is a vitamin found in food and used as a dietary supplement.[1] As a supplement it is used to treat vitamin B12 deficiency including pernicious anemia.[1][2] Other uses include treatment for cyanide poisoning, Leber's optic atrophy, and toxic amblyopia.[3][4] It is given by injection into a muscle or vein.[2]

Side effects are generally few.[2] They may include diarrhea, feeling sick, hot flushes, itchiness, low blood potassium, allergic reactions, and high blood pressure.[2] Normal doses are considered safe in pregnancy.[5] No overdosage or toxicity has been reported with this drug.[2] Hydroxocobalamin is the natural form of vitamin B12 and a member of the cobalamin family of compounds.[6][7] It is found in both raw and cooked beef, together with other cobalamins.[8] Hydroxocobalamin, or another form of vitamin B12, are required for the body to make DNA.[7]

Hydroxocobalamin was first isolated in 1949.[9] It is on the World Health Organization's List of Essential Medicines.[10] Hydroxocobalamin is available as a generic medication.[2] Commercially it is made using one of a number of types of bacteria.[11]

  1. ^ a b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 251. hdl:10665/44053. ISBN 9789241547659.
  2. ^ a b c d e f "Vitamin B12". The American Society of Health-System Pharmacists. Archived from the original on 30 December 2016. Retrieved 8 December 2016.
  3. ^ MacLennan L, Moiemen N (February 2015). "Management of cyanide toxicity in patients with burns". Burns. 41 (1): 18–24. doi:10.1016/j.burns.2014.06.001. PMID 24994676.
  4. ^ "Hydroxocobalamin 1mg in 1ml solution for injection - Summary of Product Characteristics (SPC) - (eMC)". www.medicines.org.uk. Archived from the original on 30 December 2016. Retrieved 30 December 2016.
  5. ^ "Hydroxocobalamin Use During Pregnancy". Drugs.com. Archived from the original on 1 January 2017. Retrieved 30 December 2016.
  6. ^ Bullock S, Manias E (2013). Fundamentals of Pharmacology. Pearson Higher Education AU. p. 862. ISBN 9781442564411. Archived from the original on 31 December 2016.
  7. ^ a b "Office of Dietary Supplements - Dietary Supplement Fact Sheet: Vitamin B12". ods.od.nih.gov. 11 February 2016. Archived from the original on 31 December 2016. Retrieved 30 December 2016.
  8. ^ Czerwonka M, Szterk A, Waszkiewicz-Robak B (March 2014). "Vitamin B12 content in raw and cooked beef". Meat Science. 96 (3): 1371–1375. doi:10.1016/j.meatsci.2013.11.022. PMID 24361556.
  9. ^ Eitenmiller RR, Landen WO (2010). Vitamin Analysis for the Health and Food Sciences. CRC Press. p. 467. ISBN 9781420050165. Archived from the original on 31 December 2016.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  11. ^ "Vitamins, 6. B Vitamins". Ullmann's encyclopedia of industrial chemistry. Weinheim: Wiley-VCH. 2011. ISBN 9783527303854.

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