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
 ☒NcheckY (what is this?)  (verify)

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] by pill or sublingually.

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.