Hydroxocobalamin
[CAS# 13422-51-0]

Identification

• Classification: Analytical chemistry >> Standard >> Pharmacopoeia standards and magazine standards
• Name: Hydroxocobalamin
• Synonyms: Vitamin B12b
• Molecular Formula: C₆₂H₈₉CoN₁₃O₁₅P
• Molecular Weight: 1346.37
• CAS Registry Number: 13422-51-0
• EC Number: 236-533-2
• SMILES: CC1=CC2=C(C=C1C)N(C=N2)[C@@H]3[C@@H]([C@@H]([C@H](O3)CO)OP(=O)([O-])O[C@H](C)CNC(=O)CC[C@@]4([C@H]([C@@H]5[C@]6([C@@]([C@@H](C(=N6)/C(=C7/[C@@]([C@@H](C(=N7)/C=C8/C([C@@H](C(=N8)/C(=C4[N-]5)/C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)/C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[OH-].[Co+3]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H319
• Safety Statements: P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Carcinogenicity	Carc.	2	-

Discovery and Applications

Hydroxocobalamin is a form of vitamin B12, a water-soluble vitamin that is essential for various biological functions. Its molecular formula is C62H89CoN13O15P and it is a cobalamin derivative with a cobalt ion at its core. Hydroxocobalamin is recognized for its role in treating vitamin B12 deficiency and its application as an antidote for cyanide poisoning.

The discovery of hydroxocobalamin is associated with the extensive exploration of vitamin B12 and its various forms. Vitamin B12 was first isolated in 1948 by American chemists Karl Folkers and Alexander Todd. As research progressed, different forms of this vitamin were discovered, including hydroxocobalamin. This form occurs naturally in the human body and other biological systems.

Hydroxocobalamin is usually synthesized by bacterial fermentation. Specific bacteria, such as Pseudomonas denitrificans, are cultured in a controlled environment to produce vitamin B12. The vitamin is then extracted and converted to hydroxocobalamin through a chemical process that includes oxidation and purification steps.

Hydroxocobalamin is widely used to treat vitamin B12 deficiency, a condition that can lead to anemia, neurological disorders, and other health problems. Hydroxocobalamin is particularly effective because it stays in the body longer than other forms of vitamin B12, such as cyanocobalamin. Hydroxocobalamin is administered by injection, ensuring rapid and effective absorption.

One of the most critical applications of hydroxocobalamin is as an antidote for cyanide poisoning. Cyanide binds to the enzyme cytochrome c oxidase in the mitochondria, inhibiting cellular respiration and causing cell death. Hydroxocobalamin binds to the cyanide ion to form cyanocobalamin, which can be safely excreted from the body. This application is critical in emergency medical situations such as industrial accidents or smoke inhalation from fires.

Hydroxocobalamin is used in medical imaging to assess the absorption and metabolism of vitamin B12 in the body. By labeling the compound with a radioactive isotope, doctors can track its distribution and absorption, providing valuable diagnostic information. This technique helps identify malabsorption and other metabolic disorders associated with vitamin B12.

In addition to its therapeutic applications, hydroxocobalamin is also used in nutritional supplements. It is included in multivitamins and specific B12 supplements to ensure adequate intake, especially for people with dietary restrictions, such as vegetarians and vegans, who may not get enough B12 from their diet.

Hydroxocobalamin is an important tool in biochemical and physiological research. Scientists use it to study vitamin B12 metabolism, investigate its role in cellular processes, and explore its therapeutic potential in a variety of health conditions. Its well-characterized structure and function make it a valuable reagent in laboratory research.

References

1952. Antidotal Efficacy of Vitamin B12a (Hydroxo-Cobalamin) in Experimental Cyanide Poisoning. Proceedings of the Society for Experimental Biology and Medicine, 81.
DOI: 10.3181/00379727-81-19831

2024. A Brief Overview of the Diagnosis and Treatment of Cobalamin (B12) Deficiency. Food and Nutrition Bulletin, 45(2).
DOI: 10.1177/03795721241229500

2024. Hydroxocobalamin Versus Methylene Blue for Treatment of Vasoplegic Shock Following Cardiopulmonary Bypass: A Systematic Review and Meta-analysis. Journal of Cardiothoracic and Vascular Anesthesia, 38(12).
DOI: 10.1053/j.jvca.2024.09.135```