Hydroxocobalamin

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Cat Number

API0233496

CAS Number

13422-51-0

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Product Detail Description Scientific Support Customer Q&A

CAS Number

13422-51-0

EINECS

236-533-2

Synonyms

Cyanokit, Hydroxomin, AlphaRedisol

Molecular Formula

C62H89CoN13O15P

Molecular Weight

1346.4

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(=C\7/[C@@]([C@@H](C(=N7)/C=C\8/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]

General Description

Hydroxocobalamin is a natural form of vitamin B12 (vitamin B12a) available as a sterile injectable solution for intramuscular or intravenous administration. It appears as a dark red solution and is approved for the treatment of vitamin B12 deficiency and known or suspected cyanide poisoning.

Mechanism of Action

As a vitamin B12 precursor, hydroxocobalamin is converted in the body to the active coenzymes methylcobalamin and adenosylcobalamin, which are essential for hematopoiesis and neurological function. In cyanide poisoning, each hydroxocobalamin molecule binds tightly to one cyanide ion by substituting the hydroxo ligand on the trivalent cobalt ion, forming non-toxic cyanocobalamin that is excreted in urine. It also exhibits nitric oxide and hydrogen sulfide scavenging properties, which may contribute to its hemodynamic effects.

Application

Hydroxocobalamin is indicated for the treatment of pernicious anemia and vitamin B12 deficiency resulting from various causes including malabsorption, alcoholism, and restrictive diets. It is the first-line treatment for cyanide toxicity, particularly in smoke inhalation victims where concomitant carbon monoxide poisoning may be present.

Greibe E, et al. compared the absorption of synthetic cyanocobalamin and naturally occurring hydroxocobalamin in adults with low (n=59) and normal (n=42) vitamin B12 status using the CobaSorb test, which measures increases in holotranscobalamin (holoTC). Across all doses tested (1.5–9 μg), administration of cyanocobalamin resulted in an approximately twofold greater increase in holoTC compared to hydroxocobalamin. The absorptive capacity was exceeded only at doses above 3 μg, with 6 μg producing significantly greater holoTC increases than 3 μg in both status groups.

Fig. 1 Increase in holoTC upon administration of CN-Cbl and HO-Cbl in the CobaSorb test design. (Greibe E, et al., 2018)

References

Greibe E, et al. Increase in circulating holotranscobalamin after oral administration of cyanocobalamin or hydroxocobalamin in healthy adults with low and normal cobalamin status. Eur J Nutr. 2018;57(8):2847-2855.

Does Hydroxocobalamin require protection from light during storage?

Extremely. It is highly photosensitive and rapidly degrades upon light exposure. It must be stored in its original amber glass or opaque container at all times.

What is the recommended storage temperature for Hydroxocobalamin?

Store at controlled room temperature, between 15°C and 25°C. Refrigeration is not required but may be used if protected from light and moisture.

Is Hydroxocobalamin stable in aqueous solutions for injection?

It has limited stability in solution and must be protected from light.

How is the conversion to cyanocobalamin or other analogs monitored?

We use a specific HPLC method to monitor for related cobalamin analogs, ensuring the hydroxo form remains the predominant species throughout the shelf life.