Hydroxocobalamin

Hydroxocobalamin

Basics

Hydroxocobalamin or also vitamin B12a is a synthetically produced (in the laboratory) active substance of vitamin B12. It is related to cyanocobalamin, i.e. vitamin B12, but has a higher protein binding and thus a better depot effect. Depots have the advantage that they are stored in the body (depot) and repeatedly release small amounts of the active substance into the bloodstream without further administration (application).

Hydroxocobalamin belongs to the group of cobalamins, which owe their name to the cobalt atom in their molecular structure. Hydroxocobalamin has a deep red color, is crystalline (crystal-forming), and has hydrophilic (hygroscopic) properties. Hydroxocobalamin, like the other B-group vitamins, is water-soluble and contains cobalt as its central atom. It is used to treat vitamin B12 deficiency and as an antidote for hydrogen cyanide poisoning.

Hydroxocobalamin Skelettformel von Hydroxocobalamin. Vitamin B12 chemisches Molekül (grebeshkovmaxim/iStock)

Each cobalamin consists of one cobalt atom, 5 nitrogen atoms and one exchangeable atom, which gives the cobalamin its name. In the case of cyanocobalamin it is a cyano group (R-CN), in the case of hydroxocobalamin a hydroxy group (R-OH). In the case of poisoning by prussic acid, also called hydrogen cyanide (H-CN) or cyanide, the cyano group (CN) of the prussic acid is bound to the cobalamin and at the same time the hydroxy group (OH) of the hydroxocobalamin is split off. The harmless cyanocobalamin (vitamin B12) is then obtained. The hydroxyl group (OH) of the hydroxocobalamin that is split off forms the harmless H2O, i.e. water, with the remaining hydrogen (H) of the hydrocyanic acid.

Drugs with Hydroxocobalamin

Drug Substance(s) Authorisation holder
Cyanokit 5 g powder for solution for infusion Hydroxocobalamin Merck Sante s.a.s.
Cyanokit 2.5 g powder for solution for infusion Hydroxocobalamin Merck Sante s.a.s.

Effect

Hydroxocobalamin is a prodrug, i.e. an active ingredient that is present in an inactive form and is only converted into the active form in the body after transformation. It is converted in the body to methylcobalamin and 5-deoxyadenosylcobalamin. Both are active forms of vitamin B12 and can be stored in this form in the body.

Hydroxocobalamin is taken up (absorbed) in the gastrointestinal tract, specifically in the lower part of the ileum (section of the small intestine). It is stored in the liver and is excreted in the urine.

Vitamin B12 is a key building block in metabolism. It is needed in blood formation (hematopoiesis), cell division, myelin formation (an insulating layer of nerve cells in the brain) and nucleic acid synthesis (synthesis of the components of human DNA).

Hydroxocobalamin is used to treat vitamin B12 deficiency, poor performance, fatigue and difficulty concentrating. It is used as an ointment for the treatment of psoriasis, as a dietary supplement and as an antidote for hydrocyanic acid poisoning. Hydroxocobalamin is found in meat, fish, eggs and milk.

In cases of hydrogen cyanide poisoning, the hydrogen cyanide is bound to the hydroxocobalamin and then excreted through the kidneys. Hydrogen cyanide poisoning occurs mainly in smoke inhalation, especially in indoor fires.

Hydroxocobalamin is responsible for the formation of methionine in the body. Methionine is used for the production (synthesis) of the DNA and RNA building blocks adenine, guanine and thymidine. If hydroxocobalamin is lacking, there is a deficiency of these building blocks, resulting in impaired cell division activity in the bone marrow. This leads to the absence of various blood cells, of which the deficiency of red blood cells (erythrocytes) is most noticeable.

Dosage

Always take hydroxocobalamin exactly as described in the package leaflet or as advised by your doctor.

The recommended daily requirement for adults is 3 mcg daily.

The usual dose for the treatment of hydrogen cyanide poisoning is 5 g i.v. (i.e., administration via the vein) in adults within 25-30 minutes.

For hydrogen cyanide poisoning in children, 70 mg/kg body weight is recommended.

Side Effects

The following side effects may occur:

Organ systemSide effects
Gastrointestinal tract

difficulty swallowing, nausea, vomiting, diarrhea, and stomach pain

Respiratory systemShortness of breath (dyspnea), chest discomfort, dry throat, throat tightness, and pleural effusions
Blood count

increased production of red blood cells (polycythemia); deficiency of iron, folic acid, and potassium

allergic reactions

Swelling of the eyes and tongue, swelling of the mucous membranes in the nose and throat, puffiness of the skin, and inflammation at the site of application (i.e., where the medication was administered)

Other affected organsHeadache, dizziness, memory impairment, red discoloration of the skin and urine (both reversible)

Interactions

Interactions may occur if the following drugs are taken at the same time:

  • Drugs for the treatment of diabetes (antidiabetics) of the biguanide type e.g. metformin may affect the absorption of hydroxocobalamin.
  • p-aminosalicylic acid may affect the absorption of hydroxocobalamin
  • Alcohol abuse may lower hydroxocobalamin levels

In general, hydroxocobalamin should not be taken concurrently with other medications because other agents may inhibit the absorption of hydroxocobalamin into the body.

Contraindications

Hydroxocobalamin must not be taken in the following cases:

  • in case of allergy to hydroxocobalamin
  • in case of Leber's optic atrophy

Age Restriction

Hydroxocobalamin can be administered from the completed 1st year of life.

Pregnancy & Lactation

Hydroxocobalamin can be taken both during pregnancy and while breastfeeding. There are no known mutagenic or fertility-damaging effects. Hydroxocobalamin passes into breast milk.

History to the active ingredient

Vitamin B12 was first described in 1926. Dorothy Crowfoot Hodgkin clarified its chemical structure shortly afterwards, for which she received the Nobel Prize in Chemistry in 1964. The first total synthesis was carried out by Albert Eschenmoser and Robert B. Woodward. Vitamin B12 is a very large molecule and is still considered one of the largest ever total synthesized.

Chemical & physical properties

ATC Code B03BA03, V03AB33
Formula C62H89CoN13O15P
Molar Mass (g·mol−1) 1346,3551
Physical State solid
Melting Point (°C) 200
PKS Value 1,82
CAS Number 13422-51-0
PUB Number 70689311
Drugbank ID DB00200

Editorial principles

All information used for the content comes from verified sources (recognised institutions, experts, studies by renowned universities). We attach great importance to the qualification of the authors and the scientific background of the information. Thus, we ensure that our research is based on scientific findings.
Thomas Hofko

Thomas Hofko
Author

Thomas Hofko is in the last third of his bachelor's degree in pharmacy and is a writer on pharmaceutical topics. He is particularly interested in the fields of clinical pharmacy and phytopharmacy.

Mag. pharm. Stefanie Lehenauer

Mag. pharm. Stefanie Lehenauer
Lector

Stefanie Lehenauer has been a freelance writer for Medikamio since 2020 and studied pharmacy at the University of Vienna. She works as a pharmacist in Vienna and her passion is herbal medicines and their effects.

The content of this page is an automated and high-quality translation from DeepL. You can find the original content in German here.

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