Structure via PubChem · Public domain (PubChem)
cyanocobalamin
Sign in to saveAlso known as Vitamin B 12, Rubivite, Rubramin, Nascobal, Calomist, Ruvite, Berubigen
Cyanocobalamin is a form of vitamin used to treat and prevent vitamin deficiency except in the presence of cyanide toxicity. The deficiency may occur in pernicious anemia, following surgical removal of the stomach, with fish tapeworm, or due to bowel cancer. It is given by mouth, by injection into a muscle, or as a nasal spray.
Key facts
- Drug.solubility
- 1/80
- Drug.sol_units
- g/ml
- Drug.image
- Cyanocobalamin-b12.png
- Drug.image_class
- skin-invert-image
- Drug.caption
- Skeletal formula
- Drug.image2
- Cyanocobalamin-from-xtal-3D-st-noH.png
- Drug.image_class2
- bg-transparent
- Drug.caption2
- Stick model of cyanocobalamin based on the crystal structure
- Drug.pronounce
- sye AN oh koe BAL a min
- Drug.tradename
- Cobolin-M, Depo-Cobolin, others
- Drug.MedlinePlus
- a604029
- Drug.DailyMedID
- Cyanocobalamin
- Drug.pregnancy_AU_comment
- Exempt
- Drug.routes_of_administration
- By mouth, intramuscular, nasal spray
- Drug.ATC_prefix
- B03
- Drug.ATC_suffix
- BA01
- Drug.legal_US
- OTC
- Drug.legal_US_comment
- / Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C63H88CoN14O14P
- Molecular weight
- 1355.4 g/mol
- IUPAC name
- cobalt(3+);[(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2R)-1-[3-[(2R,3R,5Z,7S,9Z,12S,13S,14Z,17S,18S,19R)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-22-id-3-yl]propanoylamino]propan-2-yl] phosphate;cyanide
- 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](C5[C@]6([C@@]([C@@H](C(=N6)/C(=C\7/[C@@]([C@@H](C(=N7)/C=C\8/C([C@@H](/C(=C(/C4=N5)\C)/[N-]8)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.[C-]#N.[Co+3]
- InChIKey
- FDJOLVPMNUYSCM-UVKKECPRSA-L
- Polar surface area
- 476 Ų
- H-bond donors
- 9
- H-bond acceptors
- 21
- Formal charge
- 0
via PubChem
Research
31,187 papers- Cyanocobalamin.Scottish medical journal · 1957
- Intranasal cyanocobalamin.JAMA · 1992
- Cyanocobalamin-loaded dissolving microneedles diminish skin inflammation in vivo.Journal of controlled release : official journal of the Controlled Release Society · 2024
- Fewer injections, less pain: Successful cyanocobalamin desensitization.Allergologia et immunopathologia · 2025
- The Role of Methylene Blue and Cyanocobalamin for Vasoplegic Syndrome in Liver Transplantation.Journal of intensive care medicine · 2025
via PubMed
Wikidata facts
- Subclass of
- cobalamin
- Has part
- phosphorus
- Mass
- 1354.567
- Has use
- medication
Show 9 more facts
- canonical SMILES
- CC1=CC2=C(C=C1C)N(C=N2)C3C(C(C(O3)CO)OP(=O)([O-])OC(C)CNC(=O)CCC4(C(C5C6(C(C(C(=C(C7=NC(=CC8=NC(=C(C4=N5)C)C(C8(C)C)CCC(=O)N)C(C7(C)CC(=O)N)CCC(=O)N)C)[N-]6)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[C-]#N.[Co+3]
- chemical formula
- C₆₃H₈₈CoN₁₄O₁₄P
- isomeric SMILES
- [Co+3].[C-]#N.C[C@H](CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)C2[N-]C1=C(C)C3=NC(=CC4=NC(=C(C)C5=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]5CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)C(C)(C)[C@@H]3CCC(N)=O)OP([O-])(=O)O[C@@H]6[C@@H](CO)O[C@@H]([C@@H]6O)N7C=NC8=C7C=C(C)C(C)=C8
- Commons category
- Cyanocobalamin
- different from
- vitamin B12
- medical condition treated
- pernicious anemia
- NCI Thesaurus ID
- C64333
- subject has role
- vitamin B
- defined daily dose
- 1
via Wikidata · CC0
~11 min read
Encyclopedic overview
12 sectionsContents
- Medical use
- Use in food
- Side effects
- Chemistry
- Chemical reactions
- Production
- Metabolism
- In the cytosol
- In mitochondria
- Absorption and transport
- See also
- References
Cyanocobalamin is a form of vitamin used to treat and prevent vitamin deficiency except in the presence of cyanide toxicity. The deficiency may occur in pernicious anemia, following surgical removal of the stomach, with fish tapeworm, or due to bowel cancer. It is given by mouth, by injection into a muscle, or as a nasal spray.
Cyanocobalamin is generally well tolerated. Minor side effects may include diarrhea, nausea, upset stomach, and itchiness. Serious side effects may include anaphylaxis, and low blood potassium resulting in heart failure. Use is not recommended in those who are allergic to cobalt or have Leber's disease. No overdosage or toxicity has been reported. It is less preferred than hydroxocobalamin for treating vitamin deficiency because it has a slightly lower bioavailability. Some studies have shown it to possess an antihypotensive effect. Vitamin is an essential nutrient meaning that it cannot be made by the body but is required for life.
Excerpted from Wikipedia’s “cyanocobalamin” article, available under the CC BY-SA 4.0 licence.