hydroxocobalamin

Also known as Alpharedisol, Hydroxomin, OH-Cbl, Vitamin B-12b, Hydroxycobalamin, Hydroxocobalamine, Hydroxocobalamin anhydrous, Hydroxocobalaminum anhydrous

Hydroxocobalamin, also known as vitamin B12a and hydroxycobalamin, is a vitamin found in food and used as a dietary supplement. As a supplement it is used to treat vitamin B12 deficiency including pernicious anemia. Other uses include treatment for cyanide poisoning, Leber's optic atrophy, and toxic amblyopia. It is given by injection into a muscle or vein, by pill or sublingually.

Key facts

Drug.KEGG: D01027
Drug.ChEMBL: 1237097
Drug.Verifiedfields: changed
Drug.verifiedrevid: 457640474
Drug.image: Hydroxocobalamin.svg
Drug.image_class: skin-invert-image
Drug.width: 250
Drug.MedlinePlus: a605007
Drug.routes_of_administration: Oral, Intramuscular, intravenous
Drug.ATC_prefix: B03
Drug.ATC_suffix: BA03
Drug.legal_NZ: Prescription only (IM ampule)
Drug.legal_US: OTC
Drug.legal_US_comment: (by prescription when injectable), not DEA-controlled
Drug.protein_bound: Very high (90%)
Drug.metabolism: Primarily liver, cobalamins are absorbed in the ileum and stored in the liver.
Drug.elimination_half life: ~6 days
Drug.CAS_number: 13422-51-0

via Wikipedia infobox

Chemical data

Formula: C62H89CoN13O15P
Molecular weight: 1346.4 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-[(1R,2R,3R,4Z,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-21-id-3-yl]propanoylamino]propan-2-yl] phosphate;hydroxide
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]
InChIKey: YOZNUFWCRFCGIH-WZHZPDAFSA-K
Polar surface area: 453 Å²
H-bond donors: 10
H-bond acceptors: 20
Formal charge: 0

via PubChem

Research

1,531 papers

[Hydroxocobalamin].Chudoku kenkyu : Chudoku Kenkyukai jun kikanshi = The Japanese journal of toxicology · 2014
Hydroxocobalamin for Vasodilatory Hypotension in Shock: A Systematic Review With Meta-Analysis for Comparison to Methylene Blue.Journal of cardiothoracic and vascular anesthesia · 2023
Hydroxocobalamin Versus Methylene Blue for Treatment of Vasoplegic Shock Following Cardiopulmonary Bypass: A Systematic Review and Meta-analysis.Journal of cardiothoracic and vascular anesthesia · 2024
Seeing Red: Hydroxocobalamin and Result Interference.Journal of cardiothoracic and vascular anesthesia · 2023
Hydroxocobalamin in cyanide poisoning.Clinical toxicology (Philadelphia, Pa.) · 2012

via PubMed

Wikidata facts

Mass: 1345.567065778

Show 7 more facts

defined daily dose: 20
chemical formula: C₆₂H₈₉CoN₁₃O₁₅P
World Health Organisation international non-proprietary name: hydroxocobalamin
isomeric SMILES: [H]O[Co+]N1\C2=C(C)/C3=N/C(=C\C4=N\C(=C(C)/C5=N[C@@](C)([C@@]1([H])[C@H](CC(=O)N)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(=O)([O-])O[C@H]1[C@@H](O)[C@H](O[C@@H]1CO)N1C=NC2=CC(C)=C(C)C=C12)[C@@](C)(CC(N)=O)[C@@H]5CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)N)/C(C)(C)[C@@H]3CCC(=O)N
NCI Thesaurus ID: C65868
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(=N6)C(=C7C(C(C(=N7)C=C8C(C(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]
Commons category: Hydroxocobalamin

Sources (3)

via Wikidata · CC0

~10 min read

Article

9 sections

Contents

Medical uses
Vitamin B<sub>12</sub> deficiency
Cyanide poisoning
Injectable hydroxocobalamin
Side effects
Properties
Mechanism of action
See also
References

Side effects are generally few. They may include diarrhea, feeling sick, hot flushes, itchiness, low blood potassium, allergic reactions, and high blood pressure. Normal doses are considered safe in pregnancy. No overdosage or toxicity has been reported with this drug. Hydroxocobalamin is the natural form of vitamin B12 and a member of the cobalamin family of compounds. It is found in both raw and cooked beef, together with other cobalamins. Hydroxocobalamin, or another form of vitamin B12, are required for the body to make DNA.