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,12S,13S,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
Basic information
- CAS
13422-51-0- Standard SMILES
CC1=C2N=C(C=C3N=C(/C(C)=C4\[N-][C@H]([C@H](CC(N)=O)[C@@]4(C)CCC(=O)NC[C@@H](C)OP(=O)([O-])O[C@H]4[C@@H](O)[C@@H](n5cnc6cc(C)c(C)cc65)O[C@@H]4CO)[C@]4(C)N=C1[C@@H](CCC(N)=O)[C@]4(C)CC(N)=O)[C@@H](CCC(N)=O)C3(C)C)[C@@H](CCC(N)=O)[C@]2(C)CC(N)=O.[Co+3].[OH-]- InChIKey
YOZNUFWCRFCGIH-WZHZPDAFSA-K- Molecular formula
- C62H89CoN13O15P
- Average molar mass
- 1,346.4 g/mol
- Monoisotopic mass
- 1,345.567065
Overview
Hydroxocobalamin, also known as vitamin B12a and hydroxycobalamin, is an injectable form of vitamin B 12 that has been used therapeutically to treat vitamin B 12 deficiency. It is also used in cyanide poisoning, Leber's optic atrophy, and toxic amblyopia.
Names & identifiers
- Preferred 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,12S,13S,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
- IUPAC
- 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,12S,13S,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
- English name
- Hydroxocobalamin
- Molecular formula
- C62H90ClCoN13O15P
- Molecular weight
- 1382.82
Names & synonyms
SCHEMBL41959590hydroxycobalaminHYDROXOCOBALAMINEaxionDepovit B12hydroxycobalamineVITAMIN B12A HYDROCHLORIDEHYDROXOCOBALAMIN VITAMIN B12HYDROXYCOBALAMIN HYDROCHLORIDEaxlonohb12
Database identifiers
- CAS
13422-51-0- PubChem CID
- 175676715
Properties
Computed structural properties
- Topological polar surface area
- 453 Ų
- Hydrogen bond donors
- 10
- Hydrogen bond acceptors
- 20
- Rotatable bonds
- 26
- Heavy atoms
- 92
- Formal charge
- 0
- Complexity
- 3,140
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 300 °C · >300 °C
- storage temp.
- 2 · 2-8°C
- solubility
- 10 mg/mL · methanol: 10 mg/mL at 20 °C, clear, dark red
- form
- Solid
- color
- Dark Brown to Black
- Odor
- odorless
- Stability
- Hygroscopic
- Major Application
- pharmaceutical (small molecule)
- InChIKey
- YOZNUFWCRFCGIH-ZKJXODNJNA-K
- LogP
- -2.812 · -2.812 (est)
- FDA UNII
- 40 X8H422O · Q40X8H422O
- ATC code
- 3 BA03,B03BA53,V03AB33 · B03BA03,B03BA53,V03AB33
- EPA Substance Registry System
- 3 · Cobinamide, Co-hydroxy-, f-(dihydrogen phosphate), inner salt, 3'-ester with (5,6-dimethyl-1-.alpha.-D-ribofuranosyl-1H-benzimidazole-.kappa.N3) (13422-51-0)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-8-10
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- GG3820000
- Toxicity
- LD50 intravenous in mouse: > 50mg/kg
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazardous Substances Data
- 13422-51-0(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Protein BindingVery high (90%). Cobalamins are extensively bound to two specific plasma proteins called transcobalamin 1 and 2; 70% to transcobalamin 1, 5% to transcobalamin 2.
Pharmacodynamics
Hydroxocobalamin is a synthetic, injectable form of Vitamin B12. Hydroxocobalamin is actually a precursor of two cofactors or vitamins (Vitamin B12 and Methylcobalamin) which are involved in various biological systems in man. Vitamin B12 is required for the conversion of methylmalonate to succinate. Deficiency of this enzyme could therefore interfere with the production of lipoprotein in myelin sheath tissue and so give rise to neurological lesions. The second cofactor, Methylcobalamin, is necessary for the conversion of homocysteine to methionine which is essential for the metabolism of folic acid. Deficiency of tetrahydrafolate leads to reduced synthesis of thymidylate resulting in reduced synthesis of DNA which is essential for cell maturation. Vitamin B12 is also concerned in the maintenance of sulphydryl groups in reduced form, deficiency leading to decreased amounts of reduced SH content of erythrocytes and liver cells. Overall, vitamin B12 acts as a coenzyme for various metabolic functions, including fat and carbohydrate metabolism and protein synthesis. It is necessary for growth, cell replication, hematopoiesis, and nucleoprotein as well as myelin synthesis. This is largely due to its effects on metabolism of methionine folic acid, and malonic acid.
Mechanism of Action
Vitamin B12 exists in four major forms referred to collectively as cobalamins; deoxyadenosylcobalamin, methylcobalamin, hydroxocobalamin, and cyanocobalamin. Two of these, methylcobalamin and 5-deoxyadenosyl cobalamin, are primarily used by the body. Methionine synthase needs methylcobalamin as a cofactor. This enzyme is involved in the conversion of the amino acid homocysteine into methionine. Methionine in turn is required for DNA methylation. 5-Deoxyadenosyl cobalamin is a cofactor needed by the enzyme that converts L-methylmalonyl-CoA to succinyl-CoA. This conversion is an important step in the extraction of energy from proteins and fats. Furthermore, succinyl CoA is necessary for the production of hemoglobin, the substances that carries oxygen in red blood cells.
Biological Half-LifeApproximately 6 days (peak plasma concentration after 8-12 hours from oral administration)
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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