Hydroxocobalamin

Hydroxocobalamin

Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a605007
Pregnancy category	US: C
Routes of administration	IM, IV
ATC code	B03BA03 (WHO) V03AB33 (WHO)
Legal status
Legal status	US: OTC (by prescription when injectable), not DEA-controlled
Pharmacokinetic data
Protein binding	Very high (90%)
Metabolism	Primarily liver, cobalamins are absorbed in the ileum and stored in the liver.
Biological half-life	~6 days
Identifiers
IUPAC name Coα-[α-(5,6-dimethylbenzimidazolyl)]- Coβ-hydroxocobamide
Synonyms	vitamin B12, vitamin B12a, hydroxycobalamin
CAS Number	13422-51-0 Y
PubChem CID	6433575
DrugBank	DB00200 Y
ChemSpider	21160115 Y
UNII	Q40X8H422O
KEGG	D01027 Y
ChEMBL	CHEMBL1237097 N
ECHA InfoCard	100.033.198
Chemical and physical data
Formula	C62H89CoN13O15P
Molar mass	1346.37 g/mol
3D model (Jmol)	Interactive image
SMILES Cc1cc2ncn(c2cc1C)C9OC(CO)C(OP3(=O)OC(C)CNC(=O)CCC5C4=C(C)C8=NC(=CC7=NC(=C(C)C6=NC(C)(C(N4[Co](O)O3)C5(C)CC(N)=O)C(C)(CC(N)=O)C6CCC(N)=O)C(C)(CC(N)=O)C7CCC(N)=O)C(CCC(N)=O)C8(C)C)C9O
InChI InChI=1S/C62H90N13O14P.Co.H2O/c1-29-20-40-41(21-30(29)2)75(28-70-40)56-52(84)53(42(27-76)87-56)89-90(85,86)88-31(3)26-69-49(83)19-15-36-50-32(4)54-58(6,7)34(12-16-43(63)77)38(71-54)22-39-35(13-17-44(64)78)59(8,23-46(66)80)55(72-39)33(5)51-37(14-18-45(65)79)61(10,25-48(68)82)62(11,74-51)57(73-50)60(36,9)24-47(67)81;;/h20-22,28,31,34-37,42,52-53,56-57,76,84H,12-19,23-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;1H2/q;+3;/p-3 Y Key:GTSMWDDKWYUXGH-UHFFFAOYSA-K Y
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Hydroxocobalamin, also known as vitamin B_12a and hydroxycobalamin, is 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 cyanide poisoning, Leber's optic atrophy, and toxic amblyopia. It is given by injection into a muscle or vein.

Side effects are generally few. They may include diarrhea, low blood potassium, allergic reactions, and high blood pressure. Normal doses are considered safe in pregnancy. Hydroxocobalamin is the natural form of vitamin B₁₂ and a member of the cobalamin family of compounds. Hydroxocobalamin, or another form of vitamin B₁₂, are required for the body to make DNA. Foods that naturally contain vitamin B₁₂ include meat, eggs, and dairy products.

Hydroxocobalamin was first isolated in 1949. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Hydroxocobalamin is available as a generic medication. The wholesale cost in the developing world is about 0.12 to 0.84 USD per dose. In the United States this amount wholesale costs about 0.84 USD. Commercially it is made from one of a number of different types of bacteria.