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Details

Stereochemistry ACHIRAL
Molecular Formula C2H4O2
Molecular Weight 60.052
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Acetic acid

SMILES

CC(O)=O

InChI

InChIKey=QTBSBXVTEAMEQO-UHFFFAOYSA-N
InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)

HIDE SMILES / InChI

Molecular Formula C2H4O2
Molecular Weight 60.052
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
StereoComments testing

Description

Hydroxocobalamin (also hydroxycobalamin, OHCbl) is a natural form, or vitamer, of vitamin B12. It is a member of the cobalamin family of compounds. Hydroxocobalamin, the active ingredient in Cyanokit, is cobinamide dihydroxide dihydrogen phosphate (ester), mono (inner salt), 3’-ester with 5,6-dimethyl-1-α-D-ribofuranosyl-1H-benzimidazole. The drug substance is the hydroxylated active form of vitamin B12 and is a large molecule in which a trivalent cobalt ion is coordinated in four positions by a tetrapyrol (or corrin) ring. It is a hygroscopic, odorless, dark red, crystalline powder that is freely soluble in water and ethanol, and practically insoluble in acetone and diethyl ether. Cyanokit contains hydroxocobalamin, an antidote indicated for the treatment of known or suspected cyanide poisoning. Cyanide is an extremely toxic poison. In the absence of rapid and adequate treatment, exposure to a high dose of cyanide can result in death within minutes due to the inhibition of cytochrome oxidase resulting in arrest of cellular respiration. Specifically, cyanide binds rapidly with cytochrome a3, a component of the cytochrome c oxidase complex in mitochondria. Inhibition of cytochrome a3 prevents the cell from using oxygen and forces anaerobic metabolism, resulting in lactate production, cellular hypoxia and metabolic acidosis. In massive acute cyanide poisoning, the mechanism of toxicity may involve other enzyme systems as well. Signs and symptoms of acute systemic cyanide poisoning may develop rapidly within minutes, depending on the route and extent of cyanide exposure. The action of Cyanokit is based on its ability to bind cyanide ions. Each hydroxocobalamin molecule can bind one cyanide ion by substituting it for the hydroxo ligand linked to the trivalent cobalt ion, to form cyanocobalamin, which is then excreted in the urine.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CYANOKIT
Curative
VOSOL

AUC

ValueDoseCo-administeredAnalytePopulation
4511.6 μM × h
5 g single, intravenous
HYDROXOCOBALAMIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
26.2 h
5 g single, intravenous
HYDROXOCOBALAMIN plasma
Homo sapiens

Doses

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
To promote continuous contact, insert a wick of cotton saturated with the drug solution (Vosol). Keep the wick in for at least 24 hours and keep it moist by adding 3 to 5 drops of solution every 4 to 6 hours. The wick may be removed after 24 hours but the patient should continue to instill 5 drops of the drug solution 3 or 4 times daily thereafter, for as long as indicated.
Route of Administration: Otic (auricular)
In Vitro Use Guide
Acetic acid inhibited Saccharomyces cerevisiae growth. The minimum inhibitory concentration (MIC) of acetic acid for yeast growth was 0.6% w/v (100 mM).
Substance Class Chemical
Record UNII
Q40Q9N063P
Record Status Validated (UNII)
Record Version