Cyanocobalamin

Cyanocobalamin is a form of vitamin B
12 used to treat and prevent vitamin B
12 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 used by mouth, by injection into a muscle, or as a nasal spray.

Cyanocobalamin
Skeletal formula
Stick model of cyanocobalamin based on the crystal structure
Clinical data
Pronunciationsye AN oh koe BAL a min
Trade namesCobolin-M, Depo-Cobolin, others
AHFS/Drugs.comProfessional Drug Facts
MedlinePlusa604029
License data
Pregnancy
category
  • AU: Exempt
Routes of
administration		By mouth, intramuscular, nasal spray
ATC code
Legal status
Legal status
  • US: OTC / Rx-only
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard100.000.618
Chemical and physical data
FormulaC63H88CoN14O14P
Molar mass1355.388 g·mol−1
3D model (JSmol)
Melting point300 °C (572 °F) +
Boiling point300 °C (572 °F) +
Solubility in water1/80g/ml
  • 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]
  • InChI=1S/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-2;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;/q;-1;+3/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57?,59-,60+,61+,62+;;/m1../s1
  • Key:FDJOLVPMNUYSCM-QJRSUKKJSA-L

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 B
12 deficiency because it has slightly lower bioavailability. Some study have shown that it has an antihypotensive effect. Vitamin B
12 is an essential nutrient meaning that it cannot be made by the body but is required for life.

Cyanocobalamin was first manufactured in the 1940s. It is available as a generic medication and over the counter. In 2021, it was the 110th most commonly prescribed medication in the United States, with more than 5 million prescriptions.

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