Cyanocobalamin

Cyanocobalamin
Skeletal formula
Stick model of cyanocobalamin based on the crystal structure[1]
Clinical data
Pronunciationsye AN oh koe BAL a min[2]
Trade namesCobolin-M,[2] Depo-Cobolin,[2] others[3]
AHFS/Drugs.comProfessional Drug Facts
MedlinePlusa604029
License data
Pregnancy
category
Routes of
administration		By mouth, intramuscular, nasal spray[5][6]
ATC code
Legal status
Legal status
  • US: OTC / Rx-only
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard100.000.618 Edit this at Wikidata
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 a form of vitamin B
12 used to treat and prevent vitamin B
12 deficiency except in the presence of cyanide toxicity.[7][8][2] The deficiency may occur in pernicious anemia, following surgical removal of the stomach, with fish tapeworm, or due to bowel cancer.[9] [5] It is used by mouth, by injection into a muscle, or as a nasal spray.[5][6]

Cyanocobalamin is generally well tolerated.[10] Minor side effects may include diarrhea, nausea, upset stomach, and itchiness.[11] Serious side effects may include anaphylaxis, and low blood potassium resulting in heart failure.[11] Use is not recommended in those who are allergic to cobalt or have Leber's disease.[9] No overdosage or toxicity has been reported.[11] It is less preferred than hydroxocobalamin for treating vitamin B
12 deficiency because it has a slightly lower bioavailability. Some studies have shown it to possess an antihypotensive effect.[5] Vitamin B
12 is an essential nutrient meaning that it cannot be made by the body but is required for life.[12][10]

Cyanocobalamin was first manufactured in the 1940s.[13] It is available as a generic medication and over the counter.[5][10] In 2022, it was the 131st most commonly prescribed medication in the United States, with more than 4 million prescriptions.[14][15]

  1. ^ Prieto L, Neuburger M, Spingler B, Zelder F (October 2016). "Inorganic Cyanide as Protecting Group in the Stereospecific Reconstitution of Vitamin B12 from an Artificial Green Secocorrinoid" (PDF). Organic Letters. 18 (20): 5292–5295. doi:10.1021/acs.orglett.6b02611. PMID 27726382.
  2. ^ a b c d "Vitamin B12 Injection: Side Effects, Uses & Dosage". Drugs.com. Retrieved 19 April 2019.
  3. ^ "Cyanocobalamin – Drug Usage Statistics, United States, 2006–2016". ClinCalc.com. Retrieved 9 November 2019.
  4. ^ "Therapeutic goods exempted from pregnancy categorisation". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 20 May 2024.
  5. ^ a b c d e British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 993–994. ISBN 9780857113382.
  6. ^ a b "Cyanocobalamin Side Effects in Detail". Drugs.com. Retrieved 19 April 2019.
  7. ^ Linnell JC, Matthews DM, England JM (November 1978). "Therapeutic misuse of cyanocobalamin". Lancet. 2 (8098): 1053–1054. doi:10.1016/s0140-6736(78)92379-6. PMID 82069. S2CID 29703726.
  8. ^ Herbert V (September 1988). "Vitamin B-12: plant sources, requirements, and assay". The American Journal of Clinical Nutrition. 48 (3 Suppl): 852–858. doi:10.1093/ajcn/48.3.852. PMID 3046314.
  9. ^ a b "DailyMed – cyanocobalamin, isopropyl alcohol". dailymed.nlm.nih.gov. Retrieved 19 April 2019.
  10. ^ a b c Lilley LL, Collins SR, Snyder JS (2019). Pharmacology and the Nursing Process E-Book. Elsevier Health Sciences. p. 83. ISBN 9780323550468.
  11. ^ a b c "Cyanocobalamin - FDA prescribing information, side effects and uses". Drugs.com. Retrieved 19 April 2019.
  12. ^ Markle HV (1996). "Cobalamin". Critical Reviews in Clinical Laboratory Sciences. 33 (4): 247–356. doi:10.3109/10408369609081009. PMID 8875026.
  13. ^ Orkin SH, Nathan DG, Ginsburg D, Look AT, Fisher DE, Lux S (2014). Nathan and Oski's Hematology and Oncology of Infancy and Childhood E-Book. Elsevier Health Sciences. p. 309. ISBN 9780323291774.
  14. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  15. ^ "Cyanocobalamin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.