Cobamamide

Identification

Name
Cobamamide
Accession Number
DB11191
Type
Small Molecule
Groups
Approved
Description

Cobamamide is one of the active forms of vitamin B12 that is also known as adenosylcobalamin or dibencozide. This drug is available as a nutritional supplement to prevent vitamin B12 deficiency.

Vitamin B12 is a collective term for these variously substituted corrinoids. The principal biochemical participants are two coenzyme forms of Vitamin B12 that are produced and activated in two separate cellular compartments: methylcobalamin in the cytosol and adenosylcobalamin in the mitochondria [7].

Vitamin B12 (cyancobalamin, Cbl) has two active co-enzyme forms, methylcobalamin (MeCbl) and adenosylcobalamin (AdCbl). There has been a shift in the treatment of vitamin B12 deficiency such that MeCbl is being extensively used and promoted. This exists despite the fact that both MeCbl and AdCbl are necessary for life and have vastly different metabolic fates and functions. MeCbl is mainly involved along with folate in hematopoiesis and the growth of the brain during childhood. Deficiency of AdCbl disturbs the carbohydrate, fat and amino-acid metabolism, and therefore interferes with the formation of myelin. It is therefore important to treat vitamin B12 deficiency with a combination of MeCbl and AdCbl or hydroxocobalamin or cobalamin [8].

Vitamin B12 has important physiological roles including DNA synthesis, myelin formation in the nervous system, red blood cell formation, as well as fatty acid and amino acid metabolism [2]. Please refer to the entry Vitamin B12 for more information on this entry.

Structure
Thumb
Synonyms
  • (5,6-Dimethylbenzimidazolyl)cobamide coenzyme
  • 5'-Deoxy-5'-adenosylcobalamin
  • Adenosylcob(III)alamin
  • Adenosylcobalamin
  • cobamamida
  • Cobamamide
  • cobamamidum
  • Cobanamida
  • Coenzyme B-12
  • Coenzyme B12
  • Vitamin B12 coenzyme
External IDs
LM 176
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Co B12Tablet1 mgOralCanat Laboratories Inc.1996-12-311999-08-28Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Acti-folic + Dibencozide CapletsCobamamide (40 mcg) + Folic Acid (1 mg)TabletOralActi Form Ltd.1991-12-312005-03-21Canada
PramLyteCobamamide (50 ug/1) + 1,2-docosahexanoyl-sn-glycero-3-phosphoserine calcium (6.4 mg/1) + 1,2-icosapentoyl-sn-glycero-3-phosphoserine calcium (800 ug/1) + Citric acid monohydrate (1.83 mg/1) + Cocarboxylase (25 ug/1) + Escitalopram oxalate (10 mg/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic Acid (1 mg/1) + Glycine betaine (500 ug/1) + Leucovorin (2.5 mg/1) + Levomefolate magnesium (7 mg/1) + Magnesium ascorbate (24 mg/1) + NADH (25 ug/1) + Phosphatidyl serine (12 mg/1) + Pyridoxal Phosphate (25 ug/1) + Sodium Citrate (3.67 mg/1) + Zinc ascorbate (1 mg/1)KitAllegis Pharmaceuticals, LLC2015-09-112016-01-04Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
BumP DHACobamamide (500 mg/1) + Flavin adenine dinucleotide (1 mg/1) + Flavin mononucleotide (2 mg/1) + Iron (15 mg/1) + Leucovorin (1 mg/1) + Levomefolate magnesium (1 mg/1) + Magnesium oxide (125 mg/1) + NADH (25 ug/1) + Omega-3 fatty acids (300 mg/1) + Potassium Iodide (250 ug/1) + Pyridoxal Phosphate (5 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Zinc glycinate (15 1/1)CapsuleOralCenturion Labs2017-03-242017-04-17Us
EnBrace HRCobamamide (50 ug/1) + 1,2-docosahexanoyl-sn-glycero-3-phosphoserine calcium (6.4 mg/1) + 1,2-icosapentoyl-sn-glycero-3-phosphoserine calcium (800 ug/1) + Cocarboxylase (25 ug/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic Acid (1 mg/1) + Glycine betaine (500 ug/1) + Leucovorin (2.5 mg/1) + Levomefolate magnesium (5.23 mg/1) + Magnesium ascorbate (24 mg/1) + NADH (25 ug/1) + Phosphatidyl serine (12 mg/1) + Pyridoxal Phosphate (25 ug/1) + Magnesium L-threonate (1 mg/1) + Zinc ascorbate (1 mg/1)Capsule, delayed release pelletsOralJaymac Pharmaceuticals, Llc2015-04-08Not applicableUs
EnLyteCobamamide (50 ug/1) + 1,2-docosahexanoyl-sn-glycero-3-phosphoserine calcium (6.4 mg/1) + 1,2-icosapentoyl-sn-glycero-3-phosphoserine calcium (800 ug/1) + Citric acid monohydrate (1.83 mg/1) + Cocarboxylase (25 ug/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic Acid (1 mg/1) + Glycine betaine (500 ug/1) + Leucovorin (2.5 mg/1) + Levomefolate magnesium (7 mg/1) + Magnesium ascorbate (24 mg/1) + NADH (25 ug/1) + Phosphatidyl serine (12 mg/1) + Pyridoxal Phosphate (25 ug/1) + Sodium Citrate (3.67 mg/1) + Magnesium L-threonate (1 mg/1) + Zinc ascorbate (1 mg/1)Capsule, delayed release pelletsOralJaymac Pharmaceuticals Llc2011-10-01Not applicableUs
PuralorCobamamide (2 mg/1) + 1-(c14-c18 esteroyl)-2-docosahexanoyl-sn-glycero-3-phosphocholine (5 mg/1) + 1-(c14-c18 esteroyl)-2-docosahexanoyl-sn-glycero-3-phosphoethanolamine (2.5 mg/1) + Acetylcysteine amide (5 mg/1) + Ascorbic acid (25 mg/1) + Cholecalciferol (100 [iU]/1) + Citric Acid (1.6 mg/1) + Egg phospholipids (42.5 mg/1) + Folic Acid (42.5 mg/1) + Gastric intrinsic factor (2.5 mg/1) + Leucovorin (3 mg/1) + Levomefolic acid (0.4 mg/1) + Magnesium glycinate (1 mg/1) + Niacin (0.5 mg/1) + Pantethine (2.5 mg/1) + Papain (20 mg/1) + Riboflavin (0.5 mg/1) + Sodium Citrate (0.8 mg/1) + Thiamine chloride (0.5 mg/1) + Magnesium L-threonate (2.5 mg/1)Tablet, chewableOralCenturion Labs2014-01-012017-09-20Us
International/Other Brands
Calomide / Cobazim (Interbat) / Comiosan (Yung Sine) / Corsete (Chen Ta) / Cotamide (Hor Chen) / Heraclene (Natrapharm) / Hicobal (Gentle) / Hokuramide (Pei Jin) / Hycobal (Eisai) / Maxibol (Sanofi-Aventis) / Neurofor (Sanofi-Aventis) / Sim-12 (Cipa)
Categories
UNII
F0R1QK73KB
CAS number
13870-90-1
Weight
Average: 1579.5818
Monoisotopic: 1578.65834557
Chemical Formula
C72H100CoN18O17P
InChI Key
ZIHHMGTYZOSFRC-OUCXYWSSSA-L
InChI
InChI=1S/C62H90N13O14P.C10H12N5O3.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;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/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);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1
IUPAC Name
(10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-1-{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-46-hydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2lambda5,9,19,26,43lambda5,44lambda5,45lambda5-heptaaza-15lambda5-phospha-1-cobaltadodecacyclo[27.14.1.1^{1,34}.1^{2,9}.1^{10,13}.0^{1,26}.0^{3,8}.0^{23,27}.0^{25,42}.0^{32,44}.0^{39,43}.0^{37,45}]heptatetraconta-2(47),3,5,7,27,29(44),32,34(45),37,39(43)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1-triuid-15-olate
SMILES
[C@H]1(C[Co-3]2345[N+]6=C7C(C)=C8N2[C@]([H])([C@H](CC(=O)N)[C@]8(CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@@H]2[C@@H](CO)O[C@H](N8C=[N+]3C3=CC(C)=C(C)C=C83)[C@@H]2O)C)[C@@]2(C)[C@@](CC(=O)N)([C@H](CCC(=O)N)C(C(C)=C3[N+]4=C(C=C6C([C@@H]7CCC(=O)N)(C)C)[C@@H](CCC(=O)N)[C@@]3(CC(=O)N)C)=[N+]52)C)O[C@@H](N2C3=C(N=C2)C(=NC=N3)N)[C@H](O)[C@@H]1O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Acute oral toxicity (LD50): 5000 mg/kg in the guinea pig [L20502]

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Thakkar K, Billa G: Treatment of vitamin B12 deficiency-methylcobalamine? Cyancobalamine? Hydroxocobalamin?-clearing the confusion. Eur J Clin Nutr. 2015 Jan;69(1):1-2. doi: 10.1038/ejcn.2014.165. Epub 2014 Aug 13. [PubMed:25117994]
  2. Cobamamide Pubchem [Link]
  3. Cobamamide Overview [Link]
  4. Vitamin B12 [Link]
  5. Cobamamide [Link]
  6. Science Labs MSDS Cobamamide [Link]
  7. Neuroenhancement with Vitamin B12—Underestimated Neurological Significance [Link]
  8. Treatment of vitamin B12 deficiency–Methylcobalamine? Cyancobalamine? Hydroxocobalamin?—clearing the confusion [Link]
  9. Cobalamin coenzyme forms are not likely to be superior to cyano- and hydroxyl-cobalamin in prevention or treatment of cobalamin deficiency [Link]
  10. Cobamamide, Drugs.com [Link]
External Links
Human Metabolome Database
HMDB0002086
KEGG Drug
D00042
PubChem Substance
347911148
ChemSpider
21864853
ChEBI
18408
ChEMBL
CHEMBL3833359
HET
B1Z
Wikipedia
Adenosylcobalamin
ATC Codes
B03BA04 — Cobamamide
MSDS
Download (313 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
CapsuleOral
TabletOral1 mg
Capsule, delayed release pelletsOral
Kit
Tablet, chewableOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitypartly miscible in waterMSDS
Predicted Properties
PropertyValueSource
logP-15ChemAxon
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area536.31 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity397.85 m3·mol-1ChemAxon
Polarizability157.77 Å3ChemAxon
Number of Rings15ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Drug created on December 03, 2015 09:51 / Updated on December 16, 2018 06:58