Cobamamide

Identification

Summary

Cobamamide is an ingredient found in a variety of supplements and vitamins.

Brand Names
EnBrace HR, EnLyte
Generic Name
Cobamamide
DrugBank Accession Number
DB11191
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 1579.5818
Monoisotopic: 1578.65834557
Chemical Formula
C72H100CoN18O17P
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

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Medicalerrors
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Toxicity

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

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

Products
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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)
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Co B12Tablet1 mg / tabOralCanat Laboratories Inc.1996-12-311999-08-28Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Acti-folic + Dibencozide CapletsCobamamide (40 mcg) + Folic acid (1 mg)TabletOralActi Form Ltd.1991-12-312005-03-21Canada flag
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) + Betaine (500 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) + 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)KitOralAllegis Pharmaceuticals, LLC2015-09-112016-01-04US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Biopar delta-FORTECobamamide (50 ug/1) + Cobalamin (50 ug/1) + Dihydrofolic Acid (1 mg/1) + Gastric intrinsic factor (50 mg/1) + Levoleucovorin (2.5 mg/1) + Levomefolate magnesium (7 mg/1)CapsuleOralJaymac Pharmacueticals LLC2020-09-01Not applicableUS flag
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 flag
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) + Betaine (500 ug/1) + Cocarboxylase (25 ug/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic acid (1 mg/1) + Magnesium L-threonate (1 mg/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) + Zinc ascorbate (1 mg/1)Capsule, delayed release pelletsOralJaymac Pharmaceuticals, Llc2011-08-12Not applicableUS flag
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) + Betaine (500 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) + Magnesium L-threonate (1 mg/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)Capsule, delayed release pelletsOralJaymac Pharmaceuticals Llc2011-08-12Not applicableUS flag
EnLyte Extra-LNCobamamide (25 ug/1) + Dihydrofolic Acid (1 mg/1) + Gastric intrinsic factor (25 mg/1) + Mecobalamin (25 ug/1)CapsuleOralJaymac Pharmacueticals LLC2019-12-16Not applicableUS flag
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) + Magnesium L-threonate (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)Tablet, chewableOralCenturion Labs2014-01-012017-09-20US flag

Categories

ATC Codes
B03BA04 — Cobamamide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as cobalamin derivatives. These are organic compounds containing a corrin ring, a cobalt atom, an a nucleotide moiety. Cobalamin Derivatives are actually derived from vitamin B12.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Tetrapyrroles and derivatives
Sub Class
Corrinoids
Direct Parent
Cobalamin derivatives
Alternative Parents
Metallotetrapyrroles / Pentose phosphates / 5'-deoxyribonucleosides / Glycosylamines / Monosaccharide phosphates / 6-aminopurines / Benzimidazoles / Aminopyrimidines and derivatives / Fatty amides / Organic phosphoric acids and derivatives
show 26 more
Substituents
5'-deoxyribonucleoside / 6-aminopurine / Alcohol / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid
show 49 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
corrinoid, cobalamins (CHEBI:18408)
Affected organisms
Not Available

Chemical Identifiers

UNII
F0R1QK73KB
CAS number
13870-90-1
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

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. [Article]
  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]
Human Metabolome Database
HMDB0002086
KEGG Drug
D00042
PubChem Substance
347911148
ChemSpider
21864853
RxNav
21373
ChEBI
18408
ChEMBL
CHEMBL3833359
PDBe Ligand
B1Z
Wikipedia
Adenosylcobalamin
MSDS
Download (313 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4WithdrawnTreatmentMenstrual Related Mood Disorder / Premenstrual Dysphoric Disorder / Premenstrual Syndrome / Premenstrual tension with edema1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
Injection, powder, lyophilized, for solutionIntramuscular
CapsuleOral
TabletOral1 mg / tab
Injection, solutionIntramuscular
Capsule
Powder, for suspensionOral
Capsule, delayed release pelletsOral
Powder, for solutionOral
KitOral
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

Drug created on December 03, 2015 16:51 / Updated on February 21, 2021 18:53