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

Nutraceutical

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Cobamamide (DB11191)

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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

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Pharmacology

Indication

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination for therapy	Malnutrition	Combination Product in combination with: Levocarnitine (DB00583)	••• •••			••••••• ••• ••••••••••
Treatment of	Vitamin b12 deficiency		••••••••••••			•••••••••• ••••••• •••••••••••• ••• ••••••••
Used in combination for therapy	Weight loss	Combination Product in combination with: Levocarnitine (DB00583)	••• •••			••••••• ••• ••••••••••

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Associated Therapies

• Nutritional supplementation

Contraindications & Blackbox Warnings

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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

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Toxicity

Acute oral toxicity (LD50): 5000 mg/kg in the guinea pig ⁶

Pathways

Not Available

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Interactions

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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.

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Food Interactions

No interactions found.

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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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Co B12	Tablet	1 mg / tab	Oral	Canat Laboratories Inc.	1996-12-31	1999-08-28

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Acti-folic + Dibencozide Caplets	Cobamamide (40 mcg) + Folic acid (1 mg)	Tablet	Oral	Acti Form Ltd.	1991-12-31	2005-03-21
PramLyte	Cobamamide (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)	Kit	Oral	Allegis Pharmaceuticals, LLC	2015-09-11	2016-01-04

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Biopar delta-FORTE	Cobamamide (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)	Capsule	Oral	Jaymac Pharma	2023-06-01	Not applicable
BumP DHA	Cobamamide (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)	Capsule	Oral	Centurion Labs	2017-03-24	2017-04-17
EnBrace HR	Cobamamide (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 pellets	Oral	Jaymac Pharma	2011-08-12	Not applicable
EnLyte Extra-LN	Cobamamide (25 ug/1) + Dihydrofolic Acid (1 mg/1) + Gastric intrinsic factor (25 mg/1) + Mecobalamin (25 ug/1)	Capsule	Oral	Jaymac Pharmacueticals LLC	2019-12-16	Not applicable
Puralor	Cobamamide (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, chewable	Oral	Centurion Labs	2014-01-01	2017-09-20

Categories

ATC Codes

B03BA04 — Cobamamide

• B03BA — Vitamin B12 (cyanocobalamin and analogues)
• B03B — VITAMIN B12 AND FOLIC ACID
• B03 — ANTIANEMIC PREPARATIONS
• B — BLOOD AND BLOOD FORMING ORGANS

Drug Categories

• Antianemic Preparations
• Blood and Blood Forming Organs
• Coenzymes
• Corrinoids
• Enzymes and Coenzymes
• Heterocyclic Compounds, Fused-Ring
• Vitamin B Complex
• Vitamin B12 and Folic Acid
• Vitamins

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 / N-substituted imidazoles / Benzenoids / Imidolactams / Pyrrolidines / Pyrrolines / Heteroaromatic compounds / Tetrahydrofurans / Secondary carboxylic acid amides / Secondary alcohols / Primary carboxylic acid amides / Lactams / Amino acids and derivatives / Metalloheterocyclic compounds / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Azacyclic compounds / Organic transition metal salts / Hydrocarbon derivatives / Carbonyl compounds / Organic oxides / Organic zwitterions / Organopnictogen compounds / Organotransition metal compounds / Primary alcohols / Primary amines / Transition metal alkyls

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Substituents

5'-deoxyribonucleoside / 6-aminopurine / Alcohol / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Cobalamin / Fatty acyl / Fatty amide / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Imidazopyrimidine / Imidolactam / Lactam / Metalloheterocycle / Metallotetrapyrrole skeleton / Monosaccharide / Monosaccharide phosphate / N-glycosyl compound / N-substituted imidazole / Organic 1,3-dipolar compound / Organic metal salt / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organic phosphoric acid derivative / Organic salt / Organic transition metal moeity / Organic transition metal salt / Organic zwitterion / Organometallic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Pentose monosaccharide / Pentose phosphate / Primary alcohol / Primary amine / Primary carboxylic acid amide / Propargyl-type 1,3-dipolar organic compound / Purine / Pyrimidine / Pyrrolidine / Pyrroline / Secondary alcohol / Secondary carboxylic acid amide / Tetrahydrofuran / Transition metal alkyl

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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]

External Links

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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Withdrawn	Treatment	Menstrual Related Mood Disorder / Premenstrual Dysphoric Disorder (PMDD) / Premenstrual Syndrome (PMS) / Premenstrual tension with edema	1
Not Available	Not Yet Recruiting	Treatment	Malnutrition	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral
Capsule		1000 mcg
Injection, powder, lyophilized, for solution	Intramuscular	1000 mcg
Injection, powder, lyophilized, for solution	Intramuscular
Powder	Oral	1000.000 mcg
Capsule	Oral
Tablet	Oral	1 mg / tab
Injection, solution	Intramuscular
Capsule
Powder, for suspension	Oral
Capsule, liquid filled	Oral
Capsule, delayed release pellets	Oral
Capsule		1 MG
Powder, for solution	Oral
Kit	Oral
Tablet, chewable	Oral

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	partly miscible in water	MSDS

Predicted Properties

Property	Value	Source
logP	-15	Chemaxon
pKa (Strongest Acidic)	1.81	Chemaxon
pKa (Strongest Basic)	3.94	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	20	Chemaxon
Hydrogen Donor Count	12	Chemaxon
Polar Surface Area	536.31 Å2	Chemaxon
Rotatable Bond Count	19	Chemaxon
Refractivity	397.85 m3·mol-1	Chemaxon
Polarizability	157.77 Å3	Chemaxon
Number of Rings	15	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

Chromatographic Properties

Collision Cross Sections (CCS)

Not Available

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Drug created at December 03, 2015 16:51 / Updated at February 03, 2022 06:26