Vitamin B12

Identification

Summary

Vitamin B12 is a vitamin available in many formulations to correct vitamin B12 deficiency.

Brand Names

Animi-3 With Vitamin D, B-12, Cobex, Concept Ob, Dodex, Ferralet 90, Folbic, Foltabs, Fortaplex, Hematogen, Infuvite, Infuvite Pediatric, Irospan 24/6 Kit, Mvc-fluoride, Mvi Pediatric, Nascobal, Natafort, Pregvit, Tandem Plus, Vitafol-one

Generic Name

Cyanocobalamin
Commonly known or available as Vitamin B12

DrugBank Accession Number

DB00115

Background

Cyanocobalamin (commonly known as Vitamin B12) is a highly complex, essential vitamin, owing its name to the fact that it contains the mineral, cobalt. This vitamin is produced naturally by bacteria ¹⁶, and is necessary for DNA synthesis and cellular energy production. Vitamin B12 has many forms, including the cyano-, methyl-, deoxyadenosyl- and hydroxy-cobalamin forms. The cyano form, is the most widely used form in supplements and prescription drugs ¹⁰, ^Label. Several pharmaceutical forms of cyanocobalamin have been developed, including the tablet, injection, and nasal spray forms ^Label, ¹⁹, ²⁰. This drug was initially approved by the FDA in 1942 ^Label.

Type

Small Molecule

Groups

Approved, Nutraceutical

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Cyanocobalamin (DB00115)

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Weight

Average: 1355.3652
Monoisotopic: 1354.5674053

Chemical Formula

C₆₃H₈₈CoN₁₄O₁₄P

Synonyms

• Cianocobalamina
• Cyanocob(III)alamin
• Cyanocobalamin
• Cyanocobalamine
• Cyanocobalaminum
• Vitamin B12
• Vitamin B12 complex
• Vitamin B12 NOS

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Pharmacology

Indication

Nasal spray

The cyanocobalamin nasal spray is indicated for the maintenance of vitamin B12 concentrations after normalization with intramuscular vitamin B12 therapy in patients with deficiency of this vitamin who have no nervous system involvement ^Label.

Note: CaloMist ^Label, the nasal spray form, has not been evaluated for the treatment of newly diagnosed vitamin B12 deficiency.

Injection forms (subcutaneous, intramuscular)

These forms are indicated for vitamin B12 deficiencies due to various causes, with or without neurologic manifestations ²⁶. Vitamin B12 deficiency is frequently caused by malabsorption, which is often associated with the following conditions ²⁰:

Addisonian (pernicious) anemia

Gastrointestinal pathology, dysfunction, or surgery, including gluten enteropathy or sprue, small bowel bacterial overgrowth, total or partial gastrectomy

Fish tapeworm infestation

Malignancy of the pancreas or bowel

Folic acid deficiency

Oral forms

Vitamin B12 supplements are widely available and indicated in patients who require supplementation for various reasons. Dose requirements for vitamin B12 which are higher than normal (caused by pregnancy, thyrotoxicosis, hemolytic anemia, hemorrhage, malignancy, hepatic and renal disease) can usually be achieved with oral supplementation ²⁰. Oral products of vitamin B12 are not recommended in patients with malabsorption, as these forms are primarily absorbed in the gastrointestinal tract ²⁷.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to treat	Anemia	Combination Product in combination with: Ferrous fumarate (DB14491)	••• •••			••••••
Used in combination to treat	Anemia, pernicious	Combination Product in combination with: Ferrous fumarate (DB14491)	••• •••			••••••
Used in combination to treat	Combined vitamin b1 and b12 deficiency	Combination Product in combination with: Lipoic acid (DB00166), Thiamine (DB00152)	••••••••••••			••••••
Used in combination for therapy	Convalescence	Combination Product in combination with: Arginine PCA (DB16025)	••••••••••••			••••••••
Used in combination to treat	Diabetic neuropathies	Combination Product in combination with: Thiamine (DB00152), Lipoic acid (DB00166)	••••••••••••			••••••

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Associated Therapies

• Nutritional supplementation
• Vitamin supplementation

Contraindications & Blackbox Warnings

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Pharmacodynamics

General effects

Cyanocobalamin corrects vitamin B12 deficiency and improves the symptoms and laboratory abnormalities associated with pernicious anemia (megaloblastic indices, gastrointestinal lesions, and neurologic damage). This drug aids in growth, cell reproduction, hematopoiesis, nucleoprotein, and myelin synthesis. It also plays an important role in fat metabolism, carbohydrate metabolism, as well as protein synthesis. Cells that undergo rapid division (for example, epithelial cells, bone marrow, and myeloid cells) have a high demand for vitamin B12 ¹⁰.

Parenteral cyanocobalamin effects

The parenteral administration of vitamin B12 rapidly and completely reverses the megaloblastic anemia and gastrointestinal symptoms of vitamin B12 deficiency. Rapid parenteral administration of vitamin B12 in deficiency related neurological damage prevents the progression of this condition ²⁰.

Nasal spray effects

In 24 vitamin B12 deficient patients who were already stabilized on intramuscular (IM) vitamin B12 therapy, single daily doses of intranasal cyanocobalamin for 8 weeks lead to serum vitamin B12 concentrations that were within the target therapeutic range (>200 ng/L) ^Label.

Mechanism of action

Vitamin B12 serves as a cofactor for methionine synthase and L-methylmalonyl-CoA mutase enzymes. Methionine synthase is essential for the synthesis of purines and pyrimidines that form DNA. L-methylmalonyl-CoA mutase converts L-methylmalonyl-CoA to succinyl-CoA in the degradation of propionate ²⁴, an important reaction required for both fat and protein metabolism. It is a lack of vitamin B12 cofactor in the above reaction and the resulting accumulation of methylmalonyl CoA that is believed to be responsible for the neurological manifestations of B12 deficiency ¹⁰. Succinyl-CoA is also necessary for the synthesis of hemoglobin ²⁴.

In tissues, vitamin B12 is required for the synthesis of methionine from homocysteine. Methionine is required for the formation of S-adenosylmethionine, a methyl donor for nearly 100 substrates, comprised of DNA, RNA, hormones, proteins, as well as lipids ²⁴. Without vitamin B12, tetrahydrofolate cannot be regenerated from 5-methyltetrahydrofolate, and this can lead to functional folate deficiency ²², ^Label. This reaction is dependent on methylcobalamin (vitamin B12) as a co-factor and is also dependent on folate, in which the methyl group of methyltetrahydrofolate is transferred to homocysteine to form methionine and tetrahydrofolate. Vitamin B12 incorporates into circulating folic acid into growing red blood cells; retaining the folate in these cells ²³. A deficiency of vitamin B12 and the interruption of this reaction leads to the development of megaloblastic anemia.

Target	Actions	Organism
AMethionine synthase	cofactor	Humans
AMethylmalonyl-CoA mutase, mitochondrial	cofactor	Humans
UMethionine synthase reductase	cofactor	Humans
UMethylmalonic aciduria type A protein, mitochondrial	binder	Humans
UMethylmalonic aciduria and homocystinuria type C protein	cofactor	Humans
UMethylenetetrahydrofolate reductase	cofactor	Humans

Absorption

Vitamin B12 is quickly absorbed from intramuscular (IM) and subcutaneous (SC) sites of injection; with peak plasma concentrations achieved about 1 hour after IM injection ²⁶.

Orally administered vitamin B12 binds to intrinsic factor (IF) during its transport through the stomach. The separation of Vitamin B12 and IF occurs in the terminal ileum when calcium is present, and vitamin B12 is then absorbed into the gastrointestinal mucosal cells. It is then transported by transcobalamin binding proteins ²⁰. Passive diffusion through the intestinal wall can occur, however, high doses of vitamin B12 are required in this case (i.e. >1 mg). After the administration of oral doses less than 3 mcg, peak plasma concentrations are not reached for 8 to 12 hours, because the vitamin is temporarily retained in the wall of the lower ileum ²⁶.

Volume of distribution

Cobalamin is distributed to tissues and stored mainly in the liver and bone marrow ^Label.

Protein binding

Very high (to specific plasma proteins called transcobalamins); binding of hydroxocobalamin is slightly higher than cyanocobalamin [FDA label.

Metabolism

Vitamin B12 or cyanocobalamin obtained from food is initially bound by haptocorrin, a protein found in the saliva with high affinity for B12. This forms a haptocorrin-B12 complex. Cyanocobalamin passes through the stomach and is protected from acid degradation due to its binding to haptocorrin. In the duodenum, pancreatic proteases release cobalamin from the haptocorrin-B12 complex and from other proteins containing protein-bound B12 that have been ingested. Following this, the binding of cobalamin to a second glycoprotein, intrinsic factor, promotes its uptake by terminal ileum mucosal cells by a process called cubilin/AMN receptor-mediated endocytosis. After absorption into enterocytes, intrinsic factor is broken down in the lysosome, and cobalamin is then released into the bloodstream. The transporter ABCC1, found in the basolateral membrane of intestinal epithelial and other cells, exports cobalamin bound to transcobalamin out of the cell ¹⁵. Cyanocobalamin then passes through the portal vein in the liver, and then reaches the systemic circulation. The active forms of cyanocobalamin are methylcobalamin and adenosylcobalamin ¹⁵, ²⁴.

Hover over products below to view reaction partners

• Cyanocobalamin
  • Mecobalamin

Route of elimination

This drug is partially excreted in the urine ²⁷. According to a clinical study, approximately 3-8 mcg of vitamin B12 is secreted into the gastrointestinal tract daily via the bile. In patients with adequate levels of intrinsic factor, all except approximately 1 mcg is reabsorbed. When vitamin B12 is administered in higher doses that saturate the binding capacity of plasma proteins and the liver, the unbound vitamin B12 is eliminated rapidly in the urine. The body storage of vitamin B12 is dose-dependent ^Label.

Half-life

Approximately 6 days (400 days in the liver) ²⁷.

Clearance

During vitamin loading, the kidney accumulates large amounts of unbound vitamin B12. This drug is cleared partially by the kidney, however, multiligand receptor megalin promotes the reuptake and reabsorption of vitamin B12 into the body ¹³, ¹⁴.

Adverse Effects

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Toxicity

LD50 Oral (mouse): > 5,000 mg/kg ²⁵.

General toxicity

Vitamin B12 is generally non-toxic, even at higher doses. Mild, transient diarrhea, polycythemia vera, peripheral vascular thrombosis, itching, transitory exanthema, a feeling of swelling of entire body, pulmonary edema and congestive heart failure in early treatment stages, anaphylactic shock and death have been observed after vitamin B12 administration ²⁶.

Carcinogenesis and mutagenesis

Long term studies in animals examining the carcinogenic potential of any of the vitamin B12 formulations have not completed to date. There is no evidence from long-term use in patients with pernicious anemia that vitamin B12 has carcinogenic potential. Pernicious anemia is known to be associated with an increased incidence of stomach carcinoma, however, this malignancy has been attributed to the underlying cause of pernicious anemia and has not been found to be related to treatment with vitamin B12 ^Label.

Use in pregnancy

No adverse effects have been reported with ingestion of normal daily requirements during pregnancy ²⁶.

A note on the use of the nasal spray in pregnancy

Although vitamin B12 is an essential vitamin and requirements are increased during pregnancy, it is currently unknown whether the nasal spray form can cause fetal harm when administered to a pregnant woman or can affect reproduction capacity. The nasal spray form should be given to a pregnant woman only if clearly needed, as it is considered a pregnancy category C drug in this form. Sufficient well-controlled studies have not been done to this date in pregnant women ^Label.

Use in lactation

Vitamin B12 has been found distributed into the milk of nursing women in concentrations similar to the maternal blood vitamin B12 concentrations. No adverse effects have been reported to date with intake of normal required doses during lactation ²⁶.

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Cyanocobalamin may decrease the excretion rate of Abacavir which could result in a higher serum level.
Aceclofenac	Aceclofenac may decrease the excretion rate of Cyanocobalamin which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Cyanocobalamin which could result in a higher serum level.
Acetazolamide	Acetazolamide may increase the excretion rate of Cyanocobalamin which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acid	Acetylsalicylic acid may decrease the excretion rate of Cyanocobalamin which could result in a higher serum level.

Food Interactions

• Take with or without food. Recommendations vary from product to product - consult individual product monographs for additional information.

Products

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Product Images

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International/Other Brands

Bedodeka (Teva) / Bedoz / Berubigen (Upjohn) / Betalin (Lilly) / Cobione (MSD) / Cobolin-M / Crystamine / Cyanoject / Cyomin / Cytakon (GlaxoSmithKline) / Cytamen (GlaxoSmithKline) / Dicopac / Neuroforte-R / Primabalt / Vitabee 12

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
B-12 1000 Inj 1000mcg/ml	Solution	1 mg / mL	Intramuscular; Subcutaneous	Omega Laboratories Ltd	1985-12-31	Not applicable
Bedoz 1000inj	Liquid	1 mg / mL	Intramuscular	Lab Nadeau LtÉe, Division Of Technilab Inc.	1951-12-31	2005-08-05
CaloMist	Spray, metered	25 ug/0.1mL	Nasal	Fleming & Company, Pharmaceuticals	2007-10-01	2010-01-26
Cobex Inj 1000mcg/ml	Solution	1 mg / mL	Intramuscular; Subcutaneous	Kripps Pharmacy Ltd.	1979-12-31	Not applicable
Crystalline Vitamin B12-liq Im Sc 1000mcg/ml	Liquid	1 mg / mL	Intramuscular; Subcutaneous	Germiphene Corporation	1996-12-31	1999-06-28

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Aj-cyanocobalamin	Solution	1000 mcg / mL	Intramuscular; Subcutaneous	Agila Jamp Canada Inc	Not applicable	Not applicable
B12 Inject Kit	Kit	1000 ug/1mL	Intramuscular; Subcutaneous	Oaklock, Llc	2015-07-08	2019-04-09
B12 Inject Kit	Kit	1000 ug/1mL	Intramuscular; Subcutaneous	Oaklock, Llc	2015-06-19	2019-03-21
Cyanocobalamin	Injection	1000 ug/1mL	Intramuscular; Subcutaneous	Gland Pharma Limited	2020-09-24	Not applicable
Cyanocobalamin	Injection, solution	1000 ug/1mL	Intramuscular	Cardinal Health	1990-09-30	2017-01-31

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
B-12 1000mcg Continuous Released Tab	Tablet, extended release	1 mg / tab	Oral	Gahler Enterprises Ltd.	1981-12-31	2000-10-03
B-plex	Tablet	50 mcg / tab	Oral	Beverly International Nutrition	1986-12-31	1998-08-01
B12 1000mcg	Tablet	1000 mcg / tab	Oral	Natural Factors Nutritional Products Ltd.	2000-09-01	2007-08-07
B12 250mcg Cyanocobalamin	Tablet	250 mcg	Oral	Wn Pharmaceuticals Ltd.	2001-10-01	2009-09-28
Coco12	Lotion	0.05 g/0.05g	Topical	SSG Ventures Inc	2019-09-26	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
24 Multivitamins + Minerals	Cyanocobalamin (25 mcg) + Ascorbic acid (150 mg) + Beta carotene (10000 unit) + Biotin (25 mcg) + Calcium (130 mg) + Cholecalciferol (400 unit) + Choline bitartrate (25 mg) + Chromium (20 mcg) + Copper (1 mg) + Ferrous fumarate (15 mg) + Folic acid (.8 mg) + Inositol (25 mg) + Magnesium (65 mg) + Manganese (2 mg) + Molybdenum (20 mcg) + Niacin (25 mg) + Calcium pantothenate (25 mg) + Potassium (15 mg) + Potassium Iodide (.1 mg) + Pyridoxine hydrochloride (25 mg) + Racemethionine (25 mg) + Riboflavin (25 mg) + Selenium (20 mcg) + Thiamine hydrochloride (25 mg) + Vanadium (20 mcg) + Vitamin A palmitate (5000 unit) + Vitamin E (50 unit) + Zinc (10 mg)	Tablet	Oral	Stanley Pharmaceuticals, A Division Of Vita Health Products Inc.	1997-04-30	2002-07-31
50 Plus	Cyanocobalamin (20 mcg) + Ascorbic acid (200 mg) + Biotin (20 mcg) + Choline bitartrate (20 mg) + Folic acid (.2 mg) + Inositol (20 mg) + Niacin (20 mg) + Calcium pantothenate (20 mg) + Pyridoxine hydrochloride (20 mg) + Racemethionine (20 mg) + Riboflavin (20 mg) + Thiamine hydrochloride (20 mg) + Vitamin A palmitate (10000 unit) + Vitamin D (400 unit) + Vitamin E (20 unit)	Tablet	Oral	Quest Vitamins A Div Of Purity Life Health Products	1998-08-04	2001-07-06
50 Plus Multiple Vitamins & Minerals	Cyanocobalamin (25 mcg) + Ascorbic acid (90 mg) + Biotin (45 mcg) + Calcium (200 mg) + Cholecalciferol (400 unit) + Chromium (10 mcg) + Copper (2 mg) + Folic acid (0.4 mg) + Magnesium (100 mg) + Manganese (5 mg) + Molybdenum (25 mcg) + Nicotinamide (40 mg) + Pantothenic acid (10 mg) + Potassium Iodide (0.15 mg) + Pyridoxine hydrochloride (3 mg) + Riboflavin (3.2 mg) + Selenium (25 mcg) + Thiamine mononitrate (2.25 mg) + Vanadium (10 mcg) + Vitamin A palmitate (6000 unit) + Zinc (15 mg)	Tablet	Oral	Gfr Pharma Ltd.	2002-10-20	2004-06-15
Adeks - Dps	Cyanocobalamin (4 mcg / mL) + Ascorbic acid (45 mg / mL) + Beta carotene (1 mg / mL) + Biotin (15 mcg / mL) + Nicotinamide (6 mg / mL) + Panthenol (3 mg / mL) + Phylloquinone (0.1 mg / mL) + Pyridoxine hydrochloride (0.6 mg / mL) + Riboflavin (0.6 mg / mL) + Thiamine (0.5 mg / mL) + Vitamin A palmitate (1500 unit / mL) + Vitamin D (400 unit / mL) + Vitamin E (40 unit / mL) + Zinc sulfate (5 mg / mL)	Solution / drops	Oral	Axcan Pharma	1995-12-31	2007-10-01
Adeks Tablets	Cyanocobalamin (12 mcg) + Ascorbic acid (60 mg) + Beta carotene (3 mg) + Biotin (50 mcg) + Cholecalciferol (400 unit) + Folic acid (0.2 mg) + Niacin (10 mg) + Calcium pantothenate (10 mg) + Phylloquinone (0.15 mg) + Pyridoxine (1.5 mg) + Riboflavin (1.3 mg) + Thiamine (1.2 mg) + Vitamin A palmitate (4000 unit) + Vitamin E (150 unit) + Zinc gluconate (7.5 mg)	Tablet	Oral	Axcan Pharma	1998-01-20	2011-04-20

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Active FE	Cyanocobalamin (30 ug/1) + Ascorbic acid (160 mg/1) + Beta carotene (2100 [iU]/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (1 mg/1) + DL-alpha tocopheryl acetate (40 [iU]/1) + Folic acid (1250 ug/1) + Iron (75 mg/1) + Magnesium oxide (30 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (4 mg/1) + Thiamine hydrochloride (4 mg/1) + Zinc oxide (20 mg/1)	Tablet	Oral	Gm Pharmaceuticals	2013-11-11	Not applicable
Active OB	Cyanocobalamin (30 ug/1) + Ascorbic acid (100 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric sulfate pentahydrate (2 mg/1) + D-alpha-Tocopherol acetate (30 [iU]/1) + Doconexent (320 mg/1) + Folic acid (1 mg/1) + Iron (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (2 mg/1) + Zinc oxide (30 mg/1)	Capsule, liquid filled	Oral	Gm Pharmaceuticals	2013-10-28	2017-03-31
Animi-3	Cyanocobalamin (500 ug/1) + Cholecalciferol (1000 [iU]/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1)	Capsule	Oral	Pbm Pharmaceuticals Inc.	2011-06-01	Not applicable
Animi-3 with Vitamin D	Cyanocobalamin (500 ug/1) + Cholecalciferol (1000 [iU]/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1)	Capsule	Oral	Pbm Pharmaceuticals Inc.	2011-06-01	Not applicable
Av-VITE FB	Cyanocobalamin (1 mg/1) + Folic acid (2.5 mg/1) + Pyridoxine hydrochloride (25 mg/1)	Tablet	Oral	Av Kare, Inc.	2015-11-05	2016-01-13

Categories

ATC Codes

B03BA01 — Cyanocobalamin

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

B03AE01 — Iron, vitamin b12 and folic acid

• B03AE — Iron in other combinations
• B03A — IRON PREPARATIONS
• B03 — ANTIANEMIC PREPARATIONS
• B — BLOOD AND BLOOD FORMING ORGANS

B03BA51 — Cyanocobalamin, combinations

• 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
• Corrinoids
• Diet, Food, and Nutrition
• Drugs that are Mainly Renally Excreted
• Food
• Growth Substances
• Heterocyclic Compounds, Fused-Ring
• Micronutrients
• Vitamin B 12, biosynthesis
• 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 / Benzimidazole ribonucleosides and ribonucleotides / Pentose phosphates / Glycosylamines / Monosaccharide phosphates / Benzimidazoles / Phosphoethanolamines / Dialkyl phosphates / Benzenoids / Fatty amides / N-substituted imidazoles / Heteroaromatic compounds / Pyrrolines / Tetrahydrofurans / Pyrrolidines / Primary carboxylic acid amides / Ketimines / Secondary alcohols / Secondary carboxylic acid amides / Oxacyclic compounds / Azacyclic compounds / Propargyl-type 1,3-dipolar organic compounds / Transition metal cyanide salts / Hydrocarbon derivatives / Organic cobalt salts / Organic oxides / Carbonyl compounds / Organic zwitterions / Organopnictogen compounds / Organotransition metal compounds / Primary alcohols

show 21 more

Substituents

1-ribofuranosylbenzimidazole / Alcohol / Alkyl phosphate / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Cobalamin / Dialkyl phosphate / Fatty acyl / Fatty amide / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Imine / Ketimine / Metallotetrapyrrole skeleton / Monosaccharide / Monosaccharide phosphate / N-glycosyl compound / N-substituted imidazole / Organic 1,3-dipolar compound / Organic cobalt salt / 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 / Phosphoethanolamine / Phosphoric acid ester / Primary alcohol / Primary carboxylic acid amide / Propargyl-type 1,3-dipolar organic compound / Pyrrolidine / Pyrroline / Secondary alcohol / Secondary carboxylic acid amide / Tetrahydrofuran / Transition metal cyanide salt

show 45 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cob(III)alamins (CHEBI:17439)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

P6YC3EG204

CAS number

68-19-9

InChI Key

RMRCNWBMXRMIRW-WZHZPDAFSA-L

InChI

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;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1

IUPAC Name

cyano[(1R,2R,3R,4R,6Z,8S,11Z,13S,14S,16Z,18S,19S)-8,13,18-tris(2-carbamoylethyl)-3,14,19-tris(carbamoylmethyl)-4-(2-{[(2R)-2-{[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl phosphonato]oxy}propyl]carbamoyl}ethyl)-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium

SMILES

C[C@H](CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)[C@H]2N=C1\C(C)=C1/N=C(/C=C3\N=C(\C(\C)=C4\[C@@H](CCC(N)=O)[C@](C)(CC(N)=O)[C@@]2(C)N4[Co+]C#N)[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)C(C)(C)[C@@H]1CCC(N)=O)OP([O-])(=O)O[C@@H]1[C@@H](CO)O[C@@H]([C@@H]1O)N1C=NC2=C1C=C(C)C(C)=C2

References

Synthesis Reference

Robert H. Allen, "Preparation of samples for vitamin B12 and/or folate assay and assay." U.S. Patent US4451571, issued October, 1982.

US4451571

General References

1. Wickramasinghe SN: Morphology, biology and biochemistry of cobalamin- and folate-deficient bone marrow cells. Baillieres Clin Haematol. 1995 Sep;8(3):441-59. [Article]
2. Sharabi A, Cohen E, Sulkes J, Garty M: Replacement therapy for vitamin B12 deficiency: comparison between the sublingual and oral route. Br J Clin Pharmacol. 2003 Dec;56(6):635-8. [Article]
3. Hall AH, Rumack BH: Hydroxycobalamin/sodium thiosulfate as a cyanide antidote. J Emerg Med. 1987;5(2):115-21. [Article]
4. Andres E, Noel E, Goichot B: Metformin-associated vitamin B12 deficiency. Arch Intern Med. 2002 Oct 28;162(19):2251-2. [Article]
5. Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. [Article]
6. Bonaa KH, Njolstad I, Ueland PM, Schirmer H, Tverdal A, Steigen T, Wang H, Nordrehaug JE, Arnesen E, Rasmussen K: Homocysteine lowering and cardiovascular events after acute myocardial infarction. N Engl J Med. 2006 Apr 13;354(15):1578-88. doi: 10.1056/NEJMoa055227. Epub 2006 Mar 12. [Article]
7. Lonn E, Yusuf S, Arnold MJ, Sheridan P, Pogue J, Micks M, McQueen MJ, Probstfield J, Fodor G, Held C, Genest J Jr: Homocysteine lowering with folic acid and B vitamins in vascular disease. N Engl J Med. 2006 Apr 13;354(15):1567-77. doi: 10.1056/NEJMoa060900. Epub 2006 Mar 12. [Article]
8. Russell-Jones GJ, Alpers DH: Vitamin B12 transporters. Pharm Biotechnol. 1999;12:493-520. [Article]
9. Seetharam B: Receptor-mediated endocytosis of cobalamin (vitamin B12). Annu Rev Nutr. 1999;19:173-95. doi: 10.1146/annurev.nutr.19.1.173. [Article]
10. O'Leary F, Samman S: Vitamin B12 in health and disease. Nutrients. 2010 Mar;2(3):299-316. doi: 10.3390/nu2030299. Epub 2010 Mar 5. [Article]
11. Scott JM: Folate and vitamin B12. Proc Nutr Soc. 1999 May;58(2):441-8. [Article]
12. Zhang M, Han W, Hu S, Xu H: Methylcobalamin: a potential vitamin of pain killer. Neural Plast. 2013;2013:424651. doi: 10.1155/2013/424651. Epub 2013 Dec 26. [Article]
13. Birn H: The kidney in vitamin B12 and folate homeostasis: characterization of receptors for tubular uptake of vitamins and carrier proteins. Am J Physiol Renal Physiol. 2006 Jul;291(1):F22-36. doi: 10.1152/ajprenal.00385.2005. [Article]
14. Moestrup SK, Birn H, Fischer PB, Petersen CM, Verroust PJ, Sim RB, Christensen EI, Nexo E: Megalin-mediated endocytosis of transcobalamin-vitamin-B12 complexes suggests a role of the receptor in vitamin-B12 homeostasis. Proc Natl Acad Sci U S A. 1996 Aug 6;93(16):8612-7. [Article]
15. Gherasim C, Lofgren M, Banerjee R: Navigating the B(12) road: assimilation, delivery, and disorders of cobalamin. J Biol Chem. 2013 May 10;288(19):13186-93. doi: 10.1074/jbc.R113.458810. Epub 2013 Mar 28. [Article]
16. Fang H, Kang J, Zhang D: Microbial production of vitamin B12: a review and future perspectives. Microb Cell Fact. 2017 Jan 30;16(1):15. doi: 10.1186/s12934-017-0631-y. [Article]
17. Amidon, Gordon L., Sadée, Wolfgang (2002). Vitamin B12 Transporters (12th ed.). Springer, Boston MA.
18. Methylcobalamin vs cyanocobalamin [Link]
19. B12, cyanocobalamin tablets, DailyMed [Link]
20. Cyanocobalamin injection, DailyMed [Link]
21. Vitamin B12 [Link]
22. The metabolic processes of folic acid and Vitamin B12 deficiency [Link]
23. University of Virginia: Megaloblastic anemia [Link]
24. Vitamin B 12 Health Professional Fact Sheet [Link]
25. Cyanocobalamin VitB12, MSDS [File]
26. Cyanocobalamin injection, monograph [File]
27. Cyanocobalamin label [File]

External Links

KEGG Drug

D00166

KEGG Compound

C02823

PubChem Compound

70678590

PubChem Substance

46509031

ChemSpider

21864832

RxNav

11248

ChEBI

17439

ChEMBL

CHEMBL2110563

PharmGKB

PA451892

PDBe Ligand

CNC

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Cyanocobalamin

FDA label

Download (208 KB)

MSDS

Download (37.1 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	Active Not Recruiting	Basic Science	Adiposity / Decreased carbohydrate and glucose tolerance / Effect of Drugs / Overweight and Obesity	1
4	Completed	Prevention	Dyslipidemia / Homocystinaemia / Menopause	1
4	Completed	Prevention	Vincristine Induced Peripheral Neuropathy (VIPN)	1
4	Completed	Treatment	Anemia, Pernicious / Megaloblastic anemia	1
4	Completed	Treatment	Anemia / Iron Deficiency (ID)	1

Pharmacoeconomics

Manufacturers

• Par pharmaceutical inc
• Pharmacia and upjohn co
• Eli lilly and co
• Watson laboratories inc
• Abraxis pharmaceutical products
• Akorn inc
• App pharmaceuticals llc
• Baxter healthcare corp anesthesia and critical care
• Bioniche pharma usa llc
• Dell laboratories inc
• Luitpold pharmaceuticals inc
• Sanofi aventis us llc
• Solopak medical products inc
• Warner chilcott inc
• Wyeth ayerst laboratories
• Merck and co inc
• Bel mar laboratories inc
• Bristol myers squibb co
• Savage laboratories inc div altana inc
• Bayer healthcare pharmaceuticals inc
• West ward pharmaceutical corp
• Bracco diagnostics inc

Packagers

• American Regent
• APP Pharmaceuticals
• Baxter International Inc.
• Bayer Healthcare
• C.O. Truxton Inc.
• Cardinal Health
• Carlisle Laboratories Inc.
• Central Pharmaceuticals
• Chain Drug
• Choice Rx Ltd.
• Clint Pharmaceutical Inc.
• CVS Pharmacy
• Darby Dental Supply Co. Inc.
• General Injectables and Vaccines Inc.
• Gonberetica
• Gyn Nutriment Pharmacology
• H and H Laboratories
• International Ethical Labs Inc.
• Ivax Pharmaceuticals
• Keene Pharmaceuticals Inc.
• Luitpold Pharmaceuticals Inc.
• Major Pharmaceuticals
• Martica Enterprises Inc.
• Martin Surgical Supply
• Mason Distributors
• Mckesson Corp.
• MDRNA Inc.
• Merck & Co.
• Merit Pharmaceuticals
• National Pharmaceuticals
• National Vitamin Company
• Neuman Distributors Inc.
• Par Pharmaceuticals
• Physicians Total Care Inc.
• Preferred Pharmaceuticals Inc.
• Primedics Laboratories
• Rite Aid Corp.
• Rugby Laboratories
• Spectrum Pharmaceuticals
• Sunmark
• Torrance Co.
• Vitaline Corp.
• Walgreen Co.

Dosage Forms

Form	Route	Strength
Powder, for solution	Intramuscular
Capsule; liquid	Oral
Tablet, coated	Oral	1 mg
Solution	Intramuscular
Solution	Intravenous	1.914 mg
Tablet	Oral	1000 ug/1
Injection, solution; kit	Intramuscular; Topical
Kit	Topical
Tablet	Oral	50 mcg / tab
Patch	Transdermal
Tablet	Oral	1000 mcg / tab
Injection, solution	Parenteral	1000 UG
Injection, solution	Parenteral	1 mg/mL
Kit	Intramuscular; Subcutaneous	1000 ug/1mL
Injection, solution	Parenteral	500 µg/mL
Tablet, delayed release	Oral
Liquid	Intramuscular	1 mg / mL
Tablet, delayed release
Tablet, coated
Injection	Intramuscular	1 mg/ml
Spray, metered	Nasal	25 ug/0.1mL
Tablet	Oral	6 mcg / tab
Injection, powder, for solution	Parenteral
Injection, powder, for solution	Intravenous
Solution	Intramuscular	1 mg
Solution	Intramuscular; Parenteral	0.1 mg
Injection, solution	Parenteral
Injection, solution	Intramuscular	1000 mcg/ml
Injection, solution
Solution	Intramuscular; Subcutaneous	1 mg / mL
Lotion	Topical	0.05 g/0.05g
Solution	Intramuscular	100.000 mg
Solution	Parenteral	4.00 mg
Liquid	Intramuscular; Subcutaneous	1 mg / mL
Injection	Intramuscular	1 mg/1mL
Injection	Intramuscular; Subcutaneous	1000 ug/1mL
Injection, solution	Intramuscular; Subcutaneous	1000 ug/1mL
Injection, solution	Subcutaneous	1000 ug/1mL
Spray, metered	Nasal	500 ug/1
Tablet, film coated
Syrup	Oral
Capsule
Capsule	Cutaneous; Oral
Solution	Intramuscular	75.000 mg
Tablet	Oral	50 mg
Injection	Intramuscular; Subcutaneous	20 mcg/ml
Injection, solution		1000 MICROGRAMMI/ML
Injection, solution		500 MICROGRAMMI/ML
Injection, solution	Intramuscular	5000 MICROGRAMMI/2ML
Solution / drops	Oral	20 MICROGRAMMI/ML
Solution	Intramuscular	1.000 mg
Tablet	Oral	0.250 mg
Tablet	Oral	1.000 mg
Tablet	Oral	1.00 mg
Tablet	Oral	50.000 mg
Liquid	Oral
Injection, solution	Intramuscular; Intravenous
Injection, powder, for solution	Intramuscular; Intravenous
Lozenge	Oral
Capsule, liquid filled; kit; tablet	Oral
Tablet	Oral	3 mcg
Liquid	Intramuscular; Intravenous
Tablet	Oral	50.0000 mg
Tablet	Oral	100.000 mg
Tablet, sugar coated	Oral	75 mcg
Gel	Oral
Capsule, delayed release	Oral
Tablet, extended release	Oral
Tablet	Oral	24 mcg / tab
Solution	Intravenous
Tablet, coated	Oral	150 mcg
Solution	Intramuscular	100 mg
Tablet, coated	Oral
Kit; tablet; tablet, film coated	Oral
Injection, solution	Parenteral	3 mg
Injection, solution, concentrate; kit	Intravenous
Injection, powder, lyophilized, for solution	Intravenous
Kit	Intravenous
Injection, powder, for solution	Intramuscular
Solution	Intramuscular	1000 μg
Elixir	Oral
Solution	Oral
Tablet	Oral
Tablet, chewable	Oral
Liquid	Intravenous
Spray	Nasal	500 ug/1
Powder, for solution	Oral
Tablet, orally disintegrating	Oral
Capsule, gelatin coated; kit; tablet	Oral
Solution	Parenteral
Injection, solution	Intramuscular
Injection
Injection	Intramuscular
Tablet, sugar coated	Oral	100 mcg
Tablet, film coated	Oral	1000 mcg
Tablet; tablet, film coated	Oral
Tablet, film coated	Oral	200 mcg
Injection, solution	Intramuscular
Tablet, sugar coated	Oral
Tablet, sugar coated	Oral	250 mcg
Gum, chewing	Oral
Injection, solution	Parenteral	1 MG
Solution	Parenteral	15.000 mg
Tablet, film coated	Oral	100 mcg
Capsule, liquid filled; kit; tablet, film coated	Oral
Powder
Injection, solution; kit	Intravenous
Injection, solution	Intravenous
Injection		1000 mcg/ml
Kit	Intramuscular; Subcutaneous; Topical
Injection	Parenteral
Solution / drops	Oral
Capsule, liquid filled; kit; tablet, coated	Oral
Tablet, film coated	Oral
Tablet	Oral	1 mcg / tab
Capsule, gelatin coated	Oral
Wafer	Oral
Tablet, effervescent	Oral
Liquid	Intramuscular; Intravenous; Subcutaneous	1 mg / mL
Injection, solution	Intramuscular	1000 ug/1mL
Liquid	Intramuscular; Subcutaneous	1000 mcg / mL
Powder, for solution	Intravenous
Injection, powder, for solution	Intravenous	100 mg
Injection	Intramuscular
Liquid; tablet	Oral
Capsule, extended release	Oral
Powder, for solution	Intramuscular; Intravenous
Solution	Intramuscular	5.0000 mg
Solution	Parenteral	10.000 mg
Solution	Parenteral	75.000 mg
Injection, solution
Capsule	Oral
Injection, powder, lyophilized, for solution	Parenteral
Capsule; kit; tablet, film coated	Oral
Capsule, coated	Oral
Capsule	Oral	0.50 mg
Capsule; kit; tablet	Oral
Injection, powder, lyophilized, for solution	Intramuscular; Intravenous
Tablet, extended release	Oral	1.2 mg / tab
Tablet	Oral	500 mcg / tab
Strip	Oral
Capsule, liquid filled; kit	Oral
Capsule, liquid filled	Oral
Capsule; kit; tablet, coated	Oral
Tablet	Oral	.025 mg
Capsule	Oral	1000 mcg / cap
Injection
Liquid	Intramuscular; Subcutaneous	100 mcg / mL
Solution	Intramuscular; Subcutaneous	1000 mcg / mL
Tablet	Oral
Tablet	Oral	1 mg / tab
Capsule	Oral	1000 mcg
Capsule	Oral	500 mcg
Tablet	Oral	500 mcg
Tablet, coated	Oral	1000 Mikrogramm
Capsule	Oral	500 mcg / cap
Injection, solution	Parenteral	3000 mcg/2mL
Solution	Intramuscular; Subcutaneous	100 mcg / mL
Injection	Intramuscular; Subcutaneous	1000 mcg/ml
Injection, solution	Parenteral	100 UG
Injection, solution	Parenteral	1000 mcg/2mL
Injection, solution	Parenteral	1000 UG/ML
Injection, solution	Parenteral	100 mcg/mL
Tablet, extended release	Oral	1 mg / tab
Tablet	Oral	100 mcg / tab
Tablet	Oral	250 mcg
Tablet	Oral	25 mcg
Tablet	Oral	5 mcg / tab
Tablet	Oral	250 mcg / tab
Injection, solution	Parenteral	121000 UG
Injection	Intramuscular	1 mg
Solution	Parenteral	1000 cg
Solution	Intramuscular; Subcutaneous	1 mg
Solution	Parenteral	1 mg
Solution	Intramuscular; Subcutaneous	0.01 g
Tablet	Oral	100 mcg
Tablet	Oral	25 mcg / tab
Tablet	Oral	3 mcg / tab
Kit	Oral
Suspension	Oral
Solution	Intramuscular	100.00 mg
Solution	Intramuscular	15.000 mg
Powder	Oral
Granule	Oral
Tablet	Oral	1000 mcg
Solution
Tablet, sugar coated	Oral	100 mcg
Tablet	Oral	50 mcg
Tablet
Tablet, coated	Oral	25 mcg
Solution		1000 mcg/1ml
Tablet, coated	Oral	100 mcg
Tablet, sugar coated	Oral	25 mcg
Suspension
Solution		10 mcg/1ml
Tablet, coated	Oral	50 mcg
Tablet, sugar coated	Oral	50 mcg
Solution		2000 mcg/1ml

Prices

Unit description	Cost	Unit
Nascobal 500 mcg/0.1ml Solution 2.3ml Bottle	277.97USD	bottle
Cyanocobalamin crystals	161.18USD	g
Infuvite pediatric vial	2.58USD	ml
Cyanocobalamin 1000 mcg/ml vial	1.44USD	vial
Cyanocobalamin 1000 mcg/ml	1.2USD	ml
Cyanocobalamin 1000 mcg/ml Solution	1.03USD	ml
Rubesol-1000 mcg/ml vial	0.48USD	ml
Vitamin B-12 1000 mcg/ml	0.47USD	ml
Vitamin b-12 2.5 mg tablet sl	0.17USD	tablet
Cyanocobalamin 1000 mcg tablet	0.16USD	tablet
Cyanocobalamin 100 mcg tablet	0.14USD	tablet
Vitamin b-12 1000 mcg tablet sl	0.08USD	tablet
B12 2500 mcg tablet sl	0.07USD	tablet
Sm vitamin b-12 500 mcg tablet	0.06USD	tablet
Vitamin b-12 1000 mcg tablet	0.06USD	tablet
Vitabee with vit c caplet	0.05USD	caplet
Vitamin b-12 500 mcg tablet	0.05USD	tablet
CVS Pharmacy vitamin b-12 1000 mcg tablet	0.04USD	tablet
CVS Pharmacy vitamin b-12 500 mcg tablet	0.04USD	tablet
Vitamin b-12 50 mcg tablet	0.04USD	tablet
CVS Pharmacy vitamin b12 100 mcg tablet	0.03USD	tablet
Pv vit b-12 1000 mcg tablet sl	0.03USD	tablet
Ra vitamin b-12 50 mcg tablet	0.03USD	tablet
Vitamin b-12 250 mcg tablet	0.03USD	tablet
Pv b-12 250 mcg tablet	0.02USD	tablet
Vitamin b-12 100 mcg tablet	0.02USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US7229636	No	2007-06-12	2024-08-01
US7879349	No	2011-02-01	2024-08-01
US8003353	No	2011-08-23	2024-08-01
US8940714	No	2015-01-27	2024-02-26
US7404489	No	2008-07-29	2024-03-12
US9415007	No	2016-08-16	2024-07-28

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	> 300	https://www.lookchem.com/Cyanocobalamin/
boiling point (°C)	> 300	http://dept.harpercollege.edu/chemistry/msds/Cyanocobalamin%20Vit%20B12.pdf
water solubility	12.5 mg/mL	http://www.hmdb.ca/metabolites/HMDB00607
logP	1.897	http://www.hmdb.ca/metabolites/HMDB00607
logS	-4.5	http://www.hmdb.ca/metabolites/HMDB00607
pKa	1.84, 8.77	http://foodb.ca/compounds/FDB013264

Predicted Properties

Property	Value	Source
Water Solubility	0.0202 mg/mL	ALOGPS
logP	2.66	ALOGPS
logP	-3.2	Chemaxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	1.82	Chemaxon
pKa (Strongest Basic)	8.68	Chemaxon
Physiological Charge	3	Chemaxon
Hydrogen Acceptor Count	18	Chemaxon
Hydrogen Donor Count	9	Chemaxon
Polar Surface Area	477.85 Å2	Chemaxon
Rotatable Bond Count	27	Chemaxon
Refractivity	337.48 m3·mol-1	Chemaxon
Polarizability	138.79 Å3	Chemaxon
Number of Rings	8	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

Property	Value	Probability
Human Intestinal Absorption	+	0.9574
Blood Brain Barrier	-	0.7447
Caco-2 permeable	-	0.6455
P-glycoprotein substrate	Substrate	0.8341
P-glycoprotein inhibitor I	Non-inhibitor	0.5082
P-glycoprotein inhibitor II	Inhibitor	0.6369
Renal organic cation transporter	Non-inhibitor	0.898
CYP450 2C9 substrate	Non-substrate	0.8104
CYP450 2D6 substrate	Non-substrate	0.8085
CYP450 3A4 substrate	Substrate	0.65
CYP450 1A2 substrate	Non-inhibitor	0.8775
CYP450 2C9 inhibitor	Non-inhibitor	0.8775
CYP450 2D6 inhibitor	Non-inhibitor	0.8737
CYP450 2C19 inhibitor	Non-inhibitor	0.7076
CYP450 3A4 inhibitor	Inhibitor	0.7118
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8125
Ames test	Non AMES toxic	0.5707
Carcinogenicity	Non-carcinogens	0.7782
Biodegradation	Not ready biodegradable	0.9972
Rat acute toxicity	2.6731 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8988
hERG inhibition (predictor II)	Non-inhibitor	0.682

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

Chromatographic Properties

Collision Cross Sections (CCS)

Not Available

Targets

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Details1. Methionine synthase

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Cofactor

General Function

Zinc ion binding

Specific Function

Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofola...

Gene Name

MTR

Uniprot ID

Q99707

Uniprot Name

Methionine synthase

Molecular Weight

140525.91 Da

References

1. Stover PJ: Vitamin B12 and older adults. Curr Opin Clin Nutr Metab Care. 2010 Jan;13(1):24-7. doi: 10.1097/MCO.0b013e328333d157. [Article]
2. Allen LH: Causes of vitamin B12 and folate deficiency. Food Nutr Bull. 2008 Jun;29(2 Suppl):S20-34; discussion S35-7. [Article]
3. O'Leary F, Samman S: Vitamin B12 in health and disease. Nutrients. 2010 Mar;2(3):299-316. doi: 10.3390/nu2030299. Epub 2010 Mar 5. [Article]

Details2. Methylmalonyl-CoA mutase, mitochondrial

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Cofactor

General Function

Modified amino acid binding

Specific Function

Involved in the degradation of several amino acids, odd-chain fatty acids and cholesterol via propionyl-CoA to the tricarboxylic acid cycle. MCM has different functions in other species.

Gene Name

MUT

Uniprot ID

P22033

Uniprot Name

Methylmalonyl-CoA mutase, mitochondrial

Molecular Weight

83133.755 Da

References

1. Worgan LC, Niles K, Tirone JC, Hofmann A, Verner A, Sammak A, Kucic T, Lepage P, Rosenblatt DS: Spectrum of mutations in mut methylmalonic acidemia and identification of a common Hispanic mutation and haplotype. Hum Mutat. 2006 Jan;27(1):31-43. [Article]
2. Brooks AJ, Vlasie M, Banerjee R, Brunold TC: Co-C bond activation in methylmalonyl-CoA mutase by stabilization of the post-homolysis product Co2+ cobalamin. J Am Chem Soc. 2005 Nov 30;127(47):16522-8. [Article]
3. Kozlowski PM, Andruniow T, Jarzecki AA, Zgierski MZ, Spiro TG: DFT analysis of co-alkyl and co-adenosyl vibrational modes in B12-cofactors. Inorg Chem. 2006 Jul 10;45(14):5585-90. [Article]
4. Moras E, Hosack A, Watkins D, Rosenblatt DS: Mitochondrial vitamin B12-binding proteins in patients with inborn errors of cobalamin metabolism. Mol Genet Metab. 2007 Feb;90(2):140-7. Epub 2006 Sep 29. [Article]
5. Stover PJ: Vitamin B12 and older adults. Curr Opin Clin Nutr Metab Care. 2010 Jan;13(1):24-7. doi: 10.1097/MCO.0b013e328333d157. [Article]
6. O'Leary F, Samman S: Vitamin B12 in health and disease. Nutrients. 2010 Mar;2(3):299-316. doi: 10.3390/nu2030299. Epub 2010 Mar 5. [Article]

Details3. Methionine synthase reductase

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Cofactor

General Function

Oxidoreductase activity, oxidizing metal ions, nad or nadp as acceptor

Specific Function

Involved in the reductive regeneration of cob(I)alamin (vitamin B12) cofactor required for the maintenance of methionine synthase in a functional state. Necessary for utilization of methylgroups fr...

Gene Name

MTRR

Uniprot ID

Q9UBK8

Uniprot Name

Methionine synthase reductase

Molecular Weight

80409.22 Da

References

1. O'Leary VB, Mills JL, Pangilinan F, Kirke PN, Cox C, Conley M, Weiler A, Peng K, Shane B, Scott JM, Parle-McDermott A, Molloy AM, Brody LC: Analysis of methionine synthase reductase polymorphisms for neural tube defects risk association. Mol Genet Metab. 2005 Jul;85(3):220-7. Epub 2005 Mar 17. [Article]
2. Miriuka SG, Langman LJ, Evrovski J, Miner SE, D'Mello N, Delgado DH, Wong BY, Ross HJ, Cole DE: Genetic polymorphisms predisposing to hyperhomocysteinemia in cardiac transplant patients. Transpl Int. 2005 Jan;18(1):29-35. [Article]
3. Berkun Y, Abou Atta I, Rubinow A, Orbach H, Levartovsky D, Aamar S, Arbel O, Dresner-Pollak R, Friedman G, Ben-Yehuda A: 2756GG genotype of methionine synthase reductase gene is more prevalent in rheumatoid arthritis patients treated with methotrexate and is associated with methotrexate-induced nodulosis. J Rheumatol. 2007 Aug;34(8):1664-9. Epub 2007 Jul 1. [Article]

Details4. Methylmalonic aciduria type A protein, mitochondrial

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Binder

General Function

Hydrolase activity

Specific Function

Probable GTPase. May function as chaperone. May be involved in the transport of cobalamin (Cbl) into mitochondria for the final steps of adenosylcobalamin (AdoCbl) synthesis.

Gene Name

MMAA

Uniprot ID

Q8IVH4

Uniprot Name

Methylmalonic aciduria type A protein, mitochondrial

Molecular Weight

46537.865 Da

References

1. Lerner-Ellis JP, Dobson CM, Wai T, Watkins D, Tirone JC, Leclerc D, Dore C, Lepage P, Gravel RA, Rosenblatt DS: Mutations in the MMAA gene in patients with the cblA disorder of vitamin B12 metabolism. Hum Mutat. 2004 Dec;24(6):509-16. [Article]
2. Dobson CM, Gradinger A, Longo N, Wu X, Leclerc D, Lerner-Ellis J, Lemieux M, Belair C, Watkins D, Rosenblatt DS, Gravel RA: Homozygous nonsense mutation in the MCEE gene and siRNA suppression of methylmalonyl-CoA epimerase expression: a novel cause of mild methylmalonic aciduria. Mol Genet Metab. 2006 Aug;88(4):327-33. Epub 2006 May 11. [Article]
3. Zhou X, Cui Y, Han J: Methylmalonic acidemia: Current status and research priorities. Intractable Rare Dis Res. 2018 May;7(2):73-78. doi: 10.5582/irdr.2018.01026. [Article]
4. Froese DS, Zhang J, Healy S, Gravel RA: Mechanism of vitamin B12-responsiveness in cblC methylmalonic aciduria with homocystinuria. Mol Genet Metab. 2009 Dec;98(4):338-43. doi: 10.1016/j.ymgme.2009.07.014. Epub 2009 Aug 3. [Article]

Details5. Methylmalonic aciduria and homocystinuria type C protein

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Cofactor

General Function

Cobalamin binding

Specific Function

May be involved in the binding and intracellular trafficking of cobalamin (vitamin B12).

Gene Name

MMACHC

Uniprot ID

Q9Y4U1

Uniprot Name

Methylmalonic aciduria and homocystinuria type C protein

Molecular Weight

31728.095 Da

References

1. Chandler RJ, Aswani V, Tsai MS, Falk M, Wehrli N, Stabler S, Allen R, Sedensky M, Kazazian HH, Venditti CP: Propionyl-CoA and adenosylcobalamin metabolism in Caenorhabditis elegans: evidence for a role of methylmalonyl-CoA epimerase in intermediary metabolism. Mol Genet Metab. 2006 Sep-Oct;89(1-2):64-73. Epub 2006 Jul 14. [Article]
2. Ben-Omran TI, Wong H, Blaser S, Feigenbaum A: Late-onset cobalamin-C disorder: a challenging diagnosis. Am J Med Genet A. 2007 May 1;143A(9):979-84. [Article]
3. Morel CF, Lerner-Ellis JP, Rosenblatt DS: Combined methylmalonic aciduria and homocystinuria (cblC): phenotype-genotype correlations and ethnic-specific observations. Mol Genet Metab. 2006 Aug;88(4):315-21. Epub 2006 May 22. [Article]
4. Lerner-Ellis JP, Tirone JC, Pawelek PD, Dore C, Atkinson JL, Watkins D, Morel CF, Fujiwara TM, Moras E, Hosack AR, Dunbar GV, Antonicka H, Forgetta V, Dobson CM, Leclerc D, Gravel RA, Shoubridge EA, Coulton JW, Lepage P, Rommens JM, Morgan K, Rosenblatt DS: Identification of the gene responsible for methylmalonic aciduria and homocystinuria, cblC type. Nat Genet. 2006 Jan;38(1):93-100. Epub 2005 Nov 27. [Article]
5. Obeid R, Fedosov SN, Nexo E: Cobalamin coenzyme forms are not likely to be superior to cyano- and hydroxyl-cobalamin in prevention or treatment of cobalamin deficiency. Mol Nutr Food Res. 2015 Jul;59(7):1364-72. doi: 10.1002/mnfr.201500019. Epub 2015 May 12. [Article]

Details6. Methylenetetrahydrofolate reductase

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Cofactor

General Function

Protein complex binding

Specific Function

Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.

Gene Name

MTHFR

Uniprot ID

P42898

Uniprot Name

Methylenetetrahydrofolate reductase

Molecular Weight

74595.895 Da

References

1. Nakamura T, Saionji K, Hiejima Y, Hirayama H, Tago K, Takano H, Tajiri M, Hayashi K, Kawabata M, Funamizu M, Makita Y, Hata A: Methylenetetrahydrofolate reductase genotype, vitamin B12, and folate influence plasma homocysteine in hemodialysis patients. Am J Kidney Dis. 2002 May;39(5):1032-9. [Article]
2. Erdogan MO, Yildiz SH, Solak M, Eser O, Cosar E, Eser B, Koken R, Buyukbas S: C677T polymorphism of the methylenetetrahydrofolate reductase gene does not affect folic acid, vitamin B12, and homocysteine serum levels in Turkish children with neural tube defects. Genet Mol Res. 2010 Jun 22;9(2):1197-203. doi: 10.4238/vol9-2gmr816. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55