Vitamin B12
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Vitamin B12
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CAS No:
68-19-9
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Formula:
C63H88CoN14O14P
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Chemical Name:
Vitamin B12
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Synonyms:
Vitamin B12;Anacobin;Betalin 12;Betaline 12;Byladoce;Cobalin;Cotel;Covit;Crystamin;Cyano-B12;Cyanocobalamin;Cyanocobalamine;Cycolamin;Cykobeminet;Cytacon;Cytamen;Cytobion;5,6-Dimethylbenzimidazolyl cyanocobamide;Dobetin;Docemine;Docibin;Docigram;Dodecabee;Dodecavite;Dodex;Ducobee;Duodecibin;Embiol;Emociclina;Eritrone;Erycytol;Erythrotin;Euhaemon;Extrinsic factor;Fresmin;Hemo-b-doze;Hemomin;Hepagon;Hepavis;Hepcovite;Lactobacillus lactis dorner factor;LLD factor;Macrabin;Megalovel;Milbedoce;Nagravon;Normocytin;Pernaemon;Pernaevit;Pernipuron;Plecyamin;Poyamin;Rebramin;Redamina;Redisol;Rhodacryst;Rubesol;Rubramin;Rubripca;Rubrocitol;Sytobex;B-Twelve;B-Twelve Ora;Vibalt;Vibisone;Virubra;Vitarubin;Vita-rubra;Vitral;Cobalamin,cyanide;Cobalamin,cyano-;Cobamin;Cykobemin;Factor II (vitamin);Cobamide,α-5,6-dimethyl-1H-benzimidazolyl-,cyanide;1H-Benzimidazole,5,6-dimethyl-1-(3-O-phosphono-α-D-ribofuranosyl)-,monoester with cobinamide cyanide,inner salt;Cobamide,cyano-5,6-dimethyl-1H-benzimidazole-;Cyano-5,6-dimethylbenzimidazolylcobamide;5,6-Dimethylbenzimidazolyl-Co-cyanocobamide;Vitamin B12 preparation;Betolvex;Cobalamin,cyano-5,6-dimethylbenzimidazole-;CN-B12;Factor II;Depinar;Cobinamide,cyanide,dihydrogen phosphate (ester),inner salt,3′-ester with 5,6-dimethyl-1-α-D-ribofuranosyl-1H-benzimidazole;Hepavit;Docivit;Behepan;Bedoz;Berubigen;Antipernicin;Rubramin PC;Millevit;Berubi;8023-26-5;8039-03-0;11037-08-4;24436-34-8
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CAS No:
Description
Vitamin B12 is a water soluble vitamin with a key role in the normal functioning of the brain and nervous system, and for the formation of blood.Target: OthersVitamin B12 is a water-soluble vitamin with a key role in the normal functioning of the brain and nervous system, and for the formation of blood. It is one of the eight B vitamins. It is normally involved in the metabolism of every cell of the human body, especially affecting DNA synthesis and regulation, but also fatty acid synthe
Vitamin B refers to several water soluble vitamins often found together in foods, all of which are necessary for normal growth and metabolism, but none of which are synthesized in adequate amounts by humans. The common forms of vitamin B include vitamin B1 (thiamine), B2 (riboflavin), B3 (niacin), B6 (pyridoxine) and B12 (cyanocobalamin). Except for niacin (when given in high doses), there is no evidence that the other B vitamins, in physiologic or even super-physiologic high doses cause liver injury or jaundice. The major forms of vitamin B and selected other water soluble vitamins (biotin, pantothenic acid, choline) are discussed briefly in this record.|A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.
Vitamin B12 Basic Attributes
1355.37000
1354.57000
200-680-0
DTXSID7044346
Dark red crystals or an amorphous or crystalline red powder|Dark-red crystals or red powder
2936260000
Characteristics
479.70000
6.57018
red crystalline powder
>300 °C
>300 °C
48.2 °F
Soluble
2-8ºC
LD50 intravenous in mouse: 2gm/kg
SPECIFIC OPTICAL ROTATION: -59 + or - 9 DEG @ 23 °C 656 NM (DILUTE AQ SOLN)
Odorless
Tasteless
Commercially available cyanocobalamin for injection has a pH of 4.5-7
Hygroscopic; when exposed to air, may absorb about 12% water; darkens at 210-220 °C; not melted at 300 °C|All vitamin B12 compounds contain the cobalt atom in its trivalent state. There are at least three active forms: cyanobalamin, hydroxycyanobalamin; nitrocobalamin
Safety Information
UN1230 - class 3 - PG 2 - Methanol, solution
1
11-23/24/25-39/23/24/25
S24/25
GG3750000
F,T
Hygroscopic. Keep cold and dry.
P210-P260-P280-P301 + P310-P311
H225-H301 + H311 + H331-H370
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Substance added directly to human food affirmed as generally recognized as safe (GRAS).|Vitamin B12 used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.
Not Classified
Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Cyanocobalamin is included on this list.
Toxicity
ABSORPTION OF VITAMINE B12 FROM THE GI TRACT MAY BE DECR BY AMINOGLYCOSIDE ANTIBIOTICS, COLCHICINE, EXTENTED-RELEASE POTASSIUM PREPN, AMINOSALICYLIC ACID & ITS SALTS, ANTICONVULSANTS (EG, PHENYTOIN, PHENOBARBITAL, PRIMADONE), COBALT IRRADIATION OF THE SMALL BOWEL, & BY EXCESSIVE ALCOHOL INTAKE LASTING LONGER THAN 2 WK.|The gastrointestinal absorption of vitamin B12 can be considerably decreased by oral neomycin. Colchicine administration appears to increase neomycin-induced malabsorption of vitamin B12.|The decreased vitamin B12 absorption induced by aminosalicylic acid may be due to the mild malabsorption syndrome that occurs in some patients treated with aminosalicylic acid (PAS).|Patients with pernicious anemia ... respond poorly to vitamin B12 therapy if chloroamphenicol is given concomitantly.|For more Interactions (Complete) data for CYANOCOBALAMIN (7 total), please visit the HSDB record page.
/Isolated from/ Streptomyces griseus or Streptomyces aureofaciens|In foods, vitamin B12 occurs only in animal products.|In nature, primary sources are certain microorganisms that grow in soil, sewage, water, or the intestinal lumen of animals, and that synthesize the vitamin.|Synthesized almost exclusively by bacteria. ... Also found in soil and water, richest sources being activated sewage sludge ... or manure.
Vitamin B12 is excreted into human breast milk. In the first 48 hours after delivery, mean colostrum levels were 2431 pg/ml & then fell rapidly to concn comparable to those of normal serum. One group of investigators also observed very high colostrum levels, ranging from 6-17.5 times that of milk. Milk:plasma ratios are approx 1.0 during lactation. Reported milk concn of B12 vary widely.
Normal serum vitamin B12 concentrations have been reported to range from 200-900 pg/ml, with a mean normal plasma concentration of 450 pg/ml.
Drug Information
Vitamin B refers to several water soluble vitamins often found together in foods, all of which are necessary for normal growth and metabolism, but none of which are synthesized in adequate amounts by humans. The common forms of vitamin B include vitamin B1 (thiamine), B2 (riboflavin), B3 (niacin), B6 (pyridoxine) and B12 (cyanocobalamin). Except for niacin (when given in high doses), there is no evidence that the other B vitamins, in physiologic or even super-physiologic high doses cause liver injury or jaundice. The major forms of vitamin B and selected other water soluble vitamins (biotin, pantothenic acid, choline) are discussed briefly in this record.
Vitamins
Hematinics|Vitamin B12 is used in the treatment of pernicious anemia and other vitamin B12 deficiency states. ... Cyanocobalamin ... usually indicated in patients with malabsorption of vitamin B12, such as those with tropical or nontropical sprue (idiopathic steatorrhea, gluten-induced enteropathy); partial or total gastrectomy; regional enteritis; gastroenterostomy; ileal resection; or malignancies, granulomas, strictures, or anastomoses involving the ileum. When the secretion of intrinsic factor is decreased by lesions that destroy the gastric mucosa (eg, following ingestion of corrosives or in patients with extensive GI neoplasia) or by gastric atrophy secondary to multiple sclerosis, certain endocrine disorders, or iron deficiency, or when antibodies to intrinsic factor are present in gastric juice, absorption of vitamin B12 is decreased and cyanocobalamin ... may be required. Malabsorption of vitamin B12 may also be caused by competition for vitamin B12 by bacteria (blind loop syndrome) or by fish tapeworm, Diphyllobothrium latum, or by admin of certain drugs.|The individual with an uncomplicated pernicious anemia, in which the abnormality is restricted to a mild or moderate anemia ... will respond quite well to the admin of vitamin B12 alone.|... Patients with neurological change or severe leukopenia or thrombocytopenia associated with infection or bleeding require emergency treatment. The older individual with a severe anemia (hematocrit less than 20%) is likely to have tissue hypoxia, cerebrovascular insufficiency, and congestive heart failure. Effective therapy must not wait for detailed diagnostic tests. ... The patient should receive intramuscular injections of 100 ug of cyanocobalamin and 1 to 5 mg of folic acid.|For more Therapeutic Uses (Complete) data for CYANOCOBALAMIN (13 total), please visit the HSDB record page.
Cyanocobalamin injection is extremely safe when given by the intramuscular or deep subcutaneous route, but it should never be given intravenously.|Cyanocobalamin should not be used in patients with early Leber's disease (hereditary optic nerve atrophy), since rapid optic nerve atrophy has been reported following admin of the drug to these patients. Vitamin B12 is contraindicated in patients who have experienced hypersensitivity reactions to the vitamin or to cobalt.|/"SHOTGUN"/ ... VITAMIN THERAPY IN TREATMENT OF ... DEFICIENCY CAN BE DANGEROUS. ... THERE IS DANGER THAT SUFFICIENT FOLIC ACID WILL BE GIVEN TO RESULT IN HEMATOLOGICAL RECOVERY; HOWEVER, THIS MAY MASK CONTINUED VIT-B DEFICIENCY & NEUROLOGICAL DAMAGE WILL DEVELOP OR PROGRESS IF ALREADY PRESENT.|Maternal Medication usually Compatible with Breast-Feeding: B12: Reported Sign or Symptom in Infant or Effect on Lactation: None. /from Table 6/|Serum potassium concn should be monitored during early vitamin B12 therapy & potassium admin is necessary, since fatal hypokalemia could occur upon conversion of megaloblastic anemia to normal erythropoesis with vitamin B12 as a result of increased erythrocyte potassium requirements. Because vitamin B12 deficiency may suppress the signs of polycythemia vera, treatment with cyanocobalamin may unmask this condition. The increase in nucleic acid degradation produced by admin vitamin B12 to vitamin B12- deficient patients could result in gout in susceptible individuals. Therapeutic response to vitamin B12 may be impaired by concurrent infection, uremia, folic acid or iron deficiency, or by drugs having bone marrow suppressant effects. Folic acid should be admin with extreme caution to patients with undiagnosed anemia, since folic acid may obscure the diagnosis of pernicious anemia by alleviating hematologic manifestations of the disease while allowing neurologic complications to progress. This may result in severe nervous system damage before the correct diagnosis is made. Vitamin preparations containing folic acid should be avoided by patients with pernicious anemia because folic acid may actually potentiate neurologic complications of vitamin B12 deficiency. Conversely, doses of cyanocobalamin exceeding 10 micrograms daily may improve folate-deficient megaloblastic anemia and obscure the true diagnosis.
A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)
IN MICE INJECTED IV WITH VITAMIN B12, THE VITAMIN ACCUMULATED RAPIDLY IN THE PLACENTA & WAS TRANSFERRED SLOWLY TO THE FETUSES. PEAK CONCN IN THE FETUSES WAS REACHED 24 HR AFTER DOSING, & FETAL ACCUMULATION WAS DOSE-DEPENDENT.|IN /MICE/ VITAMIN B12 PRESENTS UNUSUAL PATTERN OF PLACENTAL TRANSFER, FOR EVEN WITH 0.20 UG MATERNAL DOSE AVG FETAL CONCN IS 130 TIMES HIGHER THAN MATERNAL ONE. THIS INDICATES STRONGLY OPERATION OF SPECIFIC TRANSPORT MECHANISM FOR VITAMIN B12, POSSIBLY SIMILAR TO ITS GI ABSORPTION ...|IN RATS, PLACENTAL TRANSFER OF VITAMIN B12 WAS SHOWN TO INCR DURING GESTATION. ALTHOUGH QUANTITY TRANSPORTED EACH DAY WAS PROPORTIONAL TO FETAL WT, THE AMT TRANSPORTED PER G OF PLACENTA INCR TEN-FOLD FROM DAY 10 TO DAY 19.|Vitamin B12 is irregularly absorbed from the distal small intestine following oral administration. Dietary vitamin B12 is protein bound and this bond must be split by proteolysis and gastric acid before absorption. In the stomach, free vitamin B12 is attached to intrinsic factor; intrinsic factor a glycoprotein secreted by the gastric mucosa, is necessary for active absorption of the vitamin from the GI tract. The vitamin B12-intrinsic factor complex passes into the intestine, where much of the complex is transiently retained at specific receptor sites in the wall of the lower ileum before the vitamin B12 portion is absorbed into systemic circulation.|For more Absorption, Distribution and Excretion (Complete) data for CYANOCOBALAMIN (9 total), please visit the HSDB record page.
Vitamin B12 is believed to be converted to coenzyme form in the liver and is probably stored in tissues in this form.|Intracellular vitamin B12 is maintained as two active coenzymes methylcobalamin and deoxyadenasylcobalamin.
HALF-LIFE OF IV ADMIN CYANOCOBALAMIN IN SERUM IS ABOUT 6 DAYS.
CYANOCOBALAMIN STIMULATES RETICULOCYTES, THUS PLAYING IMPORTANT ROLE IN HEMATOPOIESIS IN THAT, TOGETHER WITH FOLIC ACID, IT IS INVOLVED IN FORMATION OF DEOXYRIBONUCLEOTIDES FROM RIBONUCLEOTIDES.|Vitamin B12 is converted to Coenzyme B12 in tissues, and as such is essential for conversion of methylmalonate to succinate and synthesis of methionine from homocysteine, a reaction which also requires folate. ... Vitamin B12 also may be involved in maintaining sulfhydryl (SH) groups in the reduced form required by many SH-activated enzyme systems. Through these reactions, vitamin B12 is associated with fat and carbohydrate metabolism and protein synthesis.
Vitamin B12 is usually nontoxic even in large doses; however, mild transient diarrhea, peripheral vascular thrombosis, itching, transitory exanthema, urticaria, feeling of swelling of the entire body, anaphylaxis, and death have been reported. Although allergic reactions to vitamin B12 have generally been attributed to impurities in the preparation, a few patients have reacted positively to skin testing with purified cyanocobalamin ... .
B 12, Vitamin
Vitamin B12 Use and Manufacturing
Isoln from mammalian liver: E.L. Rickes et al, Science 107, 396 (1948); from cultures of Streptomyces griseus: eidem, ibid 108, 634 (1948); E.L. Rickes, T. R. Wood, US pat 2,563,794 (1951 to Merck & Co)|BERNHAUER ET AL, US PATENT 3,120,509 (1962 TO HOFFMANN-LA ROCHE).|Purification from sewage sludge: Van Melle, US patent 3,057,851 (1962 to Armour)|Total synthesis: R.B. Woodward, Pure Appl Chem 33, 145 (1973)|Secondary metabolic product /of/ Propionibacterium species, Streptomyces species, large scale submerged culture
1) Vitamin B12 deficiency can cause anemia and nervous system disorders. It is commonly used in infant foods and fortified drinks.
2) As a nutritional fortifier in animal feed, it exhibits anti-anemia effects for pernicious anemia, nutritional anemia, anemia caused by parasites, and other forms of anemia.
3) It is primarily used for the treatment of megaloblastic anemia, malnutrition, anemia due to blood loss, neuralgia, and obstructive disorders.
4) Vitamin B12 is essential for the body's metabolism. The average total amount of vitamin B12 in the human body is 2-5mg, with 50-90% stored in the liver. The body releases it into the bloodstream for the production of red blood cells. Chronic B12 deficiency can lead to pernicious anemia. B12, along with folic acid, plays a crucial role in cell nucleic acid synthesis, participating in the synthesis of purines, pyrimidines, nucleic acids, and methionine. It also facilitates methyltransferase to promote base synthesis and increases sugar metabolism, aiding in liver fat elimination. It is often used as a therapeutic agent for liver diseases. The daily recommended intake of vitamin B12 for humans is 1 microgram, and an average diet provides around 2 micrograms to meet the normal requirements. Hydroxocobalamin in Vitamin B12 reacts with cyanide to form Vitamin B12, thereby counteracting cyanide toxicity. Consequently, individuals with vitamin B12 deficiency have a higher sensitivity to cyanide than the average person. Vitamin B12 is primarily used for the treatment of pernicious anemia, megaloblastic anemia, anemia caused by antifolate drugs, and multiple neuritis.
5) A coenzyme for synthesis of nucleic acids and metabolism carbohydrates.
Vitamin B12 is available in pure form for injection or oral admin or in combination with other vitamins and minerals for oral admin.|Grade: USP, radioactive|Cyanocobalamin injection (Redisol, rubramin PC) ... available in concentrations of 1 to 1000 ug/ml.|Ce-cobalin syrup contains in each ml cyanocobalamin 6 ug and ascorbic acid 2 mg; Cytacon: cyanocobalamin available as liquid containing 35 ug in each 5 ml (suggested diluent, syrup) and as tablets of 50 ug; Cytamen: Cyanocobalamin, available as injection containing 250 or 1000 ug per ml in ampules of 1 ml; Hepacon-B12: Cyanocobalamin, available as injection containing 100 or 1000 ug per ml in ampules of 1 ml; Hepanorm tablets: each contains cyanocobalamin 7.5 mg, intrinsic factor concentrate 25 mg, folic acid 2.5 mg, and liver fraction 150 mg.|Chromagen capsules: each capsule contains ... cyanocobalamin 10 ug; Fergon plus: each capsule contains ... vitamin B12 with intrinsic factor concentrate NF 1/2 unit; Heptune plus: each capsule contains ... vitamin B12 concentrate 25 ug; Iberet: each tablet contains ... cyanocobalamin 25 ug; Iberol: each tablet contains ... cyanocobalamin 12.5 ug; Iromin-G: each tablet contains ... vitamin B12 (crystalline or resin) 2 ug. Niferex forte: each capsule contains ... vitamin B12 25 ug; Nu-Iron plus: each 5 ml of elixir contains ... vitamin B12 25 ug; Perhemin: each capsule contains ... cyanocobalamin 50 ug; Peritinic: each tablet contains ... vitamin B12 5 ug; Pronemia: each capsule contains ... vitamin B12 (as cobalamin concentrate) 15 ug.
Vitamin B12: ACTIVE|TALC HAS A TENACIOUS AFFINTIY FOR VITAMIN B12; ALTHOUGH THIS IS NOT AN INCOMPATIBILITY, IT PRECLUDES USE OF TALC AS A FILTER AID OR LUBRICANT FOR TABLETS, PARTICULARLY IN VIEW OF POSSIBLE ASSAY DIFFICULTIES.|Prototype of the family of naturally occurring cobalt coordination cmpds known as corrinoids.|Source: (Food) Liver, eggs, milk, meats, and fish. Commercial source: produced by microbial action on various nutrients (spent antibiotic liquors, sugarbeet molasses, whey), also from sewage sludge.
SEPARATION OF COBALAMINES & OF COENZYME B12 BY HIGH-PRESSURE LIQUID CHROMATOGRAPHY.|A SEPARATION METHOD USING REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY ON VITAMIN B12 ANALOGS (MECOBALAMIN, COBAMIDE, CYANOCOBALAMIN & HYDROXOCOBALAMIN) WAS DESCRIBED.|Vitamin B1, vitamin B2, vitamin B6, and vitamin B12 were simultaneously detected in pharmaceuticals by high performance liquid chromatography on a LiChrosorb RP-18 column with a methanol-water (80:20 and 50:50) mobile phase and ultra violet detection at 254 nm. Linear relations between the peak areas and the concn for the vitamins were observed in the following ranges: 10-50 and 50-250 ng for vitamin B1, and 20-100 and 100-500 ng for vitamins B2, B6, and B12. The relative standard deviation was 4.2%.|ANALYSIS OF VITAMIN B12 BY FLAMELESS ATOMIC ABSORPTION.
A RADIOASSAY FOR ESTIMATION OF SERUM VITAMIN B12 IN PRESENCE OF NATURALLY OCCURRING VITAMIN B12 ANALOGS CAN BE OPERATED IF SERUM TRANSCOBALAMIN II IS USED AS THE BINDING PROTEIN.
Cosmetics -> Skin conditioning
Computed Properties
Molecular Weight:1355.4
Hydrogen Bond Donor Count:9
Hydrogen Bond Acceptor Count:21
Rotatable Bond Count:26
Exact Mass:1354.567399
Monoisotopic Mass:1354.567399
Topological Polar Surface Area:476
Heavy Atom Count:93
Complexity:3150
Undefined Atom Stereocenter Count:14
Undefined Bond Stereocenter Count:3
Covalently-Bonded Unit Count:3
Compound Is Canonicalized:Yes
Price Analysis
Drug Function and Efficacy
It constitutes a variety of coenzymes, participates in the metabolism, utilization and synthesis of a variety of substances, promotes bone growth, maintains the structural integrity of epithelial tissue, and maintains normal growth and development
Registered Holders
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EUROAPI FRANCE
Active
France
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Hebei Yuxing Bio-Engineering Co., Ltd.
Active
China
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Sanofi (China) Investment Co., Ltd.
Active
China
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