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?,?.1?,??.1??,??]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium

• ChemBase ID: 2
• Molecular Formular: C63H88CoN14O14P
• Molecular Mass: 1355.365181
• Monoisotopic Mass: 1354.5674002
• SMILES: [C@H]1([C@](C2=N[C@H]1[C@]1([C@]([C@@H](/C(=C(/C3=N/C(=C\C4=N/C(=C\2/C)/[C@H](C4(C)C)CCC(=O)N)/[C@H]([C@]3(C)CC(=O)N)CCC(=O)N)\C)/N1[Co+]C#N)CCC(=O)N)(CC(=O)N)C)C)(CCC(=O)NC[C@H](OP(=O)(O[C@H]1[C@H]([C@H](O[C@@H]1CO)n1cnc2c1cc(c(c2)C)C)O)[O-])C)C)CC(=O)N
• Canonical SMILES: OC[C@H]1O[C@@H]([C@@H]([C@@H]1OP(=O)(O[C@@H](CNC(=O)CC[C@@]1(C)C2=N[C@H]([C@@H]1CC(=O)N)[C@]1(C)N([Co+]C#N)/C(=C(/C)\C3=N/C(=C\C4=N/C(=C\2/C)/[C@@H](CCC(=O)N)C4(C)C)/[C@H]([C@]3(C)CC(=O)N)CCC(=O)N)/[C@H]([C@]1(C)CC(=O)N)CCC(=O)N)C)[O-])O)n1cnc2c1cc(C)c(c2)C
• 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
• InChIKey: RMRCNWBMXRMIRW-WZHZPDAFSA-L

NAMES AND DATABASE IDS

Names

• 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?,?.1?,??.1??,??]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium; 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
• IUPAC Traditional 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-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?,?.1?,??.1??,??]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium; 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-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
• Brand Name: Cyomin; Dicopac; Nascobal; Rubramin PC; Anacobin; Bedoz; Berocca PN; Berubigen; Betalin 12; Cernevit-12; Cobavite; Cobex; Cobolin-M; Crystamine; Crysti-12; Cyanocobalamin Co 57 Schilling Test Kit; Cyanoject; Depinar; Dicopac Kit; M.V.I. Pediatric; Neuroforte-R; Primabalt; Redisol; Rubivite; Rubratope-57 Kit; Rubratope-60 Kit; Ruvite; Shovite; Vi-Twel; Vibal; Vibisone; Vitabee 12; Vitaped
• Synonyms: 0.1% Cobalamin Concentrate Trituration w/Mannitol; COBALAMINE CONCENTRATE N.F.; CYANOCOBALAMIN 0.1% IN MANNITOL; VITAMIN B12 0.1% IN MANNITOL; α-(5,6-Dimethylbenzimidazolyl)cyanocobamide; Vitamin B12; Vitamin B12 complex; Cyanocob(III)alamin; Vitamine B12; Cyanocobalamin; Cobalamin; vitamin B-12; Cyanocobalamin; Vitamin b12

Database IDs

• CAS Number: 68-19-9
• EC Number: 200-680-0
• PubChem SID: 46509031; 160963465
• PubChem CID: 5311498; 44176380

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8546375
• H Acceptors: 18
• H Donor: 9
• LogD (pH = 5.5): -7.42668
• LogD (pH = 7.4): -3.669606
• Log P: -3.237631
• Molar Refractivity: 337.4833 cm^3
• Polarizability: 134.45374 Å^3
• Polar Surface Area: 477.85 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.67
• LOG S: -3.83
• Solubility (Water): 2.03e-01 g/l

PROPERTIES

Physical Property

• Solubility: 12.5 mg/mL [MERCK INDEX (1996)]
• Melting Point: >300 °C; 165-167°C
• Boiling Point: (at 3.5 mm) 290-295°C
• Density: 1.52 g/ml

Safety Information

• Storage Condition: -20°C; 2-8°C; 2-8°C, Desiccate; Room Temperature (15-30°C)
• RTECS: GG3750000
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: R:36/37/38; R:43
• Safety Statements: S:20-25-26-37/39; S:28-36

Product Information

• Purity: ~99%; 99%
• Grade: NF
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02101401

Triturated with Mannitol.
Meets N.F. standards.

MP Biomedicals - 02103271

Crystalline
Purity: ~99%

MP Biomedicals - 02103278

0.1% in Mannitol
This is 99% pure vitamin B₁₂ tritrated onto mannitol at 0.1% concentration.

DrugBank - DB00115

• Drug Groups: approved; nutraceutical
• Description: Cyanocobalamin (commonly known as Vitamin B12) is the most chemically complex of all the vitamins. Cyanocobalamin's structure is based on a corrin ring, which, although similar to the porphyrin ring found in heme, chlorophyll, and cytochrome, has two of the pyrrole rings directly bonded. The central metal ion is Co (cobalt). Cyanocobalamin cannot be made by plants or by animals, as the only type of organisms that have the enzymes required for the synthesis of cyanocobalamin are bacteria and archaea. Higher plants do not concentrate cyanocobalamin from the soil and so are a poor source of the substance as compared with animal tissues. Cyanocobalamin is naturally found in foods including meat (especially liver and shellfish), eggs, and milk products. [HMDB]
• Indication: For treatment of pernicious anemia (due to lack of or inhibition of intrinsic factor) and for prevention and treatment of vitamin B 12 deficiency.
• Pharmacology: Cyanocobalamin (Vitamin B12) is a water-soluble organometallic compound with a trivalent cobalt ion bound inside a corrin ring. It is needed for nerve cells and red blood cells, and to make DNA. Vitamin B12 deficiency is the cause of several forms of anemia.
• Toxicity: Anaphylactic reaction (skin rash, itching, wheezing)-after parenteral administration. ORL-MUS LD₅₀ > 8000 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Readily absorbed in the lower half of the ileum.
• Half Life: Approximately 6 days (400 days in the liver).
• Protein Binding: Very high (to specific plasma proteins called transcobalamins); binding of hydroxocobalamin is slightly higher than cyanocobalamin.
• References: Wickramasinghe SN: Morphology, biology and biochemistry of cobalamin- and folate-deficient bone marrow cells. Baillieres Clin Haematol. 1995 Sep;8(3):441-59. [Pubmed] ; 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. [Pubmed] ; Hall AH, Rumack BH: Hydroxycobalamin/sodium thiosulfate as a cyanide antidote. J Emerg Med. 1987;5(2):115-21. [Pubmed] ; Andres E, Noel E, Goichot B: Metformin-associated vitamin B12 deficiency. Arch Intern Med. 2002 Oct 28;162(19):2251-2. [Pubmed] ; Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1902

Research Area: Metabolic Disease
Biological Activity:
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. 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 synthesis and energy production. As the largest and most structurally complicated vitamin, it can be produced industrially only through bacterial fermentation-synthesis. [1]

REFERENCES

• Wickramasinghe SN: Morphology, biology and biochemistry of cobalamin- and folate-deficient bone marrow cells. Baillieres Clin Haematol. 1995 Sep;8(3):441-59. Pubmed
• 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. Pubmed
• Hall AH, Rumack BH: Hydroxycobalamin/sodium thiosulfate as a cyanide antidote. J Emerg Med. 1987;5(2):115-21. Pubmed
• Andres E, Noel E, Goichot B: Metformin-associated vitamin B12 deficiency. Arch Intern Med. 2002 Oct 28;162(19):2251-2. Pubmed
• Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. Pubmed
• http://en.wikipedia.org/wiki/Vitamin_B12