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68-19-9 molecular structure
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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 and InChIs

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

Cite this record

CBID:2 http://www.chembase.cn/molecule-2.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
Vitamin B12
Vitamin B12 complex
Cyanocob(III)alamin
Vitamine B12
Cyanocobalamin
Cobalamin
vitamin B-12
Cyanocobalamin
Vitamin b12
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
CAS Number
68-19-9
EC Number
200-680-0
PubChem SID
46509031
160963465
PubChem CID
5311498
44176380

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.8546375  H Acceptors 18 
H Donor LogD (pH = 5.5) -7.42668 
LogD (pH = 7.4) -3.669606  Log P -3.237631 
Molar Refractivity 337.4833 cm3 Polarizability 134.45374 Å3
Polar Surface Area 477.85 Å2 Rotatable Bonds 27 
Lipinski's Rule of Five false 
Log P 0.67  LOG S -3.83 
Solubility (Water) 2.03e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
12.5 mg/mL [MERCK INDEX (1996)] expand Show data source
Melting Point
>300 °C expand Show data source
165-167°C expand Show data source
Boiling Point
(at 3.5 mm) 290-295°C expand Show data source
Density
1.52 g/ml expand Show data source
Storage Condition
-20°C expand Show data source
2-8°C expand Show data source
2-8°C, Desiccate expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
GG3750000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
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Risk Statements
R:36/37/38 expand Show data source
R:43 expand Show data source
Safety Statements
S:20-25-26-37/39 expand Show data source
S:28-36 expand Show data source
Purity
~99% expand Show data source
99% expand Show data source
Grade
NF expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
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DETAILS

DETAILS

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals DrugBank DrugBank
MP Biomedicals - 02103278 external link
0.1% in Mannitol
This is 99% pure vitamin B12 tritrated onto mannitol at 0.1% concentration.
MP Biomedicals - 02103271 external link
Crystalline
Purity: ~99%
MP Biomedicals - 02101401 external link
Triturated with Mannitol.
Meets N.F. standards.
Selleck Chemicals - S1902 external link
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]
DrugBank - DB00115 external link
Item Information
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

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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