CAS 68-19-9|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-hy...

General Information

Structure

Molecular Formula

C₆₃H₈₈CoN₁₄O₁₄P

Molecular Mass

1355.365181

Exact Mass

1354.5674002

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

Acid pKa

1.8546375

H Acceptors

H Donor

LogD (pH = 5.5)

-7.42668

LogD (pH = 7.4)

-3.669606

Log P

-3.237631

Molar Refractivity

337.4833

Polarizability

134.45374

Polar Surface Area

477.85

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

0.67

LOG S

-3.83

Solubility (Water)

2.03e-01 g/l

Data Source

Names and Identifiers

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

Synonyms

COBALAMINE CONCENTRATE N.F.0.1% Cobalamin Concentrate Trituration w/Mannitolvitamin B-12Vitamin b12CobalaminCyanocobalaminCYANOCOBALAMIN 0.1% IN MANNITOLVITAMIN B12 0.1% IN MANNITOLα-(5,6-Dimethylbenzimidazolyl)cyanocobamideVitamin B12 complexVitamin B12CyanocobalaminVitamine B12Cyanocob(III)alamin

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

Rubratope-57 KitRuviteNeuroforte-RRubratope-60 KitBetalin 12Rubramin PCBerubigenShoviteVitapedCyanocobalamin Co 57 Schilling Test KitCrystaminePrimabaltVibalBerocca PNCyominNascobalRubiviteCobexCobolin-MDicopac KitVi-TwelCobaviteDepinarM.V.I. PediatricAnacobinCyanojectRedisolDicopacCrysti-12Vitabee 12VibisoneBedozCernevit-12

Names and Identifiers

Registration numbers

CAS Number

EC Number

PubChem CID

PubChem SID

Registration numbers

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

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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]

MP Biomedicals

02101401

Triturated with Mannitol.
Meets N.F. standards.

02103271

Crystalline
Purity: ~99%

02103278

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. 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

• http://en.wikipedia.org/wiki/Vitamin_B12

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

Synonyms

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

Registration numbers

CAS Number

EC Number

PubChem CID

PubChem SID

References

PubChem Literature

From Data Sources

• 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

• Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. 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

• http://en.wikipedia.org/wiki/Vitamin_B12

Bioactivity

PubChem BioAssay

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

Molecule Details

DrugBank

DB00115

Drug Groups

approved; nutraceutical

Description

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

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

MP Biomedicals

02101401

Triturated with Mannitol.
Meets N.F. standards.

02103271

Crystalline
Purity: ~99%

02103278

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

Molecule

ID:2