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Details

Stereochemistry ABSOLUTE
Molecular Formula C62H88N13O14P.CN.Co
Molecular Weight 1355.3652
Optical Activity UNSPECIFIED
Additional Stereochemistry Yes
Defined Stereocenters 13 / 14
E/Z Centers 0
Charge 0
Stereo Comments Octahedral trans

SHOW SMILES / InChI
Structure of CYANOCOBALAMIN

SMILES

[Co+3].[C-]#N.C[C@H](CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)C2[N-]C1=C(C)C3=NC(=CC4=NC(=C(C)C5=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]5CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)C(C)(C)[C@@H]3CCC(N)=O)OP([O-])(=O)O[C@@H]6[C@@H](CO)O[C@@H]([C@@H]6O)N7C=NC8=C7C=C(C)C(C)=C8

InChI

InChIKey=FDJOLVPMNUYSCM-UVKKECPRSA-L
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;-1;+3/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;;/m1../s1

HIDE SMILES / InChI

Molecular Formula C62H87N13O14P
Molecular Weight 1269.4066
Charge -3
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 13 / 14
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Co
Molecular Weight 58.9332
Charge 3
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula CHN
Molecular Weight 27.0253
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 is naturally found in foods including meat (especially liver and shellfish), eggs, and milk products.Vitamin B12 is essential to growth, cell reproduction, hematopoiesis, and nucleoprotein and myelin synthesis. Cells characterized by rapid division (e.g., epithelial cells, bone marrow, myeloid cells) appear to have the greatest requirement for vitamin B12. Vitamin B12 can be 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. In the absence of coenzyme B12, tetrahydrofolate cannot be regenerated from its inactive storage form, 5- methyltetrahydrofolate, and a functional folate deficiency occurs. 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 deficiency results in megaloblastic anemia, GI lesions, and neurologic damage that begins with an inability to produce myelin and is followed by gradual degeneration of the axon and nerve head. Cyanocobalamin is the most stable and widely used form of vitamin B12, and has hematopoietic activity apparently identical to that of the antianemia factor in purified liver extract. Parenteral (intramuscular) administration of vitamin B12 completely reverses the megaloblastic anemia and GI symptoms of vitamin B12 deficiency.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Cobal 1000
Primary
Cobal 1000
Primary
Cobal 1000
Primary
Cobal 1000

Cmax

ValueDoseCo-administeredAnalytePopulation
28175 pg/mL
10 mg single, oral
CYANOCOBALAMIN serum
Homo sapiens
12847 pg/mL
5 mg single, oral
CYANOCOBALAMIN serum
Homo sapiens
1239 pg/mL
5 mg single, oral
CYANOCOBALAMIN serum
Homo sapiens
221287 pg/mL
1 mg single, intravenous
CYANOCOBALAMIN serum
Homo sapiens
757.96 pg/mL
500 μg single, nasal
CYANOCOBALAMIN unknown
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
127494 pg × h/mL
10 mg single, oral
CYANOCOBALAMIN serum
Homo sapiens
54609 pg × h/mL
5 mg single, oral
CYANOCOBALAMIN serum
Homo sapiens
23165 pg × h/mL
5 mg single, oral
CYANOCOBALAMIN serum
Homo sapiens
235165 pg × h/mL
1 mg single, intravenous
CYANOCOBALAMIN serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
25.31 h
10 mg single, oral
CYANOCOBALAMIN serum
Homo sapiens
30.06 h
5 mg single, oral
CYANOCOBALAMIN serum
Homo sapiens
25.95 h
5 mg single, oral
CYANOCOBALAMIN serum
Homo sapiens
15.53 h
1 mg single, intravenous
CYANOCOBALAMIN serum
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Pernicious Anemia Initial dose: 1000 mcg intramuscularly or deep subcutaneous once a day for 6 to 7 days If clinical improvement and reticulocyte response is seen from the above dosing: -100 mcg every other day for 7 doses, then: -100 mcg every 3 to 4 days for 2 to 3 weeks, then: Maintenance dose: 100 to 1000 mcg monthly Duration of therapy: Life Usual Adult Dose for B12 Nutritional Deficiency 25 to 2000 mcg orally daily Usual Adult Dose for Schilling Test 1000 mcg intramuscularly is the flushing dose Usual Pediatric Dose for B12 Nutritional Deficiency 0.5 to 3 mcg daily
Route of Administration: Parenteral
In Vitro Use Guide
Cyanocobalamin showed a marked antiparasitic activity against epimastigotes (50% inhibitory concentration [IC(50)], 2.42 uM), amastigotes (IC(50), 10.69 uM), and trypomastigotes (IC(50), 9.46 uM) of of Trypanosoma cruzi in vitro.
Substance Class Chemical
Record UNII
P6YC3EG204
Record Status Validated (UNII)
Record Version