U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C62H88N13O14P.CH3.Co
Molecular Weight 1344.3823
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLCOBALAMIN

SMILES

[CH3-].[Co+3].[H][C@]12[N-]C(=C(C)C3=NC(=CC4=NC(=C(C)C5=N[C@]1(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)[C@](C)(CCC(=O)NC[C@H](C)OP([O-])(=O)O[C@@H]6[C@@H](CO)O[C@@H]([C@@H]6O)N7C=NC8=C7C=C(C)C(C)=C8)[C@H]2CC(N)=O

InChI

InChIKey=ZFLASALABLFSNM-QBOHGLHMSA-L
InChI=1S/C62H90N13O14P.CH3.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;;/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);1H3;/q;-1;+3/p-2/t31-,34+,35+,36+,37-,41+,52+,53+,56+,57-,59+,60-,61-,62-;;/m0../s1

HIDE SMILES / InChI
Methylcobalamin (also known as mecobalamin, MeCbl, or MeB12) is one of the two forms of biologically active vitamin B12. Methyl-B12 is the principal form of circulating vitamin B12, hence the form, which is transported into peripheral tissue. Methylcobalamin is absorbed by the intestine by a specific mechanism, which uses the intrinsic factor, and by a diffusion process in which approximately 1% of the ingested dose is absorbed. Cyanocobalamin and hydroxycobalamin are forms of the vitamin that require conversion to methylcobalamin. Methylcobalamin alone or in combination with others compound are used to treat different diseases. Being a component of CEREFOLIN NAC it is used to treat Alzheimer's dementia. As a part of METANX® tablets is used for the dietary management of endothelial dysfunction in patients with diabetic peripheral neuropathy. Methylcobalamin exerted therapeutic effects on neuropathic pain in diabetics, possibly through its neurosynthesis and neuroprotective actions. The possible mechanisms can be considered as follows. (1) Methylcobalamin improved nerve conduction velocity; (2) methylcobalamin promoted injured nerve regeneration, recovering the neuromuscular functions in peripheral hyperalgesia and allodynia; and (3) methylcobalamin inhibited the ectopic spontaneous discharges from peripheral primary sensory neurons in neuropathic pain states. Methylcobalamin is the only form that can cross the blood-brain barrier and so can directly protect brain cells from degeneration. While crossing the barrier, it also stimulates production of serotonin, a chemical neurotransmitter responsible for elevated mood; research where Alzheimer’s patients were administered methylcobalamin showcased improvements in memory, communication skills, and emotions. It also helps form the myelin sheath, the insular coating around nerve cells that allow for electrical impulses to travel through the nervous system more efficiently.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
CerefolinNAC

Approved Use

Unknown
Primary
Metanx

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Methylcobalamin prevents mutant superoxide dismutase-1-induced motor neuron death in vitro.
2017 Jan 18
Patents

Patents

Sample Use Guides

Mecobalamin injection 0.5 mg/ ml administered as injection 3 times a week for four weeks oral (Metanx): one tablet twice daily
Route of Administration: Other
In Vitro Use Guide
Unknown
Name Type Language
METHYLCOBALAMIN
DSC   MI   USP-RS   VANDF  
Common Name English
CO-METHYLCOBINAMIDE DIHYDROGEN PHOSPHATE (ESTER) INNER SALT 3'-ESTER WITH 5,6-DIMETHYL-1-.ALPHA.-D-RIBOFURANOSYL-1H-BENZIMIDAZOLE-.KAPPA.N(SIP 3)
Common Name English
mecobalamin [INN]
Common Name English
MECOBALAMIN [USAN]
Common Name English
MECOBALAMIN [MART.]
Common Name English
Mecobalamin [WHO-DD]
Common Name English
MECOBALAMIN
INN   MART.   USAN   WHO-DD  
INN   USAN  
Official Name English
ADESTOLMIN
Brand Name English
METHYL VITAMIN B12
Common Name English
METHYLCOBALAMIN [MI]
Common Name English
METHYCOBAL
Brand Name English
METHYL-5,6-DIMETHYLBENZIMIDAZOLYLCOBALAMIN
Common Name English
MECOBALAMIN [JAN]
Common Name English
METHYLCOBALAMIN [DSC]
Common Name English
METHYLCOBALAMIN [VANDF]
Common Name English
METHYLCOBALAMIN [USP-RS]
Common Name English
METHYL B12
Common Name English
Classification Tree Code System Code
WHO-VATC QB03BA05
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
DSLD 2668 (Number of products:2782)
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
WHO-ATC B03BA05
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
LIVERTOX 589
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
DSLD 520 (Number of products:2)
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
Code System Code Type Description
INN
3148
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID5048631
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
NCI_THESAURUS
C173805
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
236-535-3
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
FDA UNII
BR1SN1JS2W
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
WIKIPEDIA
METHYLCOBALAMIN
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
CHEBI
28115
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
MERCK INDEX
m7386
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY Merck Index
CAS
13422-55-4
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
EVMPD
SUB08686MIG
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
DAILYMED
BR1SN1JS2W
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
MESH
C019476
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
SMS_ID
100000088210
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
DRUG BANK
DB03614
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
RXCUI
29421
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY RxNorm
PUBCHEM
73415798
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
RS_ITEM_NUM
1424550
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY
DRUG CENTRAL
4600
Created by admin on Fri Dec 15 16:53:45 GMT 2023 , Edited by admin on Fri Dec 15 16:53:45 GMT 2023
PRIMARY