CYANOCOBALAMIN

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 Search

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	CHN
Molecular Weight	27.0253
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C62H87N13O14P
Molecular Weight	1269.4066
Charge	-3
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	13 / 14
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Co
Molecular Weight	58.933195
Charge	3
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021642s002lbl.pdf | https://www.drugbank.ca/drugs/DB00115

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 Target	Pharmacology	Condition	Potency
Methylmalonyl-CoA mutase, mitochondrial 1 Target ID: P22033 Gene ID: 4594.0 Gene Symbol: MUT Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB00115 \| https://www.ncbi.nlm.nih.gov/pubmed/17011224 \| https://www.ncbi.nlm.nih.gov/pubmed/16813422	Binding Agent 1076
Methionine synthase 4 Target ID: Q99707 Gene ID: 4548.0 Gene Symbol: MTR Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB00115	Binding Agent 1076

Conditions

Condition	Modality	Highest Phase	Product
Addisonian (pernicious) anemia 1 Sources: https://www.drugs.com/pro/b-2-inject-kit.html https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021642s002lbl.pdf	Primary	Approved 8583	Cobal 1000 Approved Use Cyanocobalamin is indicated for vitamin B 12 deficiencies due to malabsorption which may be associated with the following conditions: Addisonian (pernicious) anemia Gastrointestinal pathology, dysfunction, or surgery, including gluten enteropathy or sprue, small bowel bacteria overgrowth, total or partial gastrectomy Fish tapeworm infestation Malignancy of pancreas or bowel Folic acid deficiency Launch Date 1949
Folic acid deficiency 2 Sources: https://www.drugs.com/pro/b-2-inject-kit.html https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021642s002lbl.pdf	Primary	Approved 8583	Cobal 1000 Approved Use Cyanocobalamin is indicated for vitamin B 12 deficiencies due to malabsorption which may be associated with the following conditions: Addisonian (pernicious) anemia Gastrointestinal pathology, dysfunction, or surgery, including gluten enteropathy or sprue, small bowel bacteria overgrowth, total or partial gastrectomy Fish tapeworm infestation Malignancy of pancreas or bowel Folic acid deficiency Launch Date 1949
Fish tapeworm infestation 1 Sources: https://www.drugs.com/pro/b-2-inject-kit.html	Primary	Approved 8583	Cobal 1000 Approved Use Cyanocobalamin is indicated for vitamin B 12 deficiencies due to malabsorption which may be associated with the following conditions: Addisonian (pernicious) anemia Gastrointestinal pathology, dysfunction, or surgery, including gluten enteropathy or sprue, small bowel bacteria overgrowth, total or partial gastrectomy Fish tapeworm infestation Malignancy of pancreas or bowel Folic acid deficiency Launch Date 1949
Malignancy of pancreas or bowel 1 Sources: https://www.drugs.com/pro/b-2-inject-kit.html	Primary	Approved 8583	Cobal 1000 Approved Use Cyanocobalamin is indicated for vitamin B 12 deficiencies due to malabsorption which may be associated with the following conditions: Addisonian (pernicious) anemia Gastrointestinal pathology, dysfunction, or surgery, including gluten enteropathy or sprue, small bowel bacteria overgrowth, total or partial gastrectomy Fish tapeworm infestation Malignancy of pancreas or bowel Folic acid deficiency Launch Date 1949

C_max

Value	Dose	Co-administered	Analyte	Population
28175 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: SALCAPROZATE SODIUM	SALCAPROZATE SODIUM	CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12847 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: SALCAPROZATE SODIUM	SALCAPROZATE SODIUM	CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1239 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
221287 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
757.96 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021642s002lbl.pdf	500 μg single, nasal dose: 500 μg route of administration: Nasal experiment type: SINGLE co-administered:		CYANOCOBALAMIN plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
127494 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: SALCAPROZATE SODIUM	SALCAPROZATE SODIUM	CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
54609 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: SALCAPROZATE SODIUM	SALCAPROZATE SODIUM	CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
23165 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
235165 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
25.31 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: SALCAPROZATE SODIUM	SALCAPROZATE SODIUM	CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
30.06 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: SALCAPROZATE SODIUM	SALCAPROZATE SODIUM	CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
25.95 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
15.53 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21722960/	1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered:		CYANOCOBALAMIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
100 ug 1 times / day multiple, intramuscular Recommended Dose: 100 ug, 1 times / day Route: intramuscular Route: multiple Dose: 100 ug, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe	Other AEs: Anxiety, Incoordination... Other AEs: Anxiety (1 patient) Incoordination (1 patient) Nervousness (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe
100 ug 1 times / day multiple, subcutaneous Recommended Dose: 100 ug, 1 times / day Route: subcutaneous Route: multiple Dose: 100 ug, 1 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe	Sources: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe
500 ug 1 times / week multiple, intranasal Recommended Dose: 500 ug, 1 times / week Route: intranasal Route: multiple Dose: 500 ug, 1 times / week Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf	Other AEs: Headache, Nausea... Other AEs: Headache (1 patient) Nausea (1 patient) Rhinitis (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf

AEs

AE	Significance	Dose	Population
Anxiety	1 patient	100 ug 1 times / day multiple, intramuscular Recommended Dose: 100 ug, 1 times / day Route: intramuscular Route: multiple Dose: 100 ug, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe
Incoordination	1 patient	100 ug 1 times / day multiple, intramuscular Recommended Dose: 100 ug, 1 times / day Route: intramuscular Route: multiple Dose: 100 ug, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe
Nervousness	1 patient	100 ug 1 times / day multiple, intramuscular Recommended Dose: 100 ug, 1 times / day Route: intramuscular Route: multiple Dose: 100 ug, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=562e0ff4-a96c-4390-acbf-afa4baa0b8fe
Headache	1 patient	500 ug 1 times / week multiple, intranasal Recommended Dose: 500 ug, 1 times / week Route: intranasal Route: multiple Dose: 500 ug, 1 times / week Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf
Nausea	1 patient	500 ug 1 times / week multiple, intranasal Recommended Dose: 500 ug, 1 times / week Route: intranasal Route: multiple Dose: 500 ug, 1 times / week Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf
Rhinitis	1 patient	500 ug 1 times / week multiple, intranasal Recommended Dose: 500 ug, 1 times / week Route: intranasal Route: multiple Dose: 500 ug, 1 times / week Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19722slr006_nascobal_lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA00IBP4	https://www.aablocks.com/goods/Goods/detail?id=AA00IBP4
Aaron Chemicals	AR00ICGW	http://www.aaronchem.com/68-19-9
abcr GmbH	AB120043	http://www.abcr.de/shop/en/AB120043
Accela ChemBio Inc	SY010769	http://www.accelachem.com/cn/search.html?keyword=SY010769&attname=GoodsCode
Achemtek	0104-006654	http://www.achemtek.com/68-19-9
Acorn PharmaTech	ACN-052813	http://www.acornpharmatech.com/
AHH Chemical co.,ltd	MT-60425	http://www.ahhchemical.com/product/MT-60425.html
AK Scientific, Inc. (AKSCI)	H486	http://www.aksci.com/item_detail.php?cat=H486
AK Scientific, Inc. (AKSCI)	V0344	http://www.aksci.com/item_detail.php?cat=V0344
Alfa Chemistry	13408-78-1	https://www.alfa-chemistry.com/cas_13408-78-1.htm
Ambinter	Amb17678773	http://www.ambinter.com/reference/17678773
Ambinter	Amb22337667	http://www.ambinter.com/reference/22337667
Ambinter	Amb22349366	http://www.ambinter.com/reference/22349366
Ambinter	Amb22349379	http://www.ambinter.com/reference/22349379
Ambinter	Amb22352118	http://www.ambinter.com/reference/22352118
Aurora Fine Chemicals LLC	A17.876.689	http://online.aurorafinechemicals.com/info?ID=A17.876.689
AvaChem Scientific	3627	http://www.avachem.com/productSearch.asp?3627
Avantor Inc	200011-798	https://us.vwr.com/store/product/7520621/vitamin-b12-cyanocobalamin-96
Avantor Inc	700009-354	https://us.vwr.com/store/product/7829224/vitamin-b12-cyanocobalamin-crystalline-usp
Avantor Inc	BT130400-1G	https://us.vwr.com/store/product/16637008/vitamin-b12-cyanocobalamin-98
Avantor Inc	BT130400-25G	https://us.vwr.com/store/product/16637008/vitamin-b12-cyanocobalamin-98
Avantor Inc	BT130400-5G	https://us.vwr.com/store/product/16637008/vitamin-b12-cyanocobalamin-98
BioCrick	BCC4878	http://www.biocrick.com/Vitamin-B12-BCC4878.html
BioCyc	CPD-315	https://biocyc.org/compound?orgid=META&id=CPD-315
China MainChem Co., Ltd	MS68-19-9	https://www.mainchem.com/product/vitamin-b12/
eNovation Chemicals	D389161	https://www.enovationchem.com/ProductDetails.asp?ProductID=D389161
eNovation Chemicals	D689996	https://www.enovationchem.com/ProductDetails.asp?ProductID=D689996
Hairui	HR129121	http://www.hairuichem.com/en/product/68-19-9.html
iChemical	EBD31886	http://www.ichemical.com/products/68-19-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
LGC Standards	DRE-C11798500	https://www.lgcstandards.com/US/en/p/DRE-C11798500
LGC Standards	LGCAMP1449.00-01	https://www.lgcstandards.com/US/en/p/LGCAMP1449.00-01
LGC Standards	LGCFOR1449.00	https://www.lgcstandards.com/US/en/p/LGCFOR1449.00
LGC Standards	MM1449.00	https://www.lgcstandards.com/US/en/p/MM1449.00
MolPort	MolPort-016-633-264	https://www.molport.com/shop/molecule-link/MolPort-016-633-264
MolPort	MolPort-035-395-693	https://www.molport.com/shop/molecule-link/MolPort-035-395-693
Renno Tech	RL04605	http://www.rennotech.com/product_show.asp?id=4854
Selleck Chemicals	S1902	http://www.selleckchem.com/products/Vitamin-B12.html
Sigma-Aldrich	33-0550_SAJ	http://www.sigmaaldrich.com/catalog/product/saj/330550?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	43107_SIAL	http://www.sigmaaldrich.com/catalog/product/sial/43107?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	47869_SUPELCO	http://www.sigmaaldrich.com/catalog/product/supelco/47869?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C3000000_SIAL	http://www.sigmaaldrich.com/catalog/product/sial/c3000000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C3607_SIAL	http://www.sigmaaldrich.com/catalog/product/sial/c3607?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
TCI (Tokyo Chemical Industry)	C0449	http://www.tcichemicals.com/eshop/en/us/commodity/C0449/index.html
VladaChem	VL145048	https://www.vladachem.com/product.php?products=68-19-9
VladaChem	VL162530	https://www.vladachem.com/product.php?products=68-19-9
VladaChem	VL262179-500MG	https://www.vladachem.com/product.php?products=68-19-9
Yuhao Chemical	HL1065	http://www.chemyuhao.com/68-19-9.html

PubMed

Title	Date	PubMed
Decreased glutathione and elevated hair mercury levels are associated with nutritional deficiency-based autism in Oman.	2014-06	24676906
Prevalence and features of peripheral neuropathy in Parkinson's disease patients under different therapeutic regimens.	2014-01	24099722
Preventing Alzheimer's disease-related gray matter atrophy by B-vitamin treatment.	2013-06-04	23690582
Dietary supplementation with methyl donors reduces fatty liver and modifies the fatty acid synthase DNA methylation profile in rats fed an obesogenic diet.	2013-01	22648174
Mutations in ABCD4 cause a new inborn error of vitamin B12 metabolism.	2012-10	22922874
Evaluation of drugs with specific organ toxicities in organ-specific cell lines.	2012-03	22166485
Mechanism for prevention of alcohol-induced liver injury by dietary methyl donors.	2010-05	20118189
Methotrexate-induced myelopathy responsive to substitution of multiple folate metabolites.	2010-05	19821069
Mechanism of vitamin B12-responsiveness in cblC methylmalonic aciduria with homocystinuria.	2009-12	19700356
Influence of cobalamin on arsenic metabolism in Bangladesh.	2009-11	20049124
Delusional parasitosis in neurological patients.	2009-09-25	20430233
A case report of 46,XX,del(21)(q22) de novo deletion associated with Imerslund-Grasbeck syndrome.	1996-10	9001810
Risk factors for dideoxynucleoside-induced toxic neuropathy in patients with the human immunodeficiency virus infection.	1995-10-01	7552481
[Neonatal hemolytic and uremic syndrome, methylmalonic aciduria and homocystinuria due to intracellular vitamin B12 deficiency].	1994-08	7842113
The clinical potential of ademetionine (S-adenosylmethionine) in neurological disorders.	1994-08	7527320
[Neonatal hemolytic-uremic syndrome, methylmalonic aciduria and homocystinuria caused by intracellular vitamin B 12 deficiency. Value of etiological diagnosis].	1993-11	8060203
Uncommon chiasmal lesions: demyelinating disease, vasculitis, and cobalamin deficiency.	1993-08	8220105
Reversible dementia caused by vitamin B12 deficiency.	1993-02	8426046
Orthostatic hypotension induced by vitamin B12 deficiency.	1991-06	2037751
Maternal vegan diet causing a serious infantile neurological disorder due to vitamin B12 deficiency.	1991-01	2044594
[Regressive dementia-like syndrome caused by vitamin B 12 deficiency without hematologic abnormalities in a 92-year old patient].	1990-11-03	2147278
Glycosylated haemoglobin (HbA1c) in iron- and vitamin B12 deficiency.	1990-02	2299304
Sensory peripheral neuropathy of vitamin B12 deficiency: a primary demyelinating disease?	1988-01	2835439
A case of vitamin B12 deficiency megaloblastic anemia following total gastrectomy.	1988	3057748
Nutritional vitamin B12 deficiency in a breast-fed infant of a vegan-diet mother.	1986-04	3948463
Gaucher's disease: a case report with coincidental vitamin B12 deficiency anaemia.	1985-09	4055326
Acute organic psychosis caused by thyrotoxicosis and vitamin B12 deficiency: case report.	1985-03	3972777
[Agranulocytosis and impairment of liver functions terminating in death following vitamin B12 injection in pernicious anemia: report of a case].	1984-11	6533326
Folic acid and the nervous system.	1983-12	6685839
Totally vegetarian diets and infant nutrition.	1982-10	6812012
[A case of metabolic encephalopathy caused by vitamin B 12-dependent methylmalonicoaciduria].	1981-02	6965256
[A case of metabolic encephalopathy caused by vitamin B 12-dependent methylmalonicaciduria].	1981	7270059
Platelet monoamine oxidase activity in megaloblastic anaemia.	1980-10	7430361
The effect of vitamin B12 on tetracycline-induced fatty liver.	1980-09	7445574
The prevalence and nature of anemia among apparently normal subjects in Fiji.	1979-07	523178
[Constitutional megaloblastic anaemia due to vitamin B12 deficit (Imerslund's disease). Report of a case. (author's transl)].	1979	538553
[Anemia caused by folic acid or vitamin B-12 deficiency].	1978-12-01	749158
Management of anemia in a general city hospital: value of chart review in establishing deficiencies in care.	1978-01-07	620384
[Influence of methylcobalamin and cyanocobalamin on the neoplastic process in rats].	1977-09-01	199903
Reversal of ineffective erythropoiesis in pernicious anaemia following vitamin B12 therapy.	1977-02	857850
A qualitative platelet defect in severe vitamin B 12 deficiency. Response, hyperresponse, and thrombosis after vitamin B 12 therapy.	1973-04	4632789
[Diabetic polyneuropathy and myelopathy caused by vitamin B12 deficiency].	1973	4776668
Megaloblastic anemia after anticonvulsive therapy.	1972-11-09	4627864
[Neurologic disorders due to vitamin B 12 deficiency].	1972	4669617
Sensitivity to cyanocobalamin and hydroxocobalamin.	1971-05-01	5572387
Propionate and acetate excretion in chloramphenicol toxicity.	1968-09-21	4175520
Neuropsychiatric aspects of anticonvulsant megaloblastic anaemia.	1968-02-24	4169978
Optic neuropathy caused by vitamin-B12 deficiency in carriers of the fish tapeworm, Diphyllobothrium latum.	1966-03-26	4159602
Anemia due to vitamin B12 deficiency after treatment with folic acid in tropical sprue.	1966-02	4951496
[Cytogenetic and cytologic findings in enzymopenic panmyelopathies and pancytopenias. Familial myelopathy of Fanconi, glutathione-reductase deficiency anemia and megaloblastic B12 deficiency anemia].	1966	5984971

Patents

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 Created by `admin` on `Mon Mar 31 17:50:16 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:16 GMT 2025`
Record UNII	P6YC3EG204
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYANOCOBALAMIN

Official Name

English

Vitamin B12

Preferred Name

English

CYANOCOBALAMINUM [WHO-IP LATIN]

Common Name

English

DICOPAC KIT COMPONENT CYANOCOBALAMIN

Common Name

English

NASCOBAL

Brand Name

English

COBAVITE

Brand Name

English

DODECAVITE

Common Name

English

CYANOCOBALMIN [VANDF]

Common Name

English

RUVITE

Brand Name

English

ANTIPERNICIN

Common Name

English

CYANOCOBALAMIN [USP MONOGRAPH]

Common Name

English

Cyanocobalamin [WHO-DD]

Common Name

English

CYANOCOBALAMIN [VANDF]

Common Name

English

cyanocobalamin [INN]

Common Name

English

NSC-80365

Code

English

CYANOCOBALAMIN [WHO-IP]

Common Name

English

CYANOCOBALAMIN (CONSTITUENT OF CYANOCOBALAMIN) [DSC]

Common Name

English

BERUBIGEN

Brand Name

English

VI-TWEL

Brand Name

English

NORMOCYTIN

Common Name

English

Vitamin b12 nos [WHO-DD]

Common Name

English

CYANOCOBALAMIN [ORANGE BOOK]

Common Name

English

CYANOCOBALAMIN [MART.]

Common Name

English

CYANOCOBALAMIN [USP-RS]

Common Name

English

CYOMIN

Brand Name

English

RUBRATOPE-57 KIT COMPONENT CYANOCOBALAMIN

Common Name

English

RUBIVITE

Brand Name

English

RUBRAMIN

Brand Name

English

CYANOCOBALAMIN CO 57 SCHILLING TEST KIT COMPONENT CYANOCOBALAMIN

Common Name

English

VITAMIN B(BDI1)(BDI2)

Common Name

English

CALOMIST

Brand Name

English

VIBISONE

Brand Name

English

DEPINAR COMPONENT CYANOCOBALAMIN

Common Name

English

CYANOCOBALAMIN [JAN]

Common Name

English

PLECYAMIN

Common Name

English

CYANOCOBALAMIN [EP MONOGRAPH]

Common Name

English

CYANOCOBALAMIN [HSDB]

Common Name

English

VITAMIN B-12

Common Name

English

RUBRAMIN PC

Brand Name

English

VITAMIN B12 [FCC]

Common Name

English

RUBRATOPE-60 KIT COMPONENT CYANOCOBALAMIN

Common Name

English

REDISOL

Brand Name

English

VITAMIN B 12

Common Name

English

RUBIVAMINE

Common Name

English

VITAMIN B12 [MI]

Common Name

English

5,6-Dimethylbenzimidazolyl-Co-cyanocobamide

Common Name

English

BETALIN 12

Brand Name

English

VITAMIN B12 (AS CYANOCOBALAMIN )

Common Name

English

Classification Tree Code System Code

LIVERTOX

1034