CAS 27848-84-6|Nicergoline|Vasospan|Nimergoline|Nicergolin [German]|nicergoline|Nicergolinum [INN-Latin]|Nargoline|Nimergoline Base|Nicotergoline|Nicergolina [Dcit]|MNE|Nicergoline [Usan:Ban:Inn:Jan...

General Information

Structure

Molecular Formula

C₂₄H₂₆BrN₃O₃

Molecular Mass

484.38554

Exact Mass

483.11575371

Charge

InChI

InChI=1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1

InChIKey

YSEXMKHXIOCEJA-FVFQAYNVSA-N

Canonic Smiles

CO[C@]12C[C@@H](COC(=O)c3cncc(c3)Br)CN([C@@H]1Cc1c3c2cccc3n(c1)C)C

Isomeric Smiles

Brc1cc(C(=O)OC[C@@H]2C[C@@]3(OC)[C@H](N(C2)C)Cc2c4c3cccc4n(c2)C)cnc1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

1.1122493

LogD (pH = 7.4)

2.885367

Log P

3.695325

Molar Refractivity

123.2974

Polarizability

48.515564

Polar Surface Area

56.59

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.99

LOG S

-4.58

Solubility (Water)

1.27e-02 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

NicergolineNicergoline尼麦角林5-溴烟酸 10-甲氧基-1,6-二甲基麦角灵-8-甲酯NicotergolineSermionNimergolineNargoline

Brand Name

VasospanNimergolineNicergolin [German]Nicergolinum [INN-Latin]NargolineNimergoline BaseNicotergolineNicergolina [Dcit]MNENicergoline [Usan:Ban:Inn:Jan]Sermion

IUPAC Traditional name

nicergoline [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),9,12(16),13-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate

IUPAC name

[(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),9,12(16),13-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate

Names and Identifiers

Registration numbers

CAS Number

27848-84-6

EC Number

248-694-6

PubChem SID

2489784316096404446508741

MDL Number

MFCD00869626

PubChem CID

34040

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

3.3

Product Information

Purity

~97% (TLC)

Grade

analytical standard, for drug analysis

Application(s)

Cerebroprotective props

Has been used in treatment of senile dementia

Pharmacology Properties

Gene Information

human ... ADRA1A(148)

Mechanism of Action

a1-Adrenoceptor antagonist

Calcium channel antagonist

Peripheral vasodilator

Cholinergic

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00699

Drug Groups

approved

Description

An ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It has been suggested to ameliorate cognitive deficits in cerebrovascular disease. [PubChem]

Indication

For the treatment of senile dementia, migraines of vascular origin, transient ischemia, platelet hyper-aggregability, and macular degeneration.

Pharmacology

Nicergoline is a potent vasodilator (improves brain blood flow). On the cerebral level it prompts a lowering of vascular resistance, an increase in arterial flow and stimulates the use of oxygen and glucose. Nicergoline also improves blood circulation in the lungs and limbs and has been shown to inhibit blood platelet aggregation.

Affected Organisms

Humans and other mammals

References

• Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A: Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52. [Pubmed]

External Links

• [Wikipedia]

Sigma Aldrich

N7889

Biochem/physiol Actions
大脑和周边血管舒张剂
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N7889.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Molecule Details

References

PubChem Literature

From Data Sources

• Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A: Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52. Pubmed

• Sioufi, A. et al., Biomed. Chromatogr., 1992, 6, 9, (hplc, metab)

• Bernardi, L. et al., Farmaco, Ed. Sci., 1975, 30, 789, (synth, pharmacol)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1731

• Neumann, B.W. et al., Arzneim.-Forsch., 1979, 29, 1206, (numerous papers)

• Fumagalli, M. et al., Contact Dermatitis, 1992, 27, 256

• Carfagna, N. et al., Neurosci. Lett., 1995, 197, 195, (pharmacol)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, NDM000

• Takahashi, K. et al., Br. J. Pharmacol., 1990, 100, 705, (pharmacol)

• Arrigo, A. et al., Int. J. Clin. Pharmacol. Res., Suppl. 1, 1982, 11, 33, (use)

• Shintomi, K. et al., J. Pharmacobio-Dyn., 1987, 10, 35, (pharmacol, tox)

• Banno, K. et al., J. Chromatogr., 1991, 568, 375, (hplc)

• Arcari, G. et al., Experientia, 1972, 28, 819

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7056, (synonyms)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

Synonyms

NicergolineNicergoline尼麦角林5-溴烟酸 10-甲氧基-1,6-二甲基麦角灵-8-甲酯NicotergolineSermionNimergolineNargoline

Brand Name

VasospanNimergolineNicergolin [German]Nicergolinum [INN-Latin]NargolineNimergoline BaseNicotergolineNicergolina [Dcit]MNENicergoline [Usan:Ban:Inn:Jan]Sermion

IUPAC Traditional name

IUPAC name

Registration numbers

CAS Number

27848-84-6

EC Number

248-694-6

PubChem SID

2489784316096404446508741

MDL Number

MFCD00869626

PubChem CID

34040

Properties

Physical Property

Hydrophobicity(logP)

3.3

Product Information

Purity

~97% (TLC)

Grade

analytical standard, for drug analysis

Application(s)

Cerebroprotective props

Has been used in treatment of senile dementia

Pharmacology Properties

Gene Information

human ... ADRA1A(148)

Mechanism of Action

a1-Adrenoceptor antagonist

Calcium channel antagonist

Peripheral vasodilator

Cholinergic

Molecule Details

DrugBank

DB00699

Drug Groups

approved

Description

An ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It has been suggested to ameliorate cognitive deficits in cerebrovascular disease. [PubChem]

Indication

For the treatment of senile dementia, migraines of vascular origin, transient ischemia, platelet hyper-aggregability, and macular degeneration.

Pharmacology

Affected Organisms

Humans and other mammals

References

• Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A: Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52. [Pubmed]

External Links

• [Wikipedia]

Sigma Aldrich

N7889

References

PubChem Literature

From Data Sources

• Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A: Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52. Pubmed

• Sioufi, A. et al., Biomed. Chromatogr., 1992, 6, 9, (hplc, metab)

• Bernardi, L. et al., Farmaco, Ed. Sci., 1975, 30, 789, (synth, pharmacol)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1731

• Neumann, B.W. et al., Arzneim.-Forsch., 1979, 29, 1206, (numerous papers)

• Fumagalli, M. et al., Contact Dermatitis, 1992, 27, 256

• Carfagna, N. et al., Neurosci. Lett., 1995, 197, 195, (pharmacol)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, NDM000

• Takahashi, K. et al., Br. J. Pharmacol., 1990, 100, 705, (pharmacol)

• Arrigo, A. et al., Int. J. Clin. Pharmacol. Res., Suppl. 1, 1982, 11, 33, (use)

• Shintomi, K. et al., J. Pharmacobio-Dyn., 1987, 10, 35, (pharmacol, tox)

• Banno, K. et al., J. Chromatogr., 1991, 568, 375, (hplc)

• Arcari, G. et al., Experientia, 1972, 28, 819

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7056, (synonyms)

Bioactivity

PubChem BioAssay

Molecule

ID:581