CAS 85-79-0|dibucaine|Dibucaine|狄布卡因|2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide|Dibucaine|CINCHOCAINE|Cinchocaine|Sovcaine|Nupercainal|Dermacaine|cinchocaine hydrochloride|Heavy S...

General Information

Structure

Molecular Formula

C₂₀H₂₉N₃O₂

Molecular Mass

343.46316

Exact Mass

343.22597718

Charge

InChI

InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)

InChIKey

PUFQVTATUTYEAL-UHFFFAOYSA-N

Canonic Smiles

CCCCOc1nc2ccccc2c(c1)C(=O)NCCN(CC)CC

Isomeric Smiles

O(c1nc2c(c(C(=O)NCCN(CC)CC)c1)cccc2)CCCC

Calculated Properties

JChem

LogD (pH = 7.4)

2.05

LogD (pH = 5.5)

0.48

Log P

3.70

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.04

Polar Surface Area

54.46

Polarizability

40.93

Molar Refractivity

102.12

LOG S

-4.60

Data Source

Names and Identifiers

IUPAC Traditional name

dibucaine

Synonyms

Dibucaine狄布卡因DibucaineCINCHOCAINECINCHOCAINE2-Butoxy-quinoline-4-carboxylic acid (2-diethylamino-ethyl)-amidedibucaine basealpha-butyloxycinchonic acid-gamma-diethylethylenediaminedibucainecinchocaine2-butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamideDIBUCAINEDibucaine2-butoxy-N-(alpha-diethylaminoethyl)cinchoninamide2-butoxy-N-(2-(diethylamino)ethyl)cinchoninamidealpha-butyloxycinchoninic acid diethylethylenediamideN-(2-(diethylamino)ethyl)-2-butoxycinchoninamide2-N-butoxy-N-(2-diethylaminoethyl)cinchoninamide2-butoxyquinoline-4-carboxylic acid diethylaminoethylamide2-butoxy-N-(beta-diethylaminoethyl)cinchoninamide

IUPAC name

2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide

Brand Name

SovcaineCinchocaineDermacaineNupercainalHeavy Solution NupercaineCinchocaine HCLcinchocaine hydrochlorideNupercaineDibucaine hydrochlorideDibucaine baseDibucain

International Nonproprietary Name (INN)

cincocainiocinchocainumcinchocaine

Names and Identifiers

Registration numbers

MDL Number

MFCD00047595

CAS Number

85-79-0

EC Number

201-632-1

PubChem SID

248932381609638724650673485441075

PubChem CID

3025

ATC CODE

N01BB06S02DA04C05AD04D04AB02S01HA06

CHEMBL

1086CHEMBL1086

Unique Ingredient Identifier

L6JW2TJG99

Chemspider ID

2917

CHEBI ID

247956CHEBI:4500CHEBI:247956

KEGG ID

DrugBank ID

Wikipedia Title

BindingDB Database

BRENDA Database

3.1.1.83.1.4.112.3.1.232.7.7.15

KEGG DRUG Database

D00733

PubMed Citation Links

287322723953476

MetaboLights Database

MTBLS1642MTBLS2878MTBLS673MTBLS1411

HMDB Database

HMDB0014668

Drug Central Database

Reaxys Registry

Patent number

ACToR Database

LINCS Database

NMRShiftDB Database

CompTox Database

Beilstein Number

SureChEMBL Database

Registration numbers

Properties

Physical Property

Solubility

42 mg/L

Hydrophobicity(logP)

4.2

Product Information

Certificate of Analysis

Download link

Grade

analytical standard

Pharmacology Properties

Admin Routes

topical, intravenous (equine euthanasia)

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00527

Drug Groups

approved

Description

A local anesthetic of the amide type now generally used for surface anesthesia. It is one of the most potent and toxic of the long-acting local anesthetics and its parenteral use is restricted to spinal anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1006)

Indication

For production of local or regional anesthesia by infiltration techniques such as percutaneous injection and intravenous regional anesthesia by peripheral nerve block techniques such as brachial plexus and intercostal and by central neural techniques such as lumbar and caudal epidural blocks.

Pharmacology

Dibucaine is an amide-type local anesthetic, similar to lidocaine.

Toxicity

Subcutaneous LD₅₀ in rat is 27 mg/kg. Symptoms of overdose include convulsions, hypoxia, acidosis, bradycardia, arrhythmias and cardiac arrest.

Affected Organisms

Humans and other mammals

Biotransformation

Primarily hepatic.

Absorption

In general, ionized forms (salts) of local anesthetics are not readily absorbed through intact skin. However, both nonionized (bases) and ionized forms of local anesthetics are readily absorbed through traumatized or abraded skin into the systemic circulation.

References

• Abdel-Ghani NT, Youssef AF, Awady MA: Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry. Farmaco. 2005 May;60(5):419-24. [Pubmed]

• Souto-Padron T, Lima AP, Ribeiro Rde O: Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. Parasitol Res. 2006 Sep;99(4):317-20. Epub 2006 Apr 13. [Pubmed]

• Nounou MM, El-Khordagui LK, Khalafallah N: Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles. Acta Pol Pharm. 2005 Sep-Oct;62(5):369-79. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

MP Biomedicals

05201127

MP Biomedicals Rare Chemical collection

Wikipedia

Dibucaine

Sigma Aldrich

D0513

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
强效、长效局部麻醉剂
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D0513.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

ChEBI

CHEBI:247956

A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions.

Molecule Details

References

PubChem Literature

From Data Sources

• Abdel-Ghani NT, Youssef AF, Awady MA: Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry. Farmaco. 2005 May;60(5):419-24. Pubmed

• Souto-Padron T, Lima AP, Ribeiro Rde O: Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. Parasitol Res. 2006 Sep;99(4):317-20. Epub 2006 Apr 13. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

dibucaine

Synonyms

IUPAC name

2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide

Brand Name

SovcaineCinchocaineDermacaineNupercainalHeavy Solution NupercaineCinchocaine HCLcinchocaine hydrochlorideNupercaineDibucaine hydrochlorideDibucaine baseDibucain

International Nonproprietary Name (INN)

cincocainiocinchocainumcinchocaine

Registration numbers

MDL Number

MFCD00047595

CAS Number

85-79-0

EC Number

201-632-1

PubChem SID

248932381609638724650673485441075

PubChem CID

3025

ATC CODE

N01BB06S02DA04C05AD04D04AB02S01HA06

CHEMBL

1086CHEMBL1086

Unique Ingredient Identifier

L6JW2TJG99

Chemspider ID

2917

CHEBI ID

247956CHEBI:4500CHEBI:247956

KEGG ID

DrugBank ID

Wikipedia Title

BindingDB Database

BRENDA Database

3.1.1.83.1.4.112.3.1.232.7.7.15

KEGG DRUG Database

D00733

PubMed Citation Links

287322723953476

MetaboLights Database

MTBLS1642MTBLS2878MTBLS673MTBLS1411

HMDB Database

HMDB0014668

Drug Central Database

Reaxys Registry

Patent number

ACToR Database

LINCS Database

NMRShiftDB Database

CompTox Database

Beilstein Number

SureChEMBL Database

Molecule Details

DB00527

Drug Groups

approved

Description

Indication

Pharmacology

Dibucaine is an amide-type local anesthetic, similar to lidocaine.

Toxicity

Subcutaneous LD₅₀ in rat is 27 mg/kg. Symptoms of overdose include convulsions, hypoxia, acidosis, bradycardia, arrhythmias and cardiac arrest.

Affected Organisms

Humans and other mammals

Biotransformation

Primarily hepatic.

Absorption

References

• Abdel-Ghani NT, Youssef AF, Awady MA: Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry. Farmaco. 2005 May;60(5):419-24. [Pubmed]

• Souto-Padron T, Lima AP, Ribeiro Rde O: Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. Parasitol Res. 2006 Sep;99(4):317-20. Epub 2006 Apr 13. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

MP Biomedicals

05201127

MP Biomedicals Rare Chemical collection

D0513

References

PubChem Literature

From Data Sources

• Abdel-Ghani NT, Youssef AF, Awady MA: Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry. Farmaco. 2005 May;60(5):419-24. Pubmed

• Souto-Padron T, Lima AP, Ribeiro Rde O: Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. Parasitol Res. 2006 Sep;99(4):317-20. Epub 2006 Apr 13. Pubmed

Bioactivity

PubChem BioAssay

Properties

Physical Property

Solubility

42 mg/L

Hydrophobicity(logP)

4.2

Product Information

Certificate of Analysis

Download link

Grade

analytical standard

Pharmacology Properties

Admin Routes

topical, intravenous (equine euthanasia)

Molecule

ID:409