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Details

Stereochemistry ACHIRAL
Molecular Formula C18H22N2O2.ClH.H2O
Molecular Weight 352.856
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PHENACAINE HYDROCHLORIDE

SMILES

O.Cl.CCOC1=CC=C(N\C(C)=N\C2=CC=C(OCC)C=C2)C=C1

InChI

InChIKey=YKVNPJUSRMCNMA-UHFFFAOYSA-N
InChI=1S/C18H22N2O2.ClH.H2O/c1-4-21-17-10-6-15(7-11-17)19-14(3)20-16-8-12-18(13-9-16)22-5-2;;/h6-13H,4-5H2,1-3H3,(H,19,20);1H;1H2

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H22N2O2
Molecular Weight 298.3795
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/cfrsearch.cfm?cfrpart=310&showfr=1; https://en.wikipedia.org/wiki/Phenacaine; https://www.ncbi.nlm.nih.gov/pubmed/13108774; https://ceb.nlm.nih.gov/fdanj/bitstream/123456789/58714/3/338000410.txt;

Phenacaine (UNII: V3M4D317W8) also known as holocaine is a local anesthetic used in ophthalmic medicine. Like other local anesthetics it inhibits the specific calmodulin-dependent stimulation of erythrocyte Ca2+-ATPase (ATP phosphohydrolase) and cyclic nucleotide phosphodiesterases (3',5'-cyclic-nucleotide 5'-nucleotidohydrolase) from brain and heart. Basal activities of these enzymes in the absence of calmodulin are relatively unaffected by concentrations of local anesthetics that strongly inhibit the specific stimulation by calmodulin. Increasing calmodulin, but not Ca2+, overcomes the inhibitory action of the local anesthetics on brain phosphodiesterase. However, excess calmodulin does not fully restore activity of erythrocyte CA2+-stimulated ATPase. Although the mechanism(s) by which the local anesthetics act is unclear, they inhibit binding of 125I-labeled calmodulin to the erythrocyte membrane. Antagonism of calmodulin provides a molecular mechanism that may explain the inhibition of many Ca2+-dependent cellular processes by local anesthetics--e.g., Ca2+ transport, exocytosis, excitation-contraction coupling, non-muscle-cell motility, and aggregation. Phenacaine hydrochloride is registered by FDA as an anorectal drug product and is in the list of OTC active ingredients. The Ointment Ophthalmic Holocaine and Epinephrine (1.5% phenacaine hydrochloride) were distributed by National Drug Co., a corporation, Philadelphia, Pa. and in 1939 and was alleged to be misbranded since it contained less phenacaine hydrochloride than indicated by the labeling.

CNS Activity

Curator's Comment: Inhibits the specific calmodulin-dependent stimulation of erythrocyte Ca2+-ATPase and cyclic nucleotide phosphodiesterase from brain.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P54750|||Q9C0L3
Gene ID: 5136.0
Gene Symbol: PDE1A
Target Organism: Homo sapiens (Human)
930.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Local anesthetics, mepacrine, and propranolol are antagonists of calmodulin.
1981 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:21:02 GMT 2023
Edited
by admin
on Fri Dec 15 17:21:02 GMT 2023
Record UNII
70C1507JU9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENACAINE HYDROCHLORIDE
Common Name English
N,N'-BIS(P-ETHOXYPHENYL)ACETAMIDINE MONOHYDROCHLORIDE MONOHYDRATE
Common Name English
PHENACAINE HCL
Common Name English
PHENACAINE HYDROCHLORIDE MONOHYDRATE
MI  
Common Name English
ETHANIMIDAMIDE, N,N'-BIS(4-ETHOXYPHENOL)-, MONOHYDROCHLORIDE, MONOHYDRATE
Common Name English
N(SUP 1),N(SUP 2)-BIS(P-ETHOXYPHENYL)ACETAMIDINE HYDROCHLORIDE MONOHYDRATE
Common Name English
N,N'-BIS(4-ETHOXYPHENYL)ETHANIMIDAMIDE MONOHYDROCHLORIDE MONOHYDRATE
Systematic Name English
PHENACAINE HYDROCHLORIDE MONOHYDRATE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Dec 15 17:21:02 GMT 2023 , Edited by admin on Fri Dec 15 17:21:02 GMT 2023
Code System Code Type Description
PUBCHEM
166536
Created by admin on Fri Dec 15 17:21:02 GMT 2023 , Edited by admin on Fri Dec 15 17:21:02 GMT 2023
PRIMARY
ChEMBL
CHEMBL127123
Created by admin on Fri Dec 15 17:21:02 GMT 2023 , Edited by admin on Fri Dec 15 17:21:02 GMT 2023
PRIMARY
MERCK INDEX
m8587
Created by admin on Fri Dec 15 17:21:02 GMT 2023 , Edited by admin on Fri Dec 15 17:21:02 GMT 2023
PRIMARY Merck Index
CAS
6153-19-1
Created by admin on Fri Dec 15 17:21:02 GMT 2023 , Edited by admin on Fri Dec 15 17:21:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID00210521
Created by admin on Fri Dec 15 17:21:02 GMT 2023 , Edited by admin on Fri Dec 15 17:21:02 GMT 2023
PRIMARY
NCI_THESAURUS
C75099
Created by admin on Fri Dec 15 17:21:02 GMT 2023 , Edited by admin on Fri Dec 15 17:21:02 GMT 2023
PRIMARY
FDA UNII
70C1507JU9
Created by admin on Fri Dec 15 17:21:02 GMT 2023 , Edited by admin on Fri Dec 15 17:21:02 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY