PYRROCAINE

US Previously Marketed

First approved in 1962

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H20N2O
Molecular Weight	232.3214
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CC(C)=C1NC(=O)CN2CCCC2

InChI

InChIKey=OYCGKECKIVYHTN-UHFFFAOYSA-N

InChI=1S/C14H20N2O/c1-11-6-5-7-12(2)14(11)15-13(17)10-16-8-3-4-9-16/h5-7H,3-4,8-10H2,1-2H3,(H,15,17)

HIDE SMILES / InChI

Molecular Formula	C14H20N2O
Molecular Weight	232.3214
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4883831 | https://www.ncbi.nlm.nih.gov/pubmed/19598995 | https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/anesthetics_508.pdf | https://www.ncbi.nlm.nih.gov/pubmed/6838647

Pyrrocaine is the amide local anesthetics. It is metabolized to 2,6-xylidine. It was used mainly as an infiltration and nerve block dental anesthetic in the 1960s and favored due to its rapid onset. The potency of pyrrocaine equals that of lidocaine in both sensory and motor nerve blocking. Pyrrocaine provided to be somewhat less toxic than lidocaine. No methemoglobinemia was clinically observed. It has been classified as unsafe for use in acute porphyria. There is no evidence that it is currently used commercially.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
5-aminolevulinate synthase, nonspecific, mitochondrial 3 Target ID: P07997 Gene ID: 552895.0 Gene Symbol: ALAS1 Target Organism: Gallus gallus (Chicken) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6838647	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4883831 https://www.ncbi.nlm.nih.gov/pubmed/19598995	Preventing		Approved 8429	Dynacaine Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L2NDS
Alfa Chemistry	2210-77-7
Alfa Chemistry	ACM2210777
Alinda	IVK/0063500
Ambinter	Amb2244552	http://www.ambinter.com/reference/2244552
Aurora Fine Chemicals LLC	A21.365.984	http://online.aurorafinechemicals.com/info?ID=A21.365.984
Aurora Fine Chemicals LLC	K00.035.244	http://online.aurorafinechemicals.com/info?ID=K00.035.244
ChemDiv	Y207-4352
Chemieliva Pharmaceutical Co., Ltd	PBCM1239388
Chemspace	CSSS00025763719	https://chem-space.com/CSSS00025763719
Compound Cloud	24361
Enamine	Z46169098
Lab Network	LN02079726
MolPort	MolPort-003-666-697
MolPort	MolPort-006-114-101
NovoSeek	24361
Otava	4471046
Scientific Exchange	POD_84/0847
Smolecule	S589368	https://www.smolecule.com/products/s589368
THE BioTek	bt-427051	https://www.thebiotek.com/product/others/bt-427051
Vitas-M Laboratory	STK409086
ZINC	ZINC000000002011	http://zinc15.docking.org/substances/ZINC000000002011
eMolecules	2963303
mcule	MCULE-4424573983	https://mcule.com/MCULE-4424573983/

PubMed

Title	Date	PubMed
Double-blind evaluation of a new local anesthetic agents, pyrrocaine hydrochloride, for nerve block anesthesia.	1969 Jan-Feb	4883831
A rapid spectrophotometric assay of amide type dental anaesthetic agents.	1977 Jun	270977
Study of anaesthetic agents for their ability to elicit porphyrin biosynthesis in chick embryo liver.	1983 Mar 15	6838647

Patents

Sample Use Guides

In Vivo Use Guide

Usual, infiltration, 1 ml of a 2% solution; Nerve block, 1.5 to 2 ml of a 2% solution

Route of Administration: Other

In Vitro Use Guide

Pyrrocaine hydrochloride 0.1-300.0 uM/L significantly decreased the automatic rhythmicity of the right atrium with sinoatrial node, and 30 nmol/L of it also counteracted the increasing of the automaticity induced by isoproterenol. The drug at 10-30 uM/L reduced the excitability of the left atrium and the peak force developed in the right atrium.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:00:18 UTC 2023` Edited by `admin` on `Fri Dec 15 15:00:18 UTC 2023`
Record UNII	9D47L94CPW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PYRROCAINE

Official Name

English

PYRROCAINE [MI]

Common Name

English

1-PYRROLIDINEACETO-2',6'-XYLIDIDE.

Common Name

English

EN-1010

Code

English

Pyrrocaine [WHO-DD]

Common Name

English

PYRROCAINE [USAN]

Common Name

English

pyrrocaine [INN]

Common Name

English

NSC-52644

Code

English

1-PYRROLIDINEACETAMIDE, N-(2,6-DIMETHYLPHENYL)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245