U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H11NO2
Molecular Weight 201.2212
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBARIL

SMILES

CNC(=O)OC1=C2C=CC=CC2=CC=C1

InChI

InChIKey=CVXBEEMKQHEXEN-UHFFFAOYSA-N
InChI=1S/C12H11NO2/c1-13-12(14)15-11-8-4-6-9-5-2-3-7-10(9)11/h2-8H,1H3,(H,13,14)

HIDE SMILES / InChI

Molecular Formula C12H11NO2
Molecular Weight 201.2212
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6814883 and https://www.ncbi.nlm.nih.gov/pubmed/6804141

Carbaryl (1-naphthyl methylcarbamate) is a chemical in the carbamate family used chiefly as an insecticide. It is a white crystalline solid commonly sold under the brand name Sevin, a trademark of the Bayer Company.Union Carbide discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations. It remains the third-most-used insecticide in the United States for home gardens, commercial agriculture, and forestry and rangeland protection. As a veterinary drug, it is known as carbaril. Carbaryl is an anticholinesterase inhibitor. It is indicated for the treatment of head and pubic lice. It is available as a lotion (Carylderm) and a shampoo (Carylderm; New Suleo; Derbac). Carbaryl was developed because lice began to show resistance to organochlorine insecticides such as DDT and gamma benzene hexachloride (Quellada; Lorexane). It was introduced in the late 1960s particularly for the control of head lice; it is less effective against mites, and not recommended for scabies.

CNS Activity

Curator's Comment: Penetrant in mice and rabbits

Originator

Curator's Comment: Discovered in 1958 by Union Carbide

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
109.98 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Carylderm

Approved Use

For the treatment of head lice infections
Doses

Doses

DosePopulationAdverse events​
0.5 % single, topical
Studied dose
Dose: 0.5 %
Route: topical
Route: single
Dose: 0.5 %
Sources:
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Other AEs: Scalp irritation, Irritation skin...
Other AEs:
Scalp irritation
Irritation skin
Flaking skin
Stinging
Eyes irritation
Sources:
AEs

AEs

AESignificanceDosePopulation
Eyes irritation
0.5 % single, topical
Studied dose
Dose: 0.5 %
Route: topical
Route: single
Dose: 0.5 %
Sources:
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Flaking skin
0.5 % single, topical
Studied dose
Dose: 0.5 %
Route: topical
Route: single
Dose: 0.5 %
Sources:
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Irritation skin
0.5 % single, topical
Studied dose
Dose: 0.5 %
Route: topical
Route: single
Dose: 0.5 %
Sources:
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Scalp irritation
0.5 % single, topical
Studied dose
Dose: 0.5 %
Route: topical
Route: single
Dose: 0.5 %
Sources:
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Stinging
0.5 % single, topical
Studied dose
Dose: 0.5 %
Route: topical
Route: single
Dose: 0.5 %
Sources:
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Multiresidue screening methods for the determination of pesticides in tomatoes.
2003-09
Amperometric and spectrophotometric determination of carbaryl in natural waters and commercial formulations.
2003-09
Competitive degradation and detoxification of carbamate insecticides by membrane anodic Fenton treatment.
2003-08-27
Characterization of cholinesterase activity in three bivalves inhabiting the North Adriatic sea and their possible use as sentinel organisms for biosurveillance programmes.
2003-08-01
A simple method for the determination of carbaryl and 1-naphthol in fruit juices by high-performance liquid chromatography-diode-array detection.
2003-08
Evaluation of pesticide uptake by Lupinus seeds.
2003-08
Monitoring some phenoxyl-type N-methylcarbamate pesticide residues in fruit juices using high-performance liquid chromatography with peroxyoxalate-chemiluminescence detection.
2003-07-25
Multiresidue analysis of carbamate pesticides in soil by sonication-assisted extraction in small columns and liquid chromatography.
2003-07-25
Susceptibility of black fly larvae (Diptera: Simuliidae) to lawn-care insecticides individually and as mixtures.
2003-07
Development of a toxic bait for control of eastern lubber grasshopper (Orthoptera: Acrididae).
2003-06
Continuous ultrasound-assisted extraction coupled to on line filtration-solid-phase extraction-column liquid chromatography--post column derivatisation-fluorescence detection for the determination of N-methylcarbamates in soil and food.
2003-05-23
Photodecomposition of carbaryl in the presence of silver-doped zeolite Y and Suwannee River natural organic matter.
2003-05-15
Considerations on ultra trace analysis of carbamates in water samples.
2003-05-09
Analysis of pesticides in water and sediment under different storage conditions using gas chromatography.
2003-05
[Simultaneous determination of carbaryl and propanil in human serum and urine by on-line column-switching technique followed by automatic reversed-phase HPLC].
2003-04
Simultaneous analysis of carbamate pesticides in tap and raw water by LC/ESI/MS.
2003-04
Environmental monitoring of carbaryl applied in urban areas to control the glassy-winged sharpshooter in California.
2003-03
Inhibition of neurite outgrowth in N2a cells by leptophos and carbaryl: effects on neurofilament heavy chain, GAP-43 and HSP-70.
2003-02
Biological targets of neurotoxic pesticides analysed by alteration of developmental events in the Mediterranean sea urchin, Paracentrotus lividus.
2003-02
Turfgrass thatch effects on pesticide leaching: a laboratory and modeling study.
2003-01-29
Toxic effects of dimethoate and carbaryl pesticides on protein metabolism of the freshwater snail Lymnaea acuminata.
2003-01
Tumorigenic potential of carbaryl in the heterozygous p53 knockout mouse model.
2003-01
Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products.
2002-12
Photoinduced degradation of carbaryl in a wetland surface water.
2002-11-06
Rapid enzyme immunoassays for the detection of carbaryl and methoprene in grains.
2002-11
In vitro metabolism of carbaryl by human cytochrome P450 and its inhibition by chlorpyrifos.
2002-10-20
Effects of Sevin (carbaryl insecticide) on early life stages of zebrafish (Danio rerio).
2002-10
Effects of pesticides on DNA and protein of shrimp larvae Litopenaeus stylirostris of the California Gulf.
2002-10
Carbaryl resistance in populations of grape berry moth (Lepidoptera: Tortricidae) in New York and Pennsylvania.
2002-10
A comparison between two brine shrimp assays to detect in vitro cytotoxicity in marine natural products.
2002-09-23
Insecticide susceptibilities of cat fleas (Siphonaptera: Pulicidae) from several regions of the United States.
2002-09
Causes of ambient toxicity in the Calleguas Creek watershed of southern California.
2002-09
Derivatization reactions of carbamate pesticides in supercritical carbon dioxide.
2002-09
Hazards of insecticides to the bumble bees Bombus impatiens (Hymenoptera: Apidae) foraging on flowering white clover in turf.
2002-08
Broad-spectrum insecticide resistance in obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae) from Michigan.
2002-08
Purification and biochemical characterization of the carbamate hydrolase from Pseudomonas sp. 50432.
2002-08
Viability of textile systems for hand and body protection: effects of chemical interaction, wear, and storage conditions.
2002-08
Imidacloprid residues in Willapa Bay (Washington State) water and sediment following application for control of burrowing shrimp.
2002-07-17
[Analysis of carbaryl and other pesticides by capillary electrophoresis].
2002-07
Validation of a method for the determination of multiclass pesticide residues in fruit juices by liquid chromatography/tandem mass spectrometry after extraction by matrix solid-phase dispersion.
2002-06-27
Pesticide impact on excretory physiology of the common frog, Rana tigrina (Daud) tadpoles.
2002-05
Electrochemical detection of carbamate pesticides at conductive diamond electrodes.
2002-04-01
Carbaryl-induced alterations in biochemical metabolism of the prawn, Macrobrachium malcolmsonii.
2002-04
Toxic effects of dimethoate and carbaryl pesticides on carbohydrate metabolism of freshwater snail Lymnaea acuminata.
2002-04
Evaluation of safety and efficacy of acaricides for control of the African tortoise tick (Amblyomma marmoreum) on leopard tortoises (Geochelone pardalis).
2002-03
Effect of some insecticides on acetylcholinesterase from beneficial insects: Coccinella septempunctata, Chrysoperla carnea and Forficula auricularia.
2002
The use of the radioisotope method in studies of pesticide penetration into the eyeball.
2002
Progress toward understanding the neurophysiological basis of predator-induced morphology in Daphnia pulex.
2001-12-21
Effect of pesticides carbaryl and phorate on serum cholesterol level in fish, Clarias batrachus (Linn).
2001-07
Episodic exposures to chemicals: what relevance to chemical intolerance?
2001-03
Patents

Sample Use Guides

Carylderm solution should be applied to the hair and scalp and left for 10 to 12 hours, to ensure that all the eggs are treated. This is eventually washed out and the eggs removed from the scalp using a special nit comb. It is usually recommended that family members and close contacts be treated at the same time, if infected. In the event of early re-infestation of lice from surviving eggs, carylderm preparations may be reapplied, provided 7 days have elapsed since the first application.
Route of Administration: Topical
Rat hair cell and neuronal damage was observed at carbaryl concentrations as low as 50 uM after 96-h treatment and 100 uM after 48-h treatment.
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:30:17 GMT 2025
Edited
by admin
on Wed Apr 02 09:30:17 GMT 2025
Record UNII
R890C8J3N1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBARIL
INN   WHO-DD  
INN  
Official Name English
CARBARYL
HSDB   ISO   MART.   MI  
Preferred Name English
CARBARYL [HSDB]
Common Name English
NSC-27311
Code English
1-NAPHTHALENYL N-METHYLCARBAMATE
Systematic Name English
CARBARYL [IARC]
Common Name English
CARBARYL [ISO]
Common Name English
ENT-23969
Code English
CARBARYL [MI]
Common Name English
Carbaril [WHO-DD]
Common Name English
carbaril [INN]
Common Name English
1-NAPHTHYL METHYLCARBAMATE
Systematic Name English
CARBARYL [MART.]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 56801
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
IARC Carbaryl
WHO-VATC QP53AE01
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
Code System Code Type Description
ALANWOOD
carbaryl
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
HSDB
952
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
NCI_THESAURUS
C76389
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
MESH
D012721
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
WIKIPEDIA
Carbaryl
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
RXCUI
9724
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY RxNorm
CAS
63-25-2
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
FDA UNII
R890C8J3N1
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID9020247
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-555-0
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
CHEBI
3390
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
EVMPD
SUB06115MIG
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
SMS_ID
100000088568
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
MERCK INDEX
m3058
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY Merck Index
NSC
27311
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
DRUG CENTRAL
3066
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL46917
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
PUBCHEM
6129
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
INN
2858
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY