CAPTAN

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H8Cl3NO2S
Molecular Weight	300.589
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC(Cl)(Cl)SN1C(=O)[C@H]2CC=CC[C@H]2C1=O

InChI

InChIKey=LDVVMCZRFWMZSG-OLQVQODUSA-N

InChI=1S/C9H8Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-2,5-6H,3-4H2/t5-,6+

HIDE SMILES / InChI

Molecular Formula	C9H8Cl3NO2S
Molecular Weight	300.589
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://npic.orst.edu/factsheets/captangen.pdf
Curator's Comment: description was created based on several sources, including: https://archive.epa.gov/pesticides/reregistration/web/pdf/0120red.pdf http://www.wikidoc.org/index.php/Captan http://www.ncbi.nlm.nih.gov/pubmed/20569196

Captan is a fungicide. It is used on a variety of agricultural and greenhouse food/feed crops, indoor non-food uses, seed treatments and ornamental plant sites. People who mixed captan products or worked in fields where captan had been applied reported eye and skin irritation. A few human volunteers reported skin irritation and allergic reactions after captan was applied to their backs. Captan was previously cited as Group B2, a probable human carcinogen by the US Environmental Protection Agency (EPA), but was reclassified in 2004. The EPA now states: “Captan is not likely to be a human carcinogen nor pose cancer risks of concern when used in accordance with approved product labels.”

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Aldehyde dehydrogenase 8 Target ID: CHEMBL1935 Sources: http://www.ncbi.nlm.nih.gov/pubmed/24491970	Inhibitor 8504
Estrogen receptor alpha 134 Target ID: CHEMBL206 Sources: http://www.ncbi.nlm.nih.gov/pubmed/15253041	Binding Agent 1076		142.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

AUC

Value	Dose	Co-administered	Analyte	Population
1652 nM × h/kg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21381057/	1 mg/kg bw single, oral dose: 1 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		4-CYCLOHEXENE-1,2-DICARBOXIMIDE, CIS- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
15.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21381057/	1 mg/kg bw single, oral dose: 1 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		4-CYCLOHEXENE-1,2-DICARBOXIMIDE, CIS- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
3.75 g 1 times / day single, oral Studied dose Dose: 3.75 g, 1 times / day Route: oral Route: single Dose: 3.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	healthy, 17 years Health Status: healthy Age Group: 17 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	Other AEs: Headache, Nausea... Other AEs: Headache Nausea Weakness Numbness of limbs Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/
0.5 % 1 times / day single, topical Studied dose Dose: 0.5 %, 1 times / day Route: topical Route: single Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8365173/	healthy, 21 years Health Status: healthy Age Group: 21 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/8365173/	Other AEs: Allergic reaction... Other AEs: Allergic reaction Sources: https://pubmed.ncbi.nlm.nih.gov/8365173/
0.5 % 1 times / day single, topical Studied dose Dose: 0.5 %, 1 times / day Route: topical Route: single Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7924295/	healthy, 26 years Health Status: healthy Age Group: 26 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/7924295/	Other AEs: Contact dermatitis... Other AEs: Contact dermatitis Sources: https://pubmed.ncbi.nlm.nih.gov/7924295/
0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1839725/	healthy, 45 years Health Status: healthy Age Group: 45 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/1839725/	Other AEs: Eczema... Other AEs: Eczema Sources: https://pubmed.ncbi.nlm.nih.gov/1839725/
0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9923784/	healthy, 45 years Health Status: healthy Age Group: 45 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9923784/	Other AEs: Photosensitivity... Other AEs: Photosensitivity Sources: https://pubmed.ncbi.nlm.nih.gov/9923784/

AEs

AE	Dose	Population
Headache	3.75 g 1 times / day single, oral Studied dose Dose: 3.75 g, 1 times / day Route: oral Route: single Dose: 3.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	healthy, 17 years Health Status: healthy Age Group: 17 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/
Nausea	3.75 g 1 times / day single, oral Studied dose Dose: 3.75 g, 1 times / day Route: oral Route: single Dose: 3.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	healthy, 17 years Health Status: healthy Age Group: 17 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/
Numbness of limbs	3.75 g 1 times / day single, oral Studied dose Dose: 3.75 g, 1 times / day Route: oral Route: single Dose: 3.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	healthy, 17 years Health Status: healthy Age Group: 17 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/
Weakness	3.75 g 1 times / day single, oral Studied dose Dose: 3.75 g, 1 times / day Route: oral Route: single Dose: 3.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	healthy, 17 years Health Status: healthy Age Group: 17 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/
Allergic reaction	0.5 % 1 times / day single, topical Studied dose Dose: 0.5 %, 1 times / day Route: topical Route: single Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8365173/	healthy, 21 years Health Status: healthy Age Group: 21 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/8365173/
Contact dermatitis	0.5 % 1 times / day single, topical Studied dose Dose: 0.5 %, 1 times / day Route: topical Route: single Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7924295/	healthy, 26 years Health Status: healthy Age Group: 26 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/7924295/
Eczema	0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1839725/	healthy, 45 years Health Status: healthy Age Group: 45 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/1839725/
Photosensitivity	0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9923784/	healthy, 45 years Health Status: healthy Age Group: 45 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9923784/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP2B 32 CYP3A 142 CYP1A2 832

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inducer 1966 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 17.0	likely
CYP3A 317	inducer 1966 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 17.0	likely
CYP2B 41	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/11673071/ Page: 8.0	no
CYP1A1 272	supressor 160 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 8 to 14	yes
CYP1A2 2333	supressor 160 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 8 to 14	yes
CYP2B1 41	supressor 160 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 8 to 14	yes
CYP2E1 1146	supressor 160 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 8 to 14	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:34608	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:34608
ChemicalBook	CB4367608	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4367608
eMolecules	509613	https://www.emolecules.com/cgi-bin/more?vid=509613
MolPort	MolPort-006-109-747	https://www.molport.com/shop/molecule-link/MolPort-006-109-747

PubMed

Title	Date	PubMed
Population-based in vitro hazard and concentration-response assessment of chemicals: the 1000 genomes high-throughput screening study.	2015-05	25622337
A concentration addition model to assess activation of the pregnane X receptor (PXR) by pesticide mixtures found in the French diet.	2014-09	25028461
Gender-linked haematopoietic and metabolic disturbances induced by a pesticide mixture administered at low dose to mice.	2010-01-12	19883720
Rhinitis associated with pesticide use among private pesticide applicators in the agricultural health study.	2010	20818537
Pesticide use and adult-onset asthma among male farmers in the Agricultural Health Study.	2009-12	19541724
Estimation of estrogenic and antiestrogenic activities of selected pesticides by MCF-7 cell proliferation assay.	2004-05	15253041
Induction of hsp70 in transgenic Drosophila: biomarker of exposure against phthalimide group of chemicals.	2003-05-02	12726998
The inhibitory effect of the fungicides captan and captafol on eukaryotic topoisomerases in vitro and lack of recombinagenic activity in the wing spot test of Drosophila melanogaster.	2002-07-25	12113771
Non-Hodgkin's lymphoma and specific pesticide exposures in men: cross-Canada study of pesticides and health.	2001-11	11700263
Interaction of glutathione transferase P1-1 with captan and captafol.	1996-07-12	8678907
Evaluation of the carcinogenic potential of pesticides. 4. Chloroalkylthiodicarboximide compounds with fungicidal activity.	1993-02	8441825
Irritation and sensitization potential of pesticides.	1987-10	2962818
A test series for pesticide dermatitis.	1986-11	2949929
Cytotoxicity and mutagenicity of the fungicides captan and folpet in cultured mammalian cells CHO/HGPRT system).	1981	7274179

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Significant cytotoxicity of Captan on the human adrenocortical carcinoma cell line H295R was observed at the concentrations of 30 μM (26 %) and 100 μM (74 %).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:32:57 GMT 2025` Edited by `admin` on `Mon Mar 31 21:32:57 GMT 2025`
Record UNII	EOL5G26Q9F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CAPTAN

Official Name

English

MERPAN

Preferred Name

English

CAPTAN [II]

Common Name

English

CAPTAN [IARC]

Common Name

English

CAPTAN [HSDB]

Common Name

English

CAPTAN [ISO]

Common Name

English

VANCIDE 89

Common Name

English

NSC-36726

Code

English

CAPTAN [MI]

Common Name

English

ORTHOCIDE-406

Brand Name

English

SR-406

Code

English

1H-ISOINDOLE-1,3(2H)-DIONE, 3A,4,7,7A-TETRAHYDRO-2-((TRICHLOROMETHYL)THIO)-, (3AR,7AS)-REL-

Common Name

English

N-(TRICHLOROMETHYLTHIO)CYCLOHEX-4-ENE-1,2-DICARBOXIMIDE

Common Name

English

ENT-26538

Code

English

1H-ISOINDOLE-1,3(2H)-DIONE, 3A,4,7,7A-TETRAHYDRO-2-((TRICHLOROMETHYL)THIO)-, CIS-

Common Name

English

4-CYCLOHEXENE-1,2-DICARBOXIMIDE, N-((TRICHLOROMETHYL)THIO)-, CIS-

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 176.170