FAMPHUR

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H16NO5PS2
Molecular Weight	325.342
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COP(=S)(OC)OC1=CC=C(C=C1)S(=O)(=O)N(C)C

InChI

InChIKey=JISACBWYRJHSMG-UHFFFAOYSA-N

InChI=1S/C10H16NO5PS2/c1-11(2)19(12,13)10-7-5-9(6-8-10)16-17(18,14-3)15-4/h5-8H,1-4H3

HIDE SMILES / InChI

Molecular Formula	C10H16NO5PS2
Molecular Weight	325.342
Charge	0
Count

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

Description
Sources: https://www.pwrc.usgs.gov/eisler/CHR_27_Famphur.pdf | https://www.law.cornell.edu/cfr/text/21/520.1242g | https://www.drugs.com/international/famphur.html

Famphur is an insecticide and antihelmenthic. Famphur is approved in cattle as a pour-on (NADA 34-697; 21 CFR 524.900) and as medicated feed (NADA 34-266; 21 CFR 558.254). It is a component of the FDA-approved TRAMISOL X-TRA Combination Paste, used for the treatment of cattle infected with the following parasites: Stomach worms (Haemonchus, Trichostrongylus, Ostertagia), intestinal worms (Trichostrongylus, Cooperia, Nematodirus, Bunostomum, Oesophagostomum), lungworms (Dictyocaulus), cattle grubs (Hypoderma), biting lice (Bovicola), and sucking lice (Linognathus, Solenoptes). Famphur is a cholinesterase-inhibiting drug.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 209 Target ID: CHEMBL4768 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7284948 \| https://www.pwrc.usgs.gov/eisler/CHR_27_Famphur.pdf	Inhibitor 8504
Trichostrongylus axei 1 Target ID: CHEMBL612397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3693663	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Helminthiasis in cattle 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3693663 https://www.ncbi.nlm.nih.gov/pubmed/5816059	Curative		Approved 8583	TRAMISOL X-TRA Approved Use For treatment of cattle infected with the following parasites: 1) STOMACH WORMS: Haemonchus, Trichostrongylus, Ostertagia 2) INTESTINAL WORMS: Trichostrongylus, Cooperia, Nematodirus, Bunostomum, Oesophagostomum 3) LUNGWORMS: Dictyocaulus 4) BITING LICE: Bovicola 5) SUCKING LICE: Linognathus, Solenoptes It is not effective against lice eggs. Launch Date 1968

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 CYP2C19 2057 CYP1A2 2153	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5859#section=Biological-Test-Results Page: 13.0	inconclusive [IC50 34.6713 uM]
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5859#section=Biological-Test-Results Page: 126.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5859#section=Biological-Test-Results Page: 1.0	yes [IC50 0.055 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5859#section=Biological-Test-Results Page: 2.0	yes [IC50 0.3557 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5859#section=Biological-Test-Results Page: 10.0	yes [IC50 31.7055 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5859#section=Biological-Test-Results Page: 4.0	yes [IC50 6.9178 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5859#section=Biological-Test-Results Page: 16.0	yes [IC50 61.1306 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5859#section=Biological-Test-Results Page: 125 \| 128	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5859#section=Biological-Test-Results Page: 37.0

PubMed

Title	Date	PubMed
Longitudinal trends in organophosphate incidents reported to the National Pesticide Information Center, 1995-2007.	2009-04-20	19379510
Prediction for the mixture toxicity of six organophosphorus pesticides to the luminescent bacterium Q67.	2008-11	18308393
Avian mortality events in the United States caused by anticholinesterase pesticides: a retrospective summary of National Wildlife Health Center records from 1980 to 2000.	2004-05	15253053

Patents

Sample Use Guides

In Vivo Use Guide

TRAMISOL X-TRA Combination Paste contains levamisole resinate (50%) and famphur as active ingredients packed in a polyethylene cartridge-type container.TRAMISOL X-TRA is formulated to provide 8 mg/kg (3.6 mg/lb) of body weight oflevamisole HCl equivalent activity and 30 mg/kg (13.6 mg/lb) of body weight offamphur activity which has been demonstrated to be the optimum dose level foreffective performance the product's anthelmintic and ectoparasitic label claims.TRAMISOL X-TRA is administered to cattle in individual oral doses using thecompatible GelGun ®oral dispensing device. The product has been designed sothat each distinct depression of the Gel Gun trigger or

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:50:03 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:03 GMT 2025`
Record UNII	02UOP4Z0O0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FAMOPHOS

Preferred Name

English

FAMPHUR

Common Name

English

FAMOFOS

Common Name

English

O-4-DIMETHYLSULFAMOYLPHENYL O,O-DIMETHYL PHOSPHOROTHIOATE

Common Name

English

FAMPHUR [MART.]

Common Name

English

O-(4-((DIMETHYLAMINO)SULFONYL)PHENYL) O,O-DIMETHYL PHOSPHOROTHIOATE

Systematic Name

English

PHOSPHOROTHIOIC ACID, O-(4-((DIMETHYLAMINO)SULFONYL)PHENYL) O,O-DIMETHYL ESTER

Common Name

English

FAMPHUR [HSDB]

Common Name

English

FAMPHUR [MI]

Common Name

English

FAMPHUR [GREEN BOOK]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

59901