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Details

Stereochemistry RACEMIC
Molecular Formula C14H14O4
Molecular Weight 246.2586
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHTHALOFYNE

SMILES

CCC(C)(OC(=O)C1=CC=CC=C1C(O)=O)C#C

InChI

InChIKey=CZGIRAWWWHPJHM-UHFFFAOYSA-N
InChI=1S/C14H14O4/c1-4-14(3,5-2)18-13(17)11-9-7-6-8-10(11)12(15)16/h1,6-9H,5H2,2-3H3,(H,15,16)

HIDE SMILES / InChI

Molecular Formula C14H14O4
Molecular Weight 246.2586
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Phthalofyne (3-methyl-1-pentyn-3-yl acid phthalate) is a synthetic chemical compound demonstrated to have trichuricidal activity against both Trichuris vulpis and Trichuris trichiura. It was used in veterinary medicine against dog whipworm, Trichuris vulpis, under the brand name Whipcide.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Whipcide

Approved Use

Phthalofyne is used for the treatment of whipworm (Trichuris vulpis) infection in dogs.

Launch Date

1954
Doses

Doses

DosePopulationAdverse events​
450 mg single, rectal
Highest studied dose
Dose: 450 mg
Route: rectal
Route: single
Dose: 450 mg
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
175 mg/kg single, oral
Highest studied dose
Dose: 175 mg/kg
Route: oral
Route: single
Dose: 175 mg/kg
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Other AEs: Nausea, Regurgitation of gastric contents...
Other AEs:
Nausea
Regurgitation of gastric contents
Sources:
AEs

AEs

AESignificanceDosePopulation
Nausea
175 mg/kg single, oral
Highest studied dose
Dose: 175 mg/kg
Route: oral
Route: single
Dose: 175 mg/kg
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Regurgitation of gastric contents
175 mg/kg single, oral
Highest studied dose
Dose: 175 mg/kg
Route: oral
Route: single
Dose: 175 mg/kg
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Effects of phthalofyne in the treatment of human Trichuris trichiura infection.
1958-01
Ocular toxicity of whipcide (3-methyl-1-pentyn-3-yl acid phthalate) in humans.
1956-07-28
Trichuricidal activity of phthalofyne and certain related compounds.
1955-08
Patents

Sample Use Guides

Phthalofyne was given to 10 healthy young Filipino males harboring Trichuris trichiura. Of 7 cases who received 100 to 125 mg./kg. by mouth, alone or in combination with the same dose given by enema, 4 had rather minimal complaints of nausea and/or vomiting and none received significant therapeutic benefit. The highest oral dose, 175 mg./kg. given to a single patient, produced considerable nausea and apparently complete regurgitation of gastric contents and no therapeutic benefit, suggesting that effective single oral doses would not be easily retained. The phthalofyne enemas, containing respectively 200 mg./kg. and 450 mg./kg. of the drug, and given one week apart to a single patient, produced no side effects and no significant therapeutic effect.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:52:18 GMT 2025
Edited
by admin
on Mon Mar 31 17:52:18 GMT 2025
Record UNII
TA9XO4D05J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FTALOFYNE
INN   MART.  
INN  
Preferred Name English
PHTHALOFYNE
GREEN BOOK   MI   USAN  
USAN  
Official Name English
1,2-BENZENEDICARBOXYLIC ACID, MONO(1-ETHYL-1-METHYL-2-PROPYNYL) ESTER
Common Name English
PHTHALOFYNE [USAN]
Common Name English
NSC-25614
Code English
ftalofyne [INN]
Common Name English
PHTHALOFYNE [MI]
Common Name English
PHTHALOFYNE [GREEN BOOK]
Common Name English
FTALOFYNE [MART.]
Common Name English
Mono(1-ethyl-1-methyl-2-propynyl) phthalate
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
Code System Code Type Description
EVMPD
SUB07819MIG
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
NSC
25614
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
SMS_ID
100000080449
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
INN
2277
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
ChEMBL
CHEMBL2107106
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
NCI_THESAURUS
C75230
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
PUBCHEM
8573
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
FDA UNII
TA9XO4D05J
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
CAS
131-67-9
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
DRUG BANK
DB11449
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
MERCK INDEX
m8756
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID9057634
Created by admin on Mon Mar 31 17:52:18 GMT 2025 , Edited by admin on Mon Mar 31 17:52:18 GMT 2025
PRIMARY
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