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
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)
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Trichuris vulpis Sources: https://www.ncbi.nlm.nih.gov/pubmed/13252554 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Whipcide Approved UsePhthalofyne is used for the treatment of whipworm (Trichuris vulpis) infection in dogs. Launch Date1954 |
Doses
| Dose | Population | Adverse 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 Sources: Regurgitation of gastric contents |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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: |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13508999
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
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C250
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DTXSID9057634
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ACTIVE MOIETY