ORMETOPRIM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H18N4O2
Molecular Weight	274.3183
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(C)=C(CC2=C(N)N=C(N)N=C2)C=C1OC

InChI

InChIKey=KEEYRKYKLYARHO-UHFFFAOYSA-N

InChI=1S/C14H18N4O2/c1-8-4-11(19-2)12(20-3)6-9(8)5-10-7-17-14(16)18-13(10)15/h4,6-7H,5H2,1-3H3,(H4,15,16,17,18)

HIDE SMILES / InChI

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c74215f7-382f-4082-a950-2e38c3a15d56
Curator's Comment: description was created based on several sources, including: https://www.zoetisus.com/contact/pages/product_information/msds_pi/pi/primor.pdf https://www.drugs.com/pro/rofenaid-40.html

As an aid in the prevention of coccidiosis caused by Eimeria adenoeides, E.gallopavonis, and E.meleagrimitis; for the prevention of bacterial infections caused by Pasteurella multocida (fowl cholera); for the treatment of skin and soft tissue infections. Ormetoprim potentiates the activity of sulfadimethoxine. The in vitro antibacterial spectrum and activity of the 2 compounds are very similar. Sulfonamides competitively inhibit bacterial synthesis of folic acid (pteroylglutamic acid) from paraaminobenzoic acid. Conditions reported following use of sulfonamides or potentiated sulfonamides include polyarthritis, urticaria, facial swelling, fever, hemolytic anemia, polydypsia, polyuria, hepatitis, vomiting, anorexia, diarrhea, and neurologic disorders. In rare instances, neurologic signs including behavioral changes, ataxia, seizures, aggression, and hyperexcitability have been reported. Keratitis sicca, possibly due to prolonged use of sulfonamides, has been reported.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Folate biosynthesis 3 Target ID: map00790 Sources: https://www.zoetisus.com/contact/pages/product_information/msds_pi/pi/primor.pdf	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Coccidiosis 45 Sources: http://www.fda.gov/ohrms/dockets/98fr/cv991.pdf	Curative	Approved 8429	ROFENAID Approved Use Indicated for the prevention of coccidiosis caused by Eimeria kofoidi and E. legionensis Launch Date 1999
Fowl cholera 4 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d016a197-8b78-43d5-a267-611181b243fd	Curative	Approved 8429	ROFENAID Approved Use As an aid in the prevention of bacterial infections caused by Pasteurella multocida (fowl cholera). Launch Date 1999
Skin infections 59 Sources: https://www.zoetisus.com/contact/pages/product_information/msds_pi/pi/primor.pdf	Curative	Approved 8429	Primor Approved Use Primor is for the treatment of skin infections (wounds and abscesses) in dogs caused by strains of Staphylococcus aureus and Escherichia coli. Launch Date 1989
Soft tissue infections 4 Sources: https://www.zoetisus.com/contact/pages/product_information/msds_pi/pi/primor.pdf	Curative	Approved 8429	Primor Approved Use Primor is for the treatment of the soft tissue infections (wounds and abscesses) in dogs caused by strains of Staphylococcus aureus and Escherichia coli. Launch Date 1989
Urinary tract infections 205 Sources: https://www.zoetisus.com/contact/pages/product_information/msds_pi/pi/primor.pdf	Curative	Approved 8429	Primor Approved Use Primor is for the treatment of urinary tract infections caused by Escherichia coli, Staphylococcus spp., and Proteus mirabilis susceptible to sulfadimethoxine/ormetoprim. Launch Date 1989
Colibacillosis 1 Sources: https://www.drugs.com/pro/rofenaid-40.html	Curative	Approved 8429	ROFENAID Approved Use As an aid in the prevention of colibacillosis. Launch Date 1999
Infectious coryza 1 Sources: https://www.drugs.com/pro/rofenaid-40.html	Curative	Approved 8429	ROFENAID Approved Use As an aid in the prevention of bacterial infections caused by Haemophilus gallinarum (infectious coryza). Launch Date 1999

PubMed

Title	Date	PubMed
Prevention of coccidiosis in domestic dogs and captive coyotes (Canis latrans) with sulfadimethoxine-ormetoprim combination.	1985 Sep	4051296
Nephrotic syndrome associated with administration of sulfadimethoxine/ormetoprim in a dobermann.	2005 May	15909446

Patents

Sample Use Guides

In Vivo Use Guide

Administer an initial oral dose of 55 mg/kg of body weight on the first day of treatment. Administer subsequent daily doses at the rate of 27.5 mg/kg of body weight. Continue treatment for at least 2 days after remission of clinical signs. Do not extend treatment for more than 21 consecutive days.

Route of Administration: Oral

In Vitro Use Guide

MIC for 10 E. Ictaluri strains: Eight out of 10 strains were inhibited by concentrations of ≤0.8 ug/ml while 1 was inhibited by a concentration of 4 ug/ml.

Name

Type

Language

ORMETOPRIM

Official Name

English

RO-59754

Code

English

2,4-PYRIMIDINEDIAMINE, 5-((4,5-DIMETHOXY-2-METHYLPHENYL)METHYL)-

Systematic Name

English

ORMETOPRIM [JAN]

Common Name

English

ORMETOPRIM [GREEN BOOK]

Common Name

English

RO-5-9754

Code

English

2,4-Diamino-5-(6-methylveratryl)pyrimidine

Systematic Name

English

ORMETOPRIM [MART.]

Common Name

English

ORMETROPRIM

Common Name

English

RO 5-9754

Code

English

ORMETOPRIM [USAN]

Common Name

English

NSC-95072

Code

English

ormetoprim [INN]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.2220F