ROMAZARIT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H16ClNO4
Molecular Weight	309.745
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(COC(C)(C)C(O)=O)OC(=N1)C2=CC=C(Cl)C=C2

InChI

InChIKey=LNXXSBRGLBOASF-UHFFFAOYSA-N

InChI=1S/C15H16ClNO4/c1-9-12(8-20-15(2,3)14(18)19)21-13(17-9)10-4-6-11(16)7-5-10/h4-7H,8H2,1-3H3,(H,18,19)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1995900 | https://www.ncbi.nlm.nih.gov/pubmed/7619674 | https://www.ncbi.nlm.nih.gov/pubmed/16125391

Romazarit, (Ro 31-3948, 7), 2-[[2-(4-chlorophenyl)-4-methyl-5-oxazolyl]methoxy]-2-methylpropionic acid is a substituted heterocyclic alkoxypropionic acid. Romazarit was considered to be a potential disease-modifying antirheumatic drug. Romazarit was withdrawn due to its toxicity profile.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
inflammatory response 47 Target ID: GO:0006954 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2156999 \| https://www.ncbi.nlm.nih.gov/pubmed/1995900	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1550907 https://www.ncbi.nlm.nih.gov/pubmed/7619674 https://www.arthritisresearch.us/side-effects/romazarit.html	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
144 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2088768	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:		ROMAZARIT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
958 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2088768	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:		ROMAZARIT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
1500 mg single, oral Highest studied dose Dose: 1500 mg Route: oral Route: single Dose: 1500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2088768 Page: p.320	healthy, ,ADULT n = 6 Health Status: healthy Age Group: ,ADULT Sex: M Food Status: FASTED Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/2088768 Page: p.320	Sources: https://pubmed.ncbi.nlm.nih.gov/2088768 Page: p.320

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	36848	http://www.alfa-chemistry.com/search.aspx?q=36848
Alfa Chemistry	ACM109543762	http://www.alfa-chemistry.com/search.aspx?q=ACM109543762
Compound Cloud	71321
MuseChem	M008133	https://www.musechem.com/product/M008133.html
Tetrahedron	TS60829	http://www.thsci.com/search.do?q=TS60829

PubMed

Title	Date	PubMed
Biologic properties of romazarit (Ro 31-3948), a potential disease-modifying antirheumatic drug.	1990 Mar	2156999
Pharmacokinetics and tolerance of romazarit after oral administration of ascending single doses to healthy human volunteers.	1990 Oct-Dec	2088768
Romazarit: a potential disease-modifying antirheumatic drug.	1991 Feb	1995900
A pharmacokinetic and tolerance study of romazarit in patients with rheumatoid arthritis.	1992 Mar	1550907
Population pharmacodynamics of romazarit.	1995 Mar	7619674
Tetra substituted thiophenes as anti-inflammatory agents: exploitation of analogue-based drug design.	2005 Dec 15	16125391
Synthesis of 4-benzyl-1,3-thiazole derivatives as potential anti-inflammatory agents: an analogue-based drug design approach.	2009 Jun	19469712

Patents

Sample Use Guides

In Vivo Use Guide

patients with rheumatoid arthritis: 200 mg or 450 mg every 12 h for up to 24 weeks, 100 mg t.i.d., 350 mg b.i.d., or 350 mg t.i.d., for 6 days.

Route of Administration: Oral

In Vitro Use Guide

In vitro romazarit was an extremely weak inhibitor of prostaglandin synthetase activity in both sheep seminal vesicle (IC50 6500 microM) and rat renal medulla (IC50 greater than 300 microM) cell-free preparations.

Name

Type

Language

ROMAZARIT

Official Name

English

RO 31-3948/000

Code

English

romazarit [INN]

Common Name

English

RO-313948000

Code

English

2-((2-(P-CHLOROPHENYL)-4-METHYL-5-OXAZOLYL)METHOXY)-2-METHYLPROPIONIC ACID

Systematic Name

English

PROPANOIC ACID, 2-((2-(4-CHLOROPHENYL)-4-METHYL-5-OXAZOLYL)METHOXY)-2-METHYL-

Systematic Name

English

ROMAZARIT [USAN]

Common Name

English

RO-31-3948/000

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29634