154-85-8

Basic information

• Product Name: 6-CARBOXY-2,4-DIHYDROXYPYRIMIDINE MONOSODIUM SALT
• Synonyms: 6-CARBOXY-2,4-DIHYDROXYPYRIMIDINE MONOSODIUM SALT;URACIL-6-CARBOXYLIC ACID MONOSODIUM SALT;OROTIC ACID MONOSODIUM SALT;OROTIC ACID, NA SALT;4-pyrimidinecarboxylicacid,1,2,3,6-tetrahydro-2,6-dioxo-,sodiumsalt,hydr;ate(1:1:1);monosodiumorolatehydrate;oroticacid,sodiumsalt,hydrate(1:1:1)
• CAS NO: 154-85-8
• Molecular Formula: C₅H₃N₂O₄*Na
• Molecular Weight: 178.08
• EINECS: 205-834-0
• Mol File: 154-85-8.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-CARBOXY-2,4-DIHYDROXYPYRIMIDINE MONOSODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CARBOXY-2,4-DIHYDROXYPYRIMIDINE MONOSODIUM SALT(154-85-8)
• EPA Substance Registry System: 6-CARBOXY-2,4-DIHYDROXYPYRIMIDINE MONOSODIUM SALT(154-85-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: RM3201700
• Hazardous Substances Data: 154-85-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Orotic Acid Monosodium Salt is used in the formation of a complex with lanthanium(III) which displats cytotoxic activity on different tumor cell lines.Also, it is the unlabeled form of Orotic Acid-15N2 Monosodium Salt (O691517), which is an intermediate used in the synthesis of Orotic Acid-15N2 Monohydrate (O691504), which is a labeled analogue of Orotic Acid Monohydrade (O691500), which is used in the preparation of therapeutic agents for chronic obstructive pulmonary disease (COPD) treatment.

Definition

ChEBI: An organic sodium salt comprising equal numbers of sodium and orotate ions.

InChI:InChI=1/C5H4N2O4.Na/c8-3-1-2(4(9)10)6-5(11)7-3;/h1H,(H,9,10)(H2,6,7,8,11);/q;+1/p-1

Upstream product

• 626-48-2 6-Methyluracil 
• 65-86-1 orotic acid 
• 62881-01-0 6-trichloromethyl-1H-pyrimidine-2,4-dione 

Downstream Products

• 58-32-2 dipyridamole 
• 17687-24-0 5-nitroorotic acid 
• 7164-43-4 5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 
• 6713-54-8 2,4,6,8-tetrahydroxypyrimidine-[5,4-d]pyrimidine 
• 32980-71-5 2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine 
• 7139-02-8 2,6-dichloro-4,8-bis(piperidin-1-yl)pyrimido[5,4-d]pyrimidine 
• 3387-36-8 disodium uridine-5'-monophosphate 

Relevant articles and documents

Tri- and diorganotin(IV) complexes of biologically important orotic acid: Synthesis, spectroscopic studies, in vitro anti-cancer, DNA fragmentation, enzyme assays and in vivo anti-inflammatory activities

Tri-and diorganotin(IV) orotates of general formula, RnSn(H 2Or)m [n = 3/2, m = 1/2, R = Me, n-Bu, n-Oct and Ph; H2Or- = monoanion of orotic acid (H3Or)] (n-Bu2Sn(HOr) as an exception) have been synthesized. On the basis of various spectroscopic studies it is revealed that R3Sn(H 2Or) and R2Sn(H2Or)2 exhibit distorted trigonal-bipyramidal and distorted octahedral geometry, respectively, and n-Bu2Sn(HOr) shows both five and six coordination geometry around tin. In vitro anti-cancer screening against MCF-7 (mammary), HEK-293 (kidney), PC-3 (prostate), HCT-15 (colon) and HepG-2 (liver) cancer cell lines suggest that the n-Oct2Sn(H2Or)2 is the most active complex among all of the studied complexes. DNA fragmentation and antioxidant enzyme assays suggest that cytotoxic effect of the complexes is selectively mediated through the induction of apoptosis. They also exhibit low toxicity and good anti-inflammatory activity (in vivo).

Compositions and methods of reducing tissue levels of drugs when given as orotate derivatives

This invention is in the field of chemical restructuring of pharmaceutical agents known to cause tissue toxicity as a side effect, by producing their orotate derivatives. More particularly, it concerns orotate derivatives of the anthracyclines, doxorubicin and daunorubicin, that are found to reduce levels of the pharmaceutical agent in noncancerous tissues. There orotate derivatives are equally efficacious in inhibiting the SCCAKI-1 kidney tumor in animals and the reduction in the heart tissue of doxorubicin compared with doxorubicin HCl suggests a reduction in toxicity induced by free radical generation by the anthrracyclines.

Process for preparing orotic acid

A method for the preparation of orotic acid and thioorotic acid is described which includes the formation of carboxymethylene-hydantoin or -thiohydantoin and subsequent rearrangement and isolation of orotic acid and thioorotic acid, respectively.